Location: Windermere
Do Not Show Listings
6117 LOUISE COVE DR, WINDERMERE, FL 34786
$5,250,000107 Days on yellowkey MLS ID: O6372197
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5752 Built: 2002Monthly Fee: $1,224 Tax: $50,728 (2025)Community: Isleworth WestSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$50,728
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Nestled along the shores of Lake Louise within Isleworth West, this exceptional two-story estate represents the finest in lakefront living. Offering four bedrooms, four-and-a-half baths, and more than 5,700 square feet of living space, the residence has been fully reimagined with sophisticated, modern finishes throughout. Recent enhancements include a new roof, windows, and doors; an all-new boat dock including a new roof; a new summer kitchen; exquisite white marble flooring, a dramatic glass-and-iron double-door entry, sleek modern air vents, and a host of elevated appointments that create a seamless blend of style and comfort. Grand living spaces—including the living room, kitchen, and family room—all feature soaring ceilings and an abundance of natural light, providing an ideal backdrop for both elegant entertaining and everyday living. The first-floor primary retreat is a true sanctuary, featuring a spacious bedroom and private sitting room divided by a stunning double-sided fireplace. A secondary primary suite, also located on the first floor, offers exceptional privacy and flexibility for guests or multigenerational living. Outdoors, the estate embraces its idyllic lakefront setting with a resort-style pool, summer kitchen, and private boat dock offering direct access to Lake Louise—perfect for boating, sunset cruises, and lakeside leisure. This is a rare opportunity to experience lakefront living at its finest in one of the community’s most coveted settings.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Sarah Longwell (407-920-8451)
4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786
$3,200,000276 Days on yellowkey MLS ID: O6330108
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3745 Built: 2006Monthly Fee: $1,146 Tax: $33,607 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$33,607
High School: Olympia High
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private retreat centered around a sparkling pool, serene waterfall feature, and generous lounging areas. Whether basking in the sun or relaxing beneath the stars, this outdoor haven sets the tone for the extraordinary spaces within. Designed to embrace indoor-outdoor living, the oversized courtyard welcomes you with a seamless open-plan layout connecting the pool, summer kitchen, and a charming guest cabana. Perfect for hosting or escaping, the cabana offers a private retreat for guests or a peaceful haven for the homeowner. Inside the main residence, a sense of contemporary sophistication flows through the light-filled kitchen, elegant dining room—highlighted by a statement chandelier—and the spacious grand room. French doors throughout invite the outdoors in, offering lush views from nearly every space and extending the living area to multiple porches and verandas. The living room, centered around a calming fireplace, is the perfect spot to unwind after a long day, while the spa and cascading waterfall nearby add to the sensory appeal. Retreat to the expansive master suite, where a private porch overlooks vibrant greenery, offering a peaceful start and end to each day. Additional property highlights include a cozy morning room, a dedicated office with custom Burl wood built-ins, and a series of intimate outdoor and indoor spaces designed to inspire comfort and connection.
Listing Agent: Michelle Corbin (407-491-2690)
9648 MCCORMICK PL, WINDERMERE, FL 34786
$3,800,000212 Days on yellowkey MLS ID: O6346918
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4751 Built: 1988Monthly Fee: $1,224 Tax: $33,873 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$33,873
Remarks: Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an oversized modern built-in featuring slate stonework and lit shelves. The spacious master suite features a large sitting area and an en-suite bathroom with dual vanities, a walk-in closet, modern soaking tub and separate walk-in shower. Completing the main level are the home office, formal dining room, elegant powder bath and center-island kitchen with casual dining area. Two additional bedrooms with balcony access are on the upper level. Step outside and discover a newly reimagined outdoor living experience. The expansive pool deck has been fully updated with sleek new pavers, while fresh turf and lush landscaping create a vibrant backdrop for relaxation and entertaining. A striking glass wall encases the pool area, maximizing panoramic views of both the golf course and the lake. The outdoor kitchen has been thoughtfully upgraded with new granite, a built-in grill, pizza oven, sink, and designer lighting—seamlessly blending function with style. Enjoy evenings around the modern fire pit, take a dip in the resurfaced pool with its brand-new heater, or unwind in the extended backyard, which offers an additional 15 feet added to one side of the property. Every detail of this outdoor transformation has been designed to enhance both beauty and livability, making this property the perfect retreat for year-round enjoyment.
