Location: Windermere
Do Not Show Listings
4812 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786
$3,699,000293 Days on yellowkey MLS ID: O6339134
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4262 Built: 2007Monthly Fee: $1,146 Tax: $45,888 (2024)Community: IsleworthSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$45,888
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a private courtyard featuring a glistening pool adorned with a cascading waterfall from the pergola. An expansive covered patio houses a summer kitchen, pool bath, and attached third bedroom accessed only from the courtyard. The heart of this home is a chef's dream, with a gourmet kitchen featuring top-of-the-line Wolf appliances, striking custom cabinetry, and an open design that seamlessly connects to the family room and dining areas. The grand primary suite offers a private sitting area overlooking the peaceful pond, double walk-in closets, and a spa-like bath complete with a Jacuzzi tub and an expansive walk-in shower. The third garage was converted into a gym with air conditioning and can be converted back to additional garage space. Garden villas offer carefree living with exterior grounds maintenance included in the separate monthly fees. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
6390 SOUTHBRIDGE ST, WINDERMERE, FL 34786
$395,000118 Days on yellowkey MLS ID: O6385153
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1632 Built: 2007Monthly Fee: $249 Tax: $6,073 (2025)Community: Southbridge VillageTownhouse
Taxes:$6,073
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Immaculately maintained from top to bottom, including a NEWER A/C (2023) and newer roof (2021), this 4-bedroom, 2.5-bath townhome in the desirable Southbridge Village community delivers the ideal blend of style and location in the heart of Windermere! Framed by mature landscaping and a WOODED VIEW from the front of the home, the charming CURB APPEAL immediately sets the tone for what awaits inside. Beautiful TILE & ENGINEERED HARDWOOD FLOORS flow throughout the home, complemented by crown molding, tons of natural light, and thoughtfully designed living spaces that feel both warm and functional. The OPEN LIVING & DINING areas create an easy everyday flow, while the spacious kitchen offers ample storage, STAINLESS STEEL APPLIANCES, a tiled backsplash, and a prep ISLAND with additional cabinetry and workspace. Access to the private PAVER PATIO and rear-facing 2-CAR GARAGE adds convenience and easy indoor/outdoor living. The MAIN FLOOR PRIMARY SUITE is perfectly situated for privacy and filled with more natural light, featuring a WALK-IN CLOSET and a well-appointed en-suite bath. Upstairs, a versatile BONUS/LOFT provides additional living space ideal for a media area, playroom, or home office, along with three additional bedrooms and a second full bath. A convenient main floor half bath adds flexibility for guests. Residents of Southbridge Village enjoy access to a COMMUNITY POOL and playground, along with a highly walkable location close to Publix, shopping, dining, golf, and everyday conveniences. With easy access to 429, area theme parks, and local attractions, this move-in ready Windermere townhome is perfectly suited as a primary residence, second home, or solid investment opportunity. Call today, schedule your tour, and discover the possibilities!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
12333 VIA DERNA PL, WINDERMERE, FL 34786
$449,000209 Days on yellowkey MLS ID: O6362685
REDUCED by $9,000 (2.0%) on 06/17/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1919 Built: 2014Monthly Fee: $316 Tax: $6,305 (2024)Community: CarringtonTownhouse
Taxes:$6,305
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to this beautifully updated 1,919 sq/ft townhome in the highly desirable Carrington community of Windermere. This spacious 3-bedroom, 2.5-bath residence features a freshly renovated family room, kitchen, and shared bathroom, offering a modern and inviting living experience from the moment you enter. The open-concept layout provides excellent flow for everyday living and entertaining, enhanced by abundant natural light throughout. The home is also EV-ready, already equipped with the necessary infrastructure for an electric vehicle charger—ideal for today’s modern lifestyle. Situated just minutes from top-rated schools, shopping, dining, and major attractions, this move-in-ready townhome blends comfort, convenience, and contemporary upgrades. Please note: The Tesla charger and the window curtains are not included in the listing price; however, they may be negotiated separately. Don’t miss your chance to own in one of Windermere’s most sought-after communities!
