Location: Windermere
Do Not Show Listings
4906 AVIVA GARDEN CT, WINDERMERE, FL 34786
$4,590,00054 Days on yellowkey MLS ID: O6400218
REDUCED by $100,000 (2.1%) on 06/01/2026
Bed: 3 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6236 Built: 2016Monthly Fee: $1,146 Tax: $48,425 (2025)Community: Gardens/Isleworth Un #2Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$48,425
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to an exceptional opportunity within the gates of Isleworth, one of Central Florida’s most Acclaimed private golf communities. Perfectly positioned along a tranquil pond and scenic walking trail, this move-in ready residence offers a rare blend of privacy, natural beauty, and refined living in the heart of Windermere. Thoughtfully designed for both everyday comfort and elevated entertaining, the home features a versatile layout including a spacious primary suite, multiple guest bedrooms, an oversized office/playroom, and a dedicated theater room. Expansive living areas flow seamlessly, creating a warm yet Elegant atmosphere throughout—all easily accessible via a private elevator connecting the home’s levels. The home delivers a true turnkey experience with modern finishes and enhancements, including a fully upgraded Crestron smart home system providing whole-home audio and video distribution for effortless control and convenience. A standout feature is the exceptional garage capacity, offering four individual single-car garages two of which are equipped with vehicle lifts. The outdoor living experience is a true highlight, featuring a resort-style pool, generous covered entertaining spaces, and serene water views that create a peaceful and private backdrop. Whether enjoying quiet mornings by the water or hosting guests in the evening, the setting is both inviting and unforgettable. Located within Isleworth—renowned for its championship golf course, world-class amenities, and guard-gated privacy—residents enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes and beautifully manicured grounds. This is a rare opportunity to own a fully updated, move-in ready home that seamlessly combines luxury, technology, and exceptional outdoor living in one of Orlando’s most sought-after communities.
Listing is courtesy of: CAMPBELL CUSTOM HOMES INC (407-947-4392)
Listing Agent: William Campbell (407-947-4392)
12966 VENNETTA WAY, WINDERMERE, FL 34786
$380,00045 Days on yellowkey MLS ID: S5148828
REDUCED by $6,000 (1.6%) on 06/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2008Monthly Fee: $380 Tax: $3,153 (2025)Community: Lake Sawyer South Ph 3Townhouse
Taxes:$3,153
Elementary School: Sunset Park Elem
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: PRICE ADJUSTMENT! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 2.5-bath townhouse located in the highly sought-after Lake Sawyer South community in Windermere. Surrounded by picturesque, tree-lined streets, this well-maintained home welcomes you with a bright and open kitchen area featuring granite countertops, stainless steel appliances, and a walk-in pantry. The open living area with elegant French doors lead to a private, paved courtyard that seamlessly connects to the detached 2-car garage—perfect for indoor-outdoor living. The first floor is complete with a spacious laundry room and a half bath. Upstairs, the expansive primary suite offers a peaceful retreat with a dual vanity en suite bath, while two additional bedrooms share a full bathroom—ideal for family, guests, or a home office setup. A conveniently located downstairs laundry room adds everyday ease. Residents enjoy access to exceptional community amenities, including parks, scenic walking trails, playgrounds, tennis and basketball courts, and a resort-style swimming pool. The HOA provides added value by covering lawn care, exterior painting, and the roof—offering low-maintenance living and peace of mind. Located in the charming town of Windermere, known for its top-rated schools and high quality of life, this home is just minutes from Walt Disney World, major highways, upscale dining, and premier shopping destinations. This is one of the best values in the area—schedule your private showing today!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Mae Stigell (631-377-1205)
1924 DOWN HOLLOW LN, WINDERMERE, FL 34786
$1,680,00016 Days on yellowkey MLS ID: O6398100
0 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1962 Built: 1999 Tax: $8,460 (2025)Community: AcreageSpa: YesSingle Family
Taxes:$8,460
Elementary School: Thornebrooke Elem
High School: Olympia High
