Windermere FL Single Family Real Estate, Homes for Sale

Situated on a distinguished homesite in one of Windermere's most sought after locations, 13328 Overstreet Road impresses right when you pull into the oversized 6+ CAR PAVER DRIVWAY with parking for up to six vehicles. If any of those vehicles are electric, you can charge them using the installed TESLA CAR CHARGER and save $$ on the electric bill with the PAID-OFF SOLAR PANELS. This home defines exceptional value and modern efficiency. At the heart of the home, the GOURMET KITCHEN is an entertainer's dream, with not one, but two center islands, ample solid WOOD CABINETS with crown molding, granite counters, and a tile backsplash. A stainless steel appliance package complements these features. A spacious dining area, family room, a mini mudroom off the garage, and a multipurpose space with additional cabinetry perfect for a small office, coffee bar, or wine bar. If you are looking for some multigenerational space, take advantage of the downstairs ensuite, which includes built-in closet organizers, a new vanity and toilet and a walk in shower. There is no carpet; the entire first floor has ceramic tile and the stairs and upstairs feature newly installed hardwood flooring. Luxurious master suite provides ELECTRIC BLINDS to let the light in and out at your fingertips, a perfectly organized walk in closet with custom built ins plus a double sink vanity with vessel sinks, modern light framed mirrors and a remodeled huge walk in shower complete with a shower wand, RAINHEAD SHOWER and pebble stone floor. The second floor also offers a tremendous bonus/game room, media lounge, office or fitness studio along with 2 additional bedrooms, a full bath, and a laundry room with its own built-in sink and cabinet. Additional interior upgrades include plantation shutters on the first floor, an electric blind to the exterior and a digital thermostat. Exterior features include a SCREEN ENCLOSED LANAI overlooking the fully fenced backyard for quiet comfort, privacy and shade from the yard's mature landscaping. Pavers line the back patio, making it possible to step right outside to both grill and dine al fresco during the temperate fall, winter, and spring months here in Central Florida. Additional features include YEAR ROUND HOLIDAY LIGHTING installed on the home making you ready for every season with the flip of a switch. Neighborhood features include a community pool complete with lounge chairs and a covered pavilion, a basketball court, a tennis court, a putting green, playgrounds covered from the sun or rain, and plenty of green space. LOCATION BENEFITS include easy access to DISNEY, SR 429, SR 408 to Downtown Orlando, Florida Turnpike, I4, shopping, restaurants and much more! Combining sophisticated finishes, versatile living spaces, and cutting-edge energy-conscious upgrades, this exceptional Windermere residence offers a lifestyle as impressive as the home itself.

13328 Overstreet Road, Windermere

$539,900

3 Beds ⋅ 2 Baths ⋅ O6423262 MLS

WELCOME HOME! PRICE ENHANCEMENT! Nestled beneath majestic oak trees in one of Windermere's most desirable communities, this well-maintained 3-bedroom, 2-bath home sits on a quarter of an acre and offers the perfect blend of comfort, privacy, and location. Situated in the highly sought-after 34786 zip code, this exceptional residence features a popular split-bedroom floor plan with 1,819 square feet of thoughtfully designed living space. Silver Woods is located in the center of SW Orlando, close to Downtown Windermere, Restaurant Row, Winter Garden Village, Downtown Winter Garden, churches, schools, shopping, and more. As you enter the front door, you will be impressed with the open floor plan. New paint, new carpet, and neutral tile create a light and bright environment. Step inside to discover spacious living and dining areas that flow seamlessly into the heart of the home. The living room looks out onto the huge patio and backyard. The kitchen offers abundant cabinetry, granite countertops, ample workspace, and overlooks the main living areas, making it ideal for everyday living. Enjoy the family room, which opens to a covered, screened lanai via sliding doors, creating an incredible outdoor living space perfect for relaxing, entertaining, or simply enjoying the tranquil backyard surrounded by mature trees. The oversized, park-like shared fenced backyard provides exceptional privacy and plenty of room for gardening, play, or creating your own outdoor oasis. Let your imagination create the perfect Pool/Spa area with a summer kitchen, fire-pit, and more. The primary bedroom features sliding doors to the expansive lanai, and the en-suite features a Tub, a newer double-sink vanity, and a walk-in shower. A split-bedroom plan is perfect for today's busy family, featuring two bedrooms and a hall bath with a shower/tub. Recent improvements, including a NEW ROOF, HVAC (2016), New Garage Door (2016), Septic (2021), Electric Panel (2017), Interior paint (2026), Front Sod (2026), and Carpet (2026) in the main living areas, make this home move-in ready while still offering opportunities for a new owner to personalize and add value over time. The community offers a park and a tennis court for the residents. Ideally located just minutes from top-rated Windermere schools, shopping, dining, churches, world-famous theme parks, major highways, and Orlando's many entertainment destinations, this home offers the perfect balance of peaceful neighborhood living and everyday convenience. Don't miss your chance to make this Windermere gem your next home- schedule your private showing today!

9433 Palm Tree Drive, Windermere

$798,000

5 Beds ⋅ 5 Baths ⋅ O6422241 MLS

Discover refined living in one of Windermere's most sought-after communities. This exceptional 5-bedroom, 5-bath residence in Summerport perfectly blends timeless elegance, everyday comfort, and an unmatched location. Offering an ideal floor plan for both everyday living and entertaining, this beautifully maintained home features a dedicated office, formal dining room, spacious living room, family room, and thoughtfully designed living spaces throughout. The entire first floor showcases upgraded luxury vinyl flooring, while the gourmet kitchen is appointed with beautiful granite countertops, stainless steel appliances, abundant cabinetry, and a breakfast bar with seating, perfect for casual dining and gathering with family and friends. Situated on an oversized homesite, the backyard has been thoughtfully upgraded to create the perfect outdoor retreat. Enjoy a spacious covered lanai, an extended paver patio, and a fire pit, offering the ideal setting for entertaining or relaxing under the shade of the mature Trees. Upstairs, you'll find all 5 generously sized bedrooms, each complemented by access to a full bathroom, providing exceptional comfort and privacy for family members and guests alike. The first floor features a spacious private office that can easily be converted into a media room or 6th bedroom, complemented by a full bathroom for added flexibility. A spacious 3-car garage offers abundant room for vehicles, storage, and recreational equipment. Designed with efficiency in mind, the home is equipped with solar panels producing approximately 22–23 MWh annually, delivering substantial energy savings while reducing utility costs. Summerport is one of Windermere's most desirable communities, offering residents an exceptional lifestyle with resort-style amenities, including a community pool, fitness center, tennis courts, sand volleyball courts, playgrounds, scenic walking trails, and beautiful lakes. Families will appreciate being zoned for highly rated schools, including the sought-after Windermere High School. Ideally located just minutes from Walt Disney World, Winter Garden Village, Publix, premier shopping, dining, and major highways, this home presents a rare opportunity to enjoy luxury living in one of Central Florida's most prestigious communities.

4642 River Gem Avenue, Windermere

$3,250,000

4 Beds ⋅ 5 Baths ⋅ P4939244 MLS

BREATHTAKING WINDERMERE ESTATE!!! Situated on nearly 1.5 acres in the gated/guarded community of Bellaria, this custom built 4BR/4.5BA pool residence is the pinnacle of detail and design. Follow the long drive winding amongst the towering Italian Cypress to your expansive motor court and magnificent entry. Upon opening the massive custom double doors, you will see elegance, functionality, and breathtaking detail in every corner. Features include: over 5500SqFt of living area, soaring ceiling heights, top-notch molding and finish work, travertine floors, NEW carpet, NEW interior paint, massive kitchen with bar seating and island, walk-in pantry, game room with full bar and refrigeration, over 3000SqFt of rear pool and patio space with hot tub, outdoor bar/kitchen with vent fan and refrigeration, patio shower, multiple gas fireplaces, corner sliding pocket doors opening onto patio, NO REAR NEIGHBORS, gigantic privacy hedge, spacious primary suite with seating area and pool access, dual walk-in closets, exquisite primary bath with enormous soaking tub, spacious guest bedrooms and beautifully appointed guest bathrooms, sauna, three car garage with a hydraulic lift for a fourth vehicle, generous utility room, 22kw natural gas generator installed in 2021, office with built-ins and fireplace, fully equipped theatre with elevated seating, A BRAND NEW TILE ROOF, ample storage opportunities, and the list goes on!!! This is all just minutes from Winter Garden Village with easy access to SR429, downtown, and all the attractions!!! Schedule your showing and prepare to be amazed, this property is special. Call today!!!

13431 Bellaria Circle, Windermere

$6,700,000

8 Beds ⋅ 10 Baths ⋅ O6422852 MLS

Virtually Staged. Welcome to an extraordinary new construction waterfront estate built by Element Home Builders, located in the prestigious 24-hour guard gated community of Keene’s Pointe. Situated on a private cul-de-sac, this one of a kind residence rests on a spectacular 0.78 acre homesite with 518 feet of combined waterfront overlooking a serene pond and the beautiful waters of Lake Burden. Offering 8,133 square feet under air and 10,971 total square feet, this exceptional home features 8 bedrooms, 7 full bathrooms, and 3 half bathrooms with unparalleled craftsmanship and luxury finishes throughout. A grand marble foyer welcomes you with soaring ceilings, designer lighting, wood beams, and rich solid oak flooring. The stunning chef’s kitchen features custom solid wood cabinetry, stunning countertops, Thermador paneled refrigerator and freezer with white wine refrigeration, Wolf range, built-in convection oven, microwave, and a custom exhaust hood. The expansive great room showcases a natural stone fireplace and wall to wall sliders that open to breathtaking views of the infinity edge saltwater pool, spa, backyard oasis, and Lake Burden. The luxurious primary suite offers panoramic water views, custom illuminated walk-in closets, a spa inspired bathroom with a massive shower, designer fixtures, and a freestanding soaking tub. Additional highlights include a temperature controlled wine cellar, hidden elevator, executive study with custom built-ins, five spacious main level bedrooms, and a spectacular second floor featuring a private gym with reinforced insulation, custom theater, loft with kitchenette, balcony overlooking the water, and three ensuite bedrooms. Outdoor living is designed for entertaining with your summer kitchen including a heavy duty grill and hood, motorized screens for the entire lanai, multiple gathering areas, fire pit, private putting green, and a nature path leading to your covered boat dock with boat lift for endless Lake Burden adventures on a 125 acre skiable lake. A four-car garage with built in ceiling lighting tracks and electric vehicle charging completes this exceptional residence. Keene’s Pointe offers an unmatched lifestyle with the Golden Bear Club, featuring a championship golf course, clubhouse, fitness center, tennis courts, resort-style pool, and numerous parks and recreation areas. Ideally located just minutes from Walt Disney World, world class dining, shopping, and top rated schools, with close proximity to Windermere Preparatory School. This rare never been lived in lakefront estate is being offered for the first time and represents a unique opportunity to own one of Central Florida’s finest custom homes. Be sure to click on the virtual tour links.