Listing is courtesy of: YELLOW ROCK REALTY CORP (407-421-8056)
Listing Agent: Marco Romero (407-450-9244)
12357 VIA DERNA PL, WINDERMERE, FL 34786
$430,0007 Days on yellowkey MLS ID: O6417519
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1919 Built: 2014Monthly Fee: $316 Tax: $6,606 (2025)Community: CarringtonTownhouse
Taxes:$6,606
Elementary School: Bay Lake Elementary
Middle School: Horizon West Middle School
Remarks: Beautiful 3-bedroom, 2.5-bath townhome located in the highly desirable Carrington community. This well-maintained home features an open-concept floor plan, granite countertops, and a combination of tile and carpet flooring throughout. Enjoy your own private courtyard, perfect for relaxing, outdoor dining, or entertaining guests.Residents have access to community amenities including a sparkling pool and scenic walking paths. Conveniently situated near shopping, dining, major highways, and world-famous theme parks, this property offers both comfort and convenience. Whether you're looking for a primary residence or an investment opportunity, this exceptional townhome is a must-see and won't last long!
Listing is courtesy of: SUNNY 365 REALTY GROUP (407-574-7048)
Listing Agent: Isabel Sirizzotti (407-361-8236)
7906 JAILENE DR, WINDERMERE, FL 34786
$724,9007 Days on yellowkey MLS ID: O6416776
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2618 Built: 2011Monthly Fee: $81 Tax: $8,576 (2025)Community: Lake SawyerSpa: NoSingle Family
Taxes:$8,576
Elementary School: Sunset Park Elem
High School: West Orange High
Remarks: Virtually Staged. Enjoy exceptional privacy with beautiful conservation views behind & expansive green space beside the home, creating a peaceful setting rarely found in the community. Tucked away on a desirable homesite, 7906 Jailene Drive offers 2,618 SF, 5 bedrooms, 3 full bathrooms, 2-car garage, all filled with thoughtfully designed living spaces & ample dedicated guest parking conveniently located nearby. A welcoming front porch sets the tone as you enter the home, where a custom wood accent wall in the foyer creates a warm and inviting first impression. The open-concept layout offers spacious living & dining areas that flow seamlessly into the kitchen & family room. A dramatic two-story ceiling in the family room fills the space with natural light creating an impressive sense of openness, making it the perfect place to gather & entertain. The kitchen features granite stone countertops, abundant solid wood cabinetry, ample prep space, a kitchenette area & a functional layout overlooking the main living areas. Fresh interior paint, luxury vinyl flooring throughout & charming designer light fixtures add style and warmth throughout the home. The versatile floor plan includes a first-floor study/den which can also be used as a 5th bedroom with full bathroom. This space is ideal for a home office, family, guests, or multi-generational living. Upstairs, you’ll find four additional bedrooms, including the spacious primary suite, along with two full bathrooms & a conveniently located laundry room. Step outside to the screened lanai with tranquil conservation views, embracing nature at its best with exceptional privacy. Enhanced by a hand-painted decorative concrete finish, this outdoor retreat provides the perfect space for morning coffee, outdoor dining, or relaxing evenings, especially with a fully-fenced backyard. Located in the highly desirable Lake Sawyer community, residents enjoy access to a community pool, playground, park, and scenic sidewalks throughout the neighborhood. The home is zoned for sought-after schools, including Sunset Park Elementary, Horizon West Middle School, and Windermere High School. Just minutes from Horizon West and Hamlin Town Center, you’ll enjoy convenient access to shopping, dining, entertainment, and everyday conveniences. Major roadways are nearby, providing easy access to Walt Disney World, Disney Springs, downtown Orlando, Orlando International Airport, and all that Central Florida has to give. Combining privacy, functionality, thoughtful updates, and an exceptional location, this move-in-ready home presents a rare opportunity in one of Windermere’s most sought-after communities. Additional highlights include a brand-new roof (June 2026), HVAC 2024, abundant storage & a desirable location close to shopping, dining, schools, & major roadways. Combining privacy, functionality, & modern updates, this move-in-ready home is ready to welcome its next owners!
Listing is courtesy of: ARMEL REAL ESTATE INC (407-509-3812)
Listing Agent: Deanna Armel (407-509-3812)
6631 CRESTMONT GLEN LN, WINDERMERE, FL 34786
$809,000349 Days on yellowkey MLS ID: O6323076
REDUCED by $25,000 (3.0%) on 06/16/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3068 Built: 2002Monthly Fee: $170 Tax: $9,573 (2024)Community: GlenmuirSpa: NoSingle Family
Taxes:$9,573
Remarks: Welcome to 6631 Crestmont Glen Lane, a beautifully maintained executive home in the gated community of Glenmuir. Set on a large and spacious, landscaped lot, this 4-bedroom, 3.5-bath residence offers an ideal blend of space, comfort, and everyday functionality. Step inside to soaring ceilings, abundant natural light, and an open-concept layout designed for both entertaining and relaxed living. The gourmet kitchen features granite countertops, ample cabinetry, and a breakfast nook that flows seamlessly into the inviting family room. Enjoy year-round Florida living in your private screened lanai—perfect for quiet mornings or hosting guests. The primary suite offers a true retreat with a spa-like bath, walk-in closets, and direct access to the outdoor living space. Residents of Glenmuir enjoy a peaceful, tree-lined setting with a private park, playground, and walking paths—just minutes from top-rated schools, golf, dining, shopping, and world-renowned attractions including Walt Disney World.
