Displaying: For Sale
Location: Windermere
Property Type(s): Single Family
Price: $1,000,000+
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Windermere - 178 properties found
9648 WEATHERSTONE CT, WINDERMERE, FL 34786
$2,500,00050 Days on yellowkey MLS ID: O6400680
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4482 Built: 2000Monthly Fee: $227 Tax: $20,450 (2025)Community: Weatherstone On Lake OliviaSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$20,450
Elementary School: Thornebrooke Elem
High School: Olympia High
Tax Year: 2025
Middle School: Gotha Middle
Remarks: Set within the private gates of Weatherstone on Lake Olivia, this stunning spring fed lakefront residence offers a rare opportunity to enjoy refined living along the peaceful shoreline of Lake Olivia in Windermere. Situated on an expansive lakefront homesite, an increasingly rare find in this area, the property provides exceptional space, privacy, and unobstructed water views. Boasting 6 bedrooms and 4 full baths, the home blends classic design with thoughtful updates and an inviting, functional layout. A charming wraparound front porch creates a warm first impression, surrounded by mature landscaping and tranquil views, perfect for relaxing mornings or unwinding at the end of the day. Inside, natural light fills the home, highlighting soaring ceilings, rich wood flooring, plantation shutters, crown molding, and carefully curated designer details. The open concept design allows for effortless flow between the main living spaces, many of which capture picturesque lake views. At the center of the home, the updated kitchen serves as a true gathering place, featuring generous prep space, a large island, stainless steel appliances, and a spacious dining area. Two oversized walk in pantries, one with a concealed bar, offer both convenience and a touch of character. The primary suite is located on the first floor, offering serene lake views, a spacious custom closet, and a beautifully redesigned bathroom with dual quartz vanities, a soaking tub, and a walk in shower. The first floor also includes a private office with custom built ins, an additional family room, or optional formal dining space, and a full bath. Upstairs, a well planned layout provides flexibility and privacy with five secondary bedrooms, some connected by updated Jack and Jill baths, plus a dedicated workspace with built in features on the landing area. An additional oversized bonus room with closet can easily function as a media room or play space. The home previously had a large loft area which could quite easily be converted back. Additional highlights include a first floor laundry room, abundant storage throughout, an updated tile roof, refreshed exterior paint, and a three car garage with epoxy flooring and built in storage. Designed for entertaining, the outdoor living space features a covered lanai, summer kitchen, resort style pool, fire pit, artificial turf dog run, and a Trex dock with boat lift, all overlooking the calm waters of Lake Olivia, where you can water ski, have fun on your boat or jet ski’s or just enjoy a calm ride on your paddle boards, the fun is endless. The gently sloping homesite enhances the home’s elevated position, maximizing lake views while naturally directing rainwater away from the property, an often overlooked advantage in Florida lakefront living. It also adds character to the outdoor space, creating a more dynamic and enjoyable setting for both relaxation and play. With only 13 homes, Weatherstone Ct offers a boutique gated setting just moments from local favorites like The Yellow Dog Eats, parks, top rated schools, and the heart of Windermere. This is lakefront living at its finest, private, spacious, and beautifully appointed. Ideally located with direct access to all the major highways, the home provides seamless connectivity to destinations throughout Central Florida and beyond, while still maintaining a quiet, tucked-away feel.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Andy Neal (407-619-3517)
11015 HAWKSHEAD CT, WINDERMERE, FL 34786
$1,529,99920 Days on yellowkey MLS ID: O6405977
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
Elementary School: Windermere Elem
High School: Windermere High School
Middle School: Bridgewater Middle
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)
6117 LOUISE COVE DR, WINDERMERE, FL 34786
$5,250,000151 Days on yellowkey MLS ID: O6372197
0 Days Off yellowkey (back on 5/21/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5752 Built: 2002Monthly Fee: $1,224 Tax: $50,728 (2025)Community: Isleworth WestSingle Family
Taxes:$50,728
Remarks: Under contract-accepting backup offers. Nestled along the shores of Lake Louise within Isleworth West, this exceptional two-story estate represents the finest in lakefront living. Offering four bedrooms, four-and-a-half baths, and more than 5,700 square feet of living space, the residence has been fully reimagined with sophisticated, modern finishes throughout. Recent enhancements include a new roof, windows, and doors; an all-new boat dock including a new roof; a new summer kitchen; exquisite white marble flooring, a dramatic glass-and-iron double-door entry, sleek modern air vents, and a host of elevated appointments that create a seamless blend of style and comfort. Grand living spaces—including the living room, kitchen, and family room—all feature soaring ceilings and an abundance of natural light, providing an ideal backdrop for both elegant entertaining and everyday living. The first-floor primary retreat is a true sanctuary, featuring a spacious bedroom and private sitting room divided by a stunning double-sided fireplace. A secondary primary suite, also located on the first floor, offers exceptional privacy and flexibility for guests or multigenerational living. Outdoors, the estate embraces its idyllic lakefront setting with a resort-style pool, summer kitchen, and private boat dock offering direct access to Lake Louise—perfect for boating, sunset cruises, and lakeside leisure. This is a rare opportunity to experience lakefront living at its finest in one of the community’s most coveted settings.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Sarah Longwell (407-920-8451)
4226 DOWNEAST LN, WINDERMERE, FL 34786
$10,500,000228 Days on yellowkey MLS ID: O6355233
REDUCED by $1,300,000 (11.0%) on 04/08/2026
Bed: 5 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 5316 Built: 1980 Tax: $10,926 (2024)Community: NaSingle Family
