Location: Windermere
Do Not Show Listings
1317 GLENHEATHER DR, WINDERMERE, FL 34786
$974,90024 Days on yellowkey MLS ID: O6406551
4 Days Off yellowkey (back on 5/20/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2811 Built: 2002Monthly Fee: $183 Tax: $7,266 (2025)Community: Reserve At BelmereSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,266
Elementary School: Lake Whitney Elem
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to 1317 Glenheather Drive, a 2,811-square-foot, 4-bedroom, 3-full-bath pool home in the coveted Reserve at Belmere, one of Windermere’s most established guard-gated enclaves. Upon arrival, the home greets you with mature, curated landscaping, endearing Mediterranean-style architecture, soaring 11-foot ceilings, and high-quality upgrades that reinforce not only aesthetic appeal, but also long-term peace of mind. As you enter, the home opens to a thoughtfully reimagined interior that highlights its 2022–2023 renovation, which included a new open floor plan, new AC, new water heater, new tile roof, plantation shutters, new flooring, freshly painted interior and exterior, automated blinds, new recessed, pendant, and chandelier light fixtures, a kitchen nook, and a redesigned chef’s kitchen boasting an oversized island, quartz countertops, stainless steel appliances, dual ovens, and a gas 4-burner cooktop. The primary living areas flow seamlessly with a formal living and dining room combination, split-bedroom design, and a kitchen/family room combo toward the rear of the home overlooking the pool deck, creating a sense of openness that’s difficult to find in homes of this era. Outside, the large covered seating area and screen-enclosed pool deck offer flexibility for Florida’s celebrated indoor/outdoor lifestyle and make this home perfect for entertaining. Buyers continue to target Windermere, and specifically communities like Reserve at Belmere, for its quiet yet connected lifestyle. Its proximity to luxury lakefront hubs, major infrastructure investments, and sustained demand driven by the area’s A-rated schools have created consistent upward pressure on property values in this pocket of Central Florida. It’s the kind of location where homes don’t just serve as strategic assets, but also as foundations for cherished lifelong memories. Schedule your private tour today.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: John Goggin (321-332-3000)
6442 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786
$575,000143 Days on yellowkey MLS ID: G5106279
REDUCED by $10,000 (1.7%) on 05/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2139 Built: 2012Monthly Fee: $125 Tax: $7,649 (2024)Community: Windermere Lndgs Ph 02Single Family
Taxes:$7,649
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Short Sale. Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant courtyard, and much more. New refrigerator is 2022, water heater replaced in 2020, AC replaced in October 2021. This home is a great money saver! It is equipped with fully warranted solar panels that pays just $30.00 in electric bills. These panels are not your average solar panels; they are German technology USA made panels with top notch microinverter systems saving you thousands of dollars in utilities throughout the years!! Whether you are a first-time home buyer, investor, or a starter family this home checks all of the boxes. Wonderful Location, A Rated Schools, Shopping & Restaurants will meet all of your buyer's needs. Located within a short distance to Sunset Park Elementary, minutes to Windermere High School, CR 535, Windermere preparatory, Windermere villages, the Butler Chain of Lakes, and just 15 minutes to Disney. Book your showing today!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Yindy Reyes (732-277-2828)
11753 VINCI DR, WINDERMERE, FL 34786
$2,150,00028 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
Elementary School: Windermere Elem
High School: Windermere High School
Middle School: Bridgewater Middle
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
$3,800,000249 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
High School: Olympia High
Middle School: Chain of Lakes Middle
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 is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Michelle Corbin (407-491-2690)
1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786, WINDERMERE, FL 34786
$862,00048 Days on yellowkey MLS ID: O6398784