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
9057 BALMORAL MEWS SQ, WINDERMERE, FL 34786
$1,859,000101 Days on yellowkey MLS ID: O6390656
1 Days Off yellowkey (back on 6/17/2026)
REDUCED by $40,000 (2.1%) on 05/29/2026
Bed: 6 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5430 Built: 1997Monthly Fee: $267 Tax: $12,735 (2025)Community: BalmoralSingle Family
Taxes:$12,735
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Located within the prestigious gated community of Balmoral Estates, this spectacular 6-bedroom, 5.5-bath 4 car garage luxury estate sits on an expansive ¾-acre homesite and has been completely renovated with exceptional custom upgrades throughout. From the moment you arrive, the property makes a striking impression with a brand-new circular paver driveway centered around a dramatic custom water fountain, creating a grand sense of arrival. The residence also features a spacious four-car garage equipped with two EV charging stations, offering modern convenience for today’s lifestyle. Custom front entry doors open to an impressive grand foyer with elegant marble tile flooring, introducing the refined finishes that define the home. Inside, the residence has been beautifully transformed with brand-new flooring throughout, custom recessed lighting, upgraded designer fixtures, and crown molding across the main level. At the heart of the home is a stunning designer gourmet kitchen featuring custom white cabinetry, granite countertops, a striking tile mosaic accent wall, and premium KitchenAid stainless steel appliances, including a built-in oven, microwave, and cooktop. Perfect for entertaining or multi-generational living, the home also features a fully rebuilt second kitchen with granite countertops, custom cabinetry, and stainless steel appliances with direct access to the outdoor entertaining area. The home offers two luxurious primary suites, each thoughtfully designed as a private retreat. The upstairs primary suite features a spa-inspired bathroom with dual vanities, custom cabinetry, a dedicated makeup vanity, an oversized jacuzzi soaking tub, and a beautifully tiled walk-in shower. Outdoor living is equally impressive with a custom outdoor kitchen complete with built-in grill, professional venting, and built-in speakers, creating the perfect setting for entertaining and relaxation. Three brand-new sliding glass doors upstairs open to a private balcony, enhancing the home’s seamless indoor-outdoor lifestyle. Recent upgrades provide comfort and peace of mind, including a new Carrier 5-ton air conditioning system, new 50-gallon water heater, whole-home water purification system, and a new pool pump installed within the last six months. With extensive renovations, luxurious finishes, and exceptional indoor-outdoor living, this remarkable residence offers the sophistication, comfort, and lifestyle expected of a premier luxury estate.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ryan Rogers (407-492-0674)
11234 RAPALLO LN, WINDERMERE, FL 34786
$520,0008 Days on yellowkey MLS ID: O6416987
0 Days Off yellowkey (back on 6/16/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2236 Built: 2003Monthly Fee: $136 Tax: $3,973 (2025)Community: Belmere Village G2 48 65Single Family
Taxes:$3,973
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Located in the highly sought-after gated community of Belmere in Windermere, this beautifully maintained 4-bedroom, 2.5-bath home offers 2,236 square feet of comfortable living space and a thoughtfully designed floor plan. Filled with natural light, the home features spacious living and dining areas, a well-appointed kitchen that opens to the family room, and generously sized bedrooms, including a private primary suite. One of the home's standout features is the beautiful low-maintenance backyard courtyard, creating a private outdoor retreat perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine without the upkeep of a large yard. Residents of Belmere enjoy an exceptional amenity package including a clubhouse, fitness center, resort-style pool, tennis court, basketball court, playground, and walking areas, all within a secure gated setting. Conveniently located near top-rated schools, shopping, dining, major highways, and area attractions, this home offers the perfect combination of comfort, convenience, and community living.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kyle Grafton (203-246-8512)
