Location: Windermere, 34786
Do Not Show Listings
8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786
$322,000127 Days on yellowkey MLS ID: TB8465266
REDUCED by $3,000 (0.9%) on 05/14/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,422 (2024)Community: Lakeside/Lks/Windermere Ph 3Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,422
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: **$1000 Credit at Closing for Cosmetic Upgrades (with acceptable offer)!!!!**Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless appliances (2023 microwave, and upgraded dishwasher) lending a modern flair to the chef’s kitchen. Additional recent upgrades include a **2024 Carrier 15 SEER HVAC system** for comfort and energy efficiency throughout the year and **BRAND NEW 2025 new wood look porcelain tile** in all three bedrooms (NO CARPET). The generous primary suite and two additional bedrooms are thoughtfully separated for privacy. This floor plan features the closet OUTSIDE of the bathroom in the primary bedroom. Located just steps from the clubhouse and pool, this unit offers easy access to community amenities. Lakeside at Lakes of Windermere residents enjoy a fitness center, clubhouse and resort-style pool. The neighborhood is nestled near Lake Burden with access to a shared private dock and its own man-made lake. As a gated community, it also features a billiards room, walking paths around a central pond, and sports courts and fields. This home is just a few minutes drive from Walt Disney World (and neighboring parks) and boasts a view of the Disney fireworks EVERY night!! The combination of a well-appointed interior, wrap-around porch and enviable location near neighborhood amenities and Orlando's best entertainment make this corner-unit condo an exceptional opportunity.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Erin Aaron (727-422-1688)
4819 INDIAN DEER RD, WINDERMERE, FL 34786
$669,9009 Days on yellowkey MLS ID: O6403960
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3049 Built: 2005Monthly Fee: $131 Tax: $9,523 (2025)Community: Summerport Ph 05Spa: NoSingle Family
Taxes:$9,523
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Expansive four-bedroom, four-bathroom home in Windermere featuring a grand and thoughtfully designed floor plan. Upon entry, you are welcomed by a dramatic foyer with a sweeping staircase and an overlooking balcony. The main level offers a versatile front flex space—ideal for a formal sitting area—that flows into a chef-inspired kitchen. With abundant cabinet and counter space, the kitchen is perfectly suited for hosting and opens seamlessly into a massive living room. Additionally, the ground floor includes a dedicated private office and a full bathroom. All bedrooms are located on the second floor for maximum privacy. The primary suite is a true retreat, featuring a "Romeo and Juliet" balcony overlooking the foyer, a large walk-in closet, and a luxurious ensuite bathroom with dual vanities, a garden tub, and a separate standing shower. Ideally located just minutes from Winter Garden Village, Highway 429, and Downtown Winter Garden. This home is zoned for highly-regarded schools, including Keenes Crossing Elementary, Bridgewater Middle, and Windermere High School. Schedule your showings today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
8866 HERENCIA ALY, WINDERMERE, FL 34786
$430,0009 Days on yellowkey MLS ID: O6407518
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1577 Built: 2021Monthly Fee: $240 Tax: $5,532 (2025)Community: Legado 95/47 Lot 100Townhouse
Taxes:$5,532
Elementary School: Castleview Elementary
High School: Horizon High School
Middle School: Horizon West Middle School
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom home featuring a spacious loft area perfect for a home office, media room, or play space. This move-in ready property offers an open-concept layout, stylish finishes, abundant natural light, and comfortable living spaces throughout. Located in the highly desirable Windermere area, this home offers easy access to top-rated schools, shopping, dining, major highways, and Orlando attractions. Enjoy the perfect blend of comfort, convenience, and Florida living in a great location!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Priscila Lima (321-442-7790)
6462 DEACON CIR, WINDERMERE, FL 34786
$6,950,0009 Days on yellowkey MLS ID: O6407107
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 7178 Built: 1997Monthly Fee: $1,224 Tax: $108,011 (2025)Community: IsleworthSpa: YesSingle Family
Taxes:$108,011
Elementary School: Windermere Elem
High School: Olympia High
Middle School: Chain of Lakes Middle