Taxes:$10,926
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: Dramatic price improvement on this exceptional 5+ acre Lake Down development opportunity, offering 300 feet of pristine shoreline on the coveted Butler Chain of Lakes and positioned on the best side of Windermere with unmatched convenience to SR-408 and downtown Orlando. This rare parcel, zoned R-CE, allows for the creation of up to three luxury lakefront homes or a single premier estate compound, all while enjoying the prestige of a Windermere address with immediate access to Isleworth, Bay Hill, and downtown Windermere. The property includes an existing 5,000 sq ft home with five bedrooms, 3.1 baths, and an oversized four-car garage—ideal as a temporary residence or teardown for redevelopment. Beyond its development potential, the land itself is a natural sanctuary: mature trees and lush landscaping create a haven for native birds, passion flower vines attract vibrant butterflies, and natural Florida water plants along the shoreline provide a thriving nursery habitat for breeding wildlife and small fish. This is a rare chance for developers, custom builders, or investors to deliver exceptional lakefront homes in one of Central Florida’s most desirable luxury corridors. Also listed as Residential MLS #6367852.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Thad Czapka (407-257-4253)
12718 WINDERMERE ISLES PL, WINDERMERE, FL 34786
$1,490,00054 Days on yellowkey MLS ID: O6399958
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3487 Built: 1997Monthly Fee: $130 Tax: $6,661 (2025)Community: Isles WindermereSpa: YesSingle Family
Taxes:$6,661
Remarks: Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situated on a sprawling nearly one-acre lot, this beautifully remodeled home offers an exceptional blend of privacy, space, and elegance. Enjoy serene views of the expansive backyard and picturesque koi pond from the spacious shaded patio or the screened rear porch. The outdoor living area is designed for true Florida living, featuring a sparkling pool and spa, perfect for relaxing or entertaining. Adding to the sense of tranquility, one side of the property has no direct neighbors—only beautifully maintained green space and a scenic bridge, creating gorgeous views and a rare feeling of serenity. Inside, the home features generously sized rooms filled with comfort and charm, including an oversized family room with a wood-burning fireplace. The primary suite is a private retreat, complete with a luxurious bath featuring dual sinks, a jetted garden tub, a large walk-in shower, and a full vanity area. Every detail has been thoughtfully updated with style and functionality in mind. Additional highlights include a three-car garage with ample space for parking and storage, as well as a prime location within a top-rated public school district, just minutes from Windermere’s premier shopping, dining, and recreation. A rare opportunity to own a beautifully updated home in one of Central Florida’s most desirable communities.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Patricia Zimath, Llc (321-318-1050)
5106 TILDENS GROVE BLVD, WINDERMERE, FL 34786
$1,600,00062 Days on yellowkey MLS ID: O6397273
2 Days Off yellowkey (back on 5/20/2026)
REDUCED by $100,000 (5.9%) on 05/13/2026
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4572 Built: 2006Monthly Fee: $317 Tax: $12,584 (2025)Community: Tildens Grove Ph 02Spa: YesSingle Family
Taxes:$12,584
Remarks: Under contract-accepting backup offers. PARADISE…FOUND. Welcome to this incredible custom-built executive home in Windermere’s esteemed & highly desired Tildens Grove community which welcomes you with 24-hour guard gated security and beautiful quiet tree-lined streets. Get ready for LUXURY around every corner of this home spanning nearly 6,000 square feet of indoor & outdoor living space. Starting with one-of-a-kind curb appeal, this gorgeous home sits on a large lot measuring ½ acre with endless views of beautiful greenspace & water, mature trees & extensive landscaping…peace, privacy & serenity are all yours. Live the Florida lifestyle OUTDOORS in your fully screened resort style saltwater pool & spa with an oversized travertine lanai patio complete with summer kitchen…an incredible outdoor living space ideal for entertaining or enjoying in solitude. The fantastic & flexible floor plan begins with solid wood six lite double entry doors into a grand welcoming foyer which flows directly into the large living spaces. Extremely tall ceilings on both first & second floors with stunning coffered trim details in each room and TONS of gorgeous windows & natural light throughout. The incredible gourmet kitchen is the HEART of this home featuring a large center island, custom cabinetry, recently upgraded quartz countertops & backsplash, built-in appliances including wood-panel refrigerator, wine/beverage cooler, Fisher and Paykel double dishdrawers, walk-in pantry…for the professional chef or amateur, you couldn’t ask for more! Interior & Exterior Neutral Paint in 2022. Custom Closet Built-ins. Plantation Shutters Throughout. This functional floor plan features SIX (6) large bedrooms, FOUR (4) full bathrooms and ONE (1) half bath (four bedrooms & three full baths on first floor -- two bedrooms & one full bath PLUS huge bonus room with half bath & wet bar plumbing on second floor). Large laundry room with tons of built-in cabinets & storage spaces, desk area plus full-sized fridge/freezer. Oversized three car garage with built-in storage and large paver driveway for plenty of parking space. Whole House Aquasana Water Filtration System. Pet-Free Home. The PERFECT location -- you can be tucked AWAY FROM IT ALL, yet located just minutes from shopping, dining, golf and major highways and roadways for easy access to anywhere in Central Florida & beyond -- 18 miles to Downtown Orlando, 25 miles to Orlando International Airport (MCO), 9 miles to world-famous “Restaurant Row” and Arnold Palmer’s Bay Hill, 7 miles to Walt Disney World. In addition to the 24-hour guard gated security (one gate only for entry/exit), Tildens Grove offers a beautiful community park area with large playground, tennis & pickleball courts, basketball court & soccer field. A+ public schools plus options for Windermere Prep & Foundation Academy within minutes. This is THE ONE you have been waiting for…WELCOME HOME!