REDUCED by $18,000 (2.0%) on 05/15/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3063 Built: 2001Monthly Fee: $115 Tax: $6,661 (2025)Community: Westover Club Ph 1 RepSingle Family
Taxes:$6,661
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Now offered at an improved price, this stunning 5-bedroom estate located in the highly desirable Westover Club community. From the moment you step inside, you’re greeted by soaring ceilings and dramatic second-story windows that flood the home with natural light, creating a bright and inviting atmosphere. Just off the entry, a custom-designed office features hardwood flooring, built-in cabinetry, and a dedicated workspace—perfect for working from home in style. Designed for both everyday living and entertaining, the expansive great room opens to the second story and flows seamlessly into the heart of the home: a spacious gourmet kitchen complete with granite countertops, center island, breakfast bar, stainless steel appliances, double built-in ovens, and an elegant backsplash. A unique wine storage nook and built-in entertainment features add both charm and functionality. The split-bedroom floor plan offers privacy, with a generous primary suite on the main level featuring hardwood flooring, space for a sitting area, a contemporary ensuite bath, and a large walk-in closet. An additional first-floor bedroom and full bath with pool access provide flexibility for guests or multi-generational living. Upstairs, a versatile loft is surrounded by additional bedrooms and a full bath, offering ample space for family or guests. Step outside to your private outdoor retreat, where an extended covered lanai (2022) and screened-in pool create the perfect setting for relaxing or entertaining year-round. Additional highlights include a brand new roof (2025) and a beautifully maintained interior that is truly move-in ready. Ideally located in a gated community with amenities including tennis and pickleball courts, playground, and more, this home offers convenient access to major roadways, dining, and shopping. A perfect blend of elegance, comfort, and lifestyle—this home is not to be missed.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Michelle Melo (240-595-1876)
1028 LASCALA DR, WINDERMERE, FL 34786
$749,00042 Days on yellowkey MLS ID: O6400649
2 Days Off yellowkey (back on 5/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2208 Built: 2002Monthly Fee: $140 Tax: $8,185 (2025)Community: Belmere Village G2 48 65Spa: YesSingle Family
Taxes:$8,185
Remarks: Under contract-accepting backup offers. Introducing an EXCEPTIONAL opportunity to own a RENOVATED WATERFRONT POOL residence in the prestigious, GATED community of Belmere. Meticulously maintained, this elegant single-story home embodies refined living with a seamless blend of comfort, style, and tranquility. Designed with a desirable split floor plan, the home offers both privacy and effortless flow. The heart of the home is a newly designed chef’s kitchen featuring a generous island, integrated WINE REFRIGERATION, designer hardware, and a sleek touchless faucet—perfectly suited for both intimate gatherings and upscale entertaining. The adjoining living spaces are enhanced by luxury vinyl plank flooring, while the bedrooms offer newer carpeting for added comfort. The primary suite is a private retreat, complete with a sitting area and an en-suite bath featuring dual vanities, a soaking tub, a separate glass-enclosed shower, and a custom walk-in closet with built-ins. Through elegant Pella French doors, step into your own FLORIDA sanctuary. A SCREENED-IN SALTWATER POOL with a NEW PUMP, expansive PAED DEK, and serene water views create an atmosphere of peace and exclusivity—ideal for embracing the Florida lifestyle. Additional enhancements include a whole-home Reme Halo UV air purification system and thoughtfully included built-ins such as a TV console and mount. Set within a sought-after community offering low HOA fees, exceptional amenities, and access to top-rated schools, this residence is ideally located near fine dining, upscale shopping, and world-renowned attractions. This is more than a home—it is a lifestyle of sophistication, comfort, and serenity. Private showings available for pre-qualified buyers. Experience the home anytime through the immersive 24-hour 3D
Listing Agent: Petra Bukalo Pa (407-484-0685)
4806 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786
$4,200,00014 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.
