Location: Windermere
Do Not Show Listings
4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786
$3,200,000358 Days on yellowkey MLS ID: O6330108
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3745 Built: 2006Monthly Fee: $1,146 Tax: $33,607 (2024)Community: IsleworthSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$33,607
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private retreat centered around a sparkling pool, serene waterfall feature, and generous lounging areas. Whether basking in the sun or relaxing beneath the stars, this outdoor haven sets the tone for the extraordinary spaces within. Designed to embrace indoor-outdoor living, the oversized courtyard welcomes you with a seamless open-plan layout connecting the pool, summer kitchen, and a charming guest cabana. Perfect for hosting or escaping, the cabana offers a private retreat for guests or a peaceful haven for the homeowner. Inside the main residence, a sense of contemporary sophistication flows through the light-filled kitchen, elegant dining room—highlighted by a statement chandelier—and the spacious grand room. French doors throughout invite the outdoors in, offering lush views from nearly every space and extending the living area to multiple porches and verandas. The living room, centered around a calming fireplace, is the perfect spot to unwind after a long day, while the spa and cascading waterfall nearby add to the sensory appeal. Retreat to the expansive master suite, where a private porch overlooks vibrant greenery, offering a peaceful start and end to each day. Additional property highlights include a cozy morning room, a dedicated office with custom Burl wood built-ins, and a series of intimate outdoor and indoor spaces designed to inspire comfort and connection.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Michelle Corbin (407-491-2690)
13836 BLUEBIRD POND RD, WINDERMERE, FL 34786
$675,00080 Days on yellowkey MLS ID: TB8502779
1 Days Off yellowkey (back on 7/1/2026)
REDUCED by $23,000 (3.3%) on 06/04/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2108 Built: 2004Monthly Fee: $100 Tax: $3,052 (2025)Community: SummerportSpa: NoSingle Family
Taxes:$3,052
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Step into this impeccably maintained, move-in ready home in Summerport—one of Windermere’s most sought-after communities. With its high ceilings and elegant crown molding, the home feels both grand and inviting. The kitchen features quartz countertops, a hot water dispenser, a cozy café area, and a walk-in pantry. Recent updates include a new HVAC system and water heater, a 2021 roof, and R-38 attic insulation. Fiber optic cable is available, and the property offers room for a pool along with a one-year home warranty. Low HOA. Enjoy the spacious lanai accessible from both the family room and the primary bedroom. Start your mornings on the charming front porch overlooking the park. Summerport community amenities include a pool, fitness center, tennis, volleyball, and basketball courts, as well as a playground. Additional highlights include a rear-access two-car garage with storage shelves. Conveniently located just minutes from top-rated schools, dining, entertainment, and theme parks. Schedule your showing today and experience this beautiful home set in a garden-like setting.
Listing is courtesy of: GETMOREOFFERS (727-942-2929)
Listing Agent: Keith Gordon (727-610-8041)
11015 HAWKSHEAD CT, WINDERMERE, FL 34786
$1,489,99958 Days on yellowkey MLS ID: O6405977
REDUCED by $10,000 (0.7%) on 07/01/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3868 Built: 2004Monthly Fee: $640 Tax: $18,824 (2025)Community: Reserve At Lake Butler SoundSpa: YesSingle Family
Taxes:$18,824
Remarks: Located within the guard gated community of Reserve at Lake Sound in Windermere, this beautifull 5-bedroom, 5-bath residence offers the perfect blend of elegance, comfort, and functionality. Featuring nearly 3,900 square feet of living space, the home showcases tall ceilings, travertine flooring throughout the main living areas, and thoughtful modern updates completed in recent years. A grand double-door entry opens to formal living and dining spaces highlighted by contemporary accent walls and a striking fireplace. The spacious kitchen is designed for both everyday living and entertaining, featuring upgraded stainless steel appliances, abundant cabinetry, stylish countertops, a beverage refrigerator, and an open flow into the family room. The split-bedroom floor plan includes a private office and a spacious primary suite complete with California closets and a luxurious ensuite bath featuring dual vanities, a walk-in shower, and a freestanding soaking tub. Upstairs, the oversized bonus room with full bath offers flexibility as a guest suite, second primary suite, or media room. Sliding doors lead to an expansive screened pool area ideal for relaxing or entertaining, while the lush backyard garden creates a peaceful setting to enjoy your morning coffee. The home also features a spacious 3-car garage. *Roof and water heater was replaced 5 years ago.* Ideally located near top-rated schools, shopping, dining, and area attractions, this move-in ready Windermere home is one you won’t want to miss.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Julie Davis, Llc (407-579-7584)