Listing is courtesy of: TARA MOORE REAL ESTATE (407-738-5588)
Listing Agent: Tara Moore (407-765-3700)
11753 VINCI DR, WINDERMERE, FL 34786
$2,150,00035 Days on yellowkey MLS ID: O6404892
1 Days Off yellowkey (back on 5/20/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4037 Built: 2012Monthly Fee: $298 Tax: $22,953 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$22,953
Remarks: Under contract-accepting backup offers. Tucked away in “The Gardens” of the desirable guard gated golf course and lakefront community of Keene’s Pointe, this beautifully maintained 4-bedroom, 4.5-bath residence offers 4,037 square feet of thoughtfully designed living space on nearly a half-acre pond front homesite. Lovingly used only as a vacation home by its current original owners, the property presents in exceptional, like-new condition—showcasing pristine finishes, high-end appliances, and 12 to 14 ft ceiling heights throughout this estate home. This versatile floor plan features the primary retreat on the main floor along with two oversized secondary bedrooms that share a deluxe full bathroom and a spacious 4th Bedroom with a full bath located just steps from the pool. The floor plan’s flexibility is further enhanced by a second floor bonus room that would make a fabulous 5th Bedroom or office to include a sitting area, large full bathroom and walk in closet. Enter through elegant double doors into an inviting great room that seamlessly connects to a well-appointed kitchen and breakfast nook with pool views and an open concept living area - perfect for both everyday living and entertaining. Step outside to a covered paver patio overlooking a private backyard oasis featuring a deluxe summer kitchen with natural gas grill and wet bar as well as a saltwater pool, heated spa, and fully fenced yard. Enjoy tranquil pond views complete with a lighted fountain, stunning sunset vistas, and even Disney fireworks in the distance. Additional highlights include a three-car garage and paver driveway, enhancing both curb appeal and functionality. Built in 2012, this is one of the newer homes in Keene’s Pointe offering modern construction, double pane windows, timeless design, and an unbeatable setting.
Listing is courtesy of: KEENE'S POINTE REALTY (407-876-8879)
Listing Agent: Angela Durruthy (407-496-5811)
9648 MCCORMICK PL, WINDERMERE, FL 34786
$3,800,000256 Days on yellowkey MLS ID: O6346918
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4751 Built: 1988Monthly Fee: $1,224 Tax: $33,873 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$33,873
Remarks: Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an oversized modern built-in featuring slate stonework and lit shelves. The spacious master suite features a large sitting area and an en-suite bathroom with dual vanities, a walk-in closet, modern soaking tub and separate walk-in shower. Completing the main level are the home office, formal dining room, elegant powder bath and center-island kitchen with casual dining area. Two additional bedrooms with balcony access are on the upper level. Step outside and discover a newly reimagined outdoor living experience. The expansive pool deck has been fully updated with sleek new pavers, while fresh turf and lush landscaping create a vibrant backdrop for relaxation and entertaining. A striking glass wall encases the pool area, maximizing panoramic views of both the golf course and the lake. The outdoor kitchen has been thoughtfully upgraded with new granite, a built-in grill, pizza oven, sink, and designer lighting—seamlessly blending function with style. Enjoy evenings around the modern fire pit, take a dip in the resurfaced pool with its brand-new heater, or unwind in the extended backyard, which offers an additional 15 feet added to one side of the property. Every detail of this outdoor transformation has been designed to enhance both beauty and livability, making this property the perfect retreat for year-round enjoyment.
