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8168 Boat Hook Loop Unit 302, Windermere
$299,997
2 Beds ⋅ 2 Baths ⋅ O6445290 MLS ⋅ 8168 BLDG.
Welcome to this spacious 2-bedroom, 2-bathroom third-floor condo in an elevator building, meaning no noisy above neighbors, in a convenient Windermere location, situated within walking distance from the community clubhouse and its extensive resort-style amenities. Offering an open floor plan, generous living spaces, and a low-maintenance lifestyle, this home is well suited for a full-time residence, second home, or investment property. The open-concept living and dining areas create a comfortable space for everyday living and entertaining, while the spacious kitchen features a breakfast bar, tons of cabinet storage, and large pantry closet. Both bedrooms are generously sized with ample closet space. The primary suite includes a private en-suite bathroom and walk-in closet. An enclosed outdoor living area provides additional space to relax, enjoy your morning coffee, or unwind at the end of the day. The community clubhouse is located just steps away and offers a variety of amenities, including a large swimming pool, fitness center, library, fireplace gathering area, kitchen facilities for entertaining, volleyball court, and playground. Located in Windermere with convenient access to Walt Disney World, shopping, A rated schools, dining, entertainment, and major Central Florida attractions. Disney's Magic Kingdom is approximately 10 minutes away, making this property an attractive option for those seeking a primary residence, vacation home, or investment opportunity in the Orlando area. Schedule your private showing today and discover the convenience and lifestyle this Windermere condo has to offer.

8168 Boat Hook Loop Unit 302, Windermere
9668 Woodmont Place, Windermere
$1,295,000
6 Beds ⋅ 5 Baths ⋅ O6443475 MLS
No detail overlooked in this beautifully reimagined 6BR/5BA estate in the sought-after lakefront community of Windermere Downs! Fully renovated and expanded with high-caliber craftsmanship, this home offers the ultimate Central Florida lifestyle. The lower level boasts rich tongue-and-groove ceilings, hardwood floors, plantation shutters, double-pane vinyl windows, and bright natural light. The expansive primary suite features a custom 10’x20’ walk-in closet and spa-like bathroom. Every bedroom enjoys en-suite bath access, including the private 780 sq ft upper-level suite with stunning Lake Down sunset views. The spacious kitchen and breakfast nook anchor the home, flowing into a living room with a stunning floor-to-ceiling picture window and French doors that open to your backyard oasis. Step outside to a private resort-style paradise complete with a sport pool, sun shelf, earth-toned pavers, summer kitchen, fire pit, and remodeled pool bath. Major mechanical updates ensure total peace of mind: Spray foam insulation (2025), main HVAC (2019-2023), new water heater, upgraded plumbing, lighting, and interior laundry room. Enjoy deeded access to the Butler Chain of Lakes via Windermere Downs’ crown jewel private beach lot on Lake Down, plus tennis/pickleball courts and park spaces. Unbeatable location—10 mins to Turnpike/408/429 and 25 mins to Disney, MCO Airport, and Downtown Orlando!

9668 Woodmont Place, Windermere
6533 Cartmel Lane, Windermere
$1,598,000
4 Beds ⋅ 4 Baths ⋅ O6443650 MLS
Set on 0.54 acre at the end of a quiet cul-de-sac in the Reserve at Lake Butler Sound, 6533 Cartmel Lane offers single-story living within one of Windermere’s established guard-gated communities. Mature landscaping, a paver driveway and a substantial architectural entry frame the residence, while the private pool opens to an expansive backyard that gives the property a notable sense of space and privacy. Inside, high ceilings and generous natural light shape a thoughtfully arranged split-bedroom floor plan. The primary suite is positioned apart from the secondary bedrooms, creating a more private retreat within the home. Just beyond the bedroom, a bonus room offers a flexible extension of the suite, suited to a sitting room, study or quiet reading space. The principal living areas are distinct yet connected, allowing the home to feel open without sacrificing definition. Generous windows bring natural light throughout, while the formal dining area and multiple gathering spaces create an easy progression from one room to the next. Outdoor living is centered around the screened lanai and pool, both overlooking the broad rear lawn. The scale of the homesite gives the exterior a sense of openness, while the three-car garage provides additional parking and storage. A tile roof completes the home’s architectural profile. Reserve at Lake Butler Sound was conceived as a gated residential community of luxury homes, shaped by consistent architectural and landscape standards intended to preserve a cohesive and harmonious setting. Controlled access established landscaping and a carefully maintained residential environment contribute to a sense of privacy, permanence and distinction. Approximately six minutes away, downtown Windermere offers a refined small-town setting defined by tree-lined streets, local parks, neighborhood dining and the popular Friday farmers' market. Just beyond the community, a public boat ramp provides access to Lake Butler and the interconnected Butler Chain of Lakes, while several of Central Florida’s notable golf courses are within easy reach. Walt Disney World, Universal Orlando, Sand Lake Road, downtown Orlando and Orlando International Airport are approximately 20 to 30 minutes away. With its single-story design, generous homesite and setting within one of Windermere’s established luxury communities, 6533 Cartmel Lane offers a refined expression of Central Florida living, defined by privacy, space and convenient access to the area’s lakes, golf, entertainment and travel connections.