11564 MIZZON DR #930, WINDERMERE, FL 34786
$325,00050 Days on yellowkey MLS ID: O6404607
2 Days Off yellowkey (back on 6/16/2026)
REDUCED by $10,000 (3.0%) on 05/31/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,561 (2025)Community: Lakeside/Lks/Windermere CondoCondo
Taxes:$4,561
Remarks: Under contract-accepting backup offers. Lovely 3rd floor (Corner unit on top floor) In sought after Lakes at Lakeside of Windermere. Well-appointed 3 Bedrooms and 2 bathrooms Condo, Spacious feel. Offering an excellent layout. Newer carpets, home is ready to move in. Dine in kitchen has 42" dark cherry wood cabinets and granite countertops, stainless range and dishwasher, laminate flooring throughout the living areas and new carpet in bedrooms. Master bedroom Features walk-in closet, and Master bathroom 2 further bedrooms and other full bathroom. Step out from sliding doors to the Spacious covered/screened balcony. Elevators and stairs access to the unit. Superb community amenities. Resort style recreation, Olympic swimming pool, sand volleyball court, state-of-the-art fitness center, playground, large community clubhouse, BBQ area, & cozy outdoor fireplace! With easy access to all major highways including I-4, 429, & SR 535…Close to Disney theme parks & Restaurants, Dining, Shopping & School. Maintenance, carefree Florida living, in this well-maintained community
Listing is courtesy of: RE REALTY (321-363-6345)
Listing Agent: Reeta Gulati (321-363-6345)
2 CHASE RD, WINDERMERE, FL 34786
$2,200,000279 Days on yellowkey MLS ID: O6345197
REDUCED by $1,000,000 (31.3%) on 06/16/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3889 Built: 2026 Tax: $3,100 (2024)Community: WindermereSingle Family
Taxes:$3,100
Remarks: Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance. Property Highlights: • Total Living Area: 3,889 Sq. Ft. | Total Building Area: 5,516 Sq. Ft. • 4 Bedrooms | 4 Full Baths | 1 Powder Room | 1 Pool Bath • Expansive Living Spaces with High Ceilings & Open Floor Plan • Great Room | Dining Room | Gourmet Kitchen with Nook & Pantry • Private Elevator & Multiple Open Decks • 2-Car Garage First-Floor Features: • Grand Foyer with Staircase & High Ceilings • Great Room & Elegant Dining Room • Chef’s Gourmet Kitchen with custom cabinetry, quartz countertops, Subzero appliances, and a spacious island • Guest Suite with Private Bath & Walk-in Closet • Laundry Room & Powder Bath • Pool Bath (Outdoor Access) Second-Floor Features: • Lavish Master Suite with Private Balcony, Spa-Inspired Bath & Custom Walk-in Closet • Two Additional Bedrooms with Walk-in Closets & Shared Designer Bathroom • Two Expansive Open Decks for Outdoor Enjoyment Luxury Amenities & Smart Home Features: • State-of-the-Art Smart Home Integration • Hurricane Impact Windows for Safety & Efficiency • Custom California Closets in All Bedrooms • Heat & Glow Fireplaces in the Living Room & Master Suite • Large Format Porcelain Tile & High-End Finishes Throughout • Flat Tile Roof & Metal Truss Construction for Durability Outdoor Oasis & Entertainment Haven: • Resort-Style Custom Pool & Spa (Separate Permit) • Sunken Outdoor Kitchen & Lounge Area for Elevated Entertaining • Landscaped Backyard with Ample Space for Relaxation & Gatherings Prime Windermere Location – Unmatched Lifestyle & Convenience: • Minutes from Isleworth, Home to Celebrities & Sports Icons • Access to the Pristine Butler Chain of Lakes – Ideal for Boating & Water Sports • A-Rated Schools, Parks, & Year-Round Community Activities • Close to Luxury Shopping, Fine Dining, Golf Courses & Entertainment • Easy Access to Disney, Universal, and Orlando’s Top Attractions This exceptional luxury estate embodies a lifestyle of sophistication, exclusivity, and modern convenience. Secure this once-in-a-lifetime opportunity to own a masterpiece of design and craftsmanship in the heart of Windermere. For more details, floor plans, and customization options, contact us today!