Listing Agent: Michelle Corbin (407-491-2690)
4806 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786
$4,200,00021 Days on yellowkey MLS ID: O6408804
0 Days Off yellowkey (back on 5/19/2026)
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5695 Built: 2008Monthly Fee: $1,224 Tax: $41,679 (2025)Community: IsleworthSpa: YesSingle Family
Taxes:$41,679
Remarks: Under contract-accepting backup offers. Located within the Gardens Villas enclave of Isleworth Golf & Country Club, this updated and spacious estate epitomizes luxury living. Offering an impressive 5,695 square feet of meticulously designed living space, this villa presents an exquisite blend of elegance, comfort, and modern convenience, complemented by an array of exceptional features and amenities.The property encompasses five generously appointed ensuite bedrooms, ensuring residents and guests enjoy the utmost privacy and convenience, along with a dedicated office space ideally suited for professionals working from home. The spacious chef’s kitchen is outfitted with high-end Viking, Wolf, and TRUE appliances, abundant storage, a butler’s pantry, and an adjacent entertaining bar designed for effortless hosting. Enhancing both peace of mind and functionality, the residence is equipped with a Moen whole-home water management system, along with a sophisticated home automation and security system that controls many of the home’s key functions. Designed to embrace the Florida lifestyle, the outdoor living spaces are equally exceptional. A private pool and spa, expansive lanai, and fully appointed summer kitchen create the perfect setting for relaxing or entertaining while enjoying the picturesque surroundings. In every detail, this Garden Villa exemplifies the pinnacle of luxury living by seamlessly combining spacious design, refined finishes, advanced smart-home technology, and thoughtfully curated custom features. Whether enjoying the tranquility of the Gardens, entertaining poolside, or working from the comfort of your private office, this residence offers an unparalleled lifestyle of distinction.
105 PINE STREET, WINDERMERE, FL 34786
$2,500,00033 Days on yellowkey MLS ID: O6405163
3 Days Off yellowkey (back on 5/19/2026)
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5696 Built: 2015 Tax: $16,804 (2025)Community: WindermereSpa: YesSingle Family
Taxes:$16,804
Remarks: Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques, and the weekly farmers market. Built in 2015 and thoughtfully expanded, this 5,696 square foot home features five bedrooms and five and a half bathrooms, including a fully separate casita ideal for in-law living, guests, or private quarters. From the moment you arrive, fresh landscaping and an exposed brick front porch create a warm and inviting entrance. Inside, the open living space is both spacious and comfortable, with high ceilings, wood beams, crown molding, and a gas fireplace, complemented by shiplap and exposed brick accents. The kitchen opens seamlessly to the main living area and overlooks the backyard, featuring a large Cambria quartz island, Kohler farm sink, walk-in pantry, Bosch double ovens, Viking gas cooktop, custom hood, LG refrigerator, soft-close cabinetry, under-cabinet lighting, and a dedicated coffee bar. The primary suite offers peaceful backyard views, two custom walk-in closets, and a well-appointed bath with dual vanities, a makeup station, a garden tub, and a large walk-in shower with floor-to-ceiling tile and dual showerheads. Additional bedrooms are thoughtfully placed, including one with an ensuite bath. A versatile flex room with a coffered ceiling, storage, and its own laundry setup connects to a private office with built-ins and a walk-in closet. A secondary primary suite provides a comfortable space for extended family or guests. In total, the home offers three separate laundry areas for added convenience. Outdoor living is designed for true Florida living. Two sets of sliding glass doors, including one from the flex room, open to a covered lanai with wood plank ceiling and fans, along with a fully equipped summer kitchen featuring an Artisan natural gas grill, vent hood, sink, and icemaker. The space extends to an expansive paver patio surrounding a heated saltwater pool and spa with water features, all overlooking a large fenced backyard. The casita, completed in 2023 and offering over 1,200 square feet, lives like a private residence with its own entrance and Spanish Mediterranean character, including wood beams, hardwood flooring, and a Kiva-style fireplace. It features a full living room, a kitchen with GE Café appliances and a quartz island, and a spacious bedroom suite with a custom walk-in closet and a beautifully finished bath. A screened lanai and separate fenced yard provide added privacy. A three-car garage with high ceilings includes an oversized RV-height door, 50-amp plug, and space for additional storage or lifts, along with a third laundry area. Additional features include dual AC systems, tankless water heaters, and a Generac generator. Residents of Windermere enjoy private access to the Butler Chain of Lakes, parks, tennis courts, and a boat ramp, all golf cart accessible. Golf cart friendly with tree-lined streets and a true small-town feel. No HOA and conveniently located near top-rated schools, major roadways, and world-class dining and entertainment. This is a truly unique Windermere home designed for modern multigenerational living. Schedule your private showing today!