6533 Cartmel Lane, Windermere
12809 Holdenbury Lane, Windermere
$625,000
4 Beds ⋅ 3 Baths ⋅ S5157920 MLS
Under contract-accepting backup offers. The best sought-after Windermere location! This beautiful Lakes of Windermere 4 bedroom 2.5 bath home was just updated this summer with NEW ROOF, NEW APPLIANCES, NEW CARPETS, FRESHLY PAINTED INSIDE AND OUT, plus garage and floor fully painted. ELECTRIC VEHICLE CHARGER IN GARAGE. No rear neighbors: Enjoy a calm, quiet pond view from your covered 15x7 back porch. Or meet the neighbors by relaxing on your covered 17x12 front porch facing the tree-lined street! The kitchen/family room combo is light and bright with soaring 2-story ceiling and windows galore! All matching new SS appliances plus lots of wood cabinets and long breakfast bar in the kitchen that adjoins a dinette area with built in desk. All bedrooms are upstairs with new carpets. The extra large Primary suite includes a window seat, and bathroom with garden tub, separate shower, dual sinks, linen closet and private water closet. Three more comfortable bedrooms and bath are down the hall. The Lakes of Windermere community clubhouse and pool are a short walk away in addition to tennis, basketball, volleyball, and soccer courts, three playgrounds, a lake dock with fishing access, and scenic walking trails through the community including GAZEBO AT THE PINE LOOP PARK (Nobelton Drive and Mapperton Drive) a shaded space for community parties and events. Zoned for A+ rated Windermere High School! Short drive to Disney World, and close to 429 for easy access to Orlando and Horizon West for the best shopping and restaurants. Ready for immediate occupancy. Call to see it today!

12809 Holdenbury Lane, Windermere
7555 Tattant Boulevard, Windermere
$615,000
4 Beds ⋅ 4 Baths ⋅ O6443170 MLS
Under contract-accepting backup offers. Welcome to this 4-bedroom, 3.5-bath home in Windermere, zoned for top-rated schools including Windermere High School and Horizon West Middle School. Located near Horizon West shopping, dining, parks, and major roadways, this Windermere pool home combines a desirable location, functional layout, and the indoor-outdoor lifestyle that buyers are searching for in Central Florida.

7555 Tattant Boulevard, Windermere
12679 Calderdale Avenue, Windermere
$520,000
3 Beds ⋅ 2 Baths ⋅ O6442555 MLS
Under contract-accepting backup offers. Welcome to this beautifully located single-story home in the highly desirable Windermere area! This 3-bedroom, 2-bath home offers 1,681 sq ft of comfortable living space with an open floor plan, stone countertops, walk-in closet, spacious living and dining areas, and an attached 2-car garage. Enjoy Florida living with a covered and screened patio, plus access to community amenities including a resort-style pool, clubhouse, playground, and sidewalks. Location is a major highlight! The home is zoned for highly rated schools, including Sunset Park Elementary, Horizon West Middle School, and Windermere High School, while offering convenient access to shopping, dining, entertainment, major roadways, and everything the Windermere and Horizon West areas have to offer. Offered at $520,000, this is an excellent opportunity to own a home in one of Central Florida’s most desirable locations. Schedule your private showing today!

12679 Calderdale Avenue, Windermere
929 Lascala Drive, Windermere
$349,900
3 Beds ⋅ 2 Baths ⋅ O6435895 MLS
Virtually Staged. Welcome to this spacious 3-bedroom, 2-bathroom single-story home in the gated Belmere community of Windermere. The open floor plan provides a comfortable flow between the living spaces, with a formal living room and dining room offering flexibility for entertaining, gatherings, or everyday use. The family room features high ceilings and opens to the kitchen and breakfast area, creating a central space for relaxing and spending time together. The primary suite offers a private retreat with a walk-in closet and an ensuite bathroom featuring a garden tub, separate shower, and dual vanities. Two additional bedrooms provide comfortable space for family, guests, a home office, or other needs. A screened-in patio extends the living space outdoors and overlooks the landscaped backyard. The home also includes an attached 2-car garage and convenient interior laundry area. Belmere offers residents access to community amenities including a pool, clubhouse, fitness center, tennis courts, basketball court, and playground. Conveniently located near shopping, dining, major roadways, and Orlando-area attractions, this home offers a practical layout in a desirable Windermere community.

929 Lascala Drive, Windermere
Dingens Avenue, Windermere
$500,000
O6441380 MLS
Under contract-accepting backup offers. Build your dream home in Windermere. Opportunity is knocking in one of Central Florida’s most desirable areas! This spacious nearly half-acre vacant lot on Dingens Avenue in Windermere offers the perfect opportunity to bring your vision to life and build the home you have always wanted. One of the biggest advantages of this property is NO HOA! Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a beautiful custom estate, a spacious family home, or a private retreat, this property gives you the opportunity to create something that is truly your own. The almost 1/2-acre size provides plenty of room to design a home with the features that matter most to you, think expansive living spaces, a beautiful outdoor entertaining area, pool, garden, garage, or whatever fits your lifestyle and vision. Instead of settling for someone else’s floor plan, start with a blank canvas and make it your own. Location is everything, and this property puts you within convenient reach of the best that the Windermere and greater Orlando area have to offer. Enjoy easy access to excellent restaurants, shopping, major highways, main roads, entertainment, and some of Central Florida’s most popular attractions. Whether you are heading out for dinner, shopping, commuting to work, or enjoying a day at one of the area’s many attractions, you will appreciate the convenience of this location. Windermere is known for its beautiful surroundings, desirable residential areas, charming community atmosphere, and proximity to everything that makes Central Florida such a sought after place to live. Opportunities to purchase a sizable homesite with no HOA in a desirable location can be hard to find. This property is competitively priced to sell, making now the time to take a serious look. Stop dreaming about the perfect home and start building it. Bring your architect, your builder, and your ideas, and turn this nearly half-acre homesite into something uniquely yours. Build what your heart desires. Make your vision come to life. Make this Windermere property the place you call home! Priced competitively to sell. Don't miss this opportunity!

