Location: Windermere
Do Not Show Listings
33 MAIN ST, WINDERMERE, FL 34786
$1,575,00024 Days on yellowkey MLS ID: O6406887
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2130 Built: 1961 Tax: $9,485 (2025)Community: Davis ShoresSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,485
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2025
Middle School: Gotha Middle
Remarks: BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere residents can access Fernwood Park and boat ramp 8/10 mile away. Drive your Golf Cart to downtown Windermere. Multiple possibilities for this property in the prime location of Windermere. Home needs major renovation or demolish and rebuild. Sold AS IS.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Bruce Higgins (407-883-2728)
7644 RIPPLEPOINTE WAY, WINDERMERE, FL 34786
$435,00063 Days on yellowkey MLS ID: O6395582
2 Days Off yellowkey (back on 6/2/2026)
REDUCED by $10,000 (2.2%) on 05/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1881 Built: 2015Monthly Fee: $240 Tax: $6,847 (2025)Community: Lake Burden South Ph 2 #35 36Townhouse
Taxes:$6,847
Elementary School: Sunset Park Elem
High School: Windermere High School
Middle School: Horizon West Middle School
Remarks: Welcome to Lake Burden, one of Windermere’s most desirable and well-established communities! This corner-lot townhome offers 3 bedrooms, 2.5 bathrooms plus office. This open-concept floor plan that flows seamlessly with a well-appointed kitchen with granite countertops and backsplash, and a walk-in pantry. Large living room features high ceilings and tons of windows for natural light. French doors open to your own private paved garden courtyard, an ideal spot for morning coffee, weekend gatherings, or evening relaxation. The courtyard also provides direct access to a two-car garage via a tranquil rear alley. Upstairs laundry room has built-ins with a full-size front load washer and dryer. Enjoy a vibrant lifestyle with resort-style amenities — a sparkling community pool, shaded picnic tables, two tennis courts, a playground, and scenic walking paths around the lake ideal for peaceful evening strolls. This is a full-of-life neighborhood where pride of ownership shows everywhere. 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, Publix, 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.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Kelly Zannini (407-970-6298)
13525 GORGONA ISLE DR, WINDERMERE, FL 34786
$1,115,000108 Days on yellowkey MLS ID: O6377789
REDUCED by $5,000 (0.4%) on 05/22/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4625 Built: 2018Monthly Fee: $268 Tax: $9,351 (2025)Community: Windermere IsleSpa: NoSingle Family
Taxes:$9,351
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless entertaining. A dramatic two-story foyer creates a striking first impression, highlighted by a custom hardwood staircase with decorative iron balusters. Architectural details continue throughout with 9.5-foot ceilings, 8-foot doors, coffered ceilings, porcelain tile on the main level, and hardwood flooring upstairs. Custom Disney-inspired stained-glass window inserts throughout the home offer a subtle and charming nod to the nearby magic. The expansive open-concept living area is anchored by a chef-level gourmet kitchen featuring a natural gas cooktop, dual convection ovens, quartz countertops and backsplash, oversized island, 42-inch cabinetry, café dining area, and walk-in butler’s pantry—perfect for entertaining and daily convenience alike. The main-level primary suite serves as a tranquil retreat with a spa-style bathroom, soaking tub, glass-enclosed walk-in shower, and generous custom closet. Upstairs, five additional bedrooms include a private guest suite and well-designed shared layouts, along with a spacious upper-level great room and reading nook ideal for a media room, game space, or lounge. Significant upgrades include a 27kW commercial-grade whole-house generator, tankless water heater, gas dryer, advanced humidification and UV air filtration, and a garage with custom cabinetry, overhead storage, and durable polyaspartic flooring. Energy-efficient systems and abundant natural light enhance comfort throughout. The lot to the right of the home is Protected Green Space in perpetuity and cannot be developed so you will always have that space. Seller is providing a credit towards a 2-1 RATE BUY DOWN with full price offer. Inquire for more details.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Roo Klaers (407-493-5615)
1002 OAKDALE ST, WINDERMERE, FL 34786
$975,00051 Days on yellowkey MLS ID: TB8495717
1 Days Off yellowkey (back on 4/22/2026)
Bed: 4 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 3516 Built: 1973 Tax: $8,799 (2025)Community: Windermere TownSingle Family
Taxes:$8,799
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by. Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining. The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations. A rare offering in this location, the property features an impressive 3 bay, 30' long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs. Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home. Seller is offering up to a $25,000 closing cost credit, providing added flexibility and value for buyers. A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Frank Smith (401-644-4762)
12334 SUMMERPORT LN, WINDERMERE, FL 34786
$6,500,0006 Days on yellowkey MLS ID: O6412083