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Escape the ordinary! This charming Windermere cottage on the Butler Chain, is set on a beautiful and private wooded lot with a rare opportunity for lake and boat frontage on Lake Down! This inviting residence is nestled on nearly two acres in a serene, Florida-style setting, offering the perfect blend of privacy and convenience. Thoughtfully renovated, this 3-bed, 2.5-bath, 2-car garage home embraces a warm, relaxed style with timeless cottage appeal and inviting indoor-outdoor living. A welcoming front porch entry sets the tone for a spacious great room with a cozy fireplace, an eat-in kitchen with natural light, ample cabinets and counter top space, perfect for everyday living and hosting. The first-floor primary suite includes a walk-in closet and a private bath, featuring a dual vanity and a separate shower. The sunroom sitting areas open to an expansive deck with a recessed spa and TV, creating the perfect setting for entertaining or quiet evenings surrounded by nature. A true retreat, with a private walkway and dock leading directly to Lake Down, offering seamless access to the Butler Chain of Lakes and all the recreation the 13 interconnected lakes have to offer. Conveniently located near Downtown Windermere, top-rated schools, shopping, and dining, with easy access to major roadways and airports, delivers the best of both tranquility and accessibility.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Kari Fleck (407-925-5283)
2068 ROBERTS POINT DR, WINDERMERE, FL 34786
$2,250,00058 Days on yellowkey MLS ID: O6397543
REDUCED by $100,000 (4.3%) on 06/01/2026
Bed: 5 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4876 Built: 1999Monthly Fee: $325 Tax: $12,356 (2025)Community: Waterford Pointe Ph 02 RepSpa: YesSingle Family
Taxes:$12,356
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita and Lake Access. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts. Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs. Inside, soaring ceilings, polished marble tile flooring, detailed crown molding, and dramatic two-story living spaces create a sense of scale and elegance throughout. The thoughtfully updated chef’s kitchen is designed for gathering, featuring quartz countertops, an oversized island, premium KitchenAid and Bosch appliances, double ovens, wine refrigeration, and seamless connection to the expansive family room with custom built-ins and fireplace. The private first-floor primary suite serves as a true retreat, offering direct courtyard and pool access, a spacious custom walk-in closet, and a beautifully appointed bath with dual vanities, jetted soaking tub, and walk-in shower. A second first-floor suite provides ideal accommodations for guests or family. Upstairs, expansive, flexible living spaces include a large game room overlooking the courtyard, a dedicated office with custom built-ins, a private fitness room with balcony access, and additional secondary bedrooms thoughtfully arranged for privacy and functionality. Outdoor living is equally compelling, with a screened resort-style saltwater pool and heated spa with waterfall, covered summer kitchen, multiple entertaining spaces, and the privacy that only a homesite of this scale can provide. Waterford Pointe residents enjoy an exceptional lifestyle with private access to Lake Roberts, a waterfront clubhouse, tennis courts, playground, and beautifully tree-lined streets—all within one of Windermere’s most desirable gated communities. Additional highlights include a 4-car garage, a new whole-house generator, three HVAC systems, a newly painted exterior courtyard, and highly regarded local schools. For buyers seeking privacy, architectural character, flexible living, and established Windermere luxury—without the premium of direct lakefront pricing—this is a compelling opportunity. **Private tours available by appointment**
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: David Dorman (407-948-8295)
2230 RIDGEWIND WAY, WINDERMERE, FL 34786
$1,349,00022 Days on yellowkey MLS ID: O6410264
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3064 Built: 1999Monthly Fee: $220 Tax: $8,790 (2025)Community: Estates At WindermereSpa: YesSingle Family
Taxes:$8,790
Remarks: One or more photo(s) has been virtually staged. Spacious and beautifully maintained 5-bedroom, 4-bath pool home situated on a 1/2-acre fenced treed lot in desirable Estates at Windermere. This stunning residence offers a great split floorplan with generous living spaces, high ceilings, and abundant natural light throughout. As you enter the home the dining room is to the left and the living room on the right side could also be an office or den. The spacious family room with built-ins creates the perfect gathering space. The kitchen features granite countertops, stainless steel appliances, ample cabinetry and a breakfast area. The primary suite includes a spa-inspired bath, dual vanities, a soaking tub, and a walk-in shower. There are three spacious secondary bedrooms and two full baths offering flexibility for family and guests. There is a bonus room with a closet and full bath that provides endless possibilities like a mother-in-law suite, guest retreat, home office, media room or the 5th bedroom. Step outside to your private backyard oasis complete with a sparkling screened pool, covered lanai, and beautifully landscaped yard that backs to an expansive greenbelt common area that affords privacy. The owners have made many updates over the years and recently including new sliding hurricane doors, new carpet in all four bedrooms, painted the outside of the house and newer appliances. Conveniently located near top-rated schools, shopping, dining, attractions and major roadways. This exceptional home combines comfort, elegance, and the best of Florida living.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Tim Frush (407-284-9222)