9731 CHESTNUT RIDGE DR, WINDERMERE, FL 34786
$3,400,000253 Days on yellowkey MLS ID: O6336655
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4877 Built: 1986Monthly Fee: $1,224 Tax: $19,867 (2024)Community: IsleworthSingle Family
Taxes:$19,867
Remarks: Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.
Listing Agent: Monica Lochmandy (407-230-6888)
9669 WESTOVER CLUB CIR, WINDERMERE, FL 34786
$750,00057 Days on yellowkey MLS ID: O6386605
REDUCED by $100,000 (11.8%) on 04/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3435 Built: 2001Monthly Fee: $115 Tax: $11,111 (2024)Community: Westover Club Ph 01 44/139Spa: YesSingle Family
Taxes:$11,111
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: PRICED TO SELLLL!!! Behind the gates of Westover Club, 9669 Westover Club Circle offers a timeless Windermere setting with privacy, mature landscaping, and seamless indoor-outdoor living on nearly half an acre. Designed for both entertaining and everyday comfort, the home blends classic style with a functional layout in one of the area’s most desirable gated communities. Featuring 4 bedrooms, 4 bathrooms, and over 3,400 square feet, the home includes formal living and dining spaces and a flexible floor plan with distinct yet connected living areas. A newer AC system and roof (approx. 5 years old) provide valuable updates and peace of mind. Enjoy a screened lanai, open porch, and private pool overlooking a spacious, hedge-lined backyard. While the home would benefit from cosmetic updates, it presents an excellent opportunity to personalize, with a seller who is flexible. A Generac generator adds comfort and year-round security.
Listing is courtesy of: FIRST WORLD REALTY GROUP (954-457-0114)
Listing Agent: Regina Ferdinand (954-665-9885)
9639 WESTOVER ROBERTS RD, WINDERMERE, FL 34786
$6,395,000230 Days on yellowkey MLS ID: O6341883
Bed: 5 Bath: 8.5 Gar: 7 Liv Area Sq Ft: 11861 Built: 2017 Tax: $50,738 (2024)Community: Gotha TownSpa: YesSingle Family
Taxes:$50,738
Remarks: Welcome to a residence that transcends even the highest expectations of luxury living! This is a once-in-a-lifetime estate where architecture, scale, and location combine to create an experience that is as rare as it is breathtaking. From the moment you arrive, the home commands attention with a grand, Mediterranean-inspired façade that opens to interiors of soaring scale and meticulous marble craftsmanship. Light cascades through walls of glass, illuminating a series of living spaces designed for entertaining at the highest level. Every detail speaks of refinement: bespoke millwork, hand-selected stone, intricate ceiling treatments, and custom finishes curated with an uncompromising standard. The expansive chef’s kitchen blends culinary excellence with artful design, while the bar, wine room, and multiple gathering spaces ensure that every occasion, from intimate family dinners to grand celebrations, is unforgettable. The state-of-the-art theater begs you to slow down and enjoy the latest movie release. Conveniently adjacent to the theater is a home gym and lakefront cardio room that rivals most commercial gyms! Once the day winds down, the private retreats within the home offers warmth and convenience so you never have to leave. The first floor conveniently offers a full guest suite, and the second floor boasts an additional four bedrooms all with en-suite bathrooms. Additionally located on the second floor is a kid’s study, playroom, guest apartment and handsome cigar room. Outdoors, the estate transforms into a private resort. A sweeping terrace frames an oversized resort style pool and spa, surrounded by gardens, fountains, and tranquil seating venues. Enjoy the piece of your surroundings, from al fresco dining beneath the pergola to evenings spent overlooking Lake Olivia, one of Central Florida’s most sought-after ski lakes. Beyond the main residence, a detached guest retreat and showcase garages offering space for up to 14 cars will satisfy the most serious car collector. Set on a significant 4.43 acre parcel of land, the estate is both sanctuary