Remarks: Within the gates of Isleworth Golf & Country Club, along the shores of Lake Chase, this exceptional lakefront offers a refined and contemporary waterfront lifestyle. Ideally positioned near the driving range and just moments from Isleworth’s racquet center, clubhouse, fitness facilities, dining, and pool, the residence combines privacy with convenience.Designed by renowned architect Mark Nasrallah, the home spans more than 7,100 square feet and showcases sophisticated detailing and elevated finishes throughout. A grand foyer introduces the residence with a sweeping floating staircase and dramatic tiered crystal chandelier, leading into the formal living room where soaring ceilings, dual chandeliers, a fireplace, and expansive lake views create an impressive yet inviting setting.Marble flooring transitions seamlessly into the home’s primary living spaces, where rich hardwood floors enhance the warmth of the open-concept kitchen, casual dining area, and family room. The kitchen is both functional and elegant, featuring an oversized island, custom cabinetry, quarried quartz countertops, and professional-grade appliances by Wolf, Sub-Zero, and Bosch. A contemporary, temperature-controlled wine room accommodating over 100 bottles adds a distinctive touch. Architectural millwork in a diamond pattern defines the dining space, while custom media built-ins in the family room enhance the home’s cohesive design. Both areas open effortlessly to the lanai and pool deck.The primary suite serves as a private retreat, complete with a sitting area, designer lighting, and a spa-inspired bath featuring a soaking tub, expansive dual vanities, and a large walk-in shower. Additional interior highlights include a modern office with custom built-ins and private pool access, as well as a spacious game room with a full bar and captivating water views. Outdoors, the covered lanai extends to a resort-style pool and spa, surrounded by generous lounging areas and complemented by the private boat dock - creating an unparalleled setting for boating, entertaining, and year-round enjoyment in Florida's tropical climate.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Michelle Corbin (407-491-2690)
13609 ANCILLA BLVD, WINDERMERE, FL 34786
$749,99998 Days on yellowkey MLS ID: O6381542
0 Days Off yellowkey (back on 5/12/2026)
REDUCED by $39,001 (4.9%) on 04/14/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3360 Built: 2005Monthly Fee: $130 Tax: $9,521 (2024)Community: Summerport Ph 03Single Family
Taxes:$9,521
Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor includes a private primary suite with its own balcony, providing a serene retreat, as well as a dedicated home office perfect for remote work or study. Generous living areas are filled with natural light and create a seamless connection between indoor and outdoor living. Step outside to enjoy the covered patio and expansive backyard, offering ample space for entertaining, relaxing, or future customization. The property sits on a well-sized lot and is part of a community that features amenities such as a pool, park, playground, and sidewalks. Conveniently located near top-rated schools, shopping, dining, and major roadways, this home delivers an exceptional combination of location, space, and lifestyle. A rare opportunity to own a lake-view property in one of Windermere’s most desirable areas. Schedule your private showing today. SOME IMAGES HAVE BEEN VIRTUALLY STAGED AND/OR DIGITALLY ENHANCED TO ILLUSTRATE THE PROPERTY'S POTENTIAL AFTER UPDATES OR RENOVATIONS.
Listing Agent: Fernanda Soares Santos De Oliveira (407-840-0734)
12305 VIA DERNA PL, WINDERMERE, FL 34786
$465,000122 Days on yellowkey MLS ID: O6374964
REDUCED by $5,000 (1.1%) on 04/17/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1891 Built: 2014Monthly Fee: $316 Tax: $5,016 (2025)Community: CarringtonTownhouse
Taxes:$5,016
Elementary School: Bay Lake Elementary
Remarks: Welcome to this move-in ready 3-bedroom, 3-bath townhome in Windermere FL located in the desirable Carrington community near Walt Disney World, offering low-maintenance living and a prime Central Florida location. Major updates include a NEW ROOF (2022) for peace of mind and long-term value. From the moment you arrive, you’ll notice the curb appeal, mature landscaping, and covered entry. Inside, tile flooring flows throughout the main living areas, while bedrooms feature comfortable carpet. The open concept floor planseamlessly connects the living, dining, and kitchen—ideal for everyday living and entertaining. The kitchen features: Stainless steel appliances Center island with bar seating for casual dining Rich cabinetry and sleek countertops Stylish backsplash and pantry A highly desirable main floor bedroom and full bath offers flexibility for guests, multi-generational living, or a home office. Upstairs, the primary suite with private balcony provides a relaxing retreat, complete with a walk-in closet and en-suite bath with dual vanities and separate shower. A third bedroom, additional full bath, and loft/bonus space complete the layout. Enjoy outdoor living with a covered lanai and fenced, low-maintenance patio. The home also includes a rear-entry 2-car garage. Located just off Reams Road with easy access to 429, I-4, shopping, dining, and attractions, this home is ideal for buyers searching for a Windermere home near Disney. Carrington offers a community pool, green space, and a welcoming atmosphere, all within a family-friendly area zoned for A-rated schools. With modern upgrades, flexible living space, and a prime location, this is a turnkey opportunity in Windermere. Schedule your private showing today—this one checks all the boxes. Welcome home.