6379 SWANSON ST, WINDERMERE, FL 34786
$1,099,00086 Days on yellowkey MLS ID: O6400522
REDUCED by $20,000 (1.8%) on 06/25/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3804 Built: 2014Monthly Fee: $167 Tax: $10,769 (2025)Community: EnclaveSpa: YesSingle Family
Taxes:$10,769
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. From the moment you arrive, this Mediterranean home in the highly sought after Enclave makes an impression. It offers a balance of grand design and everyday livability. Inside, the entryway features rich paneling and an open railed staircase that sets the tone. The open floor plan flows into a bright family room and gourmet kitchen designed for both daily living and entertaining. The oversized island provides seating, while 42 inch wood cabinets with crown molding keep the space clean and functional. Large doors to the backyard bring in natural light and create an open, airy feel. The first floor also includes a full bathroom and a spacious guest bedroom, ideal for visitors or multi generational living. Upstairs, a central loft separates the primary suite from the secondary bedrooms, offering privacy. The primary suite is generously sized with a private sitting area. One secondary bedroom can be paired with a nearby bathroom to create a private ensuite, perfect for long term guests or added independence. The backyard is one of the largest in the community with a unique lot shape and side yards on both sides for added space and privacy. A covered patio spans most of the rear of the home, creating a true outdoor living area. The custom deck and private swim spa pool built for up to eight people make this space stand out for both entertaining and relaxing. Located just 1.5 miles from Windermere Preparatory School and zoned for top rated Orange County schools, the home is also minutes from the Butler Chain of Lakes, Downtown Windermere, Winter Garden Village, Disney, and major roadways.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: John Cunningham (407-801-4141)
516 JENNIFER LN, WINDERMERE, FL 34786
$1,295,00022 Days on yellowkey MLS ID: O6419731
0 Days Off yellowkey (back on 6/29/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3021 Built: 1982Monthly Fee: $333 Tax: $6,252 (2025)Community: Windermere OaksSpa: YesSingle Family
Taxes:$6,252
Remarks: OUTDOOR LIVING, ONE-STORY COMFORT & IN-TOWN WINDERMERE LIFESTYLE COME TOGETHER AT THIS RARE 1.27-ACRE WINDERMERE OAKS PROPERTY. Set within the TOWN OF WINDERMERE, this beautifully maintained one-story pool home offers privacy, space & the lifestyle buyers hope to find, with NATURAL GAS, mature landscaping, a PARTIAL BUTLER CHAIN LAKE VIEW, and exceptional outdoor living that feels like a true extension of the home. The screened pool area is the heart of the property, beautifully finished with brick pavers & designed for everyday enjoyment as well as memorable entertaining. The 35' X 20' IRREGULAR-SHAPED POOL is complemented by multiple water features, a separate step-in spa with bubbler, a custom firepit, and a highly functional summer kitchen with bar seating, grill, ice maker & refrigerator. With approximately 812 SQ FT OF OPEN FINISHED PORCH/LANAI AREA, including a main lanai approximately 62' X 12', there is room to dine, gather, relax, watch the game, host friends, or simply enjoy the peaceful setting in every season. The PRIMARY SUITE is a true highlight of the home, privately positioned and beautifully finished with a spacious bedroom, direct access to the outdoor living area, and a STUNNING PRIMARY BATH that feels calm, elegant & luxurious. Thoughtful details, generous closet space, quality finishes, and a retreat-like feel make this suite stand apart. Inside, the home offers a warm, livable floor plan with NO STAIRS & generous gathering spaces. The main living areas connect comfortably to the outdoor spaces, creating an easy flow for entertaining & everyday life. The kitchen is positioned at the center of the home with generous prep & storage space, natural gas cooking, and a connection to the main living & dining areas that keeps everyone together. Additional bedrooms & flexible rooms provide options for guests, work, hobbies, fitness, or multigenerational living. The ONE-STORY design offers long-term comfort & convenience