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6182 Built: 1966 Tax: $22,979 (2025)Community: Summerport BeachSpa: YesSingle Family
Taxes:$22,979
Middle School: Bridgewater Middle
Remarks: Under Construction. Welcome to 12334 Summerport Lane, an extraordinary lakefront estate on the prestigious Butler Chain of Lakes in Windermere. Custom built by Davila Homes and featuring the stunning Stanford floor plan, this exceptional residence offers approximately 6,182 square feet of luxurious living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Perfectly positioned on the shores of Lake Butler, this one-of-a-kind waterfront retreat showcases breathtaking panoramic lake views and includes a private covered dock with direct access to the renowned Butler Chain of Lakes, offering the ultimate Florida boating lifestyle. Designed to impress, the home welcomes you through a grand foyer with soaring ceilings and elegant architectural details. The expansive open-concept layout seamlessly connects the formal living areas, family room, and gourmet chef's kitchen, complete with an oversized island, premium appliances, custom cabinetry, and an oversized walk-in pantry. Walls of glass frame spectacular water views and fill the home with natural light. The luxurious first-floor primary suite serves as a private sanctuary overlooking the lake, featuring spa-inspired finishes, dual walk-in closets, and direct access to the outdoor living spaces. Additional guest suites provide comfort and privacy for family and visitors alike. The second level offers spacious en-suite bedrooms, a versatile loft, and a bonus room ideal for a media room, game room, or private retreat. Every detail has been thoughtfully designed to maximize comfort, functionality, and the home's incredible waterfront setting. Outdoor living reaches new heights with expansive covered lanais, resort-style entertaining areas, and endless opportunities to enjoy Windermere's spectacular sunsets over Lake Butler. Whether hosting guests, enjoying water sports, or relaxing by the lake, this property embodies the finest in luxury waterfront living. Located in one of Central Florida's most desirable addresses, 12334 Summerport Lane offers convenient access to top-rated schools, world-class golf, upscale dining, luxury shopping, and all that Windermere has to offer while delivering the exclusivity and prestige of true Butler Chain lakefront ownership.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Fernanda Negromonte (407-592-1744)
WINDERMERE, FL 34786
$369,90042 Days on yellowkey MLS ID: O6400745
INCREASED by $10,900 (3.0%) on 06/02/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1429 Built: 2006Monthly Fee: $200 Tax: $5,436 (2025)Community: Lakes/Windermere-Lk Reams TwhmSpa: NoTownhouse
Taxes:$5,436
Elementary School: Bay Lake Elementary
Remarks: Welcome to this beautifully maintained 2-bedroom, 2½-bathroom corner lot townhome in the highly desirable Windermere area! Located at 8905 Newmarket Drive, this home offers the perfect blend of comfort, style, and convenience. The spacious open floor plan is filled with natural light and designed for both everyday living and entertaining. The kitchen features clean white appliances, ample cabinetry, and a layout that flows seamlessly into the living and dining areas.The primary suite provides a relaxing retreat with a well-appointed ensuite bathroom. The second bedroom and additional baths offer flexibility for guests, home office use, or hobbies. Enjoy a private backyard and the added benefits of a corner lot, providing extra privacy and space.Situated in a sought-after community, residents enjoy easy access to top-rated schools, shopping, dining, and major roadways, with quick access to Walt Disney World. Nearby golf courses and Windermere’s charm make this location truly exceptional.Don’t miss the opportunity to own this charming corner lot townhome in a prime location—schedule your private showing today!
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
7710 FAIRGROVE AVE, WINDERMERE, FL 34786
$390,00036 Days on yellowkey MLS ID: S5148820
REDUCED by $6,000 (1.5%) on 06/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2008Monthly Fee: $380 Tax: $3,844 (2025)Community: Lake Sawyer South Ph 03Townhouse
Taxes:$3,844
Remarks: PRICE ADJUSTMENT!! Don’t miss this fantastic opportunity to own a spacious townhouse in the highly desirable Lake Sawyer South community of Windermere, Florida. Nestled among tree-lined streets, this 3-bedroom, 2.5-bath home with a 2-car garage offers comfort, style and tranquility. As you enter, a spacious living room welcomes you - perfect for entertaining. The kitchen boasts granite countertops, stainless steel appliances, and a walk-in pantry, with French doors leading to a large, paved courtyard that connects to the detached 2-car garage. A conveniently located laundry room completes the downstairs layout. Upstairs, the expansive primary suite features an en suite bath with dual vanity, while two additional bedrooms share a full hall bath with a shower/tub combo. Residents of this well-maintained community enjoy multiple parks, trails, playgrounds, tennis and basketball courts, and a refreshing swimming pool. The HOA covers lawn care, exterior painting, and the roof—adding convenience and peace of mind. Known for its top-rated schools and quality of life, Windermere offers proximity to Disney World, theme parks, major roadways, fine dining, and shopping. Start enjoying everything this exceptional home and community have to offer.