Listing is courtesy of: ALIGN REAL ESTATE LLC (305-389-2922)
Listing Agent: Tiffany Pantozzi (407-955-9716)
11449 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$1,680,00053 Days on yellowkey MLS ID: O6399319
REDUCED by $50,000 (2.9%) on 05/19/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4648 Built: 1995 Tax: $19,423 (2025)Community: Lake Butler EstatesSpa: YesSingle Family
Taxes:$19,423
Remarks: Discover Windermere’s charm and classic style from this stunning Victorian-style pool home, set on a 1-acre lot with no HOA, on one of the most desirable streets. Under the canopy of majestic oaks, this 5-bedroom residence features a dedicated office space and a versatile bonus room ideal for a private apartment or guest suite. A charming wrap-around porch welcomes you into a classic foyer featuring rich wood floors, soaring ceilings, custom millwork, and a graceful grand staircase. Throughout the home, you’ll find exquisite traditional details including dental crown molding, chair rails, and beautifully crafted trim. The spacious formal dining room is filled with natural light and accented by warm wood flooring. The kitchen blends style and function with stainless steel appliances, granite countertops, an island, walk-in pantry, custom cabinetry, and a lovely view of the pool with newly installed screen enclosure. All main living areas are carpet-free, and every bathroom has been thoughtfully updated with travertine flooring, porcelain showers, and marble countertops. The owner’s suite is located upstairs and features bay windows, wood floors, crown molding, and a walk-in closet. Its luxurious bath includes a frameless glass stone shower, dual vanities, and an elegant vessel tub. There’s an added finished and air-conditioned attic playroom above one of the bedrooms for children to explore. Plus the expansive bonus room accessible off the primary bathroom is a spacious and secluded hang out room and offers an optional private entrance leading to the large backyard—complete with a sparkling pool, generous patio space, and room to store a boat. The oversized 3-car garage provides exceptional clearance for larger vehicles, golf carts, and lake toys. Town of Windermere residents have private access available to the Butler Chain via a town boat ramp plus town tennis courts. Home is walking distance to downtown and the weekly farmer’s market, monthly food trucks, and the quaint shopping district.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
84 OAKDALE ST, WINDERMERE, FL 34786
$1,875,000148 Days on yellowkey MLS ID: O6372842
1 Days Off yellowkey (back on 5/19/2026)
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3519 Built: 2020 Tax: $12,265 (2024)Community: Davis ShoresSpa: YesSingle Family
Taxes:$12,265
Remarks: Welcome to 84 Oakdale Street, an exceptional luxury residence in the heart of Windermere, Florida, crafted by the renowned Element Home Builders—a rare opportunity to own one of their highly sought-after homes. Situated on a premium corner lot, this elegant 4-bedroom, 4 full and 2 half bath home showcases refined craftsmanship, a thoughtfully designed open floor plan, and sophisticated finishes throughout. The expansive living spaces are filled with natural light and flow seamlessly into a designer kitchen ideal for both entertaining and everyday living. The primary suite offers a serene private retreat with a spa-inspired bath, while additional bedrooms provide comfort and privacy for family and guests. Outdoor living is elevated with a private resort-style pool, creating the perfect setting for relaxing or entertaining year-round. Enjoy the convenience of being just a short golf cart ride to charming downtown Windermere, offering boutique shopping, dining, community events, and the weekly farmers market. Located in one of Windermere’s most desirable communities, just minutes from top-rated schools, upscale dining, golf, shopping, and the Butler Chain of Lakes, this home delivers timeless luxury, quality construction, and an unbeatable location. This exceptional home is a rare offering and will not last—schedule your private tour today.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Carolina Dumit (407-325-8963)
6036 GREATWATER DR, WINDERMERE, FL 34786
$1,999,99950 Days on yellowkey MLS ID: O6400277
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4013 Built: 2001Monthly Fee: $298 Tax: $15,493 (2024)Community: Keenes PointeSpa: YesSingle Family
Taxes:$15,493
Remarks: Classic elegance defined in this stately Keene’s Pointe residence, set along the 17th Fairway of the renowned Jack Nicklaus Signature Golf Course. An impressive grand foyer with warm hardwood flooring greets guests to a traditional-style home with office and formal plus family living spaces on the first floor, along with a guest suite. The primary bedroom and two other secondary bedrooms are upstairs, offering an elevated view of the golf course. A balcony spans the second floor of the home. All bedrooms feature new carpet and fresh interior paint and LED lighting. The updated kitchen features striking white cabinetry, stainless WOLF double ovens and gas cooktop with hood, Sub Zero built-in refrigerator, dishwasher, and two fridge drawers. A butler’s pantry off the dining room is perfectly suited with a beverage fridge and Miele espresso coffee bar. A covered back patio and summer kitchen is the ideal complement to the refreshing pool and paver patio, for outdoor entertaining. Roof replaced in 2023. New HVAC for the upstairs in 2024. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.