8342 Boyla Court, Windermere

$1,795,000

4 Beds ⋅ 4 Baths ⋅ O6417788 MLS

Something unexpected! Something unique! An amazing space! Welcome to 6241 Blakeford Drive, where the charm, character, and glamour of this custom-built jewel box home are sure to impress. Designed to capture natural light and stunning water views, this residence offers a floor plan that is both functional and unforgettable. At the heart of the home is a spectacular Great Room featuring soaring 30-foot ceilings and dramatic picture windows that frame breathtaking views of the pool, pond, and colorful Florida sunsets. Abundant natural light fills the space, creating an inviting atmosphere that seamlessly connects the main living areas. The thoughtfully designed split floor plan places the spacious primary suite in its own private wing, complete with French doors opening to the pool and a luxurious spa inspired bath showcasing exquisite custom tilework that is truly a work of art. On the opposite side of the home, you'll find a bright office or fifth bedroom with adjacent full bath, an additional guest bedroom, and a rear bedroom overlooking the garden and water, also with convenient pool access. The boutique-style kitchen is a showpiece, highlighted by a dramatic stacked-stone exhaust wall that beautifully complements the matching stone fireplace in the great room. Together, these elements create a warm and cohesive gathering space perfect for everyday living and entertaining. The formal dining room offers flexibility as a sitting room or entertaining space, while the breakfast nook is perfectly positioned to enjoy tranquil pond views and unforgettable sunsets. Upstairs, a spacious bonus room, fourth bedroom, full bath, and stackable washer/dryer closet create a private retreat ideal for guests, extended family, or multigenerational living. Situated on just over one-third acre with 90 feet of waterfront frontage, the property enjoys long pond views and stunning sunset vistas. The oversized three-car garage and prime location just steps from the Golden Bear Clubhouse add to the home's appeal. Move-in ready and worry free with new ACs and roof (2024) new quartz countertops (2023 & 2026), new flooring (2023) and newly painted exterior (2025).

6241 Blakeford Drive, Windermere

$1,200,000

4 Beds ⋅ 3 Baths ⋅ O6422132 MLS

Nestled within the highly sought-after Windermere Downs community this Lake-Access Residence, sitting on .74 acres, offers the ultimate Florida lifestyle surrounded by canopy-shaded, oak tree-lined streets. A walkway lined with custom pavers leads to the front door, where you're welcomed by the formal living and dining rooms on the right. Large bay windows let in plenty of natural light, creating a bright and inviting space. A barn door opens to the kitchen, which features travertine flooring, a gas stove, and stainless steel appliances—great for home cooking or entertaining. The living room is a cozy gathering space, with three skylights bringing in extra light and an Authentic Old Chicago Brick fireplace that adds warmth and character. The primary bedroom is spacious, with French doors that open to the screened-in pool lanai, offering easy access to outdoor living. The primary bathroom includes a Kohler clawfoot tub and Kohler fixtures, adding a touch of quality and comfort. Out back, the screened-in pool with travertine deck and patio provides a great spot to relax, while the larger open travertine patio off of the kitchen is perfect for hosting family and friends. The backyard is full of greenery, offering both beauty and privacy and an irrigation well. Home includes a 1,000 Underground Large Gas Tank and Full House Propane Generator and a hybrid water heater. A two-car attached garage is complemented by a large detached deep second two-car garage, perfect for extra parking, storage, or keeping your favorite lake-living toys. Living in Windermere Downs means access to a private community boat ramp, where you can launch your boat and explore Lake Down and the Butler Chain of Lakes. The community amenities include a dock with a roped-off swim area, tennis courts, pickleball courts, community park, playground—plenty of options for outdoor fun. Recent updates include whole house re-pipe (2026), freshly painted exterior and new soffit (2026).

2009 Woody Drive, Windermere

$474,900

3 Beds ⋅ 3 Baths ⋅ O6421552 MLS

Welcome to this beautifully maintained home in the highly desirable community of Summerport Trail in Windermere. This spacious residence offers a functional open floor plan with abundant natural light, generous living and dining areas, and a well-appointed kitchen featuring ample cabinetry, granite countertops, stainless steel appliances, and a large island perfect for entertaining. Throughout the home, you'll find updated luxury vinyl plank (LVP) and tile flooring, providing a modern look that's both stylish and easy to maintain. The primary suite provides a relaxing retreat with a spacious walk-in closet and an en suite bathroom featuring dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms offer flexibility for family, guests, or a home office. Conveniently located near top-rated schools, shopping, dining, major highways, and Orlando's world-famous attractions, this home offers the perfect blend of comfort, style, and convenience. Don't miss this incredible opportunity to own a beautiful home in one of Windermere's most sought-after communities. Schedule your private showing today!

13845 Bridgewater Crossings Blvd, Windermere

$650,000

5 Beds ⋅ 4 Baths ⋅ O6422064 MLS

Welcome to this beautifully maintained two-story home in the highly sought-after Lakes of Windermere, offering 5 bedrooms, 3.5 bathrooms, a private screened pool, and a brand-NEW ROOF for added value and peace of mind. Designed with both comfort and functionality in mind, the home features a bright, open floor plan with spacious living and dining areas, tile flooring throughout the main living spaces, and flexible room to accommodate everyday living, entertaining, working from home, or hosting guests. The well-appointed kitchen showcases wood cabinetry, granite countertops, stainless steel appliances, a center island, and seamless flow into the main living areas, making it the heart of the home. The spacious primary suite serves as a relaxing retreat with a large walk-in closet, dual vanities, a soaking tub, and a separate walk-in shower. Step outside to enjoy Florida living year-round in the screened lanai overlooking the private pool, brick paver deck, and fully fenced backyard—perfect for entertaining, family gatherings, or simply unwinding in your own backyard oasis. Located in the desirable Lakes of Windermere community, residents enjoy access to a playground, covered picnic area, and convenient proximity to top-rated schools, shopping, dining, Disney, major highways, and everything Southwest Orlando has to offer.

12912 Droxford Road, Windermere

$679,000

3 Beds ⋅ 3 Baths ⋅ O6421738 MLS

Under contract-accepting backup offers. Welcome to 2053 Woody Drive, where timeless Windermere charm meets modern updates. From the moment you arrive, you’ll appreciate the mature trees, spacious homesite, and the peaceful lifestyle this sought-after community offers. Through Windermere Downs HOA you will have access to a private beach -Chain of Lakes- Step inside and you’ll find a beautifully updated kitchen that’s truly the heart of the home—perfect for everyday living and entertaining family and friends. The generous living spaces, oversized lot and mature landscaping, with a prime location make this home an incredible opportunity for anyone looking to enjoy everything- Windermere. ROOF: 2020 NEW ELECTRIC PANEL (2026)-AC 2019

2053 Woody Drive, Windermere

$1,100,000

4 Beds ⋅ 3 Baths ⋅ O6422154 MLS

Welcome to a rare opportunity in the highly sought-after The Manors at Butler Bay, in the heart of Windermere. This custom-built home is situated on nearly three-quarters of an acre and a corner lot. This impressive single-story residence offers 3,478 square feet of thoughtfully designed living space with 4 bedrooms, 3 full bathrooms, a side-entry 2-car garage, an extended driveway, and a screen-enclosed pool and spa. Step through the front door into a grand foyer that opens to a spacious, flowing floor plan. The formal living room sits adjacent to the formal dining room, creating ideal space for entertaining. The expansive family room features soaring ceilings, a cozy wood-burning fireplace, and french doors that lead to the fully enclosed florida room. The oversized primary suite is a true retreat, featuring double-door entry, high ceilings, ample room for a sitting area, a walk-in closet, and french doors opening to the florida room. The spacious primary bath was remodeled approximately four years ago and offers dual vanities, a garden tub, separate shower, and a private toilet room. The open layout provides privacy and flexibility. Two secondary bedrooms share a full bathroom, while the fourth bedroom is tucked away on the opposite side of the home with its own ensuite bath, ideal for guests or multigenerational living. The kitchen is designed for both everyday living and entertaining with granite countertops, a center island with cooktop, built-in oven, dinette area, and more french doors leading to the florida room. The laundry room includes a utility sink and built-in cabinetry for added convenience. Wood-look tile flooring extends throughout the home, with carpet only in the enclosed florida room. One of the home's standout features is the expansive L-shaped florida room that wraps around the side and rear of the home, creating an abundance of bright, versatile space perfect for relaxing, entertaining, a home office, hobby room, fitness area, or additional living space, all while enjoying year-round comfort. Additional updates include an approximately 4-year-old HVAC system and 7-year-old roof, offering peace of mind for the next owner. The Manors at Butler Bay is an intimate community nestled along the shores of beautiful Lake Crescent in southwest Orange County. Residents enjoy a low HOA, golf cart friendly streets, a park with picnic area and access to Lake Crescent for launching non-motorized watercraft such as kayaks and canoes. As a resident of the Town of Windermere, you'll also enjoy access to town amenities including tennis courts and the Lake Butler boat ramp, providing entry to the renowned Butler Chain of Lakes (also known as the Windermere Chain), a 5,000-acre network of 13 interconnected lakes. Renowned for crystal-clear waters, prime bass fishing, luxury waterfront estates, and connects via 32 navigable canals for boating and water sports. The home is conveniently located within a top-rated school district and close to shopping, dining, and major roadways. This exceptional home offers the perfect combination of space, location, and lifestyle. Don't miss your opportunity to own this rare one-owner home in one of Windermere's most desirable communities!

2512 Tryon Place, Windermere

$560,000

3 Beds ⋅ 2 Baths ⋅ O6420991 MLS

Welcome to this charming and inviting home nestled in the highly desirable Lake Sawyer South community in Windermere. As you drive through the neighborhood, you'll immediately appreciate the mature landscaping, beautiful tree-lined streets, and peaceful atmosphere that make this communityso special. Upon arrival, you're greeted by a spacious covered front porch — the perfect place to relax and enjoy the Florida lifestyle. Step inside to a welcoming, wide foyer that opens to a bright and airy living room featuring soaring ceilings and an abundance of natural light. Two secondary bedrooms are thoughtfully positioned at the front of the home, offering privacy and flexibility for family members, guests, or a home office. The formal dining room is enhanced by a large window that fills the space with beautiful natural light, creating an inviting setting for entertaining. The open-concept kitchen overlooks the living room, making it ideal for gathering with family and friends. It also includes a cozy breakfast nook, perfect for casual everyday meals. Privately located at the rear of the home, the spacious primary suite is filled with natural light from three large windows. The en-suite bathroom features dual vanities, a soaking tub, a separate walk-in shower, a walk-in closet, and an additional linen closet for extra storage. Sliding glass doors from the living room lead to a covered and screened lanai and a fenced backyard with a paved patio, providing the perfect space for outdoor dining, entertaining, or simply unwinding. Offering 1,706 square feet of living space, this well-maintained home features 3 bedrooms, 2 bathrooms, a formal dining room, an open living room, a functional kitchen, a dedicated laundry room, and a two-car garage. Conveniently located just minutes from Publix, coffee shops, dinners, restaurants, shopping, personal storage facilities, and schools. This home combines comfort, convenience, and an exceptional Windermere location. Don't miss the opportunity to make this beautiful and welcoming home your own—schedule your private showing today! The existing solar panel financing is transferable to qualified buyers, offering the opportunity to enjoy energy savings without the upfront installation cost.