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
8648 POWDER RIDGE TRL, WINDERMERE, FL 34786
$499,000122 Days on yellowkey MLS ID: O6373065
1 Days Off yellowkey (back on 5/13/2026)
REDUCED by $17,000 (3.3%) on 04/13/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1876 Built: 2014Monthly Fee: $81 Tax: $6,733 (2025)Community: Windermere Trls Ph 1CSingle Family
Taxes:$6,733
Remarks: LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door. Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a spacious loft, and 1,876 square feet of thoughtfully designed living space. The open-concept kitchen and living area create a warm, inviting flow—perfect for everyday living and entertaining. Upstairs, you’ll find a versatile loft, a spacious primary suite, and two additional bedrooms with a full bathroom conveniently located between them. Wood flooring throughout the main living areas and a wooden staircase. Step outside and enjoy Florida living at its finest. From the large front porch, take in breathtaking sunsets and the Magic Kingdom nightly fireworks, while the extra-wide private balcony offers peaceful sunrise views. The rear-entry 2-car attached garage and low-maintenance yard provide both functionality and ease of ownership. *** Owned solar panel system (paid in full—no lease) designed to offset most or all of your monthly electric bill.*** The location is truly unbeatable. The home is walking distance to Bay Lake Elementary, as well as top-rated daycare and middle schools—offering unmatched peace of mind for families. Everyday conveniences such as grocery stores, dining, gyms, and shopping are also just steps away, including the newly opened Lakeside Village shopping plaza. Windermere Trails residents enjoy resort-style amenities including a large community pool, playground, dog park, scenic lakes and preserves, and miles of biking and jogging trails surrounded by beautiful retention ponds and local wildlife—perfect for morning walks and outdoor living.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Renan Serretiello (407-415-7317)
10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786
$3,450,000115 Days on yellowkey MLS ID: O6377244
REDUCED by $25,000 (0.7%) on 05/07/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 5273 Built: 1986Monthly Fee: $103 Tax: $28,092 (2025)Community: LakesSpa: YesSingle Family
Taxes:$28,092
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with artisan leaded glass. Inside, the great room makes an immediate statement with soaring 23’ cathedral ceilings and a striking Tennessee river rock fireplace. Entertain in the showstopping formal dining room, where oversized picture windows perfectly frame the lake. Designed for everyday comfort, the majority of the living space including all bedrooms is located on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a sunlit breakfast area with spectacular water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-inspired bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Generous secondary bedrooms offer ample closet space and well appointed baths, including a steam shower. Outdoors is where this home truly shines. Enjoy mature landscaping and colorful gardens, plus a motorized screened lanai with a chef-worthy summer kitchen pizza oven, prep area, grill, refrigerator, and TV alongside the pool, heated spa, and gas firepit. The desirable southern exposure delivers refreshing lake breezes and comfortable outdoor living without harsh afternoon sun. The custom floor plan maximizes lake views throughout, and the partially enclosed dock is a rare find grandfathered in, with a boat lift and side jet-ski lift. Additional highlights include newer doors and windows and a tile roof. The Lakes neighborhood also offers a community boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes from major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you. Be sure to explore the virtual tours.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
606 E 6TH AVE, WINDERMERE, FL 34786
$2,350,00065 Days on yellowkey MLS ID: O6390327
2 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4471 Built: 2016 Tax: $25,043 (2025)Community: DiamondheadSingle Family
Taxes:$25,043
Remarks: Experience elevated lakefront living in this one-of-a-kind estate, offering breathtaking views of Lake Bessie and unforgettable Florida sunsets. A private gated entry welcomes you to this exceptional residence, featuring 3 bedrooms and 3.5 bathrooms, plus a private in-law suite with its own full bath bringing the total to 4 bedrooms and 4.5 bathrooms. Thoughtfully designed for both everyday living and elegant entertaining, this home offers the perfect blend of comfort, privacy, and sophistication. The main level features formal living and dining rooms with a fireplace, along with a private office just off the foyer. The gourmet kitchen is a chef’s dream, showcasing custom cabinetry, built-in wine rack, wine refrigerator, Sub-Zero refrigerator, custom lighting, gas range, and a spacious pantry. A convenient half bath and oversized laundry room are also located on the main floor. Upstairs, you’ll find two private suites, each with its own full bathroom, plus the luxurious owner’s retreat offering stunning lake views, custom tile floors and walls, a separate walk-in shower, jetted soaking tub, custom lighting, and a large walk-in closet with built-in cabinetry. Step outside to your resort-style oasis featuring large pool with expansive deck and water feature. Two additional outdoor entertaining areas include a dedicated space with an outdoor kitchen. The pool house offers large windows with panoramic views, custom cabinetry, granite countertops, upgraded tile flooring, a Murphy bed, and a full custom bathroom, perfect for guests. Complete with a covered boat dock and located just a few blocks from downtown Windermere and nearby shopping, this extraordinary home blends luxury, comfort, and the ultimate Florida lifestyle.