without sacrificing space or privacy. The setting is what makes this property so special. With 1.27 ACRES inside the Town of Windermere, there is a sense of privacy & breathing room that is increasingly hard to find. Mature trees, established landscaping, and a long residential feel create a peaceful backdrop, while the partial lake view adds a lovely connection to the Butler Chain lifestyle without making the home solely about the view. Life in WINDERMERE OAKS means you are close to the charm of downtown Windermere, weekly farmers markets, community events, local parks, brick streets & the small-town character that makes this area so loved. You are also minutes from top schools, shopping, dining, major roadways & Central Florida attractions, making the location as practical as it is beautiful. This is the kind of Windermere property buyers hope to find but rarely do: 1.27 private acres, ONE-STORY LIVING, NATURAL GAS, exceptional outdoor living, a beautiful PRIMARY SUITE, a PARTIAL BUTLER CHAIN LAKE VIEW, and a setting that makes home feel like the best place to be. It invites you to slow down, gather often, celebrate outside & enjoy the lifestyle that makes the TOWN OF WINDERMERE so special.
Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)
Listing Agent: Cindy Rosenbloom (407-876-9175)
11861 VERMILLION AVE, WINDERMERE, FL 34786
$475,00045 Days on yellowkey MLS ID: O6410430
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1600 Built: 2015Monthly Fee: $363 Tax: $6,340 (2025)Community: Windermere Trls Prcl 3Townhouse
Taxes:$6,340
Elementary School: Bay Lake Elementary
Remarks: TOP RATED SCHOOLS. NO CARPET throughout the home!! Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Windermere Trails community! This spacious two-story home features an open-concept layout with a modern kitchen offering stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas — perfect for entertaining. Upstairs, the spacious primary suite includes a walk-in closet and private en-suite bathroom. Enjoy the convenience of a rear-entry 2-car garage and low-maintenance living in one of Windermere’s most desirable locations. Community amenities include a resort-style pool, playgrounds, walking trails, dog park, and scenic green spaces. Ideally located near top-rated schools, shopping, dining, major highways, and Disney attractions. Don’t miss this incredible opportunity!
Listing is courtesy of: KARDOSH REALTY (407-499-4466)
Listing Agent: Frederico Hexsel (407-745-8841)
11617 CAMDEN PARK DR, WINDERMERE, FL 34786
$1,375,00070 Days on yellowkey MLS ID: O6405409
REDUCED by $22,000 (1.6%) on 06/18/2026
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3463 Built: 2005Monthly Fee: $283 Tax: $7,189 (2025)Community: Keenes PointeSingle Family
Taxes:$7,189
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to one of Central Florida’s premier guard-gated golf communities. This impeccably maintained, move-in ready residence showcases refined finishes throughout, including tile and laminate flooring (no carpet), crown molding in every room, and upgraded designer lighting. An abundance of space with 6 bedrooms and 4 1/2 baths. The living room is enhanced by striking wood-look tiled accent walls, adding warmth and architectural elegance. Offering a private tiled patio with electronic screen enclosure, perfect for enjoying Florida's year-round sunshine in comfort and privacy. For buyers seeking a move-in ready luxury home in Orlando's golf course communities, this property checks every box. Major capital improvements are already done: new roof (2023), AC and water heater 2-3 years old — giving buyers the confidence and peace of mind that comes with a truly turnkey luxury purchase. Equipped with a professionally installed lightning protection system for added peace of mind. Residents enjoy exclusive access to the Golden Bear Club, a Jack Nicklaus Signature Golf Course, along with clubhouse, tennis, and Lake Tibet-Butler access. The community’s location delivers unmatched convenience with proximity to well-rated schools, along with The Grove, Westside Shoppes, Cornerstone at Summerport, and Downtown Windermere for daily essentials, local dining, and shopping adventures. Entertainment options abound with easy access to Disney, Universal, and the famed Restaurant Row in Dr. Phillips. A rare opportunity.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Carla Robles (407-462-2347)
1408 LAKE WHITNEY DRIVE, WINDERMERE, FL 34786
$2,650,00025 Days on yellowkey MLS ID: O6418721
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5433 Built: 2003Monthly Fee: $271 Tax: $24,189 (2025)Community: Reserve At Belmere Ph 02 48 144Spa: YesSingle Family
Taxes:$24,189
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: 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!