6820 THORNHILL CIR, WINDERMERE, FL 34786
$520,00055 Days on yellowkey MLS ID: V4948591
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1725 Built: 2009Monthly Fee: $82 Tax: $7,228 (2025)Community: Lakes Of WindermereSingle Family
Taxes:$7,228
Middle School: Horizon West Middle School
Remarks: Welcome to this stunning 2-story residence featuring 3 bedrooms, 2.5 bathrooms, and a spacious bonus area—ideal for a home office, gym, or playroom at The Lakes of Windermere. The expansive primary suite boasts vaulted ceilings, creating a bright and airy retreat, along with a generous walk-in closet. The primary bathroom includes a relaxing jacuzzi tub, perfect for unwinding. Upstairs, enjoy wood flooring throughout—no carpet, offering both elegance and easy maintenance. Wooden plantation shutters throughout the home. Designed for comfort and efficiency, this home includes Impact Windows, stainless steel appliances, a new washer and dryer, and ceiling fans in both the living room and primary bedroom. Step outside to a fully fenced backyard, perfect for entertaining, relaxing, or enjoying time with pets. The outdoor space features a mature mango tree and a charming pergola, creating your own private retreat. An irrigation system using reclaimed water keeps the landscaping lush and eco-friendly. The extended rear driveway, with alley access, provides ample guest parking. The 2-car garage is thoughtfully upgraded with epoxy flooring, built-in storage cabinets, an extra refrigerator, and a new garage door opener—perfect for organization and convenience. Located in the highly desirable Lakes of Windermere community, residents enjoy beautifully maintained parks, scenic lake views, playgrounds, and a community pool. The home is situated on a quiet single-entry loop, surrounded by a mix of elegant and lakefront custom homes. Just minutes from shopping, dining, Disney resorts, and more—this home offers the perfect blend of comfort, style, and location. Tenant's Lease ends July 15/ 2026
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Maria Galindez (305-803-3799)
2958 MARQUESAS CT, WINDERMERE, FL 34786
$1,875,000222 Days on yellowkey MLS ID: O6357302
REDUCED by $10,000 (0.5%) on 05/19/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4716 Built: 1984Monthly Fee: $215 Tax: $15,228 (2024)Community: Lake Crescent ReserveSingle Family
Taxes:$15,228
Elementary School: Windermere Elem
Tax Year: 2024
Remarks: PRICE IMPROVEMENT! Recently appraised - Pricing adjusted to reflect current appraised value. This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for comfort, refinement, and privacy, this home embodies Florida luxury living at its finest, where indoor grace meets outdoor serenity. The split floor plan offers a grand entry foyer, bedrooms on one side and open living/entertaining areas on the other, all wrapped around the screen-enclosed, completely private pool with a built-in summer kitchen. Through the courtyard, you’ll find the spacious guest house, complete with its own living room, bedroom, bathroom on the main floor, and a large upstairs flex room with a screened balcony overlooking the expansive backyard. This property has just undergone a modern renovation, featuring: * A brand-new primary bathroom with dual vanities, oversized shower, dedicated makeup/dressing area, and a custom walk-in closet. * A remodeled kitchen with new flooring, cabinetry, and striking quartz countertops. * Fresh interior and exterior paint, new flooring throughout half the home, and the guest house. * Additional Highlights: • 4.5 bathrooms • Generator • Water softener system • New pavers (front and pool area) • Two new A/C units — 2023 and 2025 • Plantation shutters on all windows • New paint inside & out • Two-car garage • Outdoor summer kitchen • Guest house with full kitchen. This residence is walking distance to Windermere Elementary and the Windermere Recreation Center, offering the best of both convenience and community.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786
$469,00081 Days on yellowkey MLS ID: O6392752
0 Days Off yellowkey (back on 5/31/2026)
REDUCED by $10,000 (2.1%) on 04/23/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1980 Built: 2008Monthly Fee: $315 Tax: $3,248 (2025)Community: Preston SquareTownhouse
Taxes:$3,248