13633 ANCILLA BLVD, WINDERMERE, FL 34786
$849,00031 Days on yellowkey MLS ID: O6403031
5 Days Off yellowkey (back on 5/19/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3588 Built: 2005Monthly Fee: $129 Tax: $5,951 (2025)Community: Summerport Ph 3Single Family
Taxes:$5,951
Elementary School: Keene Crossing Elementary
Remarks: Under contract-accepting backup offers. Wake up to serene pond views in this beautifully upgraded 5-bedroom, 3.5-bathroom home located in the highly sought-after Summerport community of Windermere. A charming front porch overlooks the fountain, creating a peaceful and inviting first impression. Designed for both comfort and functionality, this home features a spacious layout with a first-floor bedroom and full bathroom—ideal for guests or multigenerational living. Two living areas and two dining spaces provide flexibility for everyday living and effortless entertaining. Upstairs, the expansive primary suite serves as a private retreat with a large sitting area, a versatile sunroom perfect for a nursery or office, and dual oversized walk-in closets. The primary bathroom is thoughtfully positioned down the hall, creating a true retreat feel with added privacy. Three additional bedrooms and a full hallway bathroom complete the second level. Upgrades throughout the home include dark bamboo flooring, updated bathrooms, and granite countertops. Major system improvements include a newer roof (2021), new AC and heating system (2023), a large-capacity Rinnai gas tankless water heater, and a water softener system. Updated exterior paint and a vinyl fence enhance both curb appeal and privacy. Enjoy seamless indoor-outdoor living with an extended lanai, perfect for relaxing or entertaining. The home also features a rare 3-car rear-entry garage with an expansive driveway, accessed through a private alleyway. Summerport features resort-style amenities including a clubhouse, pool, fitness center, tennis and multi-use courts, basketball, beach volleyball, scenic walking trails, fishing docks, parks, and multiple ponds surrounded by nature. Residents can also enjoy views of Disney fireworks from within the community. Ideally located with convenient access to SR-429, near Hamlin and Winter Garden Village, and just a short drive to Disney and Universal. Zoned for highly rated schools including Windermere High School, Bridgewater Middle, and Keene’s Crossing Elementary. This home blends space, privacy, thoughtful upgrades, and lifestyle in one of Windermere’s most desirable communities.
Listing is courtesy of: JUPITER PROPERTIES, INC (386-547-6161)
Listing Agent: Marya Baqri (407-529-7200)
105 PINE STREET, WINDERMERE, FL 34786
$2,500,00026 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)
12411 MONTALCINO CIR, WINDERMERE, FL 34786
$1,495,00046 Days on yellowkey MLS ID: O6400067
REDUCED by $55,000 (3.5%) on 05/04/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3399 Built: 2011Monthly Fee: $150 Tax: $11,027 (2025)Community: Casa Del LagoSpa: YesSingle Family
Taxes:$11,027
Elementary School: Sunset Park Elem
Remarks: A custom home in the desirable Casa del Lago community. The Spanish-style exterior and elegant, clean transitional interior will surely catch your attention. This home offers 4 beds, 4.5 baths, plus an office, 3,400 sq ft under air, a saltwater pool and spa, an outdoor kitchen, and a gas fireplace near the pool. This home is full of upgrades! Porcelain floors, exotic granite throughout the home a full Carrera marble master bath with floating vanities, organize closet system in every bedroom, all bedrooms have their own private bath, $15,000 worth of plantation shutters, $5,000 security system with cameras with access from your smart phone, all of the wood in the home is African Sapele, 7.25" crown molding and base boards in every room, pre-wired surround sound, casement double pane windows as well as spray foam insulation. Too many extras to list. This home is a MUST SEE!!
Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)
Listing Agent: Mauro Costa (321-231-6800)
1136 LAKE WHITNEY DR, WINDERMERE, FL 34786
$2,295,00027 Days on yellowkey MLS ID: O6405536
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5722 Built: 2006Monthly Fee: $203 Tax: $24,153 (2025)Community: Reserve At Belmere Ph 02 48 144Spa: YesSingle Family
Taxes:$24,153
Middle School: Lakeview Middle
Remarks: Experience resort-style living in the exclusive Villa D’Este, a masterpiece of sophistication designed by the renowned Arlington Homes. Positioned on the pristine shores of Lake Whitney, this estate welcomes you with a grand 20-foot entryway featuring a custom rustic wrought-iron chandelier and immediate, unobstructed water views. The main floor is a sanctuary of luxury, featuring an Executive Office with granite built-ins and an opulent Master Retreat. The primary suite is a true escape, offering a Miele coffee system, day bar, and a spa-like bath adorned with Murano-Crystal fixtures, a body-spa shower, and a jetted tub. Culinary enthusiasts will marvel at the Chef’s Kitchen, fully equipped with a custom island, Wolf and Sub-Zero Pro-appliances, Bosch wine refrigeration, and gas cooktop. The entertainment continues outdoors on the tropical lanai, featuring a heated pool and spa with an in-floor cleaning system, a resort-style cabana with cypress ceilings, an outdoor fireplace, and a full summer kitchen. The entire estate is powered by an RTI Audio/Visual whole-house system. Upstairs, discover a private Theater Room with its own kitchen and a massive balcony perfect for sunset views over the lake. Immaculate, unique, and richly designed—this is the pinnacle of Lake Whitney living.