Dingens Avenue, Windermere
618 Ridgewood Drive, Windermere
$650,000
O6439608 MLS
Under contract-accepting backup offers. A rare opportunity to build your dream home in the heart of Old Windermere. This cleared, vacant parcel consists of 7 total lots being offered for the first time — a truly unique chance to secure land in the Town of Windermere before it's gone. Enjoy golf cart-friendly streets, access to the famed Butler Chain of Lakes, and the convenience of natural gas already available. With no HOA, you have the freedom to design and build exactly the home you envision. Just a short walk to downtown shops, restaurants, and community events, this homesite combines small-town charm with unbeatable convenience. Opportunities like this don't last long — bring your builder and make it yours! Lots approx. 100' x 167'. Lots 19-22: $650,000 each | Lot 18: $700,000 | Lot 29: $750,000 | Lot 30: $800,000. Multiple offers on lots 29 & 30. Highest and best by Friday, 9/18 at 5:00 pm.

618 Ridgewood Drive, Windermere
6243 Andreozzi Lane, Windermere
$720,000
4 Beds ⋅ 2 Baths ⋅ O6439730 MLS
Under contract-accepting backup offers. Welcome to this spacious pond-front home in Providence, featuring a private screened pool and peaceful water views. Major updates include the roof, A/C system, and water heater, all replaced in 2021. Inside, the home features plantation shutters on most windows, hardwood and tile flooring with no carpet, high ceilings, and 8-foot doors throughout. The spacious primary suite overlooks the pond and provides direct access to the oversized covered lanai and pool. The updated primary bath features dual sinks, a large walk-in tiled shower with built-in bench and niches, and a spacious walk-in closet. Generously sized secondary bedrooms provide plenty of space, while the bright family room features large windows and sliding doors overlooking the pool and pond. The updated kitchen features modern cabinetry, stainless steel appliances, contemporary lighting, generous counter space, and bar seating. Step outside to enjoy the expansive covered lanai, private screened pool, mature landscaping, and tranquil pond backdrop-an inviting setting for relaxing or entertaining. Providence includes a community pool and playground. Conveniently located near shopping, dining, Winter Garden Village, major roadways, and area attractions.

6243 Andreozzi Lane, Windermere
9155 Outlook Rock Trail, Windermere
$795,000
5 Beds ⋅ 5 Baths ⋅ O6438208 MLS
Under contract-accepting backup offers. Set against a natural preserve, this Windermere home combines a flexible floor plan, thoughtful upgrades, and a backyard setting that feels removed from the everyday. Natural light fills the main living spaces, while distinctive ceiling beams in the dining room add warmth and character. A full bedroom and bathroom on the first floor provide flexible space for guests, extended stays, a private office, or everyday living. Upstairs, the spacious primary suite features two custom walk-in closets designed for exceptional storage and organization. Paid-off solar panels provide added energy efficiency without an additional solar payment, while fresh front landscaping enhances the home’s curb appeal. Step outside to a backyard framed by preserve views, local wildlife, and an added sense of privacy. The home’s mid-street position also creates a more tucked-away setting from the neighborhood entrances. Conveniently located in the Windermere and Horizon West area, the home offers easy access to shopping, dining, major roadways, and Walt Disney World. It brings together comfortable living, useful spaces, energy-conscious features, and a natural backdrop that is increasingly difficult to find.

9155 Outlook Rock Trail, Windermere
13730 Lensdale Lane, Windermere
$375,000
4 Beds ⋅ 3 Baths ⋅ O6439354 MLS ⋅ N/A BLDG.
Under contract-accepting backup offers. Virtually Staged. Welcome home to Lensdale Lane! This 4-bedroom updated townhome and move-in ready peace of mind: fresh interior paint and trim (2025), new windows and sliding glass door (2022), a newer roof (2021), new exterior paint and siding (2021), and an updated A/C (2019). Step inside to a light and bright open-concept layout where the living, dining, and kitchen flow together effortlessly. The kitchen features sleek quartz countertops, ample storage, and a breakfast bar, perfect for everyday meals or casual entertaining. The main-floor primary suite offers privacy and convenience, while three spacious secondary bedrooms and a second full bath complete the upstairs. Ceramic tile and wood laminate flooring flow throughout; no carpet anywhere! A half bath and laundry round out the main floor. Outside, enjoy your morning coffee on the privacy-fenced courtyard patio, while the covered front porch adds instant curb appeal. The 2-car rear-facing garage keeps the streetscape clean and charming. This home pairs low-maintenance living with an impressive amenity package. The HOA covers exterior maintenance and includes access to a community POOL, clubhouse, FITNESS center, sports courts and walking trails. Zoned for TOP-RATED schools: Windermere High ,Keene's Crossing Elementary, and Bridgewater Middle and just minutes from Winter Garden Vineland Rd, the 429, shopping, dining, and Central Florida's theme parks.Southbridge, part of the sought-after Summerport/Horizon West community, offers an unbeatable sense of community and lifestyle.

13730 Lensdale Lane, Windermere
706 Oakdale Street, Windermere
$850,000
3 Beds ⋅ 3 Baths ⋅ O6439213 MLS
Under contract-accepting backup offers. Welcome to your immaculate and charming home in the heart of Downtown Windermere, where timeless traditional style meets modern convenience. Nestled beneath beautiful mature oak trees, this inviting property offers a spacious yard and a welcoming front porch perfect for relaxing in a pair of rocking chairs and enjoying the peaceful surroundings. Step through the front door into a light-filled interior featuring freshly painted walls and warm wood-look tile throughout the first floor. Your remodeled kitchen is both stylish and functional, featuring stainless steel appliances, a gas range, and granite countertops, perfect for everyday living and entertaining. Upstairs, the home showcases its original hardwood floors throughout, adding warmth and character. The spacious primary suite features a beautifully updated bathroom with custom cabinetry, walk in closets, granite countertops, and quality finishes. Two additional bedrooms and a full bathroom complete the second floor, providing plenty of space for family, guests, or a home office. The expansive, fully fenced backyard offers endless possibilities. There is ample room for a pool, playset, fire pit, outdoor games, and entertaining creating a wonderful private space to enjoy Florida’s beautiful weather. Ideally located within walking distance of the Windermere Farmers Market, local shops, restaurants, and more, with beautiful Lake Butler just blocks away, this home offers the best of the Old Windermere lifestyle. Additional highlights include a new roof installed in 2025, water softener, and newer AC unit. Don’t miss the opportunity to make this special home your own. Schedule your private showing today!

