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8259 Maritime Flag Street Unit 4, Windermere
$325,000
3 Beds ⋅ 3 Baths ⋅ O6329585 MLS ⋅ 21 BLDG.
One or more photo(s) has been virtually staged. Experience the best of Windermere living! This freshly updated two-story townhome offers resort-style amenities and unbeatable convenience, all just 10 minutes from Disney! Step inside to discover fresh paint throughout, brand new carpet, and an open-concept first floor with a kitchen/living room combo and a half bath. Upstairs, you’ll find three spacious bedrooms, two full bathrooms, and a laundry closet with washer and dryer included. Located in the resort-style community of Lakeside Villas, enjoy access to a beautiful pool, well-equipped fitness center, playgrounds, sand volleyball and tennis courts, clubhouse, dog park, and more just steps from your front door. Walk across the street to Lakeside Village’s Publix grocery store and local restaurants, or unwind at the nearby Tibet-Butler Preserve, home to 3.6 miles of peaceful walking trails. Plus, you'll enjoy quick access to Orlando’s top amusement parks, Evermore Resort and downtown Orlando, making this home the perfect full-time residence or investment opportunity. Call today for your private showing!

8259 Maritime Flag Street Unit 4, Windermere

5130 Sun Palm Drive, Windermere
$512,200
3 Beds ⋅ 2 Baths ⋅ O6390875 MLS
Welcome to 5130 Sun Palm Drive, located in the heart of WINDERMERE! This beautifully maintained 3-bedroom, 2-bath home offers 1,723 sqft of living space on a spacious ¼-acre FULLY FENCED lot — perfect for outdoor enjoyment and privacy. Recent upgrades include a new ROOF (2022) and a new AC SYSTEM (2020). ALL FLOORING HAS BEEN UPDATED. The carpet was removed and replaced with Mohawk Pergo luxury vinyl plank. The original tile was replaced with fresh ceramic tile throughout the rest of the house—NO MORE POPCORN CEILING, all was removed, and now it has a beautiful finished ceiling. A brand NEW SLIDING GLASS DOOR opens to the NEW PATIO DECK recently installed. Ideal for indoor-outdoor living. Just minutes from the famous Sand Lake Restaurant Row, conveniently located near the distinguished Bay Hill Golf Community, and backing up to the exclusive Isleworth Court private community. Zoned for top-rated schools, and ideally situated just 20 MINUTES from Walt Disney World and 10 minutes from Universal Studios — this location truly offers the best of Central Florida living!

5130 Sun Palm Drive, Windermere

4200 Down Point Lane, Windermere
$8,500,000
6 Beds ⋅ 9 Baths ⋅ O6382393 MLS
Nestled along almost 1,000’ of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2-acre peninsula reveals a masterpiece of architectural brilliance designed by Nasrallah and built by Ray Coudriet. The grand entry sets the tone, with a majestic staircase, a 25+ft hand-painted rotunda ceiling, and a stunning 10-ft Waterford chandelier. Every inch of this residence exudes sophistication, from the marble floors and corbels to the intricately carved fireplace mantels or even the ornate door hinges. Boasting 5 spacious bedroom suites, four with outdoor walk-outs, in the main home, complemented by a separate guest/staff apartment, this estate offers flexibility and privacy. A resort-style pool, cabana, along with a boathouse, dock and paver paths meandering through the property, create an outdoor haven for entertaining and relaxation. The guest quarters or a private office that takes in views from 3 sides. Architectural marvels abound, with handcrafted coffered ceilings, exposed wood beams, and a gourmet kitchen featuring a red brick barreled ceiling and appliances by Wolf and Sub-Zero. Hosting events is effortless with a separate full caterer's kitchen. The primary suite offers serene panoramic water views, complemented by an extraordinary dressing room and bathroom. For wine connoisseurs, a climate-controlled 3,000+ bottle wine cellar awaits. Verandas and terraces afford fresco dining, bar area and sweeping views, enhancing the outdoor experience. Work in the masterful office with birds’ eye 180-degree water views or step into the game room for a game of pool or a sunset view off the balcony. A large travertine parking area for events and a 4-car garage adds practicality to this extraordinary property. This masterpiece transcends the ordinary, offering a lifestyle of unparalleled luxury and sophistication. Seize the opportunity to make this stunning estate your own.