13219 Charfield Street, Windermere

$1,649,000

4 Beds ⋅ 4 Baths ⋅ O6420023 MLS

Rare opportunity to own one of the most private lakefront settings on Lake Crescent in Windermere, featuring approximately 165 feet of shoreline, breathtaking water views, and a resort-style waterfront lifestyle on a private ski lake known for its exceptional water quality. This beautifully designed custom residence offers approximately 3,086 square feet, 4 bedrooms, and 4 bathrooms, thoughtfully positioned to maximize natural light, privacy, and panoramic lake views from nearly every main living space. From the moment you arrive, the setting speaks for itself, tranquil water vistas, expansive outdoor living, and an immediate sense of calm that defines this exceptional waterfront property. A grand entrance with custom glass double doors opens into a spectacular great room where soaring vaulted ceilings and a dramatic wall of windows frame uninterrupted panoramic lake views, filling the home with natural light and creating a stunning first impression that defines the entire residence. The open concept layout seamlessly connects the living room, dining area, and spacious kitchen, creating an inviting flow ideal for both relaxed everyday living and effortless entertaining, all while the lake remains the backdrop from nearly every main living space. A truly distinctive feature of the home is its extraordinary collection of handcrafted stained glass art installations. Rich jewel tones and custom artistic designs transform sunlight into ever changing displays of color throughout the home, adding a level of artistry, warmth, and individuality rarely found in lakefront properties. The primary suite is positioned as a private sanctuary, offering soaring ceilings, peaceful lake views, and direct visual connection to the covered, screened lanai and lake beyond. The spa-inspired bath is designed for comfort and relaxation, featuring generous space and soft natural light. The expansive screened lanai overlooks the sparkling pool, spa, and poolside summer kitchen, creating a seamless indoor-outdoor living experience designed for year round Florida enjoyment. Whether entertaining guests, enjoying quiet mornings, or unwinding at sunset, this outdoor space becomes an extension of the home itself. A private dock offers direct access to Lake Crescent, where boating, skiing, paddleboarding, kayaking, and fishing become part of everyday life. Set on a beautifully landscaped homesite offering privacy and exceptional waterfront exposure, this property combines single-story convenience with one of Windermere’s most captivating lakefront settings. Located just minutes from downtown Windermere, boutique shopping, dining, golf, and top-rated schools, it offers both seclusion and convenience in one of Central Florida’s most sought after communities. Rare opportunities on Lake Crescent are limited and homes offering this level of waterfront frontage, architectural character, artistic detail, and true resort-style lake living are seldom available. This is more than a home, it is a lakefront lifestyle designed to be experienced.

2617 Butler Bay Drive N, Windermere

$560,000

3 Beds ⋅ 2 Baths ⋅ O6421270 MLS

This charming 3/2 home in the heart of Windermere is sure to make you fall in love! The covered porch and walkway provide a serene entrance to the place you'll be proud to call home. Step inside and you'll find two cozy bedrooms with a bathroom in between, also conveniently located for guests. The hallway leads to a two car garage entrance and laundry room (equipped with newer GE washer and dryer) on the left and a large flex space on the right. This space, with bamboo floors, can serve as a formal living room and family room or a formal dining room and living room - the options are endless! Across from this space is the kitchen, which also has space next to it that can be used for dining or a home office. The kitchen has a GE cooktop with separate oven, two microwaves (one can be replaced with a hood), a new Samsung fridge (2025), and walk-in pantry. The master bathroom which is conveniently located off of the kitchen has a walk in closet (with a rotating shoe rack that holds 90+ pairs), extended shower, and separate toilet room. But wait, there's more! Enjoy a screened lanai that extends the width of the house, mango and avocado trees, easy access to the newest community center with pool, and a plethora of smart features! Other features you'll be excited about include a water softener system (2024) and privacy tints on all windows - which also helps with the Florida heat! Oh and did I mention that the sun rises in the front and sets in the back?! Fall sunsets on the covered lanai are a dream! Roof installed in 2022.AC installed 2018.

13137 Penshurst Lane, Windermere

$750,000

5 Beds ⋅ 3 Baths ⋅ O6421056 MLS

Under contract-accepting backup offers. BRAND NEW TILE ROOF. Nestled within the prestigious gated community of Belmere in Windermere, Florida, this exceptional Mediterranean resort-style pool home offers a rare opportunity to own one of the community's most unique properties. Beautifully maintained and extensively updated by its meticulous owners, this move-in-ready 5-bedroom, 2.5-bathroom residence features 2,366 square feet of thoughtfully designed living space, a brand-new tile roof, and breathtaking views overlooking a tranquil private pond. Every detail has been carefully cared for, creating a home that blends timeless elegance with modern convenience. Step inside to discover a bright, open-concept floor plan designed for both entertaining and everyday living. The spacious main living areas flow seamlessly into the kitchen and dining spaces, creating an inviting atmosphere for family gatherings and special occasions. The primary suite is conveniently located on the main floor, offering privacy and comfort with generous space and a well-appointed ensuite bath. Four additional bedrooms provide flexibility for guests, a home office, or growing families. Throughout the home, you'll appreciate the pride of ownership and thoughtful updates that make this property truly turnkey. The outdoor living space is where this home truly shines. Designed as a private Mediterranean-inspired resort, the backyard features a spectacular screened-in pool and an impressive 12-person jacuzzi, creating the ultimate setting for entertaining or relaxing. In 2024, the pool system was upgraded with top-of-the-line app-controlled automation, allowing you to effortlessly control lighting, heating, water features, and more directly from your smartphone. Whether you're hosting unforgettable gatherings, enjoying peaceful evenings under the stars, or taking in the serene pond views with your morning coffee, this extraordinary outdoor oasis delivers a luxury lifestyle that is rarely found in Belmere. Located just minutes from top-rated schools, shopping, dining, and Central Florida's world-famous attractions, this exceptional Windermere home offers the perfect combination of luxury, comfort, and convenience. With its brand-new tile roof, extensive updates, resort-style amenities, and impeccable maintenance, this is a truly move-in-ready home that stands apart from the rest. UPGRADES: Brand-new tile roof (2025), new Hot water heater (2025), a fully modernized pool and spa system (2024) featuring app-controlled Wi-Fi automation, upgraded Jacuzzi, fountains, and pool heater, a new Samsung gas range (2024), all new pool enclosure screens (2025), Google Home smart thermostats on both floors, and a new overhead garage ceiling storage system.

11249 Rapallo Lane, Windermere

$1,499,000

3 Beds ⋅ 3 Baths ⋅ O6421265 MLS

Under contract-accepting backup offers. Welcome to 20 Oakdale Street, an exceptional waterfront luxury residence in the highly sought-after Town of Windermere with direct access to Lake Down and the Butler Chain of Lakes offering an ideal blend of elegance, privacy, and Florida lifestyle, this beautiful home is perfectly positioned to enjoy the area's charming small-town atmosphere while remaining just minutes from world-class dining, shopping, golf, and attractions * Incredible backyard * Summer Kitchen with Pizza Oven * Firepit with Stone Seating * Boathouse * Viking 6 Burner Gas Cooktop * Viking Fridge * Built in 2004 * 2 Suites on 1st Floor * Step inside to discover spacious living areas filled with natural light, soaring ceilings, and thoughtfully designed spaces perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into inviting gathering spaces, while the generous bedrooms provide comfort and privacy for family and guests. * Outside, enjoy your own private retreat with beautifully landscaped grounds, ample outdoor living space, and the opportunity to experience everything that makes Windermere one of Central Florida's most desirable communities. Whether relaxing by the pool, hosting friends, or taking advantage of nearby lakes and recreation, this home offers the lifestyle you've been searching for. * Located within close proximity to top-rated schools, renowned golf courses, the Butler Chain of Lakes, and just a short drive to downtown Orlando and major theme parks, this is a rare opportunity to own a premier property in one of Florida's most coveted addresses.

20 Oakdale Street, Windermere

$2,960,000

5 Beds ⋅ 6 Baths ⋅ O6418943 MLS

Under contract-accepting backup offers. Located within the prestigious guard gated community of Keene’s Pointe, this extraordinary estate offers a rare combination of luxury, privacy, and breathtaking views. Positioned on a premier lot with combined water and golf course frontage, this one-of-a-kind residence captures stunning vistas from every angle. On arrival, the expansive, multi-car, circular driveway provides ample parking for all, blending grand scale with ultimate convenience and estate-style privacy. Enter through custom wrought-iron gates into a private courtyard oasis, which makes for an unforgettable first impression. Boasting nearly 6,000 square feet of thoughtfully designed living space, the home features 5 bedrooms, including a detached casita/in-law suite with separate entrance, full bathroom, fridge and microwave. In addition, there is an equipped media room with half bathroom, also with microwave and fridge. A bonus room that can be used as a home office or gym is located off the downstairs primary suite. The gourmet kitchen is the heart of the home, showcasing custom cabinetry, granite countertops, premium appliances including a built-in Miele coffee machine, Wolf range, double oven, an incredible center island, wine cellar and generous gathering spaces. Expansive living and dining areas, with soaring ceilings, exquisite features such as, Venetian plaster, travertine floors, wood beams and custom built ins. The luxurious primary suite offers a private sanctuary with elegant finishes, dual custom closets, one with an additional washer and dryer set, a beautifully designed bathroom and private access to the office/gym/bonus rm. Three 2nd floor guest rooms include a potential second primary suite which provides exceptional accommodations for multigenerational living or visiting guests. Recently remodeled, this spacious suite has a full bathroom, walk-in closet and double door access to the balcony with its glorious golf course and water views. Outside, an oasis awaits. Floor to ceiling glass sliders in the living room offer uninterrupted views and provide access to the resort-style screened lanai featuring an expansive pool, sauna and outdoor fireplace. Indoor/outdoor speakers, security cameras, app controlled pool system with multi light show. A private sports court further enhances the lifestyle offered by this exceptional property. Keene’s Pointe is in the heart of Windermere and offers 24-hour manned security, access to the community boat ramp and optional membership to the Golden Bear Golf & Country Club, where golf, tennis, pickleball, gym, restaurant and events are included in the membership fee. Close to state-of-the-art medical facilities, theme parks, shopping, restaurants and high achieving schools, this exceptional estate represents a rare opportunity to own one of Windermere's most distinctive luxury residences.

6417 Lake Burden View Drive, Windermere

$2,099,900

4 Beds ⋅ 6 Baths ⋅ O6421211 MLS

Stunning Lakefront Mediterranean Retreat on Lake Whitney! Discover this spacious, breathtaking lakefront home nestled along the banks of Lake Whitney. Enjoy spectacular views from your private dock, deck, boat lift, & open-air boathouse, perfect for water sports, lake-side entertaining, BBQs, & catching mesmerizing sunsets. Ski friendly Lake Whitney is a great spot for wakeboarding, jet skiing or water skiing. Designed for the ultimate lake lifestyle, this home features Tuscan-inspired landscaping, an infinity pool & spa, plus expansive outdoor entertaining areas. Host unforgettable gatherings with an outdoor grill & kitchen, patio dining, outdoor fireplace, & comfortable seating, all under a screened enclosure for year-round enjoyment. The gourmet kitchen is a chef’s dream, equipped with ultra-premium Viking appliances; including a double oven, dishwasher, gas cooktop, refrigerator, & wine cooler. Granite countertops, a spacious island, walk-in pantry, dual sinks, & open layout seamlessly connect to the living & dining areas. A full-size laundry room with front-loading washer and dryer, sink, & tall cabinets adds convenience. The ground level offers a formal dining room & an office/library with built-in shelving. The massive primary suite boasts stunning lakefront views, while the luxurious master bathroom features a walk-in closet, granite countertops, dual garden baths with massage jets, a sauna, and privacy toilet and bidet. Elegant French doors lead into a welcoming foyer, with soaring ceilings and a grand staircase leading upstairs. The 2nd floor includes 3 bedrooms, 3.5 bathrooms, & a versatile game room or theater with built-in entertainment & a microwave. Three bedrooms have private baths, & an elevated outdoor covered patio offers additional lake views with ceramic tile flooring. An oversized three-car garage with electric doors, double water heaters, & ample storage completes this exceptional home. Experience the charm of Tuscany combined with the luxury of lakefront living in Central Florida! Schedule your private tour today and make this dream home yours! Sold as-is, where-is. No Seller’s disclosures. Seller is making no warranties or representations of property condition. Room dimensions are approximate & should be independently verified. Proof of funds/pre-approval letter required with all offers. Buying party is responsible for verifying whether property condition will qualify for buyer’s specific loan program. If applicable, HOA or Condominium monthly dues may be subject to changes, special assessments & must be verified by buyer. Monthly dues often adjust on January 1st of each year. Some condominiums may also charge an initial “Capital Contribution” payable at closing. MLS information deemed reliable, but not guaranteed. Parties are advised to verify. The seller requires a 10 DOM holding period prior to entertaining any offers. *Per our seller, please ensure all potential buyers view the interior of the property prior to submitting offers. Agents must always accompany buyers during showings. Seller will not entertain sight-unseen offers. Please factor any repair estimates into the offer.* There's a 7-minute interior video walk-through available under Virtual Tour in MLS.