Listing Agent: Matthew Hughes (407-619-4717)
11536 CLAYMONT CIR, WINDERMERE, FL 34786
$1,175,00089 Days on yellowkey MLS ID: O6392958
REDUCED by $75,000 (6.0%) on 05/26/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2882 Built: 2002Monthly Fee: $298 Tax: $8,766 (2025)Community: Keenes Pointe Ut 04 Sec 31 48 82Spa: YesSingle Family
Taxes:$8,766
Remarks: Virtually Staged. Price Improvement! Welcome to luxury living inside the guard-gated community of Keene’s Pointe, home to the renowned Golden Bear Club and its Jack Nicklaus Signature golf course. Perfectly positioned within one of Windermere’s most sought-after neighborhoods, this exceptional single-story residence offers a refined blend of elegance, comfort, and lifestyle. Beautifully remodeled throughout, this is truly move-in ready, showcasing a fresh, modern aesthetic while maintaining timeless architectural appeal. From the moment you enter, you’re welcomed by marble tile flooring, newly refinished wood floors, fresh interior paint, and thoughtfully selected modern light fixtures that elevate every space. The home features both a traditional dining room and formal living room, complemented by custom window treatments that add warmth and sophistication. At the heart of the home, the completely remodeled kitchen shines with all-new appliances, a gas stove, double oven, quartz countertops, and a large walk-in pantry, all wrapped in a clean, contemporary design that seamlessly opens to the family room—where a decorative modern fireplace creates the perfect gathering space. The expansive primary suite is a true retreat, featuring wood floors, direct pool access, a dedicated mini-split system for enhanced comfort and efficiency, and a spa-inspired bathroom with a stunning new garden tub, separate shower, and an oversized walk-in closet. Additional bedrooms lend to stylish comfort with new herringbone tile flooring and share a convenient Jack-and-Jill bathroom. All bathrooms throughout the home have been fully remodeled with high-end finishes. A large private office with a built-in desk provides the ideal work-from-home environment. Step outside to a spacious, fenced backyard featuring a newly repainted pool and patio—perfect for enjoying Florida living year-round. Additional highlights include a 2020 roof, paver driveway, and an oversized 3-car garage. Every detail has been thoughtfully updated, making this home completely turn-key. Residents of Keene’s Pointe enjoy 24-hour guard-gated security and a lifestyle centered around both recreation and natural beauty. The community offers private access to the Butler Chain of Lakes, ideal for boating, skiing, and sunset cruises, along with scenic walking paths, tranquil green spaces, and a peaceful, well-maintained setting throughout. There is even the opportunity for boat storage, adding convenience for those looking to fully embrace the lake lifestyle. Optional membership to the Golden Bear Club unlocks a premier lifestyle experience with championship golf, tennis, fitness, a resort-style pool, dining, and a vibrant calendar of social events. The neighborhood also features community parks, playgrounds, and gathering spaces, creating a welcoming environment that blends luxury living with everyday convenience and community connection through regular neigborhood events. Whether you're relaxing poolside, entertaining guests, or enjoying the unmatched lifestyle of this premier golf and lakefront community, this home delivers the very best of Central Florida living.
Listing is courtesy of: MATT ALLEN REAL ESTATE LLC (321-228-5555)
Listing Agent: Matt Allen (321-228-5555)
9312 BLANCHE COVE DR, WINDERMERE, FL 34786
$12,350,00022 Days on yellowkey MLS ID: O6407102
Bed: 7 Bath: 9.5 Gar: 4 Liv Area Sq Ft: 11465 Built: 2022Monthly Fee: $1,224 Tax: $116,012 (2025)Community: Isleworth 5Th AmdSpa: NoSingle Family
Taxes:$116,012
Remarks: Set along beautiful Lake Blanche within the gates of Isleworth, this extraordinary modern estate is a grand haven of remarkable scale and design. Spanning more than 11,000 square feet, the residence is thoughtfully positioned to capture sweeping views across the lakefront, with walls of glass framing the water from nearly every room and filling the interiors with natural light. Beauty and modernity define the home, where sleek architectural lines are complemented by elegant oak wood flooring throughout. The main living areas flow effortlessly, creating both an impressive setting for entertaining and a comfortable environment for everyday living. At the heart of the home, a striking kitchen features distinctive Viking appliances, a Miele espresso machine, two wine refrigerators, and a seamless connection to the family room, patio, and surrounding living and dining spaces.The estate offers 7 spacious bedrooms and 9.5 baths, with each suite designed for privacy and comfort. Multiple levels—including a rooftop terrace—provide an array of vantage points from which to enjoy the lake and surrounding grounds. Additional highlights of the estate include a private home theater; a versatile lakefront bonus room ideal for a game room, wellness studio, or creative space; and two adjoining offices with custom built-ins that can be closed off for quiet focus. A standout feature of the property is the expansive guest residence on the