Listing is courtesy of: ELITE GLOBAL REAL ESTATE LLC (407-758-2604)
Listing Agent: Maria Sarmiento Webel (305-793-6614)
7503 LAKE ALBERT DR, WINDERMERE, FL 34786
$1,650,00014 Days on yellowkey MLS ID: S5149564
3 Days Off yellowkey (back on 5/11/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4329 Built: 2015Monthly Fee: $180 Tax: $17,734 (2025)Community: Lake Burden South Phase 1Single Family
Taxes:$17,734
Remarks: 7503 Lake Albert Drive presents a beautifully renovated residence in the Lake Burden South community of Windermere. Completely renovated in 2023, the home showcases modern finishes, soaring ceilings, abundant natural light, and an open-concept layout designed for both everyday living and entertaining. Interior features include porcelain tile flooring, designer lighting, updated bathrooms, a modern kitchen, and refined details throughout. The spacious floor plan offers seamless indoor-outdoor living with a stunning backyard featuring a private pool, screened enclosure, and generous outdoor living space ideal for enjoying Florida living year-round. Additional highlights include a whole-house reverse osmosis water filtration system and beautifully updated living spaces throughout the home. Conveniently located near shopping, dining, major highways, Horizon West, and Windermere area amenities.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Mariana Haddad (858-829-7578)
111 MAIN ST, WINDERMERE, FL 34786
$889,00010 Days on yellowkey MLS ID: O6407060
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2272 Built: 1984 Tax: $9,734 (2025)Community: Windermere TownSingle Family
Taxes:$9,734
Remarks: Prime Windermere Location! Fully Renovated and Move-In Ready! Don't miss this beautifully updated 3-bedroom, 2-bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot, this property offers spacious living with two cozy fireplaces and generously sized rooms perfect for comfortable family living and entertaining. Recent Upgrades Include: Fresh interior and exterior paint. Brand-new luxury vinyl flooring Stunning 2x4 porcelain tile in the kitchen, foyer, and dining room. Sleek European-style kitchen cabinets with quartz countertops. Modern interior doors throughout. Stylishly renovated bathrooms. Energy-efficient LED recessed lighting throughout the home. As a Windermere resident, you'll also enjoy exclusive access to the community lakes perfect for boating, fishing, and relaxing outdoors.
Listing is courtesy of: CENTURY 21 CARIOTI (407-770-0322)
Listing Agent: Sammy Nakhleh (407-360-4435)
2931 SUNBITTERN CT, WINDERMERE, FL 34786
$1,199,000105 Days on yellowkey MLS ID: O6378100
2 Days Off yellowkey (back on 2/26/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 4018 Built: 1985Monthly Fee: $215 Tax: $8,710 (2024)Community: Butler BaySpa: YesSingle Family
Taxes:$8,710
Remarks: Under contract-accepting backup offers. Discover the charm of the Town of Windermere, Tree City USA, where the sparkling lakes, mature tree canopies, and a quaint ambiance create an exceptional place to call home. Deeply committed to preserving its character while embracing thoughtful cultural progress, Windermere offers a vibrant community filled with playful events. Nestled within the town proper and the gates of Lake Crescent Reserve, this freshly painted, custom 4018 sf home rests on pristine a 1.06 acre lot, showcasing an outdoor oasis. Designed for seamless indoor-outdoor living, this home also features an impressive 1100 sf flex suite with a private entrance, full kitchen, sliding doors to the pool. This area is ideal for a pool party or game area, multigenerational living, private office and work area, fitness center, or other creative space that best suits your needs. From the moment you enter, you’re welcomed into the family room featuring the vaulted ceilings, a wondrous wood-burning fireplace and wet bar conveniently located by the sliding pocket doors to the pool and outdoor entertaining spaces. Overlooking a privately landscaped yard with a new firepit, this home invites you to the perfect balance of year-round entertaining and peaceful retreat, where indoor comfort meets outdoor beauty in effortless harmony. Thoughtful home design is exhibited by a split floor plan, providing flexible spaces for separate conversations, play areas, multigenerational living, or large, scale entertaining. The spacious, well-appointed kitchen features a large eat-in area, SubZero refrigerator, quartz and granite countertops, wood cabinetry, and a center island with a cooktop and countertop eating. The owner’s suite offers a luxurious, recently updated en-suite and generous walk-in closet. Take advantage of the flex-space opportunities, which include the 1100 sf private entrance suite and the expansive second-floor loft with natural light from skylights. Notable upgrades include a Gerard stone-coated metal roof, resurfaced pool, re-sealed patio deck, and oversized septic leach field. Additional features include two water heaters, three-zone HVAC, vaulted family room ceiling, a large, covered lanai with retractable sunscreens on those days you prefer a little shade, and two outdoor kitchen plumbing access points for future expansion of the outdoor living space. Located within the Town of Windermere, residents enjoy exclusive amenities, including access to tennis courts, boat ramps to the various lakes, events, food truck night, farmers market, art and holiday special events, and other exclusive Town of Windermere residents-only events, to mention a few. The recently approved project to enhance the already meaningful community, involves the development of the Windermere Ward Trail and pedestrian bridge to provide safe and convenient access for pedestrians, bicyclists, and golf carts, to safely connect to local recreational areas, businesses, and government.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Christa Dinallo (561-702-2112)
1515 LAKE WHITNEY DR, WINDERMERE, FL 34786
$1,350,00015 Days on yellowkey MLS ID: O6405903