1238 Lake Whitney Drive, Windermere

$899,999

3 Beds ⋅ 2 Baths ⋅ O6420386 MLS

Incredible Opportunity to own a pool home with a huge lot in a fantastic neighborhood * The 1st picture is the proposed new elevation * Call for details about the proposed changes and package price * Good Floorplan * Close to Everything * Home has 3 Bedrooms * Separate Office * Formal Living Room * Breakfast Nook with Open Kitchen * Formal Dining Room * Pool Bath * Vaulted Ceilings * Inside Laundry * Screened & Covered Pool with Large Deck * Formal Dining Room * Large Family Room with Fireplace * Must see to fully appreciate the home & get more details for the remodel options

2630 Stanton Hall Court, Windermere

$6,500,000

5 Beds ⋅ 7 Baths ⋅ O6420326 MLS

Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth, this newly completed residence by premier custom homebuilder Goehring & Morgan presents a rare opportunity to enjoy the ease of modern luxury within one of the world's most distinguished golf club communities. Thoughtfully designed and never lived in, the home combines timeless architecture with professionally curated interiors by Design Specifications, creating a refined retreat where every detail has been carefully considered. Spanning more than 5,400 square feet, the five-bedroom residence unfolds through a series of light-filled living spaces distinguished by bespoke millwork, tailored cabinetry, and a sophisticated palette of designer-selected finishes. Clean architectural lines and expansive gathering areas create an atmosphere that feels both grand and inviting, while thoughtfully integrated design elements elevate everyday living. Throughout the home, custom cabinetry conceals a fully integrated Sub-Zero, Wolf, and Cove appliance suite, allowing the chef's kitchen to maintain its beautiful aesthetic while delivering professional-grade performance. Well-appointed entertaining spaces nearby transition effortlessly from intimate family gatherings to larger celebrations.Private bedroom retreats offer comfort and tranquility, while spa-inspired baths showcase carefully selected finishes, fixtures and materials that evoke exceptional craftsmanship. The primary suite serves as a sanctuary unto itself, complete with a private beverage bar and thoughtfully designed spaces that encourage both relaxation and retreat.Beyond the interiors, walls of glass open to an inviting outdoor environment designed for year-round enjoyment. A fully equipped summer kitchen anchors the outdoor living experience, creating a natural extension of the home's entertaining spaces and providing the perfect backdrop for gatherings beneath Florida's sunshine and tropical climate.Surrounded by lush landscaping, sparkling water features, and the natural beauty that defines The Gardens of Isleworth, the residence enjoys a setting that feels both private and refined. Residents of Isleworth enjoy access to a lifestyle renowned for championship golf, world-class amenities, exceptional service, and a level of privacy rarely found. Combining the freshness of brand-new construction with the prestige of an established luxury community, this is more than a home, it is an opportunity to experience Isleworth at its finest.

9316 Gladys Garden Ct, Windermere

$765,990

5 Beds ⋅ 3 Baths ⋅ O6420597 MLS

Welcome to one of the most desirable communities in Windermere! This beautifully designed home offers 5 spacious bedrooms, 3 full bathrooms, and an exceptional floor plan featuring a large family room on the main level and an additional loft upstairs, providing the perfect balance of comfort, functionality, and flexible living space. Boasting approximately 3,285 square feet of living area, this is one of the builder’s most popular and highly sought-after floor plans. Every room has been thoughtfully designed to maximize space, natural light, and everyday convenience, making it ideal for growing families, entertaining guests, or working from home. The community offers outstanding amenities and a welcoming neighborhood atmosphere. Residents enjoy convenient access to major highways, shopping centers, supermarkets, restaurants, and everyday essentials. Located in the heart of Central Florida, this home is just a short drive from Disney World, Universal Orlando Resort, SeaWorld Orlando, and many of the area’s world-famous attractions, while also providing easy access to Orlando International Airport and Downtown Orlando. If you’re looking for a spacious, move-in-ready home in one of Windermere’s most sought-after communities, this is an exceptional opportunity you won’t want to miss.

7409 Fairgrove Avenue, Windermere

$1,075,000

4 Beds ⋅ 3 Baths ⋅ O6417903 MLS ⋅ J. Richard Watson BLDG.

In Windermere homes can be renovated. Locations like this cannot be recreated. Set on more than half an acre with tranquil water views and exceptional privacy, this beautifully renovated residence offers a lifestyle that’s increasingly difficult to find. Spend weekends boating on the Butler Chain of Lakes, enjoying a match of tennis or pickleball, or unwinding by your private pool as peaceful water views become the backdrop to everyday life. Just a golf cart ride from downtown Windermere’s beloved Farmers Market, waterfront parks, dining, and community events—and with Windermere Elementary and many of Central Florida’s premier public and private schools nearby—this is a home that blends convenience with an unmatched sense of place. Inside, thoughtfully reimagined interiors pair contemporary finishes with effortless livability, creating a turnkey home where the lifestyle is every bit as compelling as the home itself. Residents of The Willows enjoy an outstanding lifestyle with neighborhood amenities including walking trails, a playground, volleyball, basketball, tennis, and pickleball courts. Windermere Elementary is within walking distance and Windermere High School and many premier private schools close by. Extensively renovated with today's most sought after finishes and design elements and designed for both everyday living and elegant entertaining, the spacious floor plan features four bedrooms and three baths. The private owner's retreat is a true sanctuary, offering direct access to the pool area and peaceful water views. A grand dining room with soaring 12-foot vaulted ceilings creates a sophisticated setting for gatherings, while the inviting living room showcases beautiful outdoor vistas. At the heart of the home, the gourmet kitchen flows seamlessly into the breakfast nook and family room, creating an open and welcoming space that extends to the covered lanai and pool area. Whether hosting guests or enjoying a quiet evening at home, the indoor/outdoor connection embodies the very best of Florida living. The thoughtfully designed split bedroom layout provides privacy and functionality, with two secondary bedrooms with walk-in closets, charming window seats with built-in storage are connected by a Jack and Jill bath. A dedicated laundry room, and abundant storage throughout add to the home's exceptional livability. Additional highlights include a central vacuum system, three-car side-entry garage, and circular driveway with ample guest parking. Convenient access to major roadways, shopping, healthcare, golf, Orlando International Airport, and world-famous attractions further enhances the appeal. Offering an unparalleled combination of location, luxury, recent renovations, and lifestyle, this remarkable property presents a rare opportunity to own one of Windermere's most desirable homes. Schedule your private showing today!

11217 Willow Gardens Drive, Windermere

$500,000

4 Beds ⋅ 3 Baths ⋅ O6419100 MLS

Virtually Staged. Nestled on a quiet cul-de-sac in the highly sought-after Lakes of Windermere – Peachtree community, this spacious 4-bedroom, 3-bath residence offers the perfect blend of comfort, functionality, and location. With over 2,100 square feet of living space, the thoughtfully designed floor plan provides ample room for both everyday living and entertaining. Residents of Lakes of Windermere enjoy access to community amenities, scenic walking paths, parks, and playgrounds while being conveniently located near top-rated schools, shopping, dining, and everyday conveniences. Just minutes from Walt Disney World, Horizon West, Winter Garden Village, and major roadways, this location provides easy access to everything Central Florida has to experience. Whether you're searching for a primary residence or an investment opportunity in one of Windermere's most desirable communities, this home presents an exceptional opportunity to enjoy the best of Florida living . (ONE OR MORE PHOTOS HAVE BEEN VIRTUALLY STAGED)

13424 Hopkinton Ct, Windermere

$624,000

4 Beds ⋅ 3 Baths ⋅ O6418877 MLS

Under contract-accepting backup offers. A rare first-time offering in the highly sought-after Lakes of Windermere, 12580 Cragside Lane is a meticulously maintained, original-owner residence with timeless appeal. Set on a desirable corner homesite, this thoughtfully designed single-story home offers 2,776 SF of living space w/ 4 bedrooms, 2 1/2 baths & a floor plan that gracefully balances formal entertaining w/ comfortable everyday living. A deep covered front porch stretches across the front elevation, creating a warm first impression. Inside, the foyer opens to elegant formal living & dining spaces highlighted by wood flooring, tall ceilings, extensive millwork, decorative niches & abundant natural light. A built-in dry bar w/ a wine refrigerator, additional cabinetry & serving space provides the perfect transition between the dining room & kitchen. At the center of the home, the kitchen opens seamlessly to the eat-in nook & family room, creating an easy flow for everyday living, casual dining & entertaining. The kitchen features a large island w/ seating, abundant wood cabinetry, generous granite countertops, stainless steel appliances & pantry. Large windows & glass doors frame views of the covered rear lanai and charming fenced backyard, where refreshed landscaping & new sod create an inviting setting for year-round outdoor living. A conveniently located powder bath, sizable indoor laundry room & separate storage closet complete the main living area. Privately positioned at the rear of the home, the primary suite serves as a quiet retreat featuring a soft entry, wood flooring, an elegant tray ceiling, private access to the lanai & an expansive walk-in closet. The spacious bath offers a garden tub, a separate glass-enclosed walk-in shower w/ neutral tile, an oversized real wood dual-sink vanity w/ extensive granite counter space, large mirrors & a private water closet. Three alternate bedrooms occupy their own wing at the front of the home, providing excellent separation for family members or guests. The secondary bathroom features a long granite-topped vanity w/ dual hammered copper sinks & a private, combined water closet with tub/shower area. Additional improvements include a recently replaced Carrier HVAC air handler (2024), water heater (2020), Kinetico water softener, some newer appliances including a front-loading Samsung Bespoke washer & dryer, and a new roof, which the seller intends to install prior to closing. Outside, mature landscaping, sidewalks & a quiet rear alleyway complement the desirable corner homesite, while a rear-entry, attached 2-car garage adds everyday convenience. Located outside a designated flood hazard area, the home is zoned for highly regarded A-rated schools, including Sunset Park Elementary, Horizon West Middle & Windermere High School. Residents of Lakes of Windermere enjoy beautifully maintained parks, playgrounds, tennis courts, a clubhouse, a community pool, sand volleyball courts, scenic ponds, a fishing pier, recreational fields & walking paths all just minutes from Walt Disney World, Horizon West, Winter Garden Village, exceptional shopping, dining & major roadways providing convenient access throughout Central Florida. Lovingly maintained by its original owner for more than two decades, this exceptional residence offers an increasingly rare opportunity to own a well-cared-for home with timeless appeal, an outstanding floor plan & an exceptional location in one of Windermere’s most established & desirable communities.

12580 Cragside Lane, Windermere

$850,000

4 Beds ⋅ 3 Baths ⋅ O6419770 MLS

All the access Windermere is known for without the rules. Most of the homes around here are beautiful, sure, but they come with a specific paint palette, and a list of things you didn't realize you'd signed up for. Not here. Host the cookout that runs late into the night. Plant a real garden. Park the boat in your own driveway. Let the dog run without thinking about it. Keep a few chickens and call it entry level homesteading. Inside, four bedrooms and two and a half baths sit on a layout that gives you more options than most homes twice the price. The primary suite is on the main floor, and there is an entire room between the bedroom and the rest of the house that gives you a private wing to do with whatever you want. It could be the work-from-home setup you've been promising yourself, or a home gym, a quiet second living room, or a nursery just steps from where you sleep. Private access to the screened lanai means the pool is right there too. Upstairs, you'll find updated LVP flooring from 2024, three more bedrooms, and a guest bath. A stone fireplace runs floor to ceiling in the great room, and out back, the screened pool was just converted to saltwater. Recent updates include a new fridge (July 2025), new pool equipment and variable speed pump (June 2025), a new pool safety fence (2025), a new variable speed air handler (May 2024), new carpet in the primary, new LVP upstairs (2024), updated showers (2022), and exterior paint (2021). You're just minutes from Yellow Dog Eats, the Butler Chain of Lakes, downtown Windermere, Winter Garden's Plant Street, Restaurant Row, and every theme park, school, and grocery store the area is known for. An acre with no HOA inside 34786 doesn't come around often. Every reason you wanted to live in Windermere, and none of the reasons you almost didn't.