706 Oakdale Street, Windermere
7033 Bramlea Lane, Windermere
$647,000
3 Beds ⋅ 3 Baths ⋅ O6438579 MLS
Modern elegance meets resort-style living in the Lakes of Windermere. Welcome to a beautifully renovated craftsman-style home. Thoughtfully updated for today's lifestyle, this move-in-ready residence blends timeless architectural character with modern comfort, quality finishes, and inviting indoor-outdoor living. From the moment you step inside, natural light fills open-concept living spaces, creating a bright and welcoming atmosphere throughout the home. The thoughtful layout and carefully selected finishes provide the perfect balance of style, functionality and everyday comfort. At the center of the home is a beautifully appointed kitchen designed for both everyday living and entertaining. It features an oversized 36-in professional Electrolux induction range with convection oven, a 36-inch range hood, built-in wine cooler, granite countertops, and a classic farmhouse sink. Whether preparing a casual meal or entertaining guests, the kitchen is designed to be both functional and impressive. The majestic dining room table, chairs, sideboard and barstools convey with the home as an attractive option. The primary suite includes an added layer of flexibility with a versatile suite located adjacent to the master. Use it as a nursery, private home office, fitness space, reading room, or whatever best fits your lifestyle. Step outside and discover one of the home's standout features: a private tropical-inspired outdoor retreat. The professionally landscaped backyard includes an outdoor kitchen, custom-paved seating area, and integrated LED lighting--creating an inviting setting for entertaining, outdoor dining, or simply enjoying your own private space. Recent upgrades & features include the following: Roof (2022); 2-stage AC system (2023); water-softening filtration system (2022); enclosed patio (2024); Ecobee thermostat (2022); B-Hyve automated irrigation system (2022); outdoor kitchen refrigerator (2026); luxury vinyl plank flooring (2022); and carpeting (2022). Beyond the property itself, residents enjoy access to desirable community amenities, including a community pool, tennis court, playgrounds, and a scenic fishing dock. This is a home designed for the way people live today, with beautiful interior spaces, meaningful upgrades, flexible living areas, and an exceptional outdoor environment.

7033 Bramlea Lane, Windermere
5379 Isleworth Country Club Drive, Windermere
$2,900,000
4 Beds ⋅ 4 Baths ⋅ O6438449 MLS
Under contract-accepting backup offers. This luxury estate in Isleworth offers a rare opportunity to remodel or create a custom estate in the highly coveted Isleworth community. Situated directly on the 17th hole of the Isleworth Country Club golf course, this property offers a unique combination of golf-course frontage and beautiful lake views. Designed for ultimate privacy, this spacious layout offers four bedroom suites each complete with a dedicated ensuite. Schedule your private tour today!!!

5379 Isleworth Country Club Drive, Windermere
8104 Jailene Drive, Windermere
$759,000
4 Beds ⋅ 4 Baths ⋅ O6437963 MLS
Under contract-accepting backup offers. Welcome to 8104 Jailene Drive, a beautifully updated 4-bedroom, 3.5-bath pool home offering nearly 2,900 square feet of thoughtfully designed living space in the desirable Lake Sawyer community in Windermere. Set against a peaceful conservation backdrop with no rear neighbors, this home pairs privacy and outdoor living with a long list of recent improvements—including a NEW ROOF completed in May 2026, fresh interior paint and landscape lighting that beautifully highlights the property after sunset. Inside, an open, light-filled floor plan creates an easy flow for both everyday living and entertaining. The centrally located kitchen features upgraded cabinetry, Topazio White granite countertops a butler pantry, stainless steel appliances with a Bosch dishwasher, and generous workspace and storage. Custom details continue throughout the home, including upgraded wood and laminate flooring, a built-in credenza in the family room and built-in shelving in the office. The spacious primary suite offers a private retreat of its own, complete with a separate sitting area, oversized walk-in closet with built-in cabinetry. Step outside to the screened pool and enjoy a private backyard setting surrounded by mature landscaping and peaceful conservation views—an ideal place to unwind, entertain, or spend a quiet Florida afternoon. Additional conveniences include a washer and dryer, Vivant security system, and an attached 2-car garage. Some furnishings may also be negotiable. Lake Sawyer residents enjoy a community pool, basketball and tennis courts, walking trails, dog-walking areas, and more, all in a sought-after Windermere location convenient to shopping, dining, top area attractions, and everything that makes this part of Central Florida such a desirable place to call home. With significant updates already completed and an inviting indoor-outdoor lifestyle, 8104 Jailene Drive is ready for its next chapter.