13304 BELLARIA CIR, WINDERMERE, FL 34786
$2,798,00071 Days on yellowkey MLS ID: O6391558
REDUCED by $70,000 (2.4%) on 05/19/2026
Bed: 6 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4920 Built: 2013Monthly Fee: $483 Tax: $30,699 (2025)Community: BellariaSpa: YesSingle Family
Taxes:$30,699
Elementary School: None
High School: None
Middle School: None
Remarks: Some residences are simply houses. Others are a statement. Welcome to Casa Pietra — an exceptional estate nestled within Bellaria, one of Windermere's most exclusive guard-gated communities, where only 64 homes share the privilege of calling this address home. Set on nearly ¾ of an acre with serene water views, this meticulously curated two-story residence offers just under 5,000 square feet of refined living space — 6 bedrooms + office, 6 full bathrooms, and a seamless open-concept floor plan designed for both grand entertaining and intimate everyday living. From the moment you arrive, the travertine-accented façade, symmetrical palm-lined circular driveway, and manicured grounds signal that this is no ordinary home. Step inside and the interiors reveal the same intentionality: soaring ceilings, wide-plank flooring, crown molding, a dramatic stone fireplace wall, custom built-in shelving, and floor-to-ceiling windows that flood every room with natural light — and frame the resort-style backyard like a living work of art. The gourmet kitchen is anchored by a generous island, custom cabinetry, Thermador stainless steel appliances, a butler's pantry, and an oversized walk-in pantry — a space where function and elegance coexist without compromise. The main-floor primary suite offers a private sanctuary with a spa-inspired bathroom designed for true restoration. Upstairs, a second primary suite with private balcony, morning kitchen, and dual custom walk-in closets provides a retreat within a retreat — along with three additional en-suite bedrooms and a loft lounge area. Outside, the resort-style pool and spa — recently resurfaced and elevated with fire bowls, deck tile, and a built-in summer kitchen — anchor a breathtaking backyard designed for the Florida lifestyle at its finest. An aerial view reveals the true scale of the grounds: a dramatic allée of mature palms flanking the pool terrace, generous green space, and total privacy secured by lush hedgerows on all sides. Additional highlights include a 3-car garage, home automation system, gas fireplace, full security system with cameras, wine refrigerator, and landscape lighting — all thoughtfully updated and impeccably maintained. Zoned for top-rated Orange County schools, minutes from Winter Garden Village, upscale dining, and with easy access to major roadways — Casa Pietra is a rare convergence of location, lifestyle, and lasting value. Elegance is not decoration. It is a way of being.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Caroline De Castro Marcellini (561-319-9009)
1330 LAKE OLIVIA, WINDERMERE, FL 34786
$5,500,00075 Days on yellowkey MLS ID: S5144942
Bed: 6 Bath: 7.0 Gar: 4 Liv Area Sq Ft: 6442 Built: 2026Monthly Fee: $400 Tax: $9,870 (2024)Community: Lake Olivia ReserveSpa: YesSingle Family
Taxes:$9,870
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. This is a lakefront estate currently under construction in Windermere, set on the shores of Lake Olivia with wide, unobstructed water views and rare privacy. This future residence will have 6 bedrooms, 6 full baths, and 2 half baths across 6,400+ sq ft, with 12’ ceilings on the main level, 10’ ceilings above, and expansive windows designed to frame the lake. Planned features include a gourmet kitchen with premium cabinetry and quartz surfaces, dual primary suites, private elevator, theater room, wet bar, and 4-car garage.Outdoor living will include a resort-style lanai, summer kitchen, custom pool and spa, and a private dock with direct lake access.Set on approximately 1.6+ acres in one of Windermere’s most desirable locations, this is a rare opportunity to secure a brand-new lakefront residence before completion.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Ana Rubio (786-207-8352)
9343 TIBET POINTE CIR, WINDERMERE, FL 34786
$7,950,000543 Days on yellowkey MLS ID: O6264629
Bed: 7 Bath: 9.0 Gar: 4 Liv Area Sq Ft: 8362 Built: 2004Monthly Fee: $283 Tax: $65,265 (2024)Community: Keenes Pointe Unit 03 46/104Spa: YesSingle Family
Taxes:$65,265
Remarks: PRICE Improvenent!! Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought iron and glass doors add a refined entry. Opening to the two-story formal areas featuring timeless elements of stone flooring, elegant ceiling details, clerestory windows, and expansive lake views set a modern tone. At the center of the home, the kitchen is a chef's dream; stone flooring and a massive working island, state-of-the-art appliances combine function and beauty with double ovens, exotic granite, stunning glazed custom cabinetry, and a huge walk-in pantry. The gourmet kitchen opens naturally to the family gathering areas, complete with sparkling lake views. A fireplace shares the media wall with a built-in entertainment center, while French doors give access to the outdoors. Just off the family area, the game room is finished with a beautiful bar area. The state-of-the-art home theatre is located just off the game room. Entertain outdoors in true Florida style; the outdoor gourmet area was added in 2019, including a large bbq grill area, massive dining/working island, wine cooler, XL Fridge as well as a pizza oven. The free-form pool, heated spa, and boat dock with lift. The master suite is private with huge master closet and beautifully finished master bath. All secondary bedrooms are ensuite. All baths have been updated. The entire home has been freshly painted and all carpet has been replaced. The detached guest house is great for extended family.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Juan Delgado (407-744-4469)