Remarks: Under contract-accepting backup offers. Welcome home to Preston Square in beautiful Windermere! This stunning corner-unit townhome with 4 bedroom, 3 bathrooms offers the perfect blend of comfort, style, and convenience, with a new roof and fresh exterior paint. Step onto the cozy front porch and into a bright, inviting two-story home filled with natural light. The main living areas feature tile flooring throughout; great room showcases a mirror accent wall along with board and batten in the dining area. Kitchen features granite countertops, breakfast bar, stainless steel appliances, and stone backsplash. Sliding glass door leads to a private paver patio, perfect for relaxing or entertaining. Downstairs bedroom with full bath, inside laundry room plus a utility sink leads to the attached two-car garage with long driveway for additional parking. Upstairs you will find 3 additional bedrooms, stunning primary suite with balcony views. Primary bath features dual sinks, large garden tub, and separate shower. Preston Square offers amenities including a stunning community pool, playground, mature landscaping, basketball court, green space for events, and fitness stations. Ideally located near local dining, shopping, top-rated schools, golf courses, hospitals, and major roadways and attractions.
Listing Agent: Morgan Horsley (256-283-8747)
10870 BAYSHORE DR, WINDERMERE, FL 34786
$2,895,000134 Days on yellowkey MLS ID: O6371471
REDUCED by $100,000 (3.3%) on 05/11/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4693 Built: 1999 Tax: $27,527 (2024)Community: Lake Down EstatesSpa: YesSingle Family
Taxes:$27,527
Remarks: Set against the shimmering waters of Little Lake Down, this extraordinary lakefront home offers an elevated expression of luxury living. Thoughtfully designed to maximize sweeping water views, the residence delivers a refined yet inviting atmosphere ideal for both intimate living and grand entertaining. As you step inside you are greeted by a spacious open floor plan, highlighted by a wood-burning fireplace, and captivating views of the pool, backyard, and lake. At the heart of the home, a chef’s kitchen stands as a true centerpiece, appointed with top-of-the-line appliances and two expansive center islands, it’s the perfect place for family gatherings. The kitchen opens to a large family room and breakfast nook providing effortless flow for daily living, enhanced by panoramic lake views that bring the outdoors in. The primary suite serves as a luxurious retreat, featuring peaceful water views and a spa-like bathroom with dual vanities, a walk-in shower, and an elegant soaking tub. Additional first floor amenities include a guest bedroom, a home office, and a pool bath. Upstairs, you will find two additional bedrooms, a spacious bonus room, and a private balcony overlooking the lake. Outdoor living rivals a private resort with a large, covered lanai, sparkling pool, spa, and an expansive backyard that leads to a private boat dock with a boat lift and jet ski parking. With direct access to the Butler Chain’s interconnected lakes there will be no shortage of things to do on the weekend. Enjoy being just minutes from Windermere A rated schools, the Friday farmers market, quaint eateries, and a short drive to world class shopping, fine dining, and the Disney and Universal theme parks. This is more than a home, it is a rare opportunity to own a private lakefront retreat on the Butler Chain of Lakes, where luxury, lifestyle, and location converge in one truly exceptional offering.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
12305 VIA DERNA PL, WINDERMERE, FL 34786
$465,000144 Days on yellowkey MLS ID: O6374964
REDUCED by $5,000 (1.1%) on 04/17/2026
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
Elementary School: Bay Lake Elementary
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)
9669 WESTOVER CLUB CIR, WINDERMERE, FL 34786
$750,000105 Days on yellowkey MLS ID: O6386605
REDUCED by $100,000 (11.8%) on 04/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3435 Built: 2001Monthly Fee: $115 Tax: $11,111 (2024)Community: Westover Club Ph 01 44/139Spa: YesSingle Family
Taxes:$11,111
Remarks: PRICED TO SELLLL!!! Behind the gates of Westover Club, 9669 Westover Club Circle offers a timeless Windermere setting with privacy, mature landscaping, and seamless indoor-outdoor living on nearly half an acre. Designed for both entertaining and everyday comfort, the home blends classic style with a functional layout in one of the area’s most desirable gated communities. Featuring 4 bedrooms, 4 bathrooms, and over 3,400 square feet, the home includes formal living and dining spaces and a flexible floor plan with distinct yet connected living areas. A newer AC system and roof (approx. 5 years old) provide valuable updates and peace of mind. Enjoy a screened lanai, open porch, and private pool overlooking a spacious, hedge-lined backyard. While the home would benefit from cosmetic updates, it presents an excellent opportunity to personalize, with a seller who is flexible. A Generac generator adds comfort and year-round security.