11449 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$1,680,00046 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 Agent: Rob Rahter (407-497-4526)
4948 WISE BIRD DR, WINDERMERE, FL 34786
$679,00019 Days on yellowkey MLS ID: O6405511
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1979 Built: 2003Monthly Fee: $130 Tax: $8,593 (2025)Community: SummerportSpa: YesSingle Family
Taxes:$8,593
Remarks: One or more photo(s) has been virtually staged. Don’t miss the opportunity to live in the HIGHLY SOUGHT-AFTER A-RATED SCHOOL DISTRICT community of Summerport. This BEAUTIFUL ONE-STORY POOL HOME features GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, and a NEW ROOF INSTALLED IN 2022. Step into a welcoming foyer that showcases the home’s OPEN LAYOUT. Two of the three bedrooms are located on the left side of the home, separated from the primary suite for added privacy. Continuing down the hallway, you’ll find a SPACIOUS FLEX ROOM currently being used as an additional bedroom, perfect as a guest room, office, gym, or playroom. The updated kitchen opens to a bright family and dining area filled with natural light. The primary suite is privately situated at the back of the home and features a WALK-IN CLOSET, dressing area, and an ensuite bathroom with DUAL SINKS, a separate shower, and a GARDEN TUB. Large sliding doors lead to your PRIVATE SCREENED-IN OASIS with a beautifully tiled lanai. The POOL AND SPA provide the perfect setting to enjoy the FLORIDA LIFESTYLE. Summerport offers excellent community amenities including a RESORT-STYLE POOL, fitness center, parks, playgrounds, and a fishing pier. Conveniently located near TOP-RATED SCHOOLS, shopping, major highways, and just MINUTES FROM DISNEY where you can enjoy the NIGHTLY FIREWORKS from the neighborhood. Don’t miss this INCREDIBLE OPPORTUNITY. Schedule your private showing today!
Listing is courtesy of: THE FLORIDA LOUNGE REALTY LLC (786-241-7619)
Listing Agent: Leo Martins Silva (786-241-7619)
84 OAKDALE ST, WINDERMERE, FL 34786
$1,875,000141 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
$1,999,99943 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
$2,798,00064 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
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
$5,500,00068 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 Agent: Ana Rubio (786-207-8352)
9343 TIBET POINTE CIR, WINDERMERE, FL 34786
$7,950,000536 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
$13,430,00043 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)
6550 CARTMEL LN, WINDERMERE, FL 34786
$2,300,00059 Days on yellowkey MLS ID: O6396111
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4257 Built: 2004Monthly Fee: $520 Tax: $23,347 (2025)Community: Reserve At Lake Butler SoundSpa: YesSingle Family
Taxes:$23,347
Remarks: This is a rare, one of a kind stunning Luxury Contemporary Home in Windermere – Over Half Acre with Private Pound View Welcome to 6550 Cartmel Ln, located in the exclusive community of Reserve at Lake Butler Sound — one of the most desirable gated neighborhoods in Windermere. This beautifully renovated, modern-contemporary residence sits on an oversized lot with over half an acre and features its own private lake view, offering a rare combination of luxury, privacy, and breathtaking outdoor living. The home offers 4 bedrooms, 4 full bathrooms, and 1 half bath across a spacious two-story layout with an open-concept design. The interior showcases elegant finishes throughout, including luxury vinyl flooring (no carpet), high ceilings, and abundant natural light. The gourmet kitchen is fully equipped with stainless steel appliances, quartz countertops, and custom cabinetry—perfect for both everyday living and entertaining. Step outside to your private backyard oasis, featuring a covered lanai with outdoor kitchen/grill area, a beautiful pool, and expansive lakefront space ideal for relaxing or hosting guests. Exterior furniture is included, making this home move-in ready. Additional highlights include a 3-car garage and partially furnished interiors. The community offers a lifestyle centered on privacy and lakefront living, featuring 24-hour guard-gated security, private access to the Butler Chain of Lakes, and beautifully maintained green spaces. Prime location just minutes from: Walt Disney World Resort Downtown Winter Garden The Mall at Millenia Top-rated schools, fine dining, shopping, and major highways This is a rare opportunity to own a fully upgraded luxury home in one of Central Florida’s premier communities. Don’t miss your chance—schedule your private showing today!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jennifer Olmeda (407-547-9242)
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