2722 Ingeborg Court, Windermere

$1,075,000

5 Beds ⋅ 4 Baths ⋅ S5152477 MLS

Fully Furnished- Located in the highly desirable Windermere Trails community, this impressive residence offers 5 bedrooms, 4 full bathrooms, a media room, loft, gym, and game room, providing plenty of space for both everyday living and entertaining. The home features elegant iron stair railings, formal living and dining areas, and an open-concept layout designed for comfort and functionality. The gourmet kitchen showcases stainless steel appliances, a 36-inch cooktop, 42-inch cabinetry with crown molding, quartz countertops, upgraded backsplash, and a spacious walk-in pantry. The primary suite includes a large walk-in closet and a luxurious bathroom with dual vanities and a private water closet. An upgraded home theater with fiber-optic illuminated ceiling and wall panels creates a unique entertainment experience. Step outside to enjoy a beautifully landscaped, fully fenced backyard with dual gate access, a tranquil water feature, and an extended covered lanai perfect for relaxing or entertaining. Residents enjoy access to community amenities including walking trails, a resort-style pool, playground, dog park, pavilions, and fitness areas. The property is being offered partially furnished, with many of the furnishings and features shown in the photos included in the sale.

8316 Lookout Pointe Drive, Windermere

$1,250,000

4 Beds ⋅ 3 Baths ⋅ O6419393 MLS

Nestled on a quiet cul-de-sac in the desirable Hamilton Village section of Keene's Pointe, this beautifully maintained one-story Golf Villa offers the perfect blend of comfort, elegance, and low-maintenance living. Featuring 4 bedrooms, 3 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space, this residence showcases extensive hardwood flooring, upgraded cabinetry, granite countertops, and an inviting open layout ideal for both everyday living and entertaining. Recent improvements provide peace of mind and exceptional value, including a brand-new metal roof, new a/c unit and fresh interior and exterior paint, enhancing both the home's appearance and long-term durability. The spacious floor plan offers generous gathering areas filled with natural light, while the well-appointed kitchen opens seamlessly to the main living spaces. The private primary suite provides a relaxing retreat, and the guest accommodations are thoughtfully positioned to offer comfort and privacy for family and visitors alike. Step outside to the screened lanai and enjoy Florida living year-round. Complete with a summer kitchen and fenced backyard, the outdoor space is perfect for dining, entertaining, or simply unwinding in a peaceful setting. Additional highlights include a two-car garage plus a dedicated golf cart garage, custom closet storage, and mature landscaping. Located within the 24-hour guard-gated community of Keene's Pointe, residents enjoy access to one of Central Florida's premier golf and lifestyle communities, with optional membership opportunities at The Golden Bear Club. Conveniently located near top-rated schools, dining, shopping, and major roadways, this exceptional Windermere home offers an outstanding opportunity to enjoy the Keene's Pointe lifestyle. Virtual Floorplan available.

6124 Foxfield Court, Windermere

$2,550,000

4 Beds ⋅ 5 Baths ⋅ O6419164 MLS

Completely renovated in 2025. State-of-the-art showpiece located in the beautiful Estates at Lake Clarice. This updated residence offers an effortless blend of generous living spaces and serene surroundings with re-designed landscaping and updated landscape lighting on a 1-Acre Private Lot! From the moment you enter through the dramatic double 12' iron and glass doors the home makes a bold statement with clean architectural lines. Large format Taj Mahal tile, soaring ceilings and OPEN concept design that feels both impressive and inviting. Formal living and dining, kitchen with eat in breakfast nook and bar, office, four en-suite bedrooms, five full bathrooms and a media room-ALL ON ONE FLOOR! Stunning chef's kitchen appointed with new custom modern premium cabinetry, newly installed high end appliances, new monolithic quartz island featuring a waterfall edge cascading to the floor all seamlessly flows into the main living and dining area-ideal for both intimate gatherings and large scale entertaining. The family room offers a glass wall of expansive sliders which fully retract blurring the line between indoors and out, enhancing the homes bright airy ambiance. The oversized screened in lanai is a, fully enclosed outdoor living space designed for year round enjoyment. This impressive retreat features a spectacular pool, generous lounge and dining areas, an outdoor kitchen and a pool bath! The Primary Suite is a private sanctuary leading out to the pool deck, along with the Spa-like bath, complete with dual vanities, separate Zen inspired soaking tub, inviting shower with multiple shower heads and bench seating. Huge walk-in closet with built-ins, a bespoke 3 way panoramic dressing alcove featuring three full-length 8' mirrors. Thoughtfully designed throughout with substantial updates including newer roof, oversized gutters and three newer air conditioners (one newly installed in the single portico/breezeway garage. Perfect for gym, hobby room or music studio). Newer water heater, two high end smart fireplaces with remotes, custom drapes, plantation shutters, shiplap ceilings and walls, newer high end ceiling fans inside and out, new custom 7 1/2 inch base molding. Just too many upgrades to mention. A must see in Windermere. Ideally located just minutes to Windermere High School, Windermere Prep, downtown Windermere, downtown Winter Garden, Walt Disney World, Universal and the Mall of Millenia.

4205 Clarice Estates Drive, Windermere

$1,569,000

5 Beds ⋅ 4 Baths ⋅ O6417606 MLS

Exceptional value in Lake Butler Sound! Welcome to 11027 Hawkshead Court, a beautifully updated luxury home in Windermere, FL offering 4 bedrooms, a dedicated office, 4 bathrooms, approximately 3,500 square feet, and a private 0.4-acre corner lot within one of Central Florida's premier guard-gated communities with 24-hour roving security. Extensively renovated between 2022 and 2026, this move-in-ready pool home blends timeless design, quality craftsmanship, and high-end finishes throughout. The open-concept floor plan is anchored by a chef's kitchen featuring upgraded countertops, a 7-foot built-in Dacor refrigerator with dual ice makers, 5-burner Dacor gas cooktop, double wall ovens with steam cooking, and abundant prep and storage space. New flooring throughout creates a seamless flow, while 12-foot ceilings in the main living areas and primary suite enhance the home's spacious feel. Designed for both everyday living and entertaining, the home showcases custom built-ins with a rolling library ladder, a striking entertainment wall with fireplace and built-in lighting, and a thoughtfully designed split floor plan. A private office with custom built-in shelving offers the perfect work-from-home space. The spacious primary suite is privately positioned away from the secondary bedrooms and features dual California Closets and a spa-inspired bath with marble tile, a custom vanity, and a freestanding soaking tub. Two secondary bedrooms share a Jack-and-Jill bathroom, while the fourth bedroom has its own full bath, making it ideal for guests, teens, or multigenerational living. Step outside to your own private backyard retreat featuring a gas-heated pool and raised spa, multiple covered and open-air entertaining areas, a turfed putting green, and an additional fenced grassy side yard. Situated on a premium corner lot bordered by two quiet cul-de-sacs, the outdoor living spaces provide exceptional privacy and tranquility. Additional upgrades include premium Pella doors, interior and exterior paint, a whole-home owned water softener system, new flooring throughout, a new septic drain field, custom California Closet systems, and numerous additional improvements that make this home truly move-in ready. Located in the Reserve at Lake Butler Sound, this exceptional property offers luxury, privacy, and convenience just minutes from downtown Windermere, top-rated schools, world-class golf, fine dining, shopping, and Orlando's premier attractions. A rare opportunity to own a meticulously updated luxury home in one of Windermere's most sought-after communities.

11027 Hawkshead Court, Windermere

$569,000

4 Beds ⋅ 3 Baths ⋅ O6418594 MLS

Under contract-accepting backup offers. Imagine living where everything you love is just a short walk away. Welcome to 5032 Beach River in Windermere's beloved Summerport community. This move-in ready 4-bedroom, 2.5-bath home offers a lifestyle that's hard to find and even harder to leave. Start your mornings with a stroll to Foxtail Coffee, cool off with an afternoon treat from Kelly's Homemade Ice Cream, walk to highly sought-after Keene's Crossing Elementary, or spend evenings enjoying Summerport's parks, playgrounds, fishing dock, community center and so much more—all just minutes from your front door. Nestled beneath mature trees that create a picturesque streetscape and added privacy, this home welcomes you with timeless curb appeal and a rear-loaded garage complemented by an extended driveway—providing plenty of parking for family and guests. Inside, you'll find a well-maintained home with recently refreshed kitchen, a functional layout, and peace of mind with a new roof installed in 2025. Step outside to the oversized screened-in patio, a true extension of the living space with endless potential for entertaining, outdoor dining, game days, or simply relaxing and enjoying Florida's beautiful weather year-round. With unmatched walkability, exceptional community amenities, and a prime Windermere location, this is more than a home—it's the lifestyle you've been waiting for.

5032 Beach River Road, Windermere

$2,650,000

5 Beds ⋅ 6 Baths ⋅ O6418721 MLS

Under contract-accepting backup offers. Presenting this stunning LAKEFRONT RESIDENCE showcasing spectacular PANORAMIC VIEWS and ideally located within the premier GUARD GATED COMMUNITY of Reserve at Belmere in WINDERMERE. The property is approached by a circular driveway with centerpiece WATER FOUNTAIN set in mature landscaping alongside an adjoining 3 car garage with side entry. Upon arrival, an impressive entryway opens to the foyer and formal living/great room with seamless glass windows framing picture perfect water views. Set over two floors, this CUSTOM-BUILT home (exterior re-painted 2024) perfectly balances grand entertainment spaces with intimate everyday living featuring soaring ceilings alongside rich architectural artistry with its ornate detailing and trim. The sizeable wood paneled EXECUTIVE HOME OFFICE is a masterpiece with its custom cabinetry, wood floor and ceiling treatment. The GOURMET KITCHEN with high-end stainless-steel appliances and granite countertops has an open floor concept flowing effortlessly into a sunlit breakfast nook, countertop seating and spacious family room with focal point fireplace and sliding doors providing direct access to the outdoor area. A formal DINING ROOM, a BILLIARD ROOM with WET BAR also provide further spaces for entertaining both family and guests. The primary bedroom suite is a true RETREAT with sweeping views and sitting area with direct patio access, two large walk-in closets and ensuite bathroom which includes a walk-in shower, tub and dual sinks. A guest bedroom with full ensuite and two further bedrooms with Jack & Jill bathroom suite are also situated on the first floor. Upstairs, the dedicated HOME THEATER with full bar opens up to an adjoining GAMES ROOM with access to a private balcony providing an additional vantage place to avail of the breathtaking sunrises and sunsets. Also on this level is a HOME GYM workout space. [Note: This upstairs area is VERSATILE as could be utilized as a secondary primary suite as there is also a full ensuite bathroom with large walk-in closet]. Nestled on the shores of Lake Whitney and with its own PRIVATE DOCK, enjoy Florida living at its finest in this PRIVATE OASIS with its resort style outdoor area highlighted by a bespoke VANISHING EDGE POOL WITH WATER FOUNTAIN AND INTEGRATED HEATED SPILLOVER SPA (re-surfaced and new pool equipment 2024). There is an expansive covered lanai with plentiful lounge and dining spaces, an outdoor fireplace in addition to a full outdoor kitchen with countertop seating. A GOLF PUTTING GREEN sits to one side of the patio area and a SERENE GARDEN AREA to the other. The residence is in close proximity to the clubhouse and the community’s many amenities which include a fitness center, playground and tennis, basketball and sand volleyball courts. Reserve at Belmere is conveniently located just minutes from historic downtown Windermere, local shops, restaurants, the theme parks, major highways and nearby top-rated schools. THIS ISN’T JUST A HOME, IT’S A LIFESTYLE! Don’t miss out, book your private showing today!