8104 Jailene Drive, Windermere
14077 Ancilla Boulevard, Windermere
$399,000
3 Beds ⋅ 3 Baths ⋅ O6437694 MLS ⋅ 14077 BLDG.
Under contract-accepting backup offers. Virtually Staged. There is something truly special about coming home to Summerport and this move-in-ready townhome captures that feeling perfectly. From the moment you arrive, the inviting front porch offers a peaceful spot to sit back and watch the sunset over Ancilla Pond. Inside, the functional main level features a highly desirable first-floor primary suite. The bright kitchen connects seamlessly to a private, fenced patio area. Upstairs, you will find an additional bedroom, a versatile loft area, and a secondary bedroom featuring a charming alcove that makes a wonderful home office or study nook. Out back, enjoy ultimate privacy with an attached garage accessed by a rear road and extended driveway. Because the property backs up to the tranquil marshland of Walsh Pond there are no rear neighbors and you are also just steps from the community playground! Summerport features resort-style amenities, including scenic walking paths, small lakes, a clubhouse pool, a fitness center, a fishing dock, volleyball, and a sand beach area right next to the tennis and basketball courts. Unbeatable Location & Convenience: * Top-Rated Schools: Just a short drive to Keene’s Crossing Elementary, Bridgewater Middle and Windermere High School. Elite private options like Windermere Preparatory School and Foundation Academy are also nearby. * Moments from Disney World and all major theme parks. * Easy Commute: Quick access to SR-429, SR-408, and the Florida Turnpike makes driving a breeze. * Shopping & Dining: Minutes from local restaurants, grocery stores, and the popular Winter Garden Village. Low-Maintenance Living, the HOA fully maintains the exterior including the lawn, exterior painting and roof replacements (new roof installed in 2022), allowing for a truly easy lifestyle. Schedule your showing today!

14077 Ancilla Boulevard, Windermere
13844 Amelia Pond Drive, Windermere
$600,000
4 Beds ⋅ 3 Baths ⋅ O6401590 MLS
Fresh interior/exterior paint and HVAC serviced! Residing in Summerport, this delightful home features a practical design with spacious room sizes and a tranquil pond view, providing the ideal atmosphere for everyday living and entertaining guests. Four comfortable bedrooms in tandem with multiple living areas and two covered patios offer ample space for any occasion, while granite countertops, extensive cabinetry, and custom accents throughout add an elegant touch to the interior. Summerport offers residents a list of amenities, including a clubhouse, community pool, sports courts, and multiple trails, parks, playgrounds, and dog parks for endless fun without leaving the neighborhood. Beyond these exceptional amenities, the location provides easy access to daily necessities, medical services, recreation activities, and major highways. The Summerport Village, Winter Garden Village, Shoppes at Lake Butler, and Shoppes at Windward Cay are moments away, placing numerous dining and retail needs right at your fingertips. Nearby Braddock Park and Tibet-Butler Nature Preserve provide natural beauty and outdoor activities close by, while just moments from Disney and Universal, making it ideal for those seeking both tranquil residential living and entertainment accessibility. This combination of a practical design, peaceful pond view, quality amenities, and strategic positioning creates the ideal living experience. Don't let this exceptional opportunity slip away – schedule your private showing today!

13844 Amelia Pond Drive, Windermere
9021 Via Di Canti, Windermere
$550,000
5 Beds ⋅ 4 Baths ⋅ O6437659 MLS ⋅ 9021 BLDG.
Under contract-accepting backup offers. Welcome to this beautifully appointed corner-unit townhome in the highly sought-after area of Windermere, Florida! Ideally located just 15 minutes from Walt Disney World, Hamlin Town Center, and an incredible selection of shopping, dining, entertainment, and everyday conveniences, this home offers the perfect combination of comfort, location, and lifestyle. As a desirable corner unit, the home provides added privacy and an abundance of natural light throughout. Featuring 5 bedrooms and 3.5 bathrooms, this spacious townhome offers a thoughtfully designed open-concept floor plan perfect for both everyday living and entertaining. The first floor includes a dedicated office, ideal for working from home, along with generous living and dining spaces that flow seamlessly into the kitchen. One of the home's standout features is the beautiful in-law suite, complete with its own private entrance, providing an ideal space for extended family, guests, or additional flexibility. Upstairs, the spacious primary suite offers a peaceful retreat along with a versatile loft area that can be used as a secondary living space, playroom, media area, or home gym. With three additional bedrooms upstairs, there is plenty of room for everyone. A two-car garage provides ample parking and storage, while the home's prime Windermere location puts you close to everything Central Florida has to offer. Whether you're looking for a primary residence, multigenerational living, or a fantastic investment opportunity, this townhome is a must-see!

9021 Via Di Canti, Windermere
4844 Flint Road, Windermere
$519,000
3 Beds ⋅ 2 Baths ⋅ O6436938 MLS
Don’t miss the opportunity to make this beautiful home in the highly sought-after Summerport community your own! Known for its A-rated schools, picturesque surroundings, and outstanding amenities. This well-maintained 3-bedroom, 2-bath home features a versatile office/den, offering flexible space to accommodate a home office, or guest room. The home features vinyl flooring throughout with no carpet, providing a clean, stylish, and low-maintenance living environment. The kitchen is equipped with a natural gas stove, perfect for those who enjoy cooking with gas. Recent improvements include a newer roof, newer A/C system, and freshly painted exterior, offering added comfort and peace of mind. From the moment you enter the welcoming foyer, you’ll appreciate the bright and open floor plan. Two secondary bedrooms are conveniently located toward the front of the home, providing separation and privacy from the primary suite. Continue down the hallway to the spacious formal living room and flexible additional living space, perfect for adapting to your family’s needs. The private primary suite offers a relaxing retreat with a walk-in closet, dressing area, and ensuite bathroom featuring dual sinks and a spacious standing glass shower. The kitchen seamlessly connects to the bright family and dining areas, creating an inviting space filled with natural light and perfect for everyday living and entertaining. The natural gas stove adds an extra touch of convenience for the home chef. Sliding glass doors open to the covered porch, extending the living space outdoors and overlooking the spacious backyard—an ideal setting for relaxing, entertaining, or enjoying the Florida lifestyle. Summerport offers an impressive array of resort-style amenities, including a community pool, fitness center, parks, playgrounds, fishing pier, and scenic walking trails. The community’s desirable location provides easy access to Windermere, Winter Garden, and Clermont, with an abundance of shopping, dining, entertainment, recreation, and highly rated schools nearby. Commuters will appreciate the convenient access to major roadways, including Highway 429, the Florida Turnpike, SR 408 (East-West Expressway), and I-4, making it easy to travel throughout Central Florida. Walt Disney World and many of Orlando’s world-renowned attractions are also just a short drive away. For Disney enthusiasts, enjoy the added bonus of being just minutes from Walt Disney World, with the opportunity to catch the nightly fireworks from select areas within the community. With vinyl flooring throughout and no carpet, a natural gas stove, a newer roof, newer A/C, freshly painted exterior, flexible living spaces, spacious backyard, desirable location, and exceptional community amenities, this home offers an outstanding opportunity in Summerport. Schedule your private showing today and come see all this home has to offer!