Listing is courtesy of: FIRST WORLD REALTY GROUP (954-457-0114)
Listing Agent: Regina Ferdinand (954-665-9885)
13448 BELLARIA CIR, WINDERMERE, FL 34786
$3,200,000264 Days on yellowkey MLS ID: O6346484
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 6308 Built: 2014Monthly Fee: $483 Tax: $29,164 (2024)Community: BellariaSingle Family
Taxes:$29,164
Remarks: Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting the elegant handcrafted staircase in the foyer. The formal living and dining areas set the tone for refined entertaining, enhanced by a gas fireplace, a well-appointed wet bar, and expansive views of the sparkling pool and two-story covered porch. Just off the entry, the study provides an intimate retreat with porcelain flooring and clerestory windows, filling the space with natural light and framing serene outdoor vistas. The open-concept family room and kitchen create the heart of the home, where a wall of glass doors seamlessly blends indoor and outdoor living. The gourmet kitchen is a chef’s delight, featuring stainless steel appliances, exotic granite, custom cabinetry, tile flooring, and a spacious walk-in pantry. The first-floor master suite, thoughtfully tucked away for privacy, serves as a true sanctuary. Its spa-inspired bath is adorned with paneled cabinetry, exotic granite, a rainforest shower, soaking tub, and expansive closet areas—both beautiful and functional. Two additional en suite guest bedrooms, a versatile bonus room, and generous living and dining spaces make the main level ideal for everyday living or hosting. Upstairs, the thoughtful layout continues with three bedrooms, a loft, a sitting area, a bonus room, and even a second laundry room for added convenience. These flexible spaces adapt easily to the needs of a growing family or guests, offering opportunities for work, play, or relaxation. Blending elegance with livability, this home captures the essence of Florida living—where interiors open gracefully to resort-style outdoor spaces, making it perfect for both intimate family life and grand entertaining.