4200 Down Point Lane, Windermere

11434 Jasper Kay Terrace Unit 1120, Windermere
$305,000
3 Beds ⋅ 2 Baths ⋅ O6382035 MLS ⋅ 11434 Jasper Kay Terrace BLDG.
Beautifully maintained condo located in the highly desirable Lakeside Lakes of Windermere community. Situated on the third floor with elevator access, this residence features a spacious split floor plan offering both privacy and functionality. The open concept living and dining area flows seamlessly to a private balcony perfect for enjoying your morning coffee or relaxing evenings. The generous primary suite includes a walk in closet and an en suite bath with dual sinks. Wood flooring runs throughout the main living areas, with ceramic tile in wet areas for added durability. Residents enjoy an array of resort style amenities including a community pool, fitness center, outdoor grilling areas, sand volleyball courts, and more. Conveniently located near Disney, Winter Garden Village, shopping, dining, and zoned for top rated schools, this property is ideal for first time buyers, investors, or as a second home. Schedule your private showing today.

11434 Jasper Kay Terrace Unit 1120, Windermere

11658 Hampstead Street, Windermere
$1,250,000
7 Beds ⋅ 5 Baths ⋅ O6376140 MLS
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 11658 Hampstead Street, a refined Windermere showpiece tucked inside the highly sought-after Enclave community, zoned for Orange County’s top-rated schools. This home defines elevated Florida living, offering 4,563 square feet of thoughtfully designed space created for both effortless entertaining and everyday comfort. Featuring 7 bedrooms plus a dedicated office (with flexibility for a second office or bonus use), 4.5 bathrooms, and an open-concept layout, the home flows seamlessly from room to room—and even better, from indoors to out. The heart of the home opens directly to a massive covered lanai, creating a true indoor-outdoor lifestyle that Florida living is known for. Step outside to your custom resort-style pool with sun shelf, recessed table, and tranquil waterfall. The space is anchored by a fully equipped outdoor kitchen and bar complete with bar seating, keg, grill, smoker, and sink—ideal for hosting game days, celebrations, or quiet evenings at home. Inside, the primary suite on the main level serves as a private retreat, featuring a spa-inspired bath and a custom walk-in closet with built-ins. A secondary primary suite upstairs provides exceptional flexibility for guests or multigenerational living, while the remaining bedrooms and bonus spaces offer endless options for work, play, or relaxation. A rare bonus, the 3-car garage features an 18,000 BTU Bluetooth-controlled AC, making it ideal for a climate-controlled home gym, hobby space, or car enthusiast’s workshop. A three-car garage, beautifully maintained finishes throughout, and access to the community neighborhood park complete the offering. Located in Enclave, you’ll enjoy tree-lined streets, a strong sense of community, and proximity to everything Windermere has to offer—including access to the Butler Chain of Lakes. This is more than a home, it’s a lifestyle.

11658 Hampstead Street, Windermere

1420 Dingens Avenue, Windermere
$1,610,000
4 Beds ⋅ 4 Baths ⋅ O6376538 MLS
One or more photo(s) has been virtually staged. No HOA custom pool home on over half an acre, offering rare space and privacy in a central Windermere location just minutes from top schools, dining, and 20–30 minutes to Disney, Universal, and Orlando International Airport. Set on 0.63 acres, the outdoor space is set up to be used, with a fully fenced yard, gas-heated saltwater pool with sunshelf, covered lanai, and outdoor kitchen. Inside, the main living area flows into a kitchen designed to anchor the home, featuring a large island, custom cabinetry, walk in pantry, natural gas cooktop with pot filler, and double wall ovens. The layout is designed to work without wasted space. The primary suite is set apart with backyard views and a well finished en suite with dual vanities, a freestanding tub, walk in shower with dual heads, and a custom closet. Secondary bedrooms are generously sized and share a well designed bath, while a fourth bedroom with direct pool access, a dedicated office with built ins, and a separate bonus room provide flexibility for guests, work, or additional living. Additional features include a mudroom and laundry space with built ins, an oversized three car garage with epoxy flooring, a large paver driveway, outdoor lighting, a security system, a fully fenced yard and paid off 20kW solar panels. Zoned for A rated Thornebrooke Elementary and just minutes from Windermere Prep, the home brings together space, layout, and location in a way that is hard to replicate in this area.