4844 Flint Road, Windermere
930 East Boulevard, Windermere
$1,895,000
4 Beds ⋅ 5 Baths ⋅ O6437093 MLS
Under contract-accepting backup offers. Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-story living. Completed in 2024, the home offers 2,868 square feet with four bedrooms, each featuring a private en-suite bath, along with a dedicated home office and an open-concept layout designed around the water views. Inside, wide-plank white oak hardwood floors, soaring ceilings and expansive black-framed glass doors create a bright, modern aesthetic while drawing the lake into the main living areas. The European-inspired kitchen anchors the home with an oversized island, quartz countertops, sleek cabinetry and smart appliances, flowing seamlessly into the dining and living spaces for easy everyday living and entertaining. The primary suite continues the home's refined design with a spa-like bath featuring a freestanding soaking tub, floating wood vanity, dual sinks and an oversized walk-in shower. Contemporary finishes and a light, neutral palette carry throughout the residence. Outdoors, a private heated pool and spa create a resort-like retreat, while the lakefront setting offers approximately 100 feet of frontage on Lake Bessie with the option to add a private dock. There is also a two car covered parking area. From morning sunrises and lake breezes to afternoons spent boating or fishing, the setting captures the relaxed lifestyle that makes Windermere so desirable. Just a short walk or golf cart ride from Downtown Windermere, the home places the weekly farmers market, parks, tennis courts, boat ramp to Lake Butler and Bessie, dining, local shops and a brewery within easy reach. Modern architecture, direct lake frontage and an exceptional in-town location come together for a rare opportunity to experience contemporary waterfront living in Windermere

930 East Boulevard, Windermere
8641 Brookvale Drive, Windermere
$410,000
3 Beds ⋅ 3 Baths ⋅ O6433201 MLS ⋅ 8641 BLDG.
Beautiful end-unit townhome in Windermere featuring the larger floor plan in the Lake Reams Townhomes community. This well-maintained 3-bedroom, 2.5-bath home offers plenty of natural light and a spacious open-concept kitchen, dining, and living area combo. The kitchen features granite countertops, tiled travertine back splash 46" wood cabinetry, and ceramic tile flooring, with kitchen and laundry appliances included. Upstairs, feel the new plush padded carpeting in the bedrooms, hallway and stairs. The spacious primary suite includes dual vanities, quartz counter top, a large walk-in closet, and walk-in shower. The guest bathroom also has a tub and shower, a single sink with a quartz counter top. Outside, enjoy a private Vinyl fenced in courtyard leading to an oversized rear-entry 2-car garage. The HOA provides low-maintenance living and includes exterior and roof maintenance, landscaping, exterior pest control, and access to the community’s Junior Olympic-size pool. Located approximately 5 minutes from Walt Disney World’s Magic Kingdom, with the added fun of being able to hear and see the Magic Kingdom fireworks each evening. Convenient to Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, major roadways, and highly rated local schools. A great opportunity to enjoy a spacious Windermere townhome in an incredibly convenient location.

8641 Brookvale Drive, Windermere
13321 Lush Lime Alley, Windermere
$556,256
3 Beds ⋅ 3 Baths ⋅ TB8542700 MLS ⋅ 3 BLDG.
Under Construction. This stylish two-story townhome features three spacious suites, including a second-floor primary suite and two additional bedrooms. The open-concept first floor offers a bright living area. Interior finishes feature the AW Collection Sapphire for a bold, modern style. This Cypress floor plan features a gourmet kitchen with 42” cabinets, quartz countertops, tiled backsplash stainless steel appliances, and luxury vinyl plank flooring. Enjoy a private courtyard and detached two-car garage. Located in the heart of Windermere near top-rated schools, Winter Garden Village, and charming downtown, with community amenities including a pool and playground.