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Alice Anne Jackson (407-520-9957)
13424 HOPKINTON CT, WINDERMERE, FL 34786
$549,99922 Days on yellowkey MLS ID: O6419100
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2190 Built: 2005Monthly Fee: $169 Tax: $7,268 (2025)Community: Lakes Of Windermere-PeachtreeSingle Family
Taxes:$7,268
Remarks: 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)
Listing is courtesy of: LJL REAL ESTATE, INC. (407-355-7889)
Listing Agent: Erik Lynch (407-694-0536)
11636 WATER RUN ALY, WINDERMERE, FL 34786
$408,000273 Days on yellowkey MLS ID: S5136888
3 Days Off yellowkey (back on 6/30/2026)
REDUCED by $17,000 (4.0%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1584 Built: 2017Monthly Fee: $332 Tax: $5,634 (2024)Community: Ashlin Park Ph 2Townhouse
Taxes:$5,634
Remarks: Under contract-accepting backup offers. This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a private interior patio between the main home and the detached two-car garage with epoxy flooring, perfect for relaxing or entertaining. Residents benefit from community amenities including a pool, clubhouse, playground, and walking trails. Conveniently situated near top-rated schools, shopping, dining, and major highways, this property combines modern comfort with an unbeatable location in the heart of Windermere.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jose Jimenez (407-394-6379)
12305 VIA DERNA PL, WINDERMERE, FL 34786
$450,000178 Days on yellowkey MLS ID: O6374964
REDUCED by $15,000 (3.2%) on 06/30/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1891 Built: 2014Monthly Fee: $316 Tax: $5,016 (2025)Community: CarringtonTownhouse
Taxes:$5,016
Remarks: Welcome to this move-in ready 3-bedroom, 3-bath townhome in Windermere FL located in the desirable Carrington community near Walt Disney World, offering low-maintenance living and a prime Central Florida location. Major updates include a NEW ROOF (2022) for peace of mind and long-term value. From the moment you arrive, you’ll notice the curb appeal, mature landscaping, and covered entry. Inside, tile flooring flows throughout the main living areas, while bedrooms feature comfortable carpet. The open concept floor planseamlessly connects the living, dining, and kitchen—ideal for everyday living and entertaining. The kitchen features: Stainless steel appliances Center island with bar seating for casual dining Rich cabinetry and sleek countertops Stylish backsplash and pantry A highly desirable main floor bedroom and full bath offers flexibility for guests, multi-generational living, or a home office. Upstairs, the primary suite with private balcony provides a relaxing retreat, complete with a walk-in closet and en-suite bath with dual vanities and separate shower. A third bedroom, additional full bath, and loft/bonus space complete the layout. Enjoy outdoor living with a covered lanai and fenced, low-maintenance patio. The home also includes a rear-entry 2-car garage. Located just off Reams Road with easy access to 429, I-4, shopping, dining, and attractions, this home is ideal for buyers searching for a Windermere home near Disney. Carrington offers a community pool, green space, and a welcoming atmosphere, all within a family-friendly area zoned for A-rated schools. With modern upgrades, flexible living space, and a prime location, this is a turnkey opportunity in Windermere. Schedule your private showing today—this one checks all the boxes. Welcome home.
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
9316 GLADYS GARDEN CT, WINDERMERE, FL 34786
$6,500,00018 Days on yellowkey MLS ID: O6420326
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5471 Built: 2026Monthly Fee: $2,370 Tax: $9,424 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$9,424
Remarks: 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.