lower level, complete with its own full kitchen, living room, two en-suite bedrooms, laundry room, and private patio—perfect for extended family or long-term guests. Practicality meets luxury with three laundry rooms throughout the estate, an elevator servicing multiple levels, and a four-bay garage. Outdoors, the expansive grounds offer both privacy and possibility, anchored by a spacious yard that leads to a private dock along the shores of Lake Blanche. A covered lanai with summer kitchen and screened living area creates an inviting setting for year-round entertaining, seamlessly blending indoor and outdoor living. This is a home that delivers on every level—scale, setting, and sophistication—offering a truly exceptional lakefront lifestyle within one of the finest golf club communities in the world.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
12720 JACOB GRACE CT, WINDERMERE, FL 34786
$2,750,000110 Days on yellowkey MLS ID: TB8476930
REDUCED by $95,000 (3.3%) on 06/16/2026
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5882 Built: 2005Monthly Fee: $300 Tax: $13,298 (2024)Community: Tildens Grove Ph 01 47/65Spa: YesSingle Family
Taxes:$13,298
Remarks: Nestled within one of **Windermere**’s most exclusive communities, this extraordinary custom-built lakefront estate with an almost 2 acres lot offers an elegant lifestyle defined by privacy, prestige, and breathtaking nightly views of the **Walt Disney World** fireworks. With nearly 6,000 square feet, six bedrooms, and six and a half baths, this residence is the pinnacle of refined Central Florida living. A long, winding driveway welcomes you, framed by mature trees and sweeping lawns. Tucked away on a quiet cul-de-sac within a 24-hour guard-gated neighborhood with a manned guard station, the property offers both grandeur and seclusion — a rare combination in today’s luxury market. Thoughtfully designed to maximize natural light and panoramic water views, the home features soaring ceilings, expansive picture windows, and seamless indoor-outdoor flow. The grand foyer opens to a spectacular living room anchored by tranquil lake vistas. The chef’s kitchen is appointed with custom cabinetry, high-end appliances, and an oversized island, effortlessly connecting to spacious dining and living areas — ideal for both intimate evenings and large-scale entertaining. The primary suite, located on the main level, is a private sanctuary with serene lake views and direct access to the outdoor living areas. The spa-inspired bath offers a soaking tub, dual vanities, walk-in shower, and generous closet space. Four additional bedrooms of which two of them include their own en-suite bath, ensuring comfort and privacy for family and guests. A detached in-law suite with private entrance, living area, bedroom, and bath provides exceptional flexibility for multigenerational living, long-term guests, or a private executive office. Step outside to your own outdoor oasis. The resort-style pool overlooks the lake, creating a stunning backdrop for entertaining or quiet relaxation. A charming pool house complete with a Murphy bed offers additional guest accommodations and enhances the estate’s resort-like ambiance. At the water’s edge, a private dock provides access to a private ski lake — perfect for boating, skiing, paddleboarding, or sunset cruises. As evening falls, the magic begins. From your backyard, dock, or expansive windows, enjoy nightly fireworks illuminating the sky above Disney — a spectacular private show reflected across the water. With nearly two acres of lakefront land, six bedrooms, six and a half baths, a detached suite, pool house, long private driveway, and location within one of Windermere’s most prestigious guard-gated communities, 12720 Jacob Grace Ct is more than a home — it is a destination, a sanctuary, and a stage for life’s most extraordinary moments.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Adrian Jacob (832-381-4670)
5500 W LAKE BUTLER RD, WINDERMERE, FL 34786
$4,700,00036 Days on yellowkey MLS ID: O6408637
0 Days Off yellowkey (back on 6/9/2026)
Bed: 8 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 7000 Built: 1997 Tax: $17,387 (2025)Community: West Lake Butler EstatesSpa: YesSingle Family
Taxes:$17,387
Remarks: Under contract-accepting backup offers. Experience the pinnacle of lakefront luxury breathtaking acres in the heart of Windermere, offering an extraordinary 320 feet of pristine ski lake frontage and an unmatched resort-style lifestyle. This one-of-a-kind waterfront compound features a stunning 6-bedroom, 5-bathroom main residence encompassing 12,323 gross square feet with 7,000 heated square feet, thoughtfully designed to maximize comfort, elegance, and breathtaking water views from nearly every angle. Adding to the property’s exceptional versatility is a private 2-bedroom, 1-bathroom guest house and separate garage apartment, creating incredible multigenerational living potential or the ideal setup for extended guests, private offices, or luxury accommodations. The showstopping covered dock pavilion is truly in a class of its own, featuring an expansive over-water lounge, designer outdoor kitchen, bar seating, dining area, and private boat slip, creating the ultimate lakeside retreat. Every detail of this estate has been curated to deliver