13321 Lush Lime Alley, Windermere
6239 Rydal Court, Windermere
$1,495,000
5 Beds ⋅ 5 Baths ⋅ O6435610 MLS
Under contract-accepting backup offers. Coming Soon! Located in the exclusive Reserve at Lake Butler Sound — one of Windermere’s premier 24-hour guard-gated communities — this custom 5-bedroom, 4.5-bath pool home offers 4,238 square feet of living space, four bedrooms on the first floor, exceptional indoor-outdoor living, and a prime Windermere location near the renowned Butler Chain of Lakes. Situated on an oversized cul-de-sac homesite and set back from the street, a long private driveway and new water feature create an impressive sense of arrival. Inside, soaring ceilings, architectural columns, graceful archways, crown molding, and abundant natural light create an elegant yet comfortable atmosphere, with views from the main living areas to the pool beyond. Formal living and dining rooms provide plenty of space for entertaining, while the spacious family room features a gas fireplace and built-in entertainment area. The generously sized kitchen offers granite countertops, extensive cabinetry and counter space, a center island, 6-burner gas cooktop, stainless steel appliances, and casual dining overlooking the pool. The flexible first-floor layout includes four bedrooms, including the primary suite. A private office with built-in bookcases overlooks the front of the home, while an additional flex space adjoining the primary suite is ideal for a second office, exercise room, den, or sitting area. All bedrooms are generously sized, and two secondary bedrooms enjoy adjoining bath access. The spacious primary suite overlooks the pool and features a spa-inspired bath with dual vanities, large walk-in shower, jetted soaking tub, and dual closets. Upstairs, the private fifth bedroom/bonus suite is currently used as a theater room and includes its own bathroom and walk-in closet. At approximately 24 feet long, this versatile space could also serve as a game room, guest suite, home gym, or oversized bonus room. Outside, the expansive screened pool and spa area offers multiple spaces for relaxing and entertaining. A covered lanai and outdoor kitchen create the perfect setting for year-round Florida living. Many major components have already been replaced or improved, including a newer roof, new septic drainfield (2021), pool resurfacing (2021), pool heater (2021), AC (2024), hot water heater (2025), and a new security camera system (2025). Reserve at Lake Butler Sound is known for its beautiful streetscapes, estate homes, neighborhood parks, and community fishing pier with access to Lake Butler and the Butler Chain of Lakes. Ideally located near Windermere shopping and dining, Restaurant Row, major roadways, golf, and Central Florida attractions. Zoned for Windermere Elementary, Bridgewater Middle, and Windermere High School and convenient to area private schools. Offering an exceptional combination of space, flexibility, major improvements, and an exclusive guard-gated Windermere setting, this is a home you’ll want to see. Coming soon — more details and professional photography to follow!

6239 Rydal Court, Windermere
5125 Sun Palm Drive, Windermere
$560,000
3 Beds ⋅ 2 Baths ⋅ O6435175 MLS
Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bath home situated on an oversized lot in the established Silver Woods community of Windermere. The heart of the home is the spacious kitchen featuring solid wood cabinetry, stainless steel appliances, marble countertops, and an impressive center island offering plenty of workspace and storage. The kitchen opens to the living and dining areas, creating a comfortable and functional layout for everyday living and entertaining. An additional flex space provides the perfect option for a home office, den, playroom, or additional living area. The spacious primary suite features both a walk-in and additional closet, along with an updated en-suite bath with dual vanities, granite countertops, and marble flooring. The split-bedroom floor plan offers two additional bedrooms and an updated guest bath. Outside, enjoy a massive fully fenced backyard with plenty of privacy and room to entertain, play, garden, or create your own outdoor oasis. The oversized lot is a standout feature and offers endless possibilities. Located in the established Silver Woods community in the heart of Windermere, enjoy a peaceful neighborhood setting surrounded by mature landscaping while still being conveniently located near Downtown Windermere, Restaurant Row, Winter Garden Village, Downtown Winter Garden, shopping, dining, schools, major roadways, and Orlando’s world-famous attractions. Silver Woods also offers community amenities including tennis courts. A wonderful opportunity to enjoy the Windermere lifestyle in the highly desirable 34786 area!

5125 Sun Palm Drive, Windermere
11348 Willow Gardens Drive, Windermere
$964,500
5 Beds ⋅ 3 Baths ⋅ O6435449 MLS
Under contract-accepting backup offers. YOUR SEARCH IS OVER! NOW AVAILABLE! Exceptional custom CAHILL pool home situated on a private sprawling .92 acre oversized lot in the highly desirable Willows at Lake Rhea in the Town Limits of Windermere. Offering 5 bedrooms, 3 bathrooms, the thoughtfully designed split floor plan provides an ideal balance of privacy, comfort and functionality. The home features elegant formal living and dining spaces , perfect for entertaining guests or enjoying special occasions. A warm wood burning fireplace serves as a beautiful focal point, creating a cozy atmosphere for relaxing with family and friends. The spacious 3 car garage provides ample room for vehicles, storage, and recreational equipment. An expansive outdoor space in complemented by a sparkling pool area creating a private retreat ideal for entertaining and enjoying Florida's year round lifestyle. Home is zoned for highly regarded schools including Windermere Elementary (walk, bike, golf cart), Bridgewater Middle School and Windermere High School. Conveniently located near world class attractions, premier shopping, dining and entertainment, this property offers the perfect combination of tranquility and accessibility. New roof in 2018. Don't miss your opportunity own a home for under $1 million dollars in this highly sought after and desirable WIndermemre neighborhood. Professional pics to come!

11348 Willow Gardens Drive, Windermere
12832 Westside Village Loop, Windermere
$760,000
5 Beds ⋅ 4 Baths ⋅ O6433322 MLS
Under contract-accepting backup offers. Water-view. Welcome to 12832 Westside Village Loop, an exceptional Windermere residence offering an impressive combination of space, location, privacy, views, and highly desirable schools. Built in 2018 and offering approximately 3,705 square feet of living space with 5 bedrooms and 4 full bathrooms, this beautifully designed home provides a spacious and versatile layout ideal for both everyday living and entertaining. What truly sets this property apart is its unique lot positioning and open surroundings. Situated on an approximately 8,975-square-foot lot, the home enjoys a desirable open rear and side setting with peaceful pond views and significantly more visual openness than a typical interior lot, creating an enhanced sense of privacy, space, and tranquility. The irregular lot configuration and expansive green space surrounding the property provide a rare feeling of separation from neighboring homes and make the outdoor setting an exceptional feature of this residence. Beyond the property itself, the location is outstanding—nestled within the sought-after Westside Village community in Windermere, with convenient access to shopping, dining, Disney, major roadways, and the rapidly growing Horizon West area. The home is also currently zoned for the highly desirable Bay Lake Elementary, Horizon West Middle School, and Windermere High School, with Horizon West Middle exceptionally close to the community. Combining a distinctive lot, beautiful pond and open-space views, added privacy, generous living space, excellent schools, and a premier Windermere location, this property delivers a combination that is increasingly difficult to find in Central Florida.