Listing Agent: Monica Lochmandy (407-230-6888)
9011 CHAPMAN OAK CT, WINDERMERE, FL 34786
$599,00092 Days on yellowkey MLS ID: S5148031
REDUCED by $30,000 (4.8%) on 06/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2050 Built: 1987Monthly Fee: $31 Tax: $8,592 (2025)Community: Silver Woods Ph 05Single Family
Taxes:$8,592
Remarks: Windermere Gem: Fully Updated & Move-In Ready! Discover the perfect blend of modern luxury and prime location in the highly sought-after Windermere area. This beautifully updated home offers an incredible opportunity for homeowners and investors alike, situated just minutes from top-rated schools, premier shopping centers, and fitness facilities. This property has been meticulously maintained, featuring an extensive list of recent high-value upgrades: Recent Upgrades & Features: Brand New Kitchen (March 2026): Fully updated with modern flooring, custom cabinetry, and premium appliances. Comprehensive Pool Refresh (2026): Newly resurfaced pool and deck (Feb 2026), plus a brand-new pool pump and filter (March 2026). New Roof: Installed August 2024. Septic System: Installed January 2018. AC System: Installed 2017. Full House Re-pipe: Completed August 2016. Additional Features: Pool rescreened (2019) and nearby access to community tennis courts. Whether you're looking for a stylish family residence or a high-performing investment property, this home is truly move-in ready.
Listing is courtesy of: TOWNE CENTER REALTY (407-447-7700)
Listing Agent: Shiran Moyal (407-716-0224)
9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786
$6,000,000196 Days on yellowkey MLS ID: O6370294
REDUCED by $150,000 (2.4%) on 05/01/2026
Bed: 7 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 8000 Built: 1999Monthly Fee: $1,043 Tax: $29,046 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$29,046
Remarks: Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
13755 BRAVANTE ALY, WINDERMERE, FL 34786
$465,000121 Days on yellowkey MLS ID: O6389321
REDUCED by $15,000 (3.1%) on 06/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1996 Built: 2017Monthly Fee: $254 Tax: $5,646 (2025)Community: Vineyards/Horizons West Ph 2BTownhouse
Taxes:$5,646
Elementary School: Independence Elementary
Remarks: **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 13755 Bravante Aly, Windermere, FL 34786, a charming two story home featuring 3 bedrooms and 2 bathrooms located in a desirable Windermere community. This home offers a bright open floor plan with comfortable living and dining areas that flow seamlessly into the kitchen, creating a welcoming space for everyday living and entertaining. The thoughtful layout provides both functionality and comfort, making it ideal for a variety of lifestyles. Upstairs, the bedrooms offer privacy and relaxation, along with a versatile second floor loft area that can be used as a home office, media space, or additional living area. The overall design maximizes space and natural light throughout the home. The property also features a covered patio on the side of the home complete with retractable screens, providing a comfortable outdoor space to relax, enjoy your morning coffee, or entertain guests year round. Residents enjoy access to community amenities including a pool and park, offering great opportunities for recreation and outdoor enjoyment. Conveniently located near shopping, dining, schools, and major roadways, this home offers comfort and convenience in the heart of Windermere.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
13366 ABUELA ALY, WINDERMERE, FL 34786
$415,000183 Days on yellowkey MLS ID: O6374298
REDUCED by $15,000 (3.5%) on 06/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1589 Built: 2020Monthly Fee: $240 Tax: $6,237 (2024)Community: LegadoTownhouse
Taxes:$6,237
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Welcome to this beautiful and move-in ready townhome located in the highly desirable Windermere area. Built in 2020, this modern residence offers the perfect combination of style, comfort, and low-maintenance living. This spacious home features 3 bedrooms, 2.5 bathrooms, and an open-concept layout ideal for both everyday living and entertaining. The kitchen showcases quartz countertops, stainless steel appliances, and generous cabinet space, seamlessly connecting to the dining and living areas to create a bright and inviting atmosphere. The primary suite offers a comfortable retreat with a walk-in closet and a well-appointed bathroom. The additional bedrooms provide flexibility for guests, a home office, or family living. Enjoy the convenience of a private garage and a well-maintained community environment. The location offers easy access to shopping, dining, major highways, and is just minutes from Disney, Winter Garden Village, and other Central Florida attractions