1408 Lake Whitney Drive, Windermere

$550,000

3 Beds ⋅ 3 Baths ⋅ O6418405 MLS

Welcome to this great maintained residence located in one of Central Florida’s most sought-after communities in Windermere. Offering approximately 2,306 square feet of thoughtfully designed living space, this home features one of the builder’s most popular and highly requested floor plans. The spacious first-floor primary suite provides privacy, comfort, and convenience, making it ideal for today’s lifestyle. Upstairs, you’ll find two generously sized secondary bedrooms along with additional living space perfect for family members or guests. The home includes 2 full bathrooms and 1 half bath, creating a functional layout for both everyday living and entertaining. This property has been meticulously maintained and is truly move-in ready. A major recent upgrade includes a brand-new HVAC system installed last year, providing peace of mind and energy efficiency for years to come. Residents will enjoy the exceptional location, just minutes from world-renowned attractions including Walt Disney World and Central Florida’s premier entertainment destinations. Everyday conveniences are right around the corner, with shopping centers, grocery stores, restaurants, pharmacies, gas stations, banks, and postal services all within close proximity. Commuters will appreciate the easy access to major highways and expressways, allowing seamless travel throughout the Orlando metropolitan area. Orlando International Airport is conveniently located within approximately 30 to 40 minutes. Windermere continues to be one of the most desirable residential markets in Central Florida, known for its beautiful surroundings, outstanding quality of life, strong property values, and excellent accessibility. Opportunities to purchase a well-maintained home with a first-floor primary suite in such a desirable location are increasingly rare. Whether you are searching for a primary residence, vacation home, or long-term investment, this exceptional property offers the perfect combination of location, lifestyle, comfort, and value. Schedule your private tour today and experience everything this remarkable Windermere home has to make.

13330 Longacre Drive, Windermere

$1,100,000

4 Beds ⋅ 4 Baths ⋅ O6418503 MLS

Why wait months for new construction when you can move into this stunning, like-new home today? Located in the desirable Windermere area, this beautifully designed residence offers the perfect blend of luxury, comfort, and convenience. Step through the welcoming foyer and immediately appreciate the thoughtful layout. To the right, you'll find the first spacious bedroom, followed by a full bathroom and a second generously sized bedroom. As you continue through the home, you'll be greeted by an expansive open-concept living area designed for gathering with family and friends. The gourmet kitchen overlooks the living and dining spaces, creating the ideal setting for entertaining and everyday living. The main level features four spacious bedrooms and four full bathrooms, providing comfort and privacy for everyone. The luxurious primary suite serves as a private retreat, complete with a spa-like bathroom designed for relaxation and tranquility. Step outside to the covered lanai and unwind while enjoying peaceful water views. Whether you're sipping your morning coffee or watching the sunset, this serene outdoor space offers the perfect place to relax and recharge. Upstairs, you'll find a versatile bonus room with its own full bathroom, ideal for a guest suite, home office, media room, or playroom. Conveniently zoned for top-rated schools, including Windermere High School, this exceptional home is just minutes from shopping centers, restaurants, entertainment, and world-famous Walt Disney World attractions. Don't miss this incredible opportunity to own a move-in-ready home that offers the benefits of new construction without the wait!

14422 Crest Palm Avenue, Windermere

$755,000

4 Beds ⋅ 4 Baths ⋅ O6418089 MLS ⋅ Ashton Woods BLDG.

***PRICE IMPROVEMENT***Welcome to this stunning FORMER MODEL HOME in the sought-after ASLIN PARK, a community in the heart of WINDERMERE. This former CUSTOM CARLISLE model was designed and built by renowned ASHTON HOMES. Perfectly positioned on a premium corner lot with not rear neighbor and pond view, located in one of Windermere desired subdivision. This exceptional former model home blends timeless architecture, upscale finishes, and a thoughtfully designed floor plan tailored for both refined entertaining and comfortable everyday living. Surrounded by tranquil lakes, beautifully manicured streets, and a picturesque neighborhood setting, the home offers an impressive sense of arrival, beginning with its inviting covered front porch and attractive curb appeal. Inside, a welcoming foyer introduces gracious formal living and dining spaces that create an elegant backdrop for gatherings, celebrations, or quiet evenings at home. Just beyond, the sunlit family room serves as the heart of the residence, featuring soaring 20-foot wood ceilings that add warmth, character, and dramatic visual impact while seamlessly connecting to the gourmet kitchen. Designed with both beauty and functionality in mind, the kitchen is appointed with an expansive quartz island with double sinks, premium stainless-steel appliances, abundant custom cabinetry, generous workspace, and convenient access to the powder room and attached two-car garage, making daily routines and entertaining effortless. A striking wood staircase with an iron handrail enhances the home’s architectural appeal and leads to the second level, where the layout continues to provide comfort, privacy, and versatility for a variety of living needs. The private primary suite serves as a relaxing retreat, complete with a custom walk-in closet and a spa-inspired bath featuring dual sinks and a separate shower. Two well-appointed secondary bedrooms share a spacious Jack & Jill bathroom with a garden tub, while the junior suite offers its own private full bath with a walk-in shower, ideal for guests, multigenerational living, or anyone seeking additional privacy. A flexible bonus room provides space for a media room, playroom, office, or lounge, and the centrally located laundry room adds everyday convenience. Outdoors, the peaceful backyard extends the living space with a private tree-lined deck that creates a serene setting for al-Fresco dining, weekend entertaining, or unwinding in the shade after a long day. Spanning 3,161 square feet, the residence is enriched with upscale details throughout, including quartz countertops, generous walk-in closets, refined interior finishes, and a wired security system that adds peace of mind. An attached private Studio further enhances the home’s versatility, offering a comfortable and separate space for extended family, In-Laws, long-term guests, or roommates, with its own distinct access through the main entrance while remaining connected to the property. Beyond the home itself, residents enjoy access to top-rated schools and an impressive selection of community amenities, including a resort-style pool, clubhouse, playgrounds, and scenic walking and biking trails that wind around picturesque ponds and lakes, creating a lifestyle that is as desirable as the home itself. Just few miles to Disney Spring and amusement attractions. Don't miss the opportunity to own this gem perfectly located in the desired Ashlin Park community!!

7211 Still Pond Lane, Windermere

$724,900

4 Beds ⋅ 3 Baths ⋅ O6416993 MLS

Virtually Staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home tucked away on a quiet cul-de-sac in the highly desirable Eden Isle community of Windermere. Offering 2,665 square feet of thoughtfully designed living space on an oversized .32-acre lot, this home combines comfort, functionality, and an unbeatable location. Step inside to discover a light and inviting floor plan featuring high ceilings, crown molding, tray ceilings, spacious living and family rooms, and a seamless flow that's perfect for both everyday living and entertaining. The kitchen is the heart of the home, complete with solid wood cabinetry, ample prep space, and an open layout overlooking the family room. The spacious primary suite offers a peaceful retreat with a walk-in closet and an oversized en-suite bath, while three additional bedrooms and two full bathrooms provide plenty of room for family, guests, or a home office. Major updates provide peace of mind, including a new HVAC system, new water heater, and fresh interior paint, making this home truly move-in ready. Outside, enjoy the privacy of a large lot with plenty of room to relax, play, or create your dream outdoor oasis. Residents of Eden Isle enjoy access to a private boat ramp on beautiful Lake Speer, offering boating, fishing, and waterfront recreation just moments from home. Located in one of Windermere's most sought-after areas, you'll love being close to top-rated schools, shopping, dining, theme parks, major roadways, and everything that makes the Windermere lifestyle so desirable. Don't miss this opportunity to own a move-in-ready home in a fantastic location with private lake access and timeless appeal.

6363 Sedona Leaf Court, Windermere

$1,575,000

4 Beds ⋅ 5 Baths ⋅ O6415932 MLS

Situated within the beautiful gated community of Waterstone, this impeccably designed custom residence blends timeless architecture, refined finishes, and resort-inspired outdoor living into one extraordinary offering. Encompassing 3,396 square feet, the thoughtfully crafted floor plan features 4 bedrooms, 4 full bathrooms, and 1 half bath, all centered around a stunning private courtyard that creates a seamless connection between indoor and outdoor spaces. Walls of glass flood the home with natural light while framing picturesque views of the pool and outdoor living areas from nearly every room. At the heart of the home, the gourmet kitchen was designed for both everyday living and effortless entertaining. Rich custom cabinetry, exotic stone countertops, premium Bosch stainless steel appliances, a natural gas cooktop, oversized center island, and designer finishes combine to create a space as functional as it is beautiful. The adjacent great room offers a warm yet elegant gathering space, highlighted by exposed wood beam ceilings, a striking gas fireplace, integrated surround sound, and elegant architectural details throughout. The luxurious primary suite serves as a private retreat, featuring direct access to the courtyard and a spa-inspired bath complete with dual vanities, a soaking tub, walk-in shower, and thoughtfully curated finishes. A separate guest suite with its own private exterior entrance offers exceptional flexibility for multigenerational living, extended-stay guests, a home office, or a private retreat. Additional bedrooms are generously sized and well-appointed, providing comfort and privacy for family and visitors alike. Outside, the home's private courtyard transforms into a true resort sanctuary. A screened saltwater pool and raised spa are surrounded by expansive travertine decking and complemented by a beautifully appointed outdoor cabana featuring a masonry fireplace—creating the perfect setting for year-round entertaining or quiet relaxation. Constructed with both quality and efficiency in mind, the residence includes a tankless natural gas water heater, foam insulation, Low-E insulated windows and doors, and high-efficiency HVAC systems. Meticulously maintained and thoughtfully designed throughout, this exceptional Waterstone residence offers an ideal balance of luxury, comfort, and privacy in one of Windermere's most sought-after gated communities.

11832 Waterstone Loop Drive, Windermere

$6,900,000

5 Beds ⋅ 7 Baths ⋅ O6417446 MLS

A rare architectural statement on Lake Down, this extraordinary contemporary waterfront estate redefines luxury living in the heart of Windermere. Positioned on the prestigious Butler Chain of Lakes, this stunning residence offers 5 bedrooms, 5 full baths, 2 half baths, and a private elevator, seamlessly blending sophisticated design with effortless lakefront living. Constructed to Miami coastal specifications, the home was engineered with exceptional attention to quality, durability, and structural integrity while maintaining its striking modern aesthetic. Floor-to-ceiling glass walls frame breathtaking water views and flood the home with natural light, while soaring ceilings and open-concept living spaces create a dramatic yet inviting atmosphere. Every detail has been thoughtfully curated, from the designer finishes and statement lighting to the seamless integration of indoor and outdoor spaces. Luxury wellness amenities, including a steam shower, further enhance the home's resort-inspired appeal. The outdoor living experience is equally impressive, featuring a spectacular pool, expansive covered entertaining areas, and a fully equipped outdoor kitchen designed for gatherings both intimate and grand. Above it all, the rooftop terrace offers panoramic views of Lake Down and the surrounding landscape, creating the perfect setting for morning coffee, sunset cocktails, or evenings under the stars. As night falls, enjoy a truly magical experience as Disney fireworks illuminate the horizon from the comfort of your private rooftop retreat. Whether spending the day on the Butler Chain, entertaining guests poolside, or relaxing while taking in the waterfront views, this residence delivers an unparalleled lifestyle defined by elegance, comfort, and connection to the water. Ideally located just minutes from Restaurant Row, Downtown Orlando, the Mall at Millenia, Disney, Universal Studios, Orlando International Airport, and major thoroughfares including SR-408, this exceptional property combines the serenity of premier lakefront living with unmatched convenience. From sunrise over Lake Down to Disney fireworks dancing across the night sky, this is a home designed to inspire, impress, and elevate everyday living.