a private luxury resort experience unlike anything else on the market. The grounds are equally spectacular with a custom screened pool and heated spa overlooking the lake, a private sandy beach, mature canopy trees, waterfront firepit lounge, multiple entertaining spaces, and beautifully manicured landscaping that creates total serenity and privacy. The property’s incredible resort-style entertaining infrastructure makes it ideal for hosting intimate gatherings or large-scale events with ease. Perfectly positioned just minutes from charming downtown Windermere, and conveniently located near Horizon West and downtown Winter Garden, this extraordinary estate also offers easy access to Orlando’s world-renowned attractions — including approximately 25 minutes to Disney and Central Florida’s premier theme parks, and only 30 minutes to Orlando International Airport (MCO). Whether enjoying peaceful mornings on the water, sunset cruises from your private dock, or entertaining on a grand scale, this extraordinary Windermere estate offers a rare opportunity to own one of Central Florida’s most impressive waterfront compounds. A true WOW property that must be experienced in person to fully appreciate its scale, setting, and lifestyle.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Julie Sanchez (817-807-3117)
9620 MAYWOOD DR, WINDERMERE, FL 34786
$2,349,00069 Days on yellowkey MLS ID: O6399315
REDUCED by $51,000 (2.1%) on 06/16/2026
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)
11539 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$3,800,0008 Days on yellowkey MLS ID: O6416913
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 5018 Built: 2017 Tax: $14,654 (2025)Community: Lake Butler EstatesSpa: NoSingle Family
Taxes:$14,654
Remarks: Welcome to this spectacular 5-bedroom, 5-bathroom custom home offering over 8,000 square feet of thoughtfully designed luxury living—spared no expense and crafted to perfection. Nestled on a sprawling acre-plus level lot, this residence redefines your Florida lifestyle with elegance and comfort. Step inside to discover more than 5,000 heated square feet filled with spacious rooms adorned with wide plank wood flooring, tongue & groove ceilings, and exposed timber beams that create a warm, inviting atmosphere. The impressive 1st floor primary suite features a huge closet offering ultimate storage and style. Guests will enjoy complete privacy in the generously sized 1st floor guest suite. The gourmet kitchen is a chef’s dream, having Natural Gas & equipped with high-end Thermador appliances and crowned by stunning quartz countertops—perfect for preparing meals or entertaining. Step outside to the fully appointed summer kitchen and enjoy the screen-enclosed swimming pool on your expansive wrap-around porch, enhanced by elegant stacked stone columns. Car enthusiasts and hobbyists will appreciate the oversized 42 x 30 - 4 car garage with 10-foot tall doors, providing ample space for all your toys and vehicles. Additional modern comforts include natural gas for efficiency and convenience throughout the home. Laundry Rooms on each Floor - Located on the most sought-after street in Windermere, this masterpiece offers privacy, style, and unparalleled craftsmanship. Truly, this is everyone’s dream home—ready for you to create lasting memories.
Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)
Listing Agent: Darrell Nunnelley (407-467-8069)
6897 NORTHWICH DR, WINDERMERE, FL 34786
$574,90062 Days on yellowkey MLS ID: O6400673
0 Days Off yellowkey (back on 5/18/2026)
REDUCED by $5,000 (0.9%) on 05/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2229 Built: 2003Monthly Fee: $82 Tax: $7,925 (2025)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$7,925
Remarks: Under contract-accepting backup offers. Welcome to the highly desirable Lakes of Windermere! Where comfort, convenience, and thoughtful updates come together in one of Central Florida’s most sought-after communities. This move-in ready 4-bedroom, 3-bathroom home offers a functional, open layout perfect for both everyday living and entertaining. Step inside to find upgraded flooring installed in 2023, creating a warm, modern feel throughout the main living areas. The kitchen has been refreshed with newer appliances, including a refrigerator (2025) and electric stove and microwave (2025), along with major systems such as roof (2018), and AC (2020) - giving buyers peace of mind and a clean, updated look from day one. Complementing the space is updated tile flooring in the kitchen (2023), blending durability with style. Major updates continue with a hot water heater (2023), adding to the home’s overall value and reducing big-ticket concerns for future homeowners. With four well-sized bedrooms and three full bathrooms, the layout offers flexibility for families, guests, or a dedicated home office. Located in the heart of Windermere, residents of Lakes of Windermere enjoy access to community amenities including a pool, playground, volleyball & tennis courts - conveniently across the street from your home. All while being just minutes from top-rated schools, shopping, dining, and major roadways. Your community now has fiber internet as an option! Don't miss out on one of the best values in Central Florida's most sought communities of Windermere!!