9621 WINDY RIDGE RD, WINDERMERE, FL 34786
$13,430,00050 Days on yellowkey MLS ID: O6400740
REDUCED by $100,000 (0.7%) on 05/19/2026
Bed: 9 Bath: 13.0 Gar: 8 Liv Area Sq Ft: 20445 Built: 2025 Tax: $13,931 (2025)Community: Windsor HillSingle Family
Taxes:$13,931
Remarks: Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.Two Pools one outdoor with a swim up bar and grill area and the other indoor pool with a spa and massage room ! Highlights: • Custom-built mansion in progress — secure it now to choose your colors, flooring, cabinetry, countertops, lighting, and finishes • Private helicopter pad for seamless arrival and departure • Luxury bowling alley in development — your private entertainment retreat of turn into extra car show storage garage area ! • Grand open floor plan, soaring ceilings, and estate-level architecture • Massive gourmet kitchen + walk-in pantry, ideal for chef-level entertaining • Space for home theater, gym, wine cellar, or guest quarters • Oversized garages and motor court • For our equestrian lovers, you are permitted one horse for each acre. Location Perks: • Situated in one of Windermere’s most coveted neighborhoods • Minutes to Lake Butler Chain, championship golf, and elite private schools • Close to Winter Garden Village and exclusive dining/shopping This is a rare opportunity to own a truly bespoke estate before completion — where every detail is yours to design, and your view is forever protected. Inquire now for private plans, customization walkthrough, and completion timeline. Step into your own private paradise with this one-of-a-kind resort-style property featuring every amenity for ultimate relaxation and recreation. Highlights include: • Lagoon-style pool with a swim-up bar, perfect for hosting or unwinding in luxury • Private spa sanctuary with a designated massage room and indoor heated pool, offering year-round wellness experiences • Full-size tennis court for active days and fun with friends or family • Charming barn – ideal for equestrian use, storage, or a stunning rustic event space Whether you’re dreaming of daily spa treatments, evening swims under the stars, or tennis matches followed by cocktails poolside, this property delivers the ultimate blend of luxury and leisure.
Listing is courtesy of: CITARELLI REALTY GROUP LLC (321-607-3586)
Listing Agent: Natalie Citarelli (321-607-3586)
2804 MARQUESAS CT, WINDERMERE, FL 34786
$1,999,00025 Days on yellowkey MLS ID: O6405937
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3649 Built: 1983Monthly Fee: $429 Tax: $13,604 (2025)Community: Lake Crescent ReserveSpa: NoSingle Family
Taxes:$13,604
Remarks: Under contract-accepting backup offers. Timeless architecture and design come together in this modern-traditional residence in the Town of Windermere, where lakefront living, community charm, and top-rated Windermere schools create one of Central Florida’s most desirable lifestyles. Rich in warmth and character with its classic brick exterior, this thoughtfully designed ranch home blends comfort, function, and classic American elegance. Set on Park Avenue, behind the gates of Lake Crescent Reserve, on a quiet cul-de-sac, this lakefront house sits on over an acre. A peaceful approach from the community entrance immediately sets a tone of privacy and serenity. The expansive windows, with water and nature views, welcome you home and fill the house with gorgeous natural light throughout the day. At 4,582 square feet under roof, with approximately 3,915 square feet of living space, the split floor plan features 5 bedrooms and 4 full baths, along with multiple gathering spaces designed for both entertaining and everyday living. From intimate to large family gatherings, the floor plan flows smoothly outdoors. This well-designed home offers a rare balance of openness, comfort, and privacy. The outdoor living experience is exceptional. The Cape Cod-style Florida room with panoramic sliders opens to the screened lanai, with a resort-style setting complete with a full summer kitchen, outdoor shower, pool, boathouse, private boat ramp, and boat mooring area, all overlooking the pristine waters of Lake Crescent. Well known for decades among water sports enthusiasts, Lake Crescent is a private 175-acre ski lake with exceptional water quality. While not part of the Butler Chain of Lakes, it shares the same water source and is listed on Florida’s Outstanding Florida Waters list, which recognizes efforts to preserve the lake’s natural beauty and quality. Adding to its appeal, Lake Crescent Reserve offers low HOA dues and is adjacent to the Windermere Recreation Center, with tennis courts, playgrounds, sports fields, and community events. Lake Crescent Reserve residents also enjoy a short bike or golf cart ride to Windermere Elementary and the charming downtown shops and restaurants along Main Street.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Kari Fleck (407-925-5283)
8340 LAKE BURDEN CIR, WINDERMERE, FL 34786
$3,250,00029 Days on yellowkey MLS ID: O6406513
0 Days Off yellowkey (back on 5/18/2026)
Bed: 6 Bath: 6.0 Gar: 4 Liv Area Sq Ft: 6848 Built: 2008Monthly Fee: $298 Tax: $28,798 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$28,798