and statement, offering numerous spaces to live, create, and entertain. Enjoy living in the heart of it all without compromising your privacy. Plus, with easy access to major highways, theme parks, downtown Windermere, and less than 10 minutes from Whole Foods, Restaurant Row, and championship golf courses, you’re never far from the very best of what Central Florida has to offer. Perfectly positioned with easy access to Windermere Prep, Lake Highland, and Montverde Academy...this location does not get any better! Rarely does a property of this magnitude become available. This is not simply a home — it is an heirloom, a landmark, and an invitation to experience luxury on a level few will ever know. Call today for an exclusive private showing.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
17521 BLACK RAIL ST, WINDERMERE, FL 34786
$1,495,000115 Days on yellowkey MLS ID: O6370115
0 Days Off yellowkey (back on 4/7/2026)
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5316 Built: 2015Monthly Fee: $167 Tax: $16,243 (2025)Community: EnclaveSpa: YesSingle Family
Taxes:$16,243
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. *** Now priced under $1.5M offering strong value at approximately $281/SF compared to similar Windermere homes*** PRIME opportunity for a LIKE NEW spacious MOVE-IN READY Windermere pool home just 1.5 miles from Windermere Preparatory School, and conveniently located near other top-rated public and private schools. Offering over 5,300 sq ft of thoughtfully designed living space, this 6 bedroom/4.5 bath home combines privacy, flexibility, and modern comfort, ideal for today’s lifestyles, including multi-generational living. The main level features wood-floored living areas and an open, airy layout anchored by a chef’s kitchen with oversized center island, stone countertops, stainless appliances, walk-in pantry, and pass-through butler’s pantry, perfect for everyday living and entertaining. Expansive glass doors open to the newly renovated screened, heated pool and spa (2024) with covered patio and summer kitchen, creating seamless indoor-outdoor living. A downstairs ensuite bedroom provides excellent flexibility for guests, extended family, or home office needs. Upstairs, the spacious primary suite is joined by a large bonus loft with wet bar and built-in desk area, and four additional bedrooms, two of which share a Jack-and-Jill bathroom. All bedrooms feature walk-in closets with built-in shelving, offering exceptional storage throughout. A well-appointed laundry room includes a sink and 2023 LG washer and dryer. Notable upgrades include variable-speed HVAC systems (2021 & 2023), fresh interior and exterior paint (2021), smart-controlled motorized window shades on the main level, a fully renovated pool and patio (2024) with 2025 Hayward pump, heater, lighting, and rescreening, 2023 vinyl fencing, and two finished garages (1-car + 2-car) with durable interlocking rubber flooring. Enjoy added privacy with neighborhood green space directly next door, all in a prime Windermere location near top schools, the Butler Chain of Lakes, Keene's Pointe, Downtown Windermere and Winter Garden, Winter Garden Village, major roadways, Disney and area attractions. A pre-listing home inspection report is available after the first showing, offering added transparency and peace of mind. Home is IMMACULATE. Schedule your private showing today.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Rebecca Puig (407-970-1149)
14371 CREST PALM AVE, WINDERMERE, FL 34786
$1,114,98920 Days on yellowkey MLS ID: G5110664
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3100 Built: 2025Monthly Fee: $245 Tax: $1,309 (2025)Community: Palms At WindermereSingle Family
Taxes:$1,309
Elementary School: Bay Lake Elementary