Listing is courtesy of: REALTY ONE GROUP INSPIRATION (321-233-2300)
Listing Agent: Blake Blahut (407-748-0484)
9621 WINDY RIDGE RD, WINDERMERE, FL 34786
$12,999,99964 Days on yellowkey MLS ID: O6400740
REDUCED by $430,001 (3.2%) on 06/15/2026
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)
12555 CRUXBURY DR, WINDERMERE, FL 34786
$350,00028 Days on yellowkey MLS ID: O6410796
2 Days Off yellowkey (back on 6/15/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1211 Built: 2005Monthly Fee: $200 Tax: $4,443 (2025)Community: Lakes Of Windermere - Lake Reams TownhomesTownhouse
Taxes:$4,443
Remarks: Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome to 12555 Cruxbury Drive in Windermere, a well-maintained 2-story townhouse offering 2 bedrooms, 2.5 bathrooms, and a practical layout in a convenient Central Florida location. Set on a quieter street with a conservation area across the way, the home offers a more open surrounding feel with added privacy. The main level features comfortable living and dining areas designed for everyday use, along with a kitchen that has a pantry closet and connects easily to the shared spaces. The home has been thoughtfully improved with a number of recent upgrades, including replaced toilets, faucets, bathroom fixtures, dishwasher, washing machine, dryer, kitchen light fixture, and exterior lighting. Additional updates include a new kitchen backsplash, LED flood lights, epoxy-coated bathroom walls, and electrical improvements completed following the previous inspection. The mirrored bathroom walls were also removed, giving the spaces a cleaner and more updated appearance. Upstairs, both bedrooms are separated from the main living area, creating a practical setup for privacy, guests, roommates, or a home office arrangement. With 2 full bathrooms upstairs and a half bath on the first floor, the layout works well for both daily living and entertaining. Outside, the patio offers a manageable area for seating, plants, or a small outdoor dining setup. The exterior lighting adds function and curb appeal, while the conservation area across the way contributes to the home’s quieter setting. The exterior of the home was also freshly repainted last year through the HOA, helping maintain a clean and updated appearance. Adding to the home’s appeal is the low-maintenance lifestyle provided by the HOA, which handles roof repairs, exterior painting (touchup 2025), and landscaping maintenance, allowing for easier day-to-day ownership and added peace of mind. Located in Windermere, the property is close to restaurants, daycare options, nearby elementary schools, Disney University, shopping, parks, area employers, and major Central Florida roadways. With its low-maintenance layout, recent updates, HOA-covered exterior maintenance, patio space, and well-connected location, 12555 Cruxbury Drive offers a solid opportunity in a desirable Windermere area.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,450,00039 Days on yellowkey MLS ID: O6407352
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3997 Built: 1999Monthly Fee: $108 Tax: $9,227 (2025)Community: Windsor HillSingle Family
Taxes:$9,227
Remarks: Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throughout the home, combining sophistication with durability and low-maintenance living. Designed for both everyday comfort and entertaining, the flexible floor plan includes an oversized upstairs BONUS ROOM, with a built-in-closet and a full bathroom, ideal for a home theater, game room, executive office, fitness studio, or private guest retreat/in-law suite. Major upgrades provide exceptional value and peace of mind, including a 2021 roof, dual high-efficiency HVAC systems (2 units/ 2026), new water heater, upgraded sliding glass doors, and an epoxy-coated garage. The expansive backyard offers endless possibilities to create your dream outdoor oasis, resort-style pool, or entertaining space. Located just minutes from the renowned Butler Chain of Lakes, championship golf courses, upscale dining, shopping, and top-rated schools, this exceptional property combines luxury, privacy, and convenience in one of Central Florida’s most desirable locations. Rarely does a fully updated home with this level of quality, land, and location become available. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
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