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3931 Built: 2005Monthly Fee: $272 Tax: $12,979 (2025)Community: Reserve At Belmere 48 23Spa: YesSingle Family
Taxes:$12,979
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to an exceptional opportunity in the highly sought-after, guard-gated community of Reserve at Belmere in Windermere, where elegance, space, and lifestyle come together seamlessly. This beautifully designed residence offers over 3500 square feet of refined living space, featuring 5 spacious bedrooms and 5 full bathrooms, salt water pool/spa, 3 car garage and thoughtfully laid out to provide both comfort and flexibility for modern living. From the moment you arrive, you are welcomed by a custom waterfall fountain in the front yard, setting the tone for the level of detail and care found throughout the home. Inside, you are greeted by soaring ceilings, elegant finishes, and an abundance of natural light that creates a warm and inviting atmosphere. The indoor fireplace adds a cozy focal point, perfect for relaxing evenings. At the heart of the home is a spacious gourmet kitchen featuring a gas stove, ideal for those who love to cook and entertain. With a large center island, ample cabinetry, flush fridge and wine fridge with an open flow into the main living areas, this space is designed for both everyday living and hosting with ease. The bedrooms throughout the home are generously sized, each offering comfort and privacy, along with spacious closets featuring custom built-ins. The primary suite is a true retreat, complete with a custom-designed closet with built-in cabinetry, providing both luxury and functionality. In addition to the primary suite there is a second en-suite bedroom. The second-floor bonus room adds incredible versatility, featuring one of the five full bathrooms, making it an ideal space for a private en-suite bedroom, home office, media room, or guest retreat. The home features crown molding, tray ceilings in the primary and a surround sound system throughout the living areas and back patio. Step outside to your own private backyard oasis, beautifully maintained, and incredibly private. Designed for true Florida living, this space is perfect for summer pool days and year-round entertaining. Enjoy the saltwater pool and spa a fully equipped summer kitchen, and a custom outdoor fire pit, creating multiple areas to gather, relax, and entertain. The size and privacy of the yard provide a peaceful, resort-style setting rarely found. The rear yard is fully fenced. Situated on a spacious lot within this premier community, residents enjoy access to top-tier amenities including a fitness center, tennis courts and park areas. Located just minutes from Downtown Windermere, top-rated schools, dining, shopping, and major roadways, this home offers the perfect balance of privacy and convenience. This is more than just a home, it’s a lifestyle.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Michelle Dunkley (407-908-4477)
2635 TRYON PL, WINDERMERE, FL 34786
$1,475,00017 Days on yellowkey MLS ID: O6402029
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4027 Built: 1997Monthly Fee: $60 Tax: $8,425 (2026)Community: Manors At Butler BaySingle Family
Taxes:$8,425
Tax Year: 2026
Remarks: Under contract-accepting backup offers. Come tour the epitome of southern charm mixed with stately elegance located in the heart of Windermere- this beautiful colonial estate was masterfully crafted by Jim Akers and sits on an expansive 0.78 acre lot within the premier Manors at Butler Bay, offering shady oak trees within minutes of downtown Windermere and her chain of lakes. The home was custom built and showcases exceptional millwork, rich hardwood floors, and an updated chef’s kitchen featuring Viking and Thermador appliances. Warm natural light streams in through expansive window packages bracketed by plantation shutters, making the main level warm and welcoming. French doors and windows throughout the newly painted living space, breakfast room and primary suite provide sweeping views of the covered lanai and private pool in this tranquil oasis. The primary suite, with two walk in closets and a spacious bathroom with jetted tub, is on the main floor, while the second level provides an additional five bedrooms, including a versatile mini-master- perfect for multigenerational families, an au pair suite, or a flexible bonus space. An oversized side-entry 3 car garage comes equipped with built in closets, storage shelving, and car charging unit. The expansive front and back yards are unique for this neighborhood, allowing for a myriad of outdoor living options, as well as providing a sense of peace and privacy. Landscaping was recently updated after the 2026 freeze and includes one of the coveted centennial legacy trees from the town of Windermere. This gem has been well maintained, including a NEW ROOF (2021), WHOLE HOME GENERATOR with 500 gallon in ground propane tank (2023), gas fireplace remodel (2022), new AC units (2023, 2023, 2018), a built in Thermador coffee maker (2025), and a Pool Heater/Chiller (2025) that encourages swimming year round. This is truly the perfect family home- it is ideally positioned within minutes of downtown Windermere and is zoned for A rated Windermere Elementary (right around the corner). Come experience the Windermere lifestyle - a unique blend of of lake life, vibrant community, and small town charm. Residents of this neighborhood have access to the Town of Windermere Chain of Lakes private BOAT RAMPs, and downtown Windermere, with its enchanting shopping district, farmer’s market, local restaurants and brewery, is only a short bike or golf cart ride away. With easy access to major highways, downtown Orlando, Disney World, Universal Studios, Winter Garden and Restaurant Row, as well as two major hospitals, are all just minutes away. Don’t miss this rare opportunity to own a home of this caliber in the sought-after Manors at Butler Bay. Washer/Dryer, breakfast and dining rooms light fixtures do not convey.