Remarks: One or more photo(s) has been virtually staged. Arlington Floorplan – 3,140 Sq. Ft. | 4 Beds | 4Baths | 2.5-Car Garage | Move-In ReadyWelcome to the Arlington with Bonus – a thoughtfully designed, 2-story home that perfectly blends luxury, functionality, and comfort. This brand new 3,140 square foot residence sits on an wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in.Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet.4 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, large center island, upgraded cabinetry, quartz countertops, walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living.2.5-Car Garage: Ample space for two vehicles plus additional storage or hobby area.Oversized Lot: Extra space for a garden,—ideal for entertaining or relaxing outdoors.Move-In Ready: No waiting required.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
58 MAIN ST, WINDERMERE, FL 34786
$3,725,00080 Days on yellowkey MLS ID: O6370886
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4875 Built: 1953 Tax: $21,723 (2024)Community: Lake Butler Park Pt RepSingle Family
Taxes:$21,723
Elementary School: None
High School: None
Middle School: None
Remarks: Nestled in the heart of Old Town Windermere, this exceptional lakefront residence offers direct access to the Butler Chain of Lakes from the tranquil waters of Wauseon Bay, prized for its reduced boat traffic and peaceful setting. Set on an oversized waterfront lot with western exposure, the home captures breathtaking lake views from nearly every room—delivering spectacular sunsets and a seamless indoor-outdoor lifestyle. Over 4800sq 5 bedrooms, 4 full bathrooms, Recently enhanced by renovations completed in 2020, the residence now features a newly added owner’s retreat with spa-inspired bathroom, thoughtfully designed to maximize comfort, privacy, and sweeping lake views. Additional updated interior in 2022 showcases refined craftsmanship and high-end finishes, including Provenza engineered hardwood flooring, vaulted tongue-and-groove ceilings, cedar beams, updated bathrooms, custom drapery, and plantation shutters. The large open kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, two oversized kitchen islands, a GE Profile refrigerator, and an Advantium double oven, all seamlessly connected to the main living areas. The great room opens effortlessly to the outdoor living spaces through fully retractable sliding doors, creating an ideal setting for gatherings of any size. Outdoor amenities rival those of a private resort, featuring a saltwater pool with pebble-tech finish and shallow lounging shelf, summer kitchen with natural gas Artisan grill, motorized patio screens, indoor/outdoor surround sound, and a luxury boat dock with electric cradle and Trex decking—perfect for enjoying the Butler Chain lifestyle year-round. Additional highlights include interior and exterior security systems, natural gas, city water, roof 2020, and a newer septic tank. Located just steps from downtown Windermere, residents enjoy a charming small-town atmosphere with farmers markets, cafés, local shops, and dining, while remaining only minutes from Restaurant Row and Orlando’s premier amenities. A rare opportunity to own a fully updated lakefront retreat in one of Central Florida’s most coveted communities.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Michelle Ingrassia (407-756-9164)
8737 IRON MOUNTAIN TRL, WINDERMERE, FL 34786
$725,00027 Days on yellowkey MLS ID: O6389224
1 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2260 Built: 2014Monthly Fee: $81 Tax: $5,709 (2025)Community: Windermere Trls Ph 1CSpa: NoSingle Family
Taxes:$5,709
Remarks: Under contract-accepting backup offers. Located in the desirable Windermere Trails community, this beautifully updated and exceptionally well-maintained home offers outstanding curb appeal and a welcoming feel from the moment you arrive. A standout feature of the property is the fantastic backyard retreat highlighted by a heated saltwater pool built in 2022 with a travertine paver deck, screened enclosure with privacy screens, and a vinyl privacy fence for added seclusion. The home also features a fully paid off whole house solar system, providing impressive energy efficiency and long-term savings. Inside, the open floor plan seamlessly connects the living room, kitchen, and dining area, creating a bright and inviting space