9061 Ron Den Lane, Windermere

$1,550,000

6 Beds ⋅ 5 Baths ⋅ O6416690 MLS

Welcome to an exceptional residence in the prestlgious gated community of Oxford Moor, where timeless elegance meets modern comfort. This impressive 6-bedroom, 4.5-bathroom estate offers over-the-top space for both refined living and effortless entertaining, complete with a spacious 3-car garage and an expansive, thoughtfully designed floor plan. From the moment you enter, you’ll appreciate the home’s grand scale, abundant natural light, and inviting living spaces designed to accommodate both intimate gatherings and large celebrations. The luxurious primary suite and generously sized secondary bedrooms provide comfort and privacy for family and guests alike. Step outside to your private resort-style oasis, featuring a beautifully redesigned pool and spa completely renovated in 2025, creating the perfect backdrop for relaxation and outdoor entertaining. Meticulously maintained and extensively updated, this home offers exceptional peace of mind with both HVAC systems replaced in 2020, fresh interior and exterior paint completed in 2022, a new water heater installed in 2023, and both the well pump and pool pump replaced in 2026. Perfectly positioned in one of Windermere’s most coveted communities, Oxford Moor offers a serene setting while remaining just minutes from top-rated schools, upscale shopping, fine dining, championship golf, major roadways, and Central Florida’s renowned attractions. A rare opportunity to own a beautifully updated luxury residence that seamlessly combines sophistication, comfort, and enduring value. Experience the lifestyle you deserve—schedule your private tour today.

5741 Oxford Moor Boulevard, Windermere

$930,000

5 Beds ⋅ 5 Baths ⋅ O6417680 MLS

Virtually Staged. Enjoy the best of Central Florida living in a highly sought-after neighborhood, just minutes from local schools, shopping, great restaurants, and magic of Disney. This 5-bedroom, 4.5-bathroom pool home is clean, well-maintained, and ready for move-in, featuring a freshly painted interior along with a newly painted exterior stucco, patio, and doors. THE FIRST FLOOR Walking in from the two-car garage and paver driveway, the covered front porch opens into a bright floorplan with high ceilings and tile floors. Right off the entrance is a formal sitting room that works perfectly as a quiet reading nook or music space. Down the hall, there's a convenient half-bath and a coat closet, leading into a large formal dining room made for family dinners. The kitchen connects right to the family room and comes with a large island and breakfast bar, plenty of counter and cabinet space, a big pantry, stainless steel appliances, recessed lighting, and a hidden back scullery. Tucked away at the back of the main floor is a guest bedroom and full bath, which is great for a mother-in-law suite or a playroom. THE SECOND FLOOR Upstairs, a large loft gives you a flexible second living area or media space. The laundry room is also on this level, making laundry a lot easier. The primary suite is set apart for privacy and includes separate individual vanities, a soaking tub, a glass shower, and a walk-in closet big enough to be a small room on its own. On the left side of the house, bedrooms 3 and 4 share a Jack-and-Jill bathroom. Across the way, bedroom 5 sits directly next to the home's fourth full bath. OUTDOOR LIVING Out back, the home looks out over a quiet pond. The covered, screened patio leads to a heated pool, giving you a great spot to hang out during the day and watch the nightly Disney fireworks from your own backyard

12929 Westside Village Loop, Windermere

$699,000

5 Beds ⋅ 3 Baths ⋅ O6416776 MLS

Virtually Staged. Enjoy exceptional privacy with beautiful conservation views behind & expansive green space beside the home, creating a peaceful setting rarely found in the community. Tucked away on a desirable homesite, 7906 Jailene Drive offers 2,618 SF, 5 bedrooms, 3 full bathrooms, 2-car garage, all filled with thoughtfully designed living spaces & ample dedicated guest parking conveniently located nearby. A welcoming front porch sets the tone as you enter the home, where a custom wood accent wall in the foyer creates a warm and inviting first impression. The open-concept layout offers spacious living & dining areas that flow seamlessly into the kitchen & family room. A dramatic two-story ceiling in the family room fills the space with natural light creating an impressive sense of openness, making it the perfect place to gather & entertain. The kitchen features granite stone countertops, abundant solid wood cabinetry, ample prep space, a kitchenette area & a functional layout overlooking the main living areas. Fresh interior paint, luxury vinyl flooring throughout & charming designer light fixtures add style and warmth throughout the home. The versatile floor plan includes a first-floor study/den which can also be used as a 5th bedroom with full bathroom. This space is ideal for a home office, family, guests, or multi-generational living. Upstairs, you’ll find four additional bedrooms, including the spacious primary suite, along with two full bathrooms & a conveniently located laundry room. Step outside to the screened lanai with tranquil conservation views, embracing nature at its best with exceptional privacy. Enhanced by a hand-painted decorative concrete finish, this outdoor retreat provides the perfect space for morning coffee, outdoor dining, or relaxing evenings, especially with a fully-fenced backyard. Located in the highly desirable Lake Sawyer community, residents enjoy access to a community pool, playground, park, and scenic sidewalks throughout the neighborhood. The home is zoned for sought-after schools, including Sunset Park Elementary, Horizon West Middle School, and Windermere High School. Just minutes from Horizon West and Hamlin Town Center, you’ll enjoy convenient access to shopping, dining, entertainment, and everyday conveniences. Major roadways are nearby, providing easy access to Walt Disney World, Disney Springs, downtown Orlando, Orlando International Airport, and all that Central Florida has to give. Combining privacy, functionality, thoughtful updates, and an exceptional location, this move-in-ready home presents a rare opportunity in one of Windermere’s most sought-after communities. Additional highlights include a brand-new roof (June 2026), HVAC 2024, abundant storage & a desirable location close to shopping, dining, schools, & major roadways. Combining privacy, functionality, & modern updates, this move-in-ready home is ready to welcome its next owners!

7906 Jailene Drive, Windermere

$3,300,000

5 Beds ⋅ 5 Baths ⋅ O6416913 MLS

Welcome to this spectacular 5-bedroom, 5-bathroom custom home offering over 8,000 square feet of thoughtfully designed luxury living—spared no expense and crafted to perfection. Nestled on a sprawling acre-plus level lot, this residence redefines your Florida lifestyle with elegance and comfort. Step inside to discover more than 5,000 heated square feet filled with spacious rooms adorned with wide plank wood flooring, tongue & groove ceilings, and exposed timber beams that create a warm, inviting atmosphere. The impressive 1st floor primary suite features a huge closet offering ultimate storage and style. Guests will enjoy complete privacy in the generously sized 1st floor guest suite. The gourmet kitchen is a chef’s dream, having Natural Gas & equipped with high-end Thermador appliances and crowned by stunning quartz countertops—perfect for preparing meals or entertaining. Step outside to the fully appointed summer kitchen and enjoy the screen-enclosed swimming pool on your expansive wrap-around porch, enhanced by elegant stacked stone columns. Car enthusiasts and hobbyists will appreciate the oversized 42 x 30 - 4 car garage with 10-foot tall doors, providing ample space for all your toys and vehicles. Additional modern comforts include natural gas for efficiency and convenience throughout the home. Laundry Rooms on each Floor - Located on the most sought-after street in Windermere, this masterpiece offers privacy, style, and unparalleled craftsmanship. Truly, this is everyone’s dream home—ready for you to create lasting memories.

11539 Lake Butler Boulevard, Windermere

$13,995,000

6 Beds ⋅ 11 Baths ⋅ O6411245 MLS

BRAND NEW ESTATE. A truly exceptional one-of-one on the shores of Lake Down, boasting over 12,000SF, 6BR's, 6/5BA's, and unmatched multigenerational flexibility. Designed by Mark Nasrallah and curated by Sorenson Construction, every inch of this estate was crafted with intention and the finest materials. Two 4-car garages flank either side of the oversized motor court, offering private entry to both the main house and the attached guest house. Off the main foyer, you'll find the formal dining room with Calacatta marble floors, and geometric coffered ceiling. Just beyond the elevator lies a 17x19 laundry room with an expansive island. The east wing is home to the gourmet kitchen, breakfast room, and family room. The chef's kitchen includes a Wolf six-burner gas stove with a built-in range hood, stacked double oven, and Sub-Zero double-wide refrigerator. Two Calacatta Macchia Vecchia marble islands create the ultimate statement. Beyond the main kitchen, behind a hidden door, is the prep/messy kitchen, with a Monogram 4-burner gas stove, Bosch refrigerator, walk-in pantry and butler's pantry. On the opposite side of the kitchen, the spacious breakfast room is bathed in natural light with access to the summer kitchen and pool deck through glass sliding doors. The open-concept layout flows effortlessly to the family room, where a backlit, custom media wall offers endless entertainment options. At the center of the main house is the expansive living room, the heartbeat of the estate. From the backlit coffered ceilings to the handcrafted millwork, and an overwhelming wall of glass, every part of this room feels larger than life. Rich hardwood flooring, built-in bookshelves, and a custom brass fireplace make it feel as charming as it is expansive. For guests, there is a first-floor ensuite bedroom complete with a separate generous lounge room, all overlooking spectacular lake views. Beyond the custom iron staircase on the first floor is the executive office, with built-in library, wood desk, and beautiful herringbone flooring. Adjacent is a stunning powder bath, followed by the interior guesthouse entry, which opens to a generous living room, a full-size kitchen with a Wolf 6-burner gas stove and a beautiful Arpell Azul mosaic backsplash, its own prep/messy kitchen, and full butler's pantry. The guest house's primary suite is its own oasis, with sweeping lake views, an ensuite bathroom, double vanity, clawfoot tub, and a huge walk-in closet. Two additional ensuite bedrooms — one designed for staff — a full-sized laundry room, and a flex room complete the guest house. Upstairs, the primary suite spans the entire east wing, with handcrafted coffered and backlit ceilings that are mesmerizing, plus panoramic views of Lake Down from the balcony. The master ensuite bathroom boasts a freestanding massage bath, his-and-hers vanities, and Walden Onyx designer wall coverings. The immersive primary walk-in closet will simply take your breath away, featuring designated his-and-hers areas, a center island, custom-built-in cabinetry, and an adjacent laundry room for the upper level. Directly next to the primary suite lies a spa retreat with a sauna room. A media room and entertainment den complete with its own kitchenette boast a flex room directly across the hall as well as an oversized ensuite guest suite. Outside, the limestone pool deck & covered summer kitchen, the disappearing-edge pool and spa with retractable screens provide the perfect retreat.

3057 Porto Lago Court, Windermere

$824,900

4 Beds ⋅ 5 Baths ⋅ O6416526 MLS

Welcome home, to a bright and spacious 4 bedroom, 3 full and 2 half baths home in a highly desirable Windermere area. With no HOA where you can bring your boat or RV and your vision for the property you've looking for. Open living space with soaring ceilings, offers a flexible layout full of potential. The master suite includes private bath with hot tub and separate shower, kitchen features ample storage and eat in bar, the upstairs has three bedrooms with two full baths given family and guest room to spread out. Out back, a pool and patio are ready for quiet mornings and weekends BBQs-with plenty of space to make it your own. All this minutes from downtown Windermere, top-rated schools, Orlando's best attractions and major highways. Opportunities like this - space, location no HOA - rarely come available. Come and make it your own.