Remarks: Under contract-accepting backup offers. Come visit this majestic and dreamy LAKEFRONT custom built Windermere estate that boasts 6,848 square feet in the prestigious guard gated Keene’s Pointe community on the pristine shores of Lake Burden. This home was designed to have lake views from practically every room which create a dramatic and magical setting to your every day living. This estate will impress your most discerning buyer. This home can either be 6 bedrooms or 5 bedrooms with an office plus 7 bathrooms! (5 full baths and 2 half baths). Feeling tired? Take the ELEVATOR to the second story and relax in your extravagant theatre overlooking the lake while watching your favorite movies. The upstairs theater could also be used as a loft, flex space, playroom, or gym. The sunsets are absolutely breathtaking from every vantage point and set this estate apart from all the rest. There are luxury details around every corner – from Wolff appliances, two dishwashers, custom built in’s, travertine flooring, stone details, intricate moldings, plantation shutters, and surround sound in practically every room. Come enjoy the massive sized mud room that was recently renovated and even has it’s own refrigerator and sink. Do you have a lot of cars or golf carts? Come enjoy the 4 CAR GARAGE with epoxy flooring to house your luxury automobiles. Another unique feature that this home has is two laundry spaces! One downstairs and one upstairs and all washers and dryers convey with property. You never have to worry about carrying clothes upstairs or downstairs. The owners retreat is located downstairs and the exquisite master closet has impeccable built in features with lots of storage. Everything in this home has been designed for comfort and convenience and no stone has been left unturned. The outdoor space will make you feel like your on vacation every day – from the outdoor kitchen, fireplace, resort style saltwater pool/spa, and sunset views for days. Upstairs you will find a spacious outdoor balcony that wraps around to enjoy more lake views. This estate has amazing curb appeal from the minute you pull up. There is a grand feel with the cathedral ceilings and magnificent foyer that showcases the desirable open floor plan that is great for entertaining. You will notice the remarkable architecture and charm that this home exudes. Your buyer will benefit from all the recent updates that the seller has done with this house. NEWER TILED ROOF. NEWER HVAC. BRAND NEW Tankless water heaters. A generator was also recently installed. Also, enjoy the lower water bill since irrigation is pumped from the lake (under $20 dollars per month!). Keene’s Pointe offers access to the Butler Chain of Lakes, a Jack Nicklaus Signature golf course, the Golden Bear Club, resort-style pool, tennis courts, fitness center, basketball court, a clubhouse. Come live the country club lifestyle all while living close to Disney and the theme parks!
Listing Agent: Jill Davis (407-579-5347)
9620 MAYWOOD DR, WINDERMERE, FL 34786
$2,400,00055 Days on yellowkey MLS ID: O6399315
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3004 Built: 1979 Tax: $20,433 (2025)Community: Lake Down ShoresSpa: NoSingle Family
Taxes:$20,433
Remarks: Lakefront living on the Butler Chain of Lakes in the heart of Windermere. This rare offering on Lake Down presents 100 feet of direct frontage, expansive water views and a private setting on a quiet cul-de-sac with no HOA. Set across 1.35 acres, this two-story pool home captures the essence of Windermere’s enduring lakefront lifestyle, where space, privacy, and natural beauty come together in a setting that feels refined and relaxed. From sunrise to sunset, the backdrop is nothing short of extraordinary. Sweeping views stretch across Lake Down, where calm morning waters give way to vibrant evening skies, and a nightly Disney fireworks view adds a subtle sense of wonder to the horizon. The property is thoughtfully oriented to take full advantage of its surroundings, featuring a private beach area, a two-story dock and direct access to the Butler Chain, one of Central Florida’s sought-after and interconnected lake systems, known for its recreational appeal and timeless value. Inside, the home offers a layout designed for everyday living and effortless entertaining. Spacious living and family rooms are complemented by an open kitchen appointed with granite countertops and stainless steel appliances, creating a central gathering space that flows naturally to the outdoors. A dedicated office or den provides flexibility for work or quiet retreat, while an upstairs loft captures elevated, panoramic views of Lake Down, an ideal setting for a secondary lounge, media space or creative studio. The outdoor experience is equally compelling. A resort-style pool anchors the backyard, accompanied by a screened porch and expansive lawn that extends toward the water’s edge. The setting invites relaxed afternoons and large-scale gatherings, with ample room to further enhance or personalize the landscape. A greenhouse and additional storage add charm and functionality, supporting a variety of lifestyle needs. A second-story balcony offers yet another vantage point, where elevated lake views and evening fireworks create a memorable daily backdrop. Whether enjoying a quiet morning coffee or winding down at sunset, this space reinforces the home’s seamless connection to its environment. Positioned in a peaceful and private location, yet just moments from renowned restaurants, shopping and everyday conveniences, the property offers a rare balance of seclusion and accessibility. Its location on one of the desirable stretches of Lake Down further underscores its long-term appeal. This is a compelling opportunity to enjoy the home as it exists today or to reimagine the site as an exceptional custom waterfront estate. In a setting defined by natural beauty, established luxury and enduring demand, properties of this caliber and positioning are increasingly rare.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Linda O'Grady (407-970-6880)
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