Listing is courtesy of: KENNEDY REALTY GROUP LLC (407-590-6192)
Listing Agent: Shawn Kennedy (407-590-6192)
11564 MIZZON DR #930, WINDERMERE, FL 34786
$325,00040 Days on yellowkey MLS ID: O6404607
REDUCED by $10,000 (3.0%) on 05/31/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,561 (2025)Community: Lakeside/Lks/Windermere CondoCondo
Taxes:$4,561
Remarks: Lovely 3rd floor (Corner unit on top floor) In sought after Lakes at Lakeside of Windermere. Well-appointed 3 Bedrooms and 2 bathrooms Condo, Spacious feel. Offering an excellent layout. Newer carpets, home is ready to move in. Dine in kitchen has 42" dark cherry wood cabinets and granite countertops, stainless range and dishwasher, laminate flooring throughout the living areas and new carpet in bedrooms. Master bedroom Features walk-in closet, and Master bathroom 2 further bedrooms and other full bathroom. Step out from sliding doors to the Spacious covered/screened balcony. Elevators and stairs access to the unit. Superb community amenities. Resort style recreation, Olympic swimming pool, sand volleyball court, state-of-the-art fitness center, playground, large community clubhouse, BBQ area, & cozy outdoor fireplace! With easy access to all major highways including I-4, 429, & SR 535…Close to Disney theme parks & Restaurants, Dining, Shopping & School. Maintenance, carefree Florida living, in this well-maintained community
Listing is courtesy of: RE REALTY (321-363-6345)
Listing Agent: Reeta Gulati (321-363-6345)
9144 ISLEWORTH GARDENS DR, WINDERMERE, FL 34786
$4,450,00065 Days on yellowkey MLS ID: O6397842
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 5004 Built: 2019Monthly Fee: $1,146 Tax: $35,432 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$35,432
Middle School: Chain of Lakes Middle
Remarks: Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed residence offers three expansive bedrooms, each with its own beautifully appointed en-suite bathroom, along with two elegant half baths to accommodate guests with ease. From the moment you arrive, the home’s striking Mediterranean-inspired architecture, circular tower entry, and meticulously landscaped grounds set the tone for the sophistication that awaits inside. Step through the grand entrance into interiors defined by soaring ceilings, abundant natural light, and exquisite craftsmanship at every turn. The gourmet kitchen serves as the heart of the home, showcasing custom cabinetry, premium Sub-Zero appliances, an oversized center island, and designer finishes that seamlessly blend form and function—perfect for both intimate family moments and upscale entertaining. Flowing effortlessly into the main living areas, the open-concept layout creates a warm yet refined atmosphere, enhanced by elegant lighting, stone flooring, and thoughtful architectural details throughout. Retreat to the luxurious primary suite, a private sanctuary featuring a spa-inspired bathroom with soaking tub, walk-in shower, dual vanities, and custom finishes that evoke a five-star resort experience. Each additional bedroom offers generous proportions, privacy, ensuring comfort and convenience for family members and guests alike. The inclusion of two half bathrooms further elevates the home’s functionality for entertaining. The outdoor living spaces are equally impressive, offering the perfect backdrop for enjoying Florida’s year-round sunshine. Whether hosting gatherings or savoring quiet evenings, the seamless indoor-outdoor connection enhances the overall living experience. Located within the exclusive Isleworth community—renowned for its world-class golf, privacy, and unparalleled lifestyle, this residence presents a rare opportunity to own a home that embodies elegance, comfort, and timeless design in one of Central Florida’s most sought-after communities while being close to shopping, world class dining and attractions.
Listing is courtesy of: MEGAN DOWDY REALTY, LLC (407-509-9279)
Listing Agent: Megan Dowdy (407-509-9279)
6412 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786
$550,00014 Days on yellowkey MLS ID: O6412095
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1984 Built: 2012Monthly Fee: $130 Tax: $6,210 (2025)Community: Windermere Lndgs Ph 02Single Family
Taxes:$6,210
Remarks: RARE OPPORTUNITY IN WINDERMERE LANDINGS! Beautifully upgraded 4-bedroom home in one of Windermere's most desirable communities, just steps from Windermere Preparatory School. Originally designed with an expansive downstairs living and family room layout, the spacious loft was thoughtfully converted into a versatile fourth bedroom, creating exceptional value rarely found at this price point. The result is a flexible floor plan ideal for families, remote work, guests, or a growing household. Pride of ownership shines throughout this one-owner home. Elegant porcelain tile flooring, custom wood accent walls, designer finishes, and abundant natural light create a sophisticated yet welcoming atmosphere. Every detail has been carefully maintained and thoughtfully enhanced. The location is simply unmatched. Enjoy a short walk to the community pool and playground, while being just minutes from top-rated schools, shopping, dining, and everyday conveniences. Disney, major attractions, and Orlando's world-class entertainment are only a short drive away. Whether you're searching for a primary residence, a relocation home, or an investment in one of Central Florida's most sought-after areas, this property delivers the perfect combination of location, upgrades, functionality, and value. Homes offering this level of quality, flexibility, and proximity to Windermere Prep rarely become available. Schedule your private showing today.
Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)
Listing Agent: Jose Rojo (786-502-6162)
1407 HEMPEL AVE, WINDERMERE, FL 34786
$1,090,00014 Days on yellowkey MLS ID: O6410840
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2842 Built: 1989 Tax: $10,727 (2025)Community: Gotha TownSingle Family
Taxes:$10,727
Remarks: Welcome to this incredible investment opportunity located in one of the most desirable areas in Central Florida. This beautiful property offers the perfect combination of space, privacy, freedom, and location. Featuring 4 spacious bedrooms and 3 full bathrooms, this home sits on more than half an acre of land, giving you and your family the opportunity to truly enjoy comfort and outdoor living. One of the greatest advantages of this property is that it has NO HOA, allowing you the freedom to enjoy your property without restrictive association rules or expensive monthly fees. Whether you are looking for a primary residence, vacation home, or investment property, this home offers endless possibilities. The property features a beautiful swimming pool and stunning water views, creating the perfect atmosphere to relax, entertain guests, and enjoy the Florida lifestyle all year round. The oversized lot provides plenty of space for family gatherings, outdoor activities, parking, or future improvements.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Lina Abi Hanna De El Bonney (407-227-1740)
11326 LEDGEMENT LN, WINDERMERE, FL 34786
$939,00023 Days on yellowkey MLS ID: O6409714
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3182 Built: 2002Monthly Fee: $170 Tax: $9,509 (2025)Community: Glenmuir 48 39Single Family
Taxes:$9,509
Remarks: One or more photo(s) has been virtually staged. Experience refined living in this beautifully updated 5-bedroom home, nestled in an exclusive gated community zoned for top-rated schools. The open-concept main level boasts soaring high ceilings, abundant natural light, elegant tile flooring, and a convenient primary suite for ultimate privacy. At the heart of the home is a fully remodeled kitchen (2021) featuring upgraded cabinetry and modern finishes. Upstairs, you'll find premium luxury vinyl plank flooring, newly replaced in 2026. Additional high-value upgrades include a whole-house water filtration system and a private well irrigation system (both installed in 2022). 2 Air Conditioning units installed in October, 2020. Combining security, style, and efficiency, this thoughtfully upgraded home is completely move-in ready!
Listing is courtesy of: AAA GLOBAL VENTURES PA (407-717-5232)
Listing Agent: Jingjing Guan (713-820-3325)
2002 WATER KEY DR, WINDERMERE, FL 34786
$1,299,00017 Days on yellowkey MLS ID: O6408915
0 Days Off yellowkey (back on 5/30/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3695 Built: 2002Monthly Fee: $335 Tax: $16,085 (2025)Community: Reserve At Waterford Pointe Ph 01Spa: YesSingle Family
Taxes:$16,085
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Set behind the gates of Reserve at Waterford Pointe, this exceptional 5-bedroom, 5-bathroom estate spans 3,695 square feet on more than half an acre of beautifully manicured grounds, delivering refined everyday living in one of Central Florida's most sought-after lakeside communities. Framed by freshly updated landscaping and mature greenery, the residence commands attention with its stately presence, expansive lot, and genuine sense of privacy. Recent upgrades elevate both comfort and longevity, including a new HVAC system, new water heater, fresh carpet in the main living areas, and tile flooring throughout the primary rooms. A grand entry introduces spectacular formal living and dining spaces designed to elevate both intimate gatherings and large-scale entertaining. At the heart of the home, the chef's kitchen is thoughtfully designed with a large center island, bar seating, stainless steel appliances, abundant cabinetry, and an open-concept layout that flows effortlessly into the main living areas. Overlooking the kitchen, the family room feels both warm and dramatic, anchored by a striking floor-to-ceiling stone feature wall with a gas fireplace that creates an inviting focal point. Privately positioned, the primary suite serves as a luxurious retreat with direct access to the outdoor living spaces. Spacious and serene, it is complemented by a spa-inspired bath with dual vanities, a soaking tub, walk-in shower, and an oversized walk-in closet designed for both comfort and functionality. Upstairs, a generous bonus room doubles as a private movie theatre with a wet bar, offering an ideal space for entertaining, relaxing, or hosting guests in a setting that feels distinctly elevated. Beyond the interiors, the home opens into a private outdoor oasis featuring a sprawling screened lanai, sparkling pool and spa, and a fully equipped summer kitchen with grill and bar seating. The expansive backyard delivers exceptional space and privacy, framed by lush mature landscaping that creates a tranquil, secluded atmosphere. Residents of The Reserve at Waterford Pointe enjoy an exclusive lifestyle with access to private community amenities, including a boat ramp to Lake Roberts, tennis courts, a playground, and beautifully maintained park spaces. Ideally positioned just minutes from Disney, Universal Orlando, SR 429, the Florida Turnpike, and some of Central Florida's finest shopping and dining destinations, this remarkable residence offers a rare combination of luxury, privacy, and convenience.