Listing is courtesy of: REIKI REALTY LLC (407-435-8909)
Listing Agent: Nipul Shah (407-435-8909)
6137 GROSVENOR SHORE DR, WINDERMERE, FL 34786
$8,495,000414 Days on yellowkey MLS ID: O6294487
4 Days Off yellowkey (back on 5/12/2026)
Bed: 6 Bath: 7.5 Gar: 5 Liv Area Sq Ft: 9571 Built: 2010Monthly Fee: $283 Tax: $54,933 (2024)Community: Keenes PointeSpa: YesSingle Family
Taxes:$54,933
Remarks: Under contract-accepting backup offers. Experience luxury lakefront living on a grand scale in this custom-built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three-story residence spans 9,571 square feet of living space on over 2.2 acres in the guard-gated community of Keene’s Pointe in sought-after Windermere. Built by Goehring & Morgan, this architectural masterpiece offers refined craftsmanship, exquisite details and seamless indoor-outdoor living with stunning water views from almost every space. The 26-foot grand entry sets the tone for soaring handcrafted coffered ceilings, travertine marble and mahogany wood floors, custom cabinetry, designer interior and exterior finishes and an open floor plan. Inside you'll find six bedrooms, five en suite, nine baths, formal living and dining rooms, wine cellar, family room, captivating saltwater aquarium, game room, lounge/loft, two offices, a mudroom, and a home theater constructed of concrete block to also serve as a safe room. The chef’s kitchen is outfitted with Sub-Zero and Dacor appliances, Esmeralda Brazil granite countertops, LED lighting, a large walk-in pantry, a prep kitchen with additional appliances and a built-in Miele coffee station with beverage refrigerator. The owner’s retreat features a private sitting room, fireplace, wet bar, oversized custom closet, spa-like bath and a covered balcony with breathtaking lake views. A spiral staircase leads to the third floor, the highest elevation in Keene’s Pointe, where you’ll find a private study and an observation deck. Massive sliding doors open to a spectacular outdoor living space with retractable screens, tongue-and-groove ceilings, fireplace, TV and a full summer kitchen with Viking gas grill, sink and refrigerator. The resort-style saltwater pool features a Beadcrete finish, sun shelf, lazy river, slide, grotto, swim-up table and stools, island planter with palm trees, spa and dramatic water, fire and lighting effects. A putting green and built-in trampoline complete the backyard oasis. One of only two, two-story docks in Keene’s Pointe, the home's private boathouse includes two boat slips with lifts and touchless covers, plus a floating dock for jet skis. Additional features include an elevator, in-floor vacuum system, attached in-law suite with private entry plumbed for a future kitchen, two garages with room for five cars and a gated dog run. The barrel tile roof, stone entry columns, motor court with fountains and professionally designed landscaping further elevate the estate. Keene’s Pointe offers access to the Butler Chain of Lakes, a 250-acre Jack Nicklaus Signature golf course, the Golden Bear Club, resort-style pool, tennis courts, fitness center, multiple playgrounds and a clubhouse for private events. Windermere offers small-town charm with proximity to downtown Orlando, fine dining, world-class shopping, championship golf courses, top-rated schools, international and private airports, and theme parks.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
8411 WOBURN CT, WINDERMERE, FL 34786
$1,200,00057 Days on yellowkey MLS ID: O6391980
REDUCED by $50,000 (4.0%) on 05/12/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2582 Built: 1999Monthly Fee: $222 Tax: $12,964 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$12,964
Middle School: Lakeview Middle
Remarks: Welcome to this beautifully reimagined luxury residence in the highly sought-after Keene’s Pointe, ideally positioned on a quiet cul-de-sac and backing onto the serene natural beauty of the Tibet Butler Preserve. This exceptional 4 bedroom, 3 bathroom home with a dedicated office has been extensively renovated to an outstanding standard, offering a perfect blend of modern design, comfort, and privacy in one of Windermere’s premier guard-gated communities. From the moment you arrive, the custom iron front door sets the tone for the quality found throughout. Inside, the entire home has been thoughtfully updated with smooth finished walls and ceilings, elegant crown molding in every room, and wood-look ceramic flooring that flows seamlessly throughout. Every space has been freshly painted, creating a light, bright, and cohesive feel, while feature walls, custom trim detailing, and designer touches elevate the overall aesthetic. The heart of the home is the fully remodeled kitchen, showcasing custom cabinetry, granite countertops, and WiFi-enabled LG appliances, perfectly designed for both everyday living and entertaining. The open layout connects effortlessly to the main living areas, enhanced