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Mae Stigell (631-377-1205)
4906 AVIVA GARDEN CT, WINDERMERE, FL 34786
$4,590,00045 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
Taxes:$48,425
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
$380,00036 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
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!
1924 DOWN HOLLOW LN, WINDERMERE, FL 34786
$1,680,0007 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
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)
7174 BEEK ST, WINDERMERE, FL 34786
$725,00031 Days on yellowkey MLS ID: O6402279
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2464 Built: 2013Monthly Fee: $115 Tax: $5,627 (2025)Community: Windermere TerraceSingle Family
Taxes:$5,627
Remarks: Welcome to this solid built 1-story 5 bedroom split plan, 3 full baths home with 2464 square feet of well designed living space, plus a 3 car garage and no rear neighbor as it backs to the brick wall of Windermere Terrace. Inside you'll find soaring 10' ceilings & 6-incht baseboards throughout, crown moldings in the family/kitchen area, ceramic tile in the kitchen & bathrooms and engineered wood floors in the foyer, dining & family rooms & carpet in the bedrooms. As you enter the foyer, the view draws you to the family room and kitchen/dining area plus the triple sliding doors to the large covered porch (21x15). The kitchen has all granite counters, a breakfast bar and plenty of cabinets & a closet pantry. The dining room is at the end of the kitchen with a view to the rear yard. The additional multiple purpose room with granite counters opens to the family room, and can be a computer room, mud room, dry bar or butler pantry, extra storage with the cabinets. It also opens to the inside laundry room then to the 3-car garage with brand new door openers (April 2026). The primary bedroom has an ensuite bathroom with dual sinks, granite counters, garden tub plus separate shower, and walk-in closet with built in custom made Italian clothes storage cabinets. The community pool is a short distance away exclusive for Windermere Terrace residents. The electric power to the home is efficiently supplied by the Leased Solar system in connection with Duke. Reduces the electric bill. The recent upgrades will greatly make this home worry free for your family, They are: (1) The 4 ton air conditioner was replaced on 3-30-2023. (2) The entire roof was replaced in October 2025 (3) The 50 gallon water heater was replaced on 11-12-2024. (4) Both garage door openers were replaced in April 2026. Great location and close to all shopping, major roads and more. Shop and compare, your family deserves this home. Click the tour button above for Virtual Tour and floor plan..
Listing is courtesy of: RE/MAX CENTRAL REALTY (407-333-4400)
Listing Agent: Ron Hernquist (407-257-2700)
2068 ROBERTS POINT DR, WINDERMERE, FL 34786
$2,250,00049 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)
2428 BUTLER BAY DR N, WINDERMERE, FL 34786
$1,150,0006 Days on yellowkey MLS ID: O6410967
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3387 Built: 1990Monthly Fee: $199 Tax: $9,842 (2025)Community: Butler BaySingle Family
Taxes:$9,842
Remarks: This stunning updated 4 bedroom/4 bathroom executive pool home in exclusive Windermere Club has been meticulously maintained and is the perfect place to call home!!! Upon entering the gated community you will be impressed by the oversized lots and sprawling custom homes. When arriving to the residence and turning into the circular paver driveway you will enjoy the homes classic elevation with a tall center gable and a neutral exterior palette with classic French blue shutters. Upon stepping through the double entry doors you will immediately sense this home is special with a fabulous floorpan, open and spacious, perfect for entertaining. Soaring vaulted ceilings, wood moldings, wood flooring, French doors and neutral interior tones all contribute to the allure of a classic and timeless residence. The home offers a study with double doors located off the entry Foyer with custom built-in cabinetry/shelves. The oversized Dining Room overlooks the beautiful swimming pool and patio and is open to the kitchen. The Gourmet Kitchen with 42" cabinets, gorgeous granite counters tops, beautiful glass tile backsplash, a center island, stainless steel appliances is open to the large Breakfast Nook and spacious Family room featuring a gas fireplace with a custom wood mantel making it the perfect space for winding down after a long day or enjoying family gatherings and holidays. The home also benefits from tremendous natural light through its many windows. The oversized Primary Bedroom is fit for a King and Queen with French Doors overlooking the pool, a spa-like 5-piece Travertine bathroom featuring a shower, soaking tub, double vanities and two large walk-in closets with custom built-in shelving systems. The 3 additional bedrooms include 2 with ensuite bathrooms and a 3rd that is served by a hall bathroom. All of the bathrooms have been updated with high-end finishes. The 3 car side-entry garage with spacious car park area offers convenience and significant storage. The Pool area with covered space, an outdoor kitchen/grilling station and nature views is perfect for Florida entertaining! Schedule a showing today and see this amazing home before it's gone!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Randall Gill (407-756-0071)