ideal for both everyday living and entertaining. Elegant porcelain tile flooring spans the entire first floor, while bamboo flooring adds warmth and character upstairs. The primary suite is conveniently located on the first floor and features dual walk-in closets and a well-appointed bath. Upstairs you will find two additional bedrooms along with a versatile loft or bonus room that can serve as a second living area, office, or playroom. The kitchen flows easily to the interior laundry room, and a half bath is located downstairs near the mudroom and main living area for guests. Covered front and rear porches provide additional outdoor living space to relax or entertain. Ideally situated just minutes from top rated schools, shopping, restaurants, Publix, and the attractions of Walt Disney World, this Windermere Trails home offers both convenience and an exceptional lifestyle.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Matt Kester (772-494-8550)
13145 ZORI LN, WINDERMERE, FL 34786
$775,00030 Days on yellowkey MLS ID: O6394437
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3597 Built: 2003Monthly Fee: $102 Tax: $10,490 (2025)Community: ProvidenceSingle Family
Taxes:$10,490
Remarks: One or more photo(s) has been virtually staged. Priced right and move-in ready! Situated in the Windermere community of Providence, this home offers spacious living across two floors. Upon entering, you are greeted by the formal living and dining rooms. The family room is open to the kitchen for easy entertaining. The primary suite along with three other bedrooms are on the first floor. On the second floor, there is a large loft with full bathroom and private guest bedroom. The 5 bedroom home scans over 3,500 Sq Ft and sits on 0.21 acres. The private, fenced backyard features a screened patio accessible by the primary suite and family room. Providence features a community pool, playground and sidewalks throughout offering scenic vistas whether you are jogging, walking your dog or strolling to take in the fresh Florida air.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Toni Cafferty (904-449-2184)
13448 BELLARIA CIR, WINDERMERE, FL 34786
$3,200,000216 Days on yellowkey MLS ID: O6346484
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 6308 Built: 2014Monthly Fee: $483 Tax: $29,164 (2024)Community: BellariaSingle Family
Taxes:$29,164
Remarks: Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting the elegant handcrafted staircase in the foyer. The formal living and dining areas set the tone for refined entertaining, enhanced by a gas fireplace, a well-appointed wet bar, and expansive views of the sparkling pool and two-story covered porch. Just off the entry, the study provides an intimate retreat with porcelain flooring and clerestory windows, filling the space with natural light and framing serene outdoor vistas. The open-concept family room and kitchen create the heart of the home, where a wall of glass doors seamlessly blends indoor and outdoor living. The gourmet kitchen is a chef’s delight, featuring stainless steel appliances, exotic granite, custom cabinetry, tile flooring, and a spacious walk-in pantry. The first-floor master suite, thoughtfully tucked away for privacy, serves as a true sanctuary. Its spa-inspired bath is adorned with paneled cabinetry, exotic granite, a rainforest shower, soaking tub, and expansive closet areas—both beautiful and functional. Two additional en suite guest bedrooms, a versatile bonus room, and generous living and dining spaces make the main level ideal for everyday living or hosting. Upstairs, the thoughtful layout continues with three bedrooms, a loft, a sitting area, a bonus room, and even a second laundry room for added convenience. These flexible spaces adapt easily to the needs of a growing family or guests, offering opportunities for work, play, or relaxation. Blending elegance with livability, this home captures the essence of Florida living—where interiors open gracefully to resort-style outdoor spaces, making it perfect for both intimate family life and grand entertaining.