by upgraded LED lighting and stylish ceiling fans throughout. The primary suite offers a true retreat, featuring a beautifully redesigned bathroom with custom cabinetry, upgraded finishes, and a luxurious soaking tub. Guest bathrooms have also been fully renovated with new flooring, showers, and modern fixtures. Additional highlights include custom closet systems with integrated lighting, a redesigned pantry with barn-style doors, and upgraded ceilings in both the dining room and sunroom. Step outside to your private outdoor oasis, where the oversized screened lanai, pool, and spa create the perfect setting for relaxation or entertaining. The pool has been enhanced with an acid wash, updated tile, and a resurfaced pool deck, complemented by a new spa heater, WiFi-enabled pool controls, and thoughtfully designed landscaping with ambient lighting that adds to the home’s tranquil atmosphere. This home is as smart as it is stylish, featuring a comprehensive ADT security system with cameras, glass break sensors, water detection, CO2, and fire monitoring, along with an air purification system integrated into the HVAC for added comfort and peace of mind. Additional upgrades include new garage door openers, updated exterior lighting, and professionally enhanced landscaping. Located toward the front of Keene’s Pointe, the home also benefits from convenient access to CR 535 and I-4, offering a meaningful time-saving advantage compared to properties deeper within the community. With its private setting, extensive high-end upgrades, and prime location, this is a rare opportunity to own a truly turnkey luxury home in one of Windermere’s most desirable communities.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Andy Neal (407-619-3517)
11617 CAMDEN PARK DR, WINDERMERE, FL 34786
$1,450,00014 Days on yellowkey MLS ID: O6405409
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3463 Built: 2005Monthly Fee: $283 Tax: $7,189 (2025)Community: Keenes PointeSingle Family
Taxes:$7,189
Remarks: Welcome to one of Central Florida’s premier guard-gated golf communities. This impeccably maintained, move-in ready residence showcases refined finishes throughout, including tile and laminate flooring (no carpet), crown molding in every room, and upgraded designer lighting. An abundance of space with 6 bedrooms and 4 1/2 baths. The living room is enhanced by striking wood-look tiled accent walls, adding warmth and architectural elegance. Offering a private tiled patio with electronic screen enclosure, perfect for enjoying Florida's year-round sunshine in comfort and privacy. For buyers seeking a move-in ready luxury home in Orlando's golf course communities, this property checks every box. Major capital improvements are already done: new roof (2023), AC and water heater 2-3 years old — giving buyers the confidence and peace of mind that comes with a truly turnkey luxury purchase. Residents enjoy exclusive access to the Golden Bear Club, a Jack Nicklaus Signature Golf Course, along with clubhouse, tennis, and Lake Tibet-Butler access. The community’s location delivers unmatched convenience with proximity to well-rated schools, along with The Grove, Westside Shoppes, Cornerstone at Summerport, and Downtown Windermere for daily essentials, local dining, and shopping adventures. Entertainment options abound with easy access to Disney, Universal, and the famed Restaurant Row in Dr. Phillips. A rare opportunity.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Carla Robles (407-462-2347)
6001 CAYMUS LOOP, WINDERMERE, FL 34786
$1,599,000108 Days on yellowkey MLS ID: O6379564
0 Days Off yellowkey (back on 2/10/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3520 Built: 2005Monthly Fee: $298 Tax: $9,709 (2024)Community: Keenes PointeSpa: YesSingle Family
Taxes:$9,709
Remarks: Under contract-accepting backup offers. Stunning Remodeled Golf Home in Keene’s Pointe – Windermere’s Premier Golf Community. Discover this unique, fully remodeled home in the highly sought-after Keene’s Pointe neighborhood, nestled in the picturesque lake community of Windermere. Offering privacy, breathtaking golf course views, and upgrades at every turn, this move-in-ready gem is the perfect blend of elegance and modern convenience. Home Features: • Total 4 suites Bedrooms, 5 Baths, a Gym & a Office. • 3 spacious suites on the first floor. • 1 converted in-law suite on the second floor. • Dedicated office space for work-from-home convenience. • 3 Car garage with a huge driveway/ parking. • Open-Concept Living with high-end finishes throughout including plantation shutters. Home also features a whole Home Water Filtration System. • Gourmet Kitchen: • Expansive granite island with seating. • Built-in appliances & wine bar. • Double-door dishwasher & trash compactor. • Touchless faucet & instant filtered boiling water. • Natural gas cooktop & pantry. Recent Replacements: • New Gas Water Heater (November 2024). • New