Listing Agent: Christopher Christensen (407-312-8003)
10520 PARK RIDGE GOTHA RD, WINDERMERE, FL 34786
$2,400,00017 Days on yellowkey MLS ID: O6409659
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3101 Built: 1979 Tax: $3,341 (2025)Community: NoneSingle Family
Taxes:$3,341
Remarks: This listing presents two distinct 1+ acre residential properties, located at 10532 & 10520 Park Ridge Gotha Rd, offering a unique opportunity: a 2.522-acre residential estate parcel situated in Windermere, Florida. The two adjacent lots, both exceeding one acre, currently feature vacant, yet well-maintained, older single-family homes. Windermere is renowned as one of Central Florida's most desirable, high-end luxury communities. Orange County's A1 zoning permits one single-family home per acre, in addition to horses, agricultural activities, barns, nurseries, sheds, etc. The property offers ample space for various amenities, including a pool, summer kitchen, tennis court, playground, or horses and stables. The neighborhood is predominantly comprised of large, luxury residences. The land is high and dry & flat and level, with only a few mature trees. This premium location provides convenient access to numerous retail developments, hospitals, expressways, restaurants, entertainment venues, golf courses, Publix, Walmart, and other popular shopping areas. Please be advised that these two parcels can only be purchased together as a package; they are not available for individual purchase. Note the attachments for aerial video, surveys, floor plans, and other descriptions.
Listing is courtesy of: DAVID WEAVER, REALTOR (407-230-4778)
Listing Agent: David Weaver (407-230-4778)
11434 JASPER KAY TER #106, WINDERMERE, FL 34786
$320,00015 Days on yellowkey MLS ID: S5150874
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1455 Built: 2007Monthly Fee: $485 Tax: $4,640 (2025)Community: Lakeside/Lks/WindermereCondo
Taxes:$4,640
Remarks: investment property with a very high rental demand for its location and comfort or a vacation retreat, this condo is perfect for you. Beautiful condo located in Lakeside at Lakes of Windermere, corner unit on the first floor (ground floor) with covered lanai Welcome to this stunning condo located in one of the best and most exclusive areas of Orlando Fl such as Windermere, with 3 bedrooms and 2 bathrooms, this condo which is in perfect condition of care and maintenance, offers a spacious and open layout that perfectly combines the kitchen, dining and living areas, ideal for both everyday life and entertaining. The master suite, located to one side for privacy, has a generous bathroom with a garden-style tub/shower and a large walk-in closet. The kitchen is beautifully equipped with wood cabinets. On the opposite side, you will find the secondary bedrooms along with the second bathroom, a convenient laundry closet and ample storage space throughout. The gated resort-style community includes a clubhouse, pool, fitness room, walkways, green areas, parks, sports areas, on-site management and valet trash service, ensuring convenience and comfort. Located in the heart of Windermere in a strategic location just minutes from Walt Disney World and Downtown Winter Garden, easy access to major streets and highways that bring you closer to other important areas of the city and other local attractions such as Universal Studios, it is close to Publix, shops, restaurants and stores.
Listing is courtesy of: NUMBER 1 BROKER, LLC (407-566-3400)
Listing Agent: Eric Jia (407-401-1431)
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