Listing is courtesy of: BAHIA INTERNATIONAL REALTY (407-608-5308)
Listing Agent: Alexandra Mateu (321-332-8039)
1554 LAKE RHEA DR, WINDERMERE, FL 34786
$1,350,00070 Days on yellowkey MLS ID: O6406297
REDUCED by $50,000 (3.6%) on 05/29/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3427 Built: 2004Monthly Fee: $241 Tax: $9,102 (2025)Community: Reserve At BelmereSpa: YesSingle Family
Taxes:$9,102
Remarks: Price Improvement! Located behind the gates of the prestigious Reserve at Belmere in sought-after Windermere, this exceptional Mediterranean-inspired estate offers a rare blend of timeless architecture, modern luxury and thoughtful custom enhancements. Built in 2004 by the original owners and expanded during construction, the residence offers more than 3,427 square feet of refined living space and over 4,528 total square feet, creating a larger footprint than many comparable homes within the community. Extensively upgraded with more than $250,000 in recent improvements, this meticulously maintained home showcases true pride of ownership. Significant updates completed within the last three years include three new Trane HVAC systems, replacement windows, premium appliances, pool renovations, designer lighting and numerous interior and exterior enhancements. From the moment you enter, soaring 24-foot ceilings and elegant architectural details set the tone. Crown molding, coffered ceilings, engineered hardwood flooring, custom window treatments and a marble wood-burning fireplace create a sophisticated yet inviting atmosphere. Expansive glass sliding doors frame the outdoor living spaces and provide seamless indoor-outdoor flow ideal for everyday living and entertaining. The chef’s kitchen has been thoughtfully curated with luxurious quartzite countertops, custom pullout cabinetry with rotating shelving systems and an impressive suite of premium German appliances, including a Miele built-in coffee system, convection oven, dishwasher and refrigerator. A professional-grade 48-inch chef gas range with six burners and a griddle, custom lighting and a built-in three-stage water filtration system complete the space. Privately on the main level, the primary suite offers a tranquil retreat with coffered ceilings, newly installed commercial-grade carpeting, serene pool views and direct patio access. The spa-inspired primary bath is appointed with marble and travertine finishes, a soaking tub, a separate shower and custom walk-in closet built-ins. Upstairs, generously sized secondary bedrooms and a spacious loft overlook the formal living and dining areas below. Designed for elevated outdoor living, the resort-style backyard features a resurfaced saltwater pool and spa, an updated pool heater, decorative fountains, remote-controlled pool systems and multiple entertaining areas surrounded by lush European-inspired landscaping, stone pathways and manicured grounds. Canary palms and mature landscaping create a private, luxurious setting. Additional highlights include a new front entry door, an oversized three-car garage, an upgraded security system, a partial roof replacement and designer chandeliers and lighting throughout. Ideally located in one of Windermere’s premier gated communities, residents of Reserve at Belmere enjoy convenient access to top-rated schools, dining, shopping, golf, major roadways and the area’s renowned luxury lifestyle offerings.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Adam Shuler, Ii (407-949-4495)
11401 EVESHAM DR, WINDERMERE, FL 34786
$425,00056 Days on yellowkey MLS ID: O6410182
REDUCED by $10,000 (2.3%) on 06/15/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1847 Built: 2008Monthly Fee: $315 Tax: $3,077 (2024)Community: Preston SquareTownhouse
Taxes:$3,077