12832 Westside Village Loop, Windermere
2031 Willow Lauren Lane Unit L, Windermere
$1,179,000
5 Beds ⋅ 5 Baths ⋅ O6429898 MLS
Stunning William P Campbell custom home on a private, oversized lot of more than half an acre in one of the most desirable communities in the Town of Windermere-Willows at Lake Rhea! From the moment you arrive, the soaring 14-foot ceilings, abundant windows, and elegant glass French doors create a light-filled, inviting atmosphere with beautiful views of the pool and spa from nearly every room. Mature landscaping surrounds the property, creating a peaceful and private setting that is increasingly rare. Designed for both sophisticated entertaining and comfortable everyday living, the open-concept layout seamlessly connects the living room, dining room, gourmet kitchen, and family room, creating an exceptional space for gatherings. The chef’s kitchen is truly the heart of the home, featuring an induction cooktop, Wolf double ovens, Sub-Zero refrigerator, Bosch dishwasher, brand-new disposal, upgraded granite countertops, farmhouse sink, prep sink and an abundance of custom cabinetry for exceptional storage. The expansive private primary suite overlooks the sparkling pool and spa and offers two oversized walk-in closets. The luxurious primary bath features a massive walk-in-shower with dual shower heads, jetted tub, and an impressive dual vanity. Two additional generously sized bedrooms share a Jack-and-Jill bath, while the fourth bedroom offers privacy and direct access to the pool bath-perfect for guests. Upstairs an oversized bonus room/fifth bedroom provides incredible flexibility and includes a full bath and wet bar, making it an ideal guest suite, media room, office, or entertaining space. Step outside to your private pool and spa and enjoy the Florida lifestyle in complete comfort, with a fabulous outdoor kitchen, creating the perfect setting for al fresco dining and entertaining. This exceptional home is truly move-in ready with a new roof in 2016, newer AC systems in 2021 and 2026, and a repipe completed in 2024. A three-car side-entry garage, expansive brick-paver driveway, and circular drive provide impressive curb appeal and abundant parking. Enjoy all the benefits of living in the Town of Windermere, including access to the Butler Chain of Lakes boat ramp, weekly Farmers Market, Public Library, and year-round community events. Willows At Lake Rhea offers an exceptional setting within one of Windermere’s most desirable communities, combining an outstanding custom home, a rare oversized private lot, and the lifestyle, charm and amenities that make Windermere so sought after.

2031 Willow Lauren Lane Unit L, Windermere
9600 Ambleside Drive, Windermere
$975,000
3 Beds ⋅ 3 Baths ⋅ O6433478 MLS
Welcome to this beautifully updated home situated on a full 1-acre homesite in a highly desirable, established community surrounded by mature trees. Enjoy access to the Butler Chain of Lakes for just $100 annually, offering an incredible opportunity for boating, fishing, and the Florida lake lifestyle. Inside, the home features a spacious open layout with an updated kitchen, white cabinetry, stone countertops, stainless-steel appliances, and a large island overlooking the living area. A rare double primary suite configuration provides exceptional flexibility for guests, multigenerational living, or a private retreat. The home also offers three full bathrooms, including beautifully updated baths with spacious walk-in showers. Two separate A/C systems help keep the home comfortable year-round. Generous living spaces and large bedrooms provide plenty of room to spread out. Outside, the acre-sized property and mature trees offer privacy and space that are increasingly hard to find. Add in an outstanding location with convenient access to shopping, dining, entertainment, and area attractions, and this home truly delivers. One-acre living, Butler Chain access, and a fantastic location—this is Florida living at its best.

9600 Ambleside Drive, Windermere
12303 Langstaff Drive, Windermere
$400,000
3 Beds ⋅ 3 Baths ⋅ O6430630 MLS ⋅ Na BLDG.
Under contract-accepting backup offers. Accepting Back Up Offers!!!!!!! ABSOLUTELY STUNNING WINDERMERE END-UNIT TOWNHOME! Welcome home to this exceptional end-unit townhome, perfectly positioned in one of the most desirable locations within the community. Nestled against tranquil wooded conservation and lush green space, this home offers a rare sense of privacy with no front neighbors and direct access to a scenic community walking path. One of the largest floor plans in the neighborhood, this beautifully maintained 3-bedroom, 2.5-bath residence is filled with natural light, creating a bright, open, and inviting atmosphere throughout. The spacious open-concept kitchen, dining, and living area is ideal for both everyday living and entertaining. The kitchen is tastefully upgraded with granite countertops, a stylish tile backsplash, rich wood cabinetry, and quality flooring. Best of all, there is no carpet anywhere in the home! All kitchen and laundry appliances are included, making this home truly move-in ready. The thoughtfully designed floor plan provides each bedroom with convenient access to a bathroom. The generous primary suite features dual vanities, a large walk-in closet, and a spacious ensuite bath designed for comfort and functionality. Step outside to enjoy the private fenced courtyard leading to the oversized rear-entry two-car garage with a pedestrian door, offering both convenience and privacy. Enjoy low-maintenance living with an HOA that covers exterior maintenance, landscaping, roof maintenance, pest control, and access to the beautiful resort-style community pool and clubhouse. Located in the heart of Windermere, this home offers an unbeatable location with top-rated A schools and easy access to Disney, Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, and major roadways. This is a rare opportunity to own one of the finest townhomes to come on the market in quite some time. Don't miss your chance to make this exceptional home yours!

12303 Langstaff Drive, Windermere