1420 Dingens Avenue, Windermere

1329 Glenheather Drive, Windermere
$835,000
3 Beds ⋅ 3 Baths ⋅ O6395704 MLS
Impeccably maintained one-story pool home in the 24/7 guard gated community of Reserve at Belmere in Windermere. This move-in-ready residence offers peaceful pond views and stunning postcard-worthy sunsets from the expansive screened lanai overlooking the stocked pond in the backyard. Step inside to discover elegant one-story living with soaring high ceilings, an updated kitchen featuring a natural gas cooktop, built-in double convection ovens, abundant cabinet storage, and a walk-in pantry. The spacious family room includes an entertainment system with the TV conveying. A large dedicated home office provides flexibility and could easily serve as a fourth bedroom if desired. The primary suite is a true retreat, complete with two walk-in closets, a luxurious jacuzzi garden tub, separate walk-in shower, and dual vanities. The oversized premium lot backs directly to the serene pond, creating a private oasis designed for the ultimate Florida lifestyle. Enjoy the sparkling screened pool, deep covered lanai, and custom summer kitchen—perfect for outdoor entertaining while watching nightly western sunsets. A pocketing glass wall opens to.the lanai and extended pool deck, the outdoor shower is perfect to rinse off. Additional highlights include a three-car garage with a large paver driveway, mature landscaping that enhances incredible curb appeal, a tile roof, and a full hurricane shutter system on all windows and entries. The Reserve at Belmere delivers resort-style living with 24/7 guarded entry, a state-of-the-art fitness center, tennis courts, basketball courts, beach volleyball, and a fishing pier on Lake Reams. Families appreciate the sought-after A-rated K-12 schools in the area, along with convenient access to top private school campuses. Endless shopping and dining options are just minutes away in every direction, with quick commutes via the 429, Florida turnpike, 408 ,I-4, Winter Garden Village, and Downtown Orlando. Pride of ownership shines throughout this lovingly cared-for home, making it one of the best values in the community. Don't miss the opportunity to call this exceptional pond-view pool home yours.

1329 Glenheather Drive, Windermere

8350 Bowden Way, Windermere
$1,115,000
3 Beds ⋅ 4 Baths ⋅ O6395966 MLS
Gated/24-hour attended Keene's Pointe. Home of The Golden Bear Club, a private membership club offering golf, tennis, fitness, dining and swimming. This thoughtfully designed home offers both space and functionality for modern living. Upon entry, you’re welcomed by a spacious formal dining room, formal living room, and a private office featuring classic French doors—perfect for working from home. Wood-look tile flooring flows seamlessly throughout the entire first floor, adding warmth and durability.The private primary suite is a true retreat, complete with a large walk-in closet featuring custom shelving and an en suite bathroom. The updated kitchen boasts white shaker cabinets, stainless appliances, ample storage, and a cozy breakfast nook that opens to the inviting family room—ideal for everyday living and entertaining.The first floor also includes two additional bedrooms, a fully renovated bathroom, and bonus space for work or play, offering flexibility for family or guests. Upstairs, you’ll find a spacious bonus room that can easily serve as a fourth bedroom along with a full bathroom—perfect for a guest suite or multi-purpose space.The back yard provides plenty of space for a future pool or entertaining area. There is also a garage with 2 spaces for cars and a tandem third space for golf cart or storage.Tankless gas water heater, water softner system, NEW ROOF in 2022, updated HVAC units (2026 and 2021), new paver driveway in 2026, designer touches throughout, and much more! This home combines comfort, style, and versatility—ready for you to move in and make it your own.

8350 Bowden Way, Windermere

11044 Hawkshead Court, Windermere
$1,335,000
5 Beds ⋅ 5 Baths ⋅ O6388401 MLS
Stunning home in the Reserve at Lake Butler Sound-Windermere. This luxury living at its finest located in the prestigious 24 hour guarded community. The property features 5 bedrooms, 4.5 bathrooms, a 3-car garage, and a private heated pool, perfect for relaxing or entertaining. The owner has invested more than $100,000 upgrades..... newly renovated kitchen boasts brand new cabinetry and countertops., creating a modern and stylish space for cooking and gathering. Upstairs, the loft includes brand new hardwood flooring and a full bathroom, making it ideal as a guest suite, media room, office, or versatile multi purpose space. The 3 car garage offers a Tesla charger, Epoxy flooring, Storage Racks, and Shelves..... Enjoy the comfort, elegance, and security of one of Windermere's most sought-after communities.Roof (2023). Air conditions (2020 and 2022). ... No rear neighbor... Please schedule your private viewing today ....