Listing is courtesy of: KENNEDY REALTY GROUP LLC (407-590-6192)
Listing Agent: Shawn Kennedy (407-590-6192)
14377 CREST PALM AVE, WINDERMERE, FL 34786
$970,00020 Days on yellowkey MLS ID: G5110662
0 Days Off yellowkey (back on 4/6/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3239 Built: 2025Monthly Fee: $215 Tax: $1,309 (2024)Community: Palms At WindermereSingle Family
Remarks: One or more photo(s) has been virtually staged. Tidewater Floorplan – 3,100 Sq. Ft. | 4 Beds | 2.5 Baths | 2-Car Garage | Oversized Lot | Move-In ReadyWelcome to the Tidewater– a thoughtfully designed, single-story home by Dream Finders Homes that perfectly blends luxury, functionality, and comfort. This brand new 2,687 square foot residence sits on an oversized lot, offering expansive indoor and outdoor living space, ready for immediate move-in.Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet.2.5 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, large center island, upgraded cabinetry, quartz countertops, walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living. 2-Car Garage: Ample space for two vehicles plus additional storage or hobby area.: Extra space for a future pool, garden, or play area—ideal for entertaining or relaxing outdoors.Move-In Ready: No waiting required. Price reduced, no incentives apply.
106 PALM ST, WINDERMERE, FL 34786
$1,399,00032 Days on yellowkey MLS ID: O6391350
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3082 Built: 1960 Tax: $12,903 (2025)Community: Windermere TownSingle Family
Taxes:$12,903
Remarks: Under contract-accepting backup offers. Set on a large, tree-lined lot just moments from historic downtown Windermere, this fully reimagined residence blends modern luxury with timeless charm—delivering a level of craftsmanship and detail that truly stands out. Every inch of this home has been thoughtfully redesigned, including a newly configured floor plan, all new interior doors and trim, and beautiful wide-plank flooring throughout. Light pours into the home, creating a bright, inviting atmosphere from the moment you step inside. At the center of it all is a completely NEW kitchen—designed for both everyday living and elevated entertaining. Featuring an impressive 10-foot quartz island with seating, custom wood cabinetry, a double-door pantry, and a stunning suite of GE Café appliances including a four-panel refrigerator, double ovens, 6-burner gas cooktop, microwave drawer, dishwasher, and a custom hood. A dedicated coffee bar adds the perfect finishing touch. The family room is equally striking, with high ceilings and a custom dry bar complete with dual beverage refrigerators—creating a seamless space for gathering and hosting. The private primary suite has been elevated to feel like a true retreat, now featuring dual walk-in closets and a beautifully renovated spa-style bathroom with a quartz-topped double vanity and a luxurious walk-in shower with rain head. A newly created private office with glass French doors and a decorative fireplace offers a quiet, stylish workspace. The home also features a newly added fourth bathroom and additional bedroom / or flex space, enhancing both functionality and flexibility. Step outside to your own backyard escape, where a private pool is surrounded by mature trees, offering both shade and privacy. Beyond the stunning design, this home offers true peace of mind with major system upgrades including a 50-year architectural shingle roof, full home replumb (2024), new tankless water heater (2025), and a new well, pump, and irrigation system (2025). All of this just minutes from the charm of downtown Windermere and the shops and restaurants along Conroy-Windermere Road. This is more than a renovation—it’s a complete reimagination of what Windermere living can be.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
6550 CARTMEL LN, WINDERMERE, FL 34786
$2,300,00022 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)
11675 SNAIL KITE WAY, WINDERMERE, FL 34786
$596,400103 Days on yellowkey MLS ID: O6373317
2 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2139 Built: 2012Monthly Fee: $130 Tax: $4,433 (2025)Community: Windermere LandingsSingle Family
Taxes:$4,433
Remarks: Under contract-accepting backup offers. Welcome to 11675 Snail Kite Way—a rare end-unit single-family home perfectly positioned on a serene park and green space, just steps from the community pool and playgrounds, in one of Windermere’s most desirable areas: the Chase Road corridor. Surrounded by luxury homes and zoned for A-rated schools including Windermere High School, this beautifully renovated, one-owner home is truly move-in ready. With its west-facing, fenced backyard and end-unit location, this home enjoys extra sunlight, a larger lot feel, and an open, airy vibe that’s perfect for everyday living and entertaining. From the moment you arrive, the charming front porch welcomes you with freshly painted exterior, custom coach lighting, and thoughtful upgrades—giving off that “was this a model home?” impression. Step inside to find stunning engineered wood floors throughout the main living area, with the living room overlooking peaceful park views. The open-concept kitchen is a showstopper, featuring dark stainless appliances, 42" maple cabinets, stone counters and backsplash, and seamless flow to the glass French doors leading to the screened-in lanai. Outside, enjoy your private retreat with pavers & turf backyard, pergola, and easy access to the 2-car garage. Upstairs, a versatile loft offers the perfect space for a home office, playroom, or lounge. The spacious primary suite easily fits a king-size bed and includes a walk-in closet and a spa-like bath with dual vanities. If you’re looking for location, lifestyle, and a home that’s been lovingly maintained and upgraded, this is it. Come see why 11675 Snail Kite Way stands out as one of the best opportunities under $600k in Windermere.