Remarks: Under contract-accepting backup offers. Virtually Staged. Brand New Roof just installed! Listed below market value. Welcome to this stunning corner unit townhome in the highly sought after Preston Square community in Windermere. Offering 3 bedrooms, 2.5 baths, and an exceptional layout.This beautifully maintained home perfectly combines elegance, comfort, and convenience. Ideally situated directly across from the community amenities, you’ll enjoy easy access to everything Preston Square has to offer while still enjoying the charm and privacy of a welcoming neighborhood setting. From the inviting front porch to the light filled interior, every detail of this home has been thoughtfully designed. Expansive wrap around windows flood the space with natural light, accentuating the soaring 10 foot ceilings and rich hardwood flooring throughout the main living areas. The open and functional floor plan is ideal for both everyday living and effortless entertaining. One of the home’s standout features is the private courtyard, a tranquil outdoor oasis perfect for hosting gatherings, grilling with friends, or simply unwinding after a long day. Inside, the gourmet kitchen is sure to impress with 42 inch solid wood cabinetry, granite countertops, stainless steel appliances, and ample prep and storage space for any home chef. The spacious first floor primary suite offers a peaceful retreat with a tray ceiling and a luxurious ensuite bath featuring dual vanities, a relaxing garden tub, and a walk in shower with dual shower heads. Upstairs, an oversized open concept loft provides flexible living space along with two additional bedrooms, creating ideal separation and privacy for family members or guests. Additional highlights include a laundry room with a utility sink and natural light, plus a rear entry two car garage complete with overhead storage racks and an extended driveway for extra parking. Residents of Preston Square enjoy resort style amenities including a sparkling community pool, beautifully landscaped grounds, basketball court, playground, fitness stations, and a large community park that regularly hosts movie nights and food truck events. Conveniently located near top rated schools, shopping, dining, golf courses, hospitals, and major roadways, this home offers easy access to Orlando, Winter Garden, and Central Florida’s world famous theme parks. This is an incredible opportunity to own a stylish and move in ready home in one of Windermere’s most desirable communities.
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Chris Courtney (407-406-0506)
9110 PALM TREE DR, WINDERMERE, FL 34786
$650,00035 Days on yellowkey MLS ID: O6414631
REDUCED by $25,000 (3.7%) on 06/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1819 Built: 1985Monthly Fee: $32 Tax: $8,182 (2025)Community: Silver Woods Ph 02Spa: NoSingle Family
Taxes:$8,182
Remarks: 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.
Listing is courtesy of: VICARI REALTY CORP (407-415-4401)
Listing Agent: Tony Vicari (407-415-4401)
8744 DANFORTH DR, WINDERMERE, FL 34786
$350,00030 Days on yellowkey MLS ID: O6414301
2 Days Off yellowkey (back on 6/29/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1375 Built: 2005Monthly Fee: $200 Tax: $2,938 (2025)Community: Lakes Of Windermere - Lake Reams TownhomesTownhouse
Taxes:$2,938
Remarks: Under contract-accepting backup offers. **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 8744 Danforth Drive in Windermere, a FRESHLY UPDATED 2-story townhouse offering 2 bedrooms, 2.5 bathrooms, and a functional layout designed for comfortable everyday living. EVERY BEDROOM FEATURES ITS OWN EN-SUITE FULL BATHROOM, providing maximum privacy and convenience for residents, guests, or work-from-home needs. Inside, the main level flows effortlessly between the living, dining, and kitchen areas, with a half bath conveniently serving the common spaces. The home received a FRESH INTERIOR PAINT JOB in 2026 and BRAND NEW FLOORING on the stairs and upper level in 2026, giving it a crisp, move-in ready feel throughout. The primary suite features a RECENTLY UPDATED WALK-IN SHOWER, adding a modern touch to your daily routine. Step outside to your OWN PRIVATE BACKYARD, a rare and UNIQUE feature amongst townhomes, offering a dedicated green space to relax, garden, entertain, or make entirely your own. The backyard is also home to a MATURE GUAVA TREE, providing fresh fruit and a charming touch for those who appreciate outdoor living. Parking is a breeze with a PRIVATE 2-CAR GARAGE tucked in the rear, plus ADDITIONAL OPEN STREET PARKING right in front of the home. The community delivers resort-style living with a POOL, PLAYGROUND, CLUBHOUSE, and ample walking space, and the HOA covers exterior maintenance so you can enjoy your home stress-free. The neighborhood stays lively year-round with food truck events and holiday celebrations that bring the community together, making this a truly FAMILY-FRIENDLY place to call home. And the location? UNBEATABLE, just MINUTES FROM DISNEY with fireworks visible right from the home, plus easy access to Winter Garden, Horizon West, shopping, dining, parks, schools, and all of greater Orlando.
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