11044 Hawkshead Court, Windermere

6013 Greatwater Drive, Windermere
$6,700,000
5 Beds ⋅ 7 Baths ⋅ O6387953 MLS
One of a kind extraordinary lakefront estate, perfectly positioned along the shores of Lake Tibet Butler on the renowned Butler Chain of Lakes, offers over 7,600 square feet of refined living in the beautiful guard-gated community of Keene’s Pointe. Tucked at the end of a quiet cul-de-sac on coveted Greatwater Drive, the residence enjoys one of the most picturesque settings in the community, where timeless architecture, exceptional craftsmanship, and breathtaking water views create a truly remarkable Florida lifestyle. A brick-paver circular drive and stately entry introduce interiors where thoughtful design and luxurious finishes are evident throughout. Expansive living spaces are framed by large windows capturing stunning lake views and filling the home with natural light. The residence features five spacious bedrooms, each with its own private en-suite bath and custom-designed closet systems, along with two additional half baths for residents and guests. The primary suite serves as a private retreat with a natural gas fireplace, automated window shades, completely updated modernized spa-inspired bath and dual closets. At the heart of the home, the chef’s kitchen is designed for both everyday living and entertaining, featuring premium Wolf appliances, a concealed Sub-Zero refrigerator, warming drawer, ice maker, and extensive custom cabinetry. Adjacent living and dining spaces flow seamlessly for effortless gatherings. Designed with entertaining in mind, the home offers two wet bars — one in the main living area and another in the expansive game room , both completely remodeled to reflect todays best design standard's— along with a dedicated theater room for an immersive cinematic experience. Outdoor living is equally impressive. A large screen-enclosed lanai with summer kitchen overlooks the resort-style pool and sparkling lake beyond. The infinity-edge saltwater pool with cascading waterfall and adjoining spa creates a private oasis ideal for relaxing or entertaining while enjoying panoramic water views. Other recent upgrades and remodels include a complete new Savant Smart home system, new floors throughout, new offices 2, upstairs game room, master bedroom , bath and closets, upgraded kitchen and AC Dog run with new laundry. The beautifully landscaped grounds extend to a private dock with two boat lifts, providing effortless access to Lake Tibet Butler and the Butler Chain of Lakes — one of Central Florida’s most sought-after recreational waterways. Furnishings available. Additional highlights include a four-plus car garage with a dedicated golf cart bay for added convenience. Residents of Keene’s Pointe enjoy 24-hour guard-gated security, a private community boat ramp, playground, and the opportunity to join The Golden Bear Club, home to the Jack Nicklaus Signature golf course, clubhouse, dining, fitness, and tennis. This exceptional lakefront estate presents a rare opportunity to experience refined waterfront living in one of Windermere’s most desirable communities.

6013 Greatwater Drive, Windermere

7432 Leighside Drive, Windermere
$465,000
4 Beds ⋅ 3 Baths ⋅ O6383362 MLS ⋅ N/A BLDG.
Welcome to this beautifully upgraded 4-bedroom, 2.5-bath, home with a 2-car garage, located in a quiet and highly desirable Windermere community that truly invites you to enjoy the Florida lifestyle. The spacious primary suite is conveniently located on the first floor, offering comfort and privacy. The home features recent upgrades including a renovated kitchen, updated bathrooms, and new flooring, making it move-in ready. Residents enjoy wonderful community amenities such as a clubhouse, resort-style swimming pool, tennis courts, and scenic walking paths, perfect for relaxing or staying active. Ideally situated just minutes from Walt Disney World, major highways, top-rated A schools, shopping centers, supermarkets, restaurants, and everyday conveniences. This property offers the perfect combination of location, lifestyle, and value, ideal as a primary residence, vacation home, or investment opportunity in one of Central Florida’s most sought-after areas..

7432 Leighside Drive, Windermere

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