2230 RIDGEWIND WAY, WINDERMERE, FL 34786
$1,349,00013 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 Agent: Tim Frush (407-284-9222)
5074 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786
$7,250,000141 Days on yellowkey MLS ID: O6373191
REDUCED by $345,000 (4.5%) on 05/21/2026
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 7099 Built: 1988Monthly Fee: $1,224 Tax: $21,279 (2024)Community: IsleworthSingle Family
Taxes:$21,279
Tax Year: 2024
Remarks: A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 7,000 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the two-story home features 5 bedrooms, 6.5 bathrooms, and a seamless blend of timeless modern design and resort-style living. A striking 10-foot custom pivot door welcomes you into light-filled interiors, where elegant European porcelain tile and expansive open living spaces create a bright, elevated ambiance. Designed for both entertaining and everyday living, the main living areas flow effortlessly through expansive sliding glass doors to a stunning outdoor retreat, complete with a fully retractable screen enclosure. The chef’s kitchen serves as the centerpiece of the home, appointed with top-of-the-line appliances, custom European cabinetry, designer countertops, and an oversized island. A hidden chef’s pantry and temperature-controlled wine cellar enhance both functionality and style. The main-level primary suite offers a private, resort-inspired retreat, featuring a custom walk-in closet, a versatile bonus room ideal for fitness or wellness, and a dedicated in-home spa room. The spa-like primary bath includes a soaking tub, expansive walk-in shower, and a tropical outdoor shower, creating a tranquil escape. Upstairs, the newly constructed addition includes a secondary primary suite with a luxurious bath and walk-in closet, additional en-suite bedrooms, a spacious game room with access to a grand balcony overlooking panoramic golf course views, and a refined home theater. Outdoor living is equally impressive, featuring a sleek pool and heated spa, outdoor kitchen, wet bar, surround sound, and lush, manicured landscaping designed for privacy and enjoyment. Additional highlights include a fully integrated Crestron smart home system controlling lighting, audio, climate, and security, as well as a brand-new Generac generator for uninterrupted comfort. Fully remodeled and upgraded throughout, this residence presents a rare opportunity to own a like-new luxury estate in one of Central Florida’s most prominent communities.
Listing is courtesy of: MEM REALTY GROUP (407-/58-3702)
Listing Agent: Armaan Memarpouri (407-583-7028)
13327 LAKE CLARICE DR, WINDERMERE, FL 34786
$2,180,0006 Days on yellowkey MLS ID: O6411453
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4867 Built: 2007Monthly Fee: $200 Tax: $23,806 (2025)Community: The Estates At Lake ClariceSpa: YesSingle Family
Taxes:$23,806
Remarks: Nestled on 1.26 pristine lakefront acres within the exclusive Estates at Lake Clarice community and zoned for top-rated public schools, this custom-built estate offers an extraordinary blend of luxury, privacy, and lifestyle in the heart of Windermere. With expansive lake frontage and the opportunity to build your own private dock or gazebo, the property showcases breathtaking water views and even nightly Disney fireworks displays from the comfort of home. Adding to its rare appeal, HOA-owned land and a pond directly across the street ensure no front or rear neighbors, creating a truly serene and private setting. Designed with both elegance and functionality in mind, this impressive 5-bedroom, 4-bath residence features formal living and dining rooms, a private office, and an upstairs bonus/theater room. Complementing the home’s timeless architecture, soaring 12-foot ceilings on the main level and 9-foot ceilings upstairs create a bright and airy atmosphere throughout. From the moment you step through the grand wrought iron and glass entry doors, custom details shine with extensive moldings, intricate ceiling details, and rich hardwood flooring. The private office/study offers a wine cellar, while the luxurious primary suite features a sitting alcove, dual vanities, and a customized walk-in closet. At the heart of the home, the open-concept kitchen is designed for gathering and entertaining, complete with stainless steel appliances, stacked cabinetry with glass accents and lighting, granite countertops, an oversized island, breakfast bar, gas range, and seamless flow into the family room. Framed by expansive windows and French doors, the family room showcases a stunning stone gas fireplace, custom