11994 Mckinnon Road, Windermere

$635,000

3 Beds ⋅ 2 Baths ⋅ O6414631 MLS

Welcome home. This wonderfully kept move-in ready 3 bedroom, 2 bathroom pool home is located in one of SouthWest Orlando's sought after communities, Silver Woods. It features travertine tile flooring throughout most of the home with engineered hardwood flooring in all the bedrooms, an open kitchen with stainless steel appliances and granite countertops overlooking the family room and an inside laundry room for your convenience. After long days, step outside on the patio and enjoy lounging around the open-air sparkling pool. The back yard also has plenty of space for the kids and pets to play. The major components of the home: roof 2022, A/C 2015, water heater 2023, GE electrical panel and CPVC plumbing.

9110 Palm Tree Drive, Windermere

$500,000

3 Beds ⋅ 2 Baths ⋅ O6416099 MLS

Welcome home to this charming single story, 3-bedroom, 2-bath home located in the highly desired gated community, Lakes of Windermere – Peachtree. Step inside to an inviting open layout with brand new carpet, abundant natural light, spacious living and dining areas ideal for everyday living and entertaining. The kitchen features ample cabinetry, a kitchen island, and stunning views of the serene backyard. The split-bedroom floor plan provides a private primary suite with a walk in closet and en-suite bath, while two additional bedrooms and a full bath offers flexibility for family, guests, or a home office. Enjoy outdoor living in the fully fenced backyard and a screen enclosed patio overlooking lush conservation with no rear neighbors — a perfect setting for relaxing, gardening, or play. For added peace of mind, a NEW ROOF WILL BE INSTALLED PRIOR TO CLOSING, offering exceptional value to the next owner. Residents of Lakes of Windermere enjoy access to community amenities including a community pool, playground, and beautifully maintained green spaces, all just minutes from top-rated schools, dining, shopping, and the best of Windermere and Horizon West. Move in ready with meaningful updates and a premium lot — this home is the ideal blend of comfort, convenience, and Florida living. GET YOUR RATE BOUGHT DOWN by using SELLERS PREFERRED LENDER.

8662 Abbotsbury Drive, Windermere

$1,400,000

5 Beds ⋅ 4 Baths ⋅ O6410847 MLS

Welcome to this exceptional luxury residence offering 5 spacious bedrooms, 4 beautifully appointed bathrooms, and 3,929 square feet of refined living space on an expansive homesite of over half an acre. Perfectly positioned in a highly sought-after location, this stunning property combines elegance, comfort, and privacy with resort-style outdoor living. Surrounded by lush, mature landscaping, the home makes a striking first impression and provides a serene setting for everyday living. Inside, thoughtfully designed interiors feature generous living and entertaining spaces, abundant natural light, and sophisticated finishes throughout. The spacious layout seamlessly accommodates both intimate family gatherings and large-scale entertaining. The outdoor retreat is equally impressive, highlighted by a sparkling pool and expansive patio areas ideal for relaxation and year-round enjoyment. The oversized lot offers exceptional privacy while providing ample space for outdoor activities and future enhancements. Residents enjoy access to outstanding community amenities and the convenience of a prime location close to premier shopping, dining, entertainment, top-rated schools, and major transportation routes. Offering an unparalleled blend of luxury, space, and lifestyle, this remarkable property presents a rare opportunity to own a distinguished home in one of the area’s most desirable communities. You're also nestled within a well-established community, this property enjoys an enviable location close to major highways, ensuring convenient access to all amenities. Just minutes away, residents can indulge in excellent shopping opportunities, dine at a variety of luxury and casual eateries, and explore nearby theme parks for entertainment. The neighborhood benefits from proximity to brand-new, state-of-the-art hospitals and a top notch school system, providing peace of mind for residents seeking quality healthcare services and high end education for their family. This vibrant community offers an abundance of options to suit every lifestyle need and preference. Call today to schedule a private tour.

1700 Lake Roberts Court, Windermere

$624,900

4 Beds ⋅ 3 Baths ⋅ O6416272 MLS

***NEW ROOF IS DONE.***Welcome to this spacious 4-bedroom, 3-bath Victorian-style home in the highly desirable Lakes of Windermere community. Boasting over 3,000 square feet of living space, this beautifully designed home offers an exceptional layout ideal for both everyday living and entertaining. A charming covered front porch and elegant curved staircase create a warm and inviting first impression. The open-concept family room flows seamlessly into the upgraded kitchen, featuring granite countertops, stainless steel appliances, a center island, and abundant cabinet space. The oversized primary suite is conveniently located on the first floor, complete with a spacious walk-in closet and a private ensuite bath. Upstairs, you'll find three generously sized bedrooms and additional full bath accommodations, providing flexibility and comfort for family and guests. Situated on a premium corner lot directly across from a community playground, this home also features a rear-entry attached garage and an ideal location within the neighborhood. Residents of Lakes of Windermere enjoy outstanding amenities, including a community pool, fishing dock, playgrounds, tennis courts, scenic lakes, and recreational areas. The home is also zoned for highly rated A+ schools and is conveniently located just minutes from shopping, dining, major roadways, and Central Florida's world-famous attractions. Don't miss this incredible opportunity to own a beautiful home in one of Windermere's most sought-after communities!

6601 Duncaster Street, Windermere

$12,750,000

6 Beds ⋅ 10 Baths ⋅ O6416194 MLS

Virtually Staged. A true Lake Butler trophy estate. Set within the world-famous gates of Isleworth and commanding panoramic western sunset water views of Lake Butler from virtually every room, 9832 Laurel Valley Drive offers over 11,000 square feet of luxury lakefront living, situated upon 150 feet of expanded sandy beachfront, thoughtfully enlarged by the current owners, in one of Florida’s most well known communities. This statement home features six bedrooms, seven full bathrooms, and three half bathrooms, a newly installed bespoke theater room with custom seating, an infrared sauna and dedicated wellness and fitness area, two full bars, a private pub and game room, an elegant pool and spa, a fully equipped summer kitchen, and multiple levels of outdoor living and lounge space overlooking the lake. Complemented by countless additional spaces designed for both grand-scale entertaining and everyday enjoyment, every room exudes elegance and has been meticulously designed and expertly executed down to the finest detail. Beyond its unmatched location and architecture, the home has benefited from several million dollars’ worth of enhancements and upgrades, further elevating an already impressive estate into something truly magnificent. The result is a residence that blends timeless luxury with modern comfort while offering one of the most desirable waterfront settings in Central Florida. Not all lakefront homes are created equal, and Laurel Valley is a shining example of that. More than a home, 9832 Laurel Valley Drive is a statement. A trophy estate befitting a legacy. A rare opportunity to own one of Florida’s most compelling waterfront properties ever. The home may be negotiated to include select furniture, a brand-new pontoon boat, two new Sea-Doo jet skis, and a golf cart.

9832 Laurel Valley Drive, Windermere

$479,500

3 Beds ⋅ 3 Baths ⋅ O6410344 MLS

PRICE IMPROVMENT– INCREDIBLE VALUE IN ONE OF CENTRAL FLORIDA'S MOST DESIRABLE COMMUNITIES If you've been searching for the perfect combination of location, condition, lifestyle, and value, this is the home you've been waiting for. Welcome to this beautifully maintained single-family home in the highly sought-after Windermere area, offering an opportunity that's becoming harder and harder to find in today's market. Why settle for a townhome when you can own a standalone home on a premium corner lot with more privacy, more outdoor space, and all the benefits of one of Central Florida's premier communities? This move-in-ready home has been extensively refreshed and improved, making it one of the best values currently available in the area. Property Highlights: • Premium corner lot with added space and privacy • Freshly painted interior, exterior, and garage • Brand-new AC system (inside and outside units) • Water softener system already installed • Freshly pressure-washed driveway and sidewalks • Spacious floor plan with a half bath downstairs • Versatile loft area upstairs • Newer construction home • Excellent curb appeal and move-in-ready condition Beyond the home itself, you'll love the lifestyle this community offers. Enjoy beautiful walking trails, abundant green spaces, playgrounds, a community clubhouse and pool, and an active neighborhood atmosphere where residents enjoy walking, exercising, biking, and outdoor activities year-round. Conveniently located just minutes from Disney, major highways, shopping, restaurants, fitness centers, entertainment, and everyday conveniences, this location truly puts everything within reach. Whether you're a first-time homebuyer, relocating, downsizing, or looking for a smart investment, this home delivers exceptional value and peace of mind with many of the major items already updated. Homes with this combination of condition, location, lifestyle, and value do not come along often. Schedule your private showing today and see why this may be one of the best opportunities currently available in Windermere. For more information or to schedule a private tour, contact: Mahmoud Mango, Realtor® The Mango Group

8266 Bryce Canyon Avenue, Windermere

$2,474,000

5 Beds ⋅ 7 Baths ⋅ S5151608 MLS

Positioned on a corner homesite along the 18th hole of the Golden Bear Club within the guard-gated community of Keene's Pointe, this thoughtfully updated custom home offers five bedrooms, four full bathrooms, and three half bathrooms, combining exceptional golf-front living with breathtaking views of the golf course, pool, and surrounding landscape. A grand foyer welcomes guests with a soaring 22-foot ceiling, while oversized tile flooring extends throughout the first floor. Expansive windows fill the home with natural light while creating a seamless connection to the outdoor living spaces. The well-designed floor plan features a dedicated office with a coffered ceiling, spacious living and dining areas, and a beautifully appointed kitchen with beautiful cabinetry, granite countertops, a professional-grade gas range, center island, and abundant storage. Just off the kitchen and family room is a spectacular custom entertainment bar featuring extensive cabinetry, generous serving space, and four under-counter refrigerators, creating the ultimate setting for entertaining. The first-floor primary suite serves as a private retreat with direct access to the lanai and pool area. The updated spa-inspired bath features designer cabinetry, quartz countertops, a freestanding soaking tub, oversized walk-in shower, premium fixtures, and elegant floor-to-ceiling tilework. Completing the owner's retreat are two spacious walk-in closets, including a large walk-in closet directly off the bedroom and an additional oversized walk-in closet conveniently located off the bathroom, providing exceptional storage and organization. The secondary bedroom layout offers both comfort and privacy for family and guests. Two bedrooms feature en-suite bathrooms, while two additional bedrooms are connected by a Jack-and-Jill bathroom. The expansive second-floor bonus room serves as a versatile gathering space, ideal as a media room, game room, lounge, or secondary family room. A dramatic vaulted tongue-and-groove wood ceiling creates architectural interest and warmth, while large windows and French doors fill the space with natural light and provide direct access to the covered second-floor terrace overlooking the pool and golf course. A conveniently located half bath serves the bonus room and outdoor terrace, making the space perfectly suited for entertaining family and guests. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers an abundance of covered outdoor living space. The resort-style outdoor area features a covered lanai, summer kitchen, pool, spa, dedicated pool bath, and multiple gathering spaces thoughtfully positioned to capture views of the Golden Bear Club's signature finishing hole. An expansive covered second-floor terrace with a tongue-and-groove wood ceiling is accessible from multiple bedrooms as well as the bonus room, providing stunning views of the pool and golf course. A spiral staircase leads to a private third-story observation deck featuring a wet bar and panoramic views across the fairways and surrounding treetops, creating the perfect setting for entertaining, enjoying evening sunsets, or watching play unfold along the Golden Bear Club's signature finishing hole.

6288 Blakeford Drive, Windermere

Browse All Windermere FL Single Family Properties for Sale

Windermere Single Family Real Estate

Adair Realty, Inc.

Search

Resources

About