Roof (September 2023). • Fairly New Air Conditioning Units (September/2019). Outdoor Oasis – Perfect for Entertaining! • Lanai with unobstructed picture screen for breathtaking views. • Heated pool with built-in bench & jets. • Full Summer Kitchen: • Ice maker, dishwasher, BBQ grill. • Hibachi Japanese grill & pizza oven. • Built-in Gas Fire Pit – perfect for cozy evenings • 5-Person Infrared Jacuzzi Sauna. • Outdoor Bath & Shower for convenience. Prime Location & Community Perks: • A-rated school zone. • Close to theme parks, fine dining, and shopping. • Keene’s Pointe Amenities: • Guarded gate, parks, trails, and clubhouse. • Optional Membership to The Golden Bear Club: • Championship golf course, tennis courts, gym, pool, restaurant & more. Stop searching—this home has it all! Experience luxury, privacy, and resort-style living in one of Windermere’s most exclusive communities. Schedule your private showing today! ****Feel free to Text Listing Agent asking the video of the property****
Listing is courtesy of: QUATTRO R E SOLUTIONS LLC (407-929-6120)
Listing Agent: Stella Freeman (407-285-1281)
5603 MARLEON DR, WINDERMERE, FL 34786
$27,000,00011 Days on yellowkey MLS ID: O6404938
Bed: 7 Bath: 9.0 Gar: 10 Liv Area Sq Ft: 22108 Built: 2008 Tax: $138,635 (2025)Community: NaSpa: YesSingle Family
Taxes:$138,635
Remarks: A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private acres with over 440 feet of pristine frontage on Cypress Lake. Masterfully designed to deliver the ultimate blend of grandeur, privacy, and resort-inspired living, the residence is statement of uncompromising luxury. Beyond the gated entrance, a sweeping motor court and dramatic porte-cochère introduce the home’s commanding Mediterranean-inspired architecture, where turreted wings, natural stone detailing, and elegant arched windows create an unforgettable arrival experience. Inside, a breathtaking 28-foot grand foyer unfolds beneath soaring ceilings, anchored by a spectacular double staircase with intricate custom ironwork that evokes the elegance of a world-class villa. Flooded with natural light through towering arched windows, the space immediately establishes the scale and sophistication that define the estate. Designed for intimate living and large-scale entertaining, the interiors blend timeless craftsmanship with modern refinement. The gourmet chef’s kitchen is a showpiece of its own, featuring custom wood cabinetry, expansive stone countertops, professional-grade appliances, a dramatic custom range hood, oversized center island, hidden pantry and richly detailed ceiling treatments that elevate the space into a culinary centerpiece. Adjacent gathering areas showcase exposed wood beams, designer lighting and seamless indoor-outdoor connectivity, creating warm yet grand living environments ideal for entertaining on any scale. Every amenity within the residence has been thoughtfully curated to rival the finest luxury resorts. Highlights include a state-of-the-art theater, golf simulator, multiple game rooms, an expansive wine room, private elevator, smart home automation system and a fully equipped fitness center. Elegant fireplaces and sophisticated entertaining spaces add warmth and intimacy throughout the home. A private guest wing with two bedrooms, its own living room, and separate entrance offers luxurious accommodations for extended family, guests or staff. The outdoor experience is nothing short of spectacular. The rear elevation unfolds around a breathtaking 125,000-gallon resort-style pool complete with cascading waterfalls, bordered by natural stones, a water slide, diving board and expansive terraces that rival five-star destinations. At twilight, the towering palms and illuminated architecture reflect across the shimmering water, creating a setting reminiscent of an exclusive private resort with intimate lounge settings that invite grand entertaining and quiet moments of retreat. For the automotive enthusiast, the estate includes a 10-car garage equipped with two vehicle lifts. Recreational amenities continue across the grounds with a private basketball court, boat dock and private community boat ramp, which provide effortless access to the desired Butler Chain of Lakes for world-class boating and waterfront living. Surrounded by expansive lawns, mature landscaping and unmatched privacy, this extraordinary residence represents a once-in-a-generation opportunity to own a waterfront legacy estate, a property designed not only to impress, but to endure for generations to come.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Llin Lu, Pa (954-907-3868)
33 MAIN ST, WINDERMERE, FL 34786
$1,575,00011 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
Taxes:$9,485
Remarks: BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP. 90 Ft wide x 177 ft to center of canal. 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)
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