built-ins, and panoramic lake views that beautifully bring the outdoors in. Upstairs, four oversized secondary bedrooms and a spacious bonus/theater room are connected by a second staircase leading directly to the family room below. Outdoor living is equally impressive, with expansive covered porches on both levels — a standout architectural feature admired throughout the neighborhood — offering the perfect spaces to unwind and enjoy the picturesque surroundings. The screened resort-style pool and spa with paver decking, reaching 6 feet deep, provide ample space for recreation and entertaining, while the covered lanai and summer kitchen with grill, refrigeration, and gas outdoor grill connection create the ultimate outdoor retreat. Additional highlights include a spacious laundry room, oversized 3-car garage, Andersen windows newly installed on two-thirds of the home in 2025, and ample room on the expansive lot to build an additional garage, guest house, or mother-in-law suite. This remarkable lakefront estate offers timeless elegance, unmatched privacy,
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Rita Phillips (407-928-0573)
7867 BERKSHIRE OAK ALY, WINDERMERE, FL 34786
$539,00013 Days on yellowkey MLS ID: S5149947
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2221 Built: 2017Monthly Fee: $133 Tax: $7,755 (2025)Community: Westside VillageSpa: NoSingle Family
Taxes:$7,755
Remarks: Luxury Living in the Heart of Windermere! Welcome to this beautifully maintained 4 bedrooms and 2.5 bathrooms, single family home, located in the highly desirable community of Windermere. Situated on a charming alley-style streetscape, this elegant property offers the perfect blend of comfort, style, and convenience in one of Central Florida’s most sought-after locations. This spacious home features an open and functional floor plan with abundant natural light, generous living and dining areas, and thoughtfully designed spaces ideal for both everyday living and entertaining. Enjoy a fresh updated feel with NEW interior paint and NEW exterior paint, enhancing both the beauty and curb appeal of the home. The kitchen offers ample cabinetry, modern appliances, and a functional layout overlooking the main living area. The primary suite provides a relaxing private retreat with an en-suite bathroom and spacious closet space, while additional bedrooms flexibility for family, guests, or a home office. Enjoy outdoor Florida living with a private patio/backyard area perfect for relaxing or hosting gatherings. The community features beautifully maintained surroundings and convenient access to nearby parks, walking trails, and recreational areas. Ideally located just minutes from shopping, dining, top-rated schools, major highways, and world-famous attractions, including nearby Walt Disney World Resort. Easy access to Orlando, Winter Garden, and surrounding areas makes this an exceptional opportunity for homeowners seeking both convenience and lifestyle. Don’t miss your opportunity to own this beautiful Windermere home—schedule your private showing today!
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: James Song (407-405-3140)
6820 THORNHILL CIR, WINDERMERE, FL 34786
$520,00046 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
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
$1,875,000213 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
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)
12633 HADDON DR, WINDERMERE, FL 34786
$650,0007 Days on yellowkey MLS ID: O6411199
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3000 Built: 2003Monthly Fee: $82 Tax: $7,410 (2025)Community: Lakes WindermereSpa: NoSingle Family
Taxes:$7,410
Remarks: Sitting on a premium corner lot with mature landscaping, this beautiful Kensington model by Ashton Woods is located in the highly sought-after Lakes of Windermere community! Offering nearly 3,000 sq ft, this move-in ready home has been meticulously cared for and features room for a future pool. Recent updates include a new roof (2024), new downstairs A/C (2026), upstairs A/C (2023), upgraded Stainmaster PetProtect carpet (2026), quartz countertops, marble backsplash, cabinet lighting, paver patio, aluminum fencing, and updated landscaping. Inside, you’ll love the open split-bedroom floor plan, crown molding, upgraded flooring, and spacious kitchen with tons of cabinet space and stainless steel appliances overlooking the family room with custom built-in entertainment center wired for home theater. Upstairs 5th bedroom with full bath could also make the perfect theater room, game room, and guest suite. Lakes of Windermere offers a welcoming small-town atmosphere with resort-style amenities including a fishing dock, junior Olympic-size community pool, tennis courts, playgrounds, and organized recreational activities. Ideally located just minutes from Disney, Winter Garden Village, I-4, SR 408, and the Florida Turnpike.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Amy Brown (443-851-1508)
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