Listing is courtesy of: ORLANDO PROPERTY ADVISORS (407-808-3695)
Listing Agent: Justin Pekarek (407-808-3695)
6142 GROSVENOR SHORE DR, WINDERMERE, FL 34786
$5,150,00048 Days on yellowkey MLS ID: O6388222
Bed: 4 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 6950 Built: 2009Monthly Fee: $298 Tax: $69,198 (2026)Community: Keenes PointeSpa: NoSingle Family
Taxes:$69,198
Tax Year: 2026
Remarks: Located in Grosvenor Village within Keene’s Pointe, this estate overlooks a pond and the Tibet-Butler Preserve. Updated with interior design by Goehring & Morgan, the home includes professionally designed spaces by Angela Neel Interiors, lighting from Fine Art Handcrafted Lighting, and finishes including Emperador marble and Venetian plaster. The floor plan features a formal living room with a groin-vault ceiling leading to a central kitchen with Busby cabinetry, Emperador marble countertops, and two islands. Appliances include Miele steam oven, gas cooktop, wall oven, warming drawer, dishwashers, and a Sub-Zero refrigerator. The kitchen connects to the family room, dining area, and elevator lobby and is located near a home gym equipped with Cybex Eagle equipment. The primary suite includes a sitting area with fireplace, Busby built-in wet bar, wardrobe storage, and a bath with dual vanities, soaking tub, and walk-through shower. Additional interior features include a home office with wood flooring and display cabinetry, spiral staircase to the upper level, game room with kitchen, walk-in closet, and attic access, a laundry room, and a four-car split garage. Outdoor amenities include a covered lanai with fireplace, seating area, and sunset views over the pond and conservation area. The outdoor space also features a summer kitchen with gas grill and refrigerator, heated saltwater pool with sun shelf, travertine pool deck, and fire bowls with marble column accents. Sold fully furnished.
414 E 5TH AVE, WINDERMERE, FL 34786
$1,200,00052 Days on yellowkey MLS ID: O6387808
1 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2521 Built: 2000 Tax: $7,227 (2024)Community: Windermere RepSingle Family
Taxes:$7,227
Remarks: Under contract-accepting backup offers. CHARMING LAKEVIEW HOME IN THE HEART OF WINDERMERE! Enjoy unobstructed views of Lake Down from this beautifully located 3-bedroom, 2-bath home in the Town of Windermere. A stunning 44-foot-wide front porch provides the perfect place to relax and take in the peaceful lake scenery, morning sunrises, and evening breezes. Inside, the home offers comfortable living spaces designed for everyday living and entertaining. The backyard provides privacy and mature landscaping perfect for entertaining and family recreational activities! The property also features an impressive 33’ x 23’ oversized garage, providing abundant space for vehicles, storage, a workshop, or recreational gear. Located in the charming and highly sought-after Town of Windermere, residents enjoy a true small-town atmosphere with exceptional local amenities. Stroll or bike to nearby shopping, cozy coffee shops, wine boutiques, and the popular Windermere Brewery. The town also offers a public library, Town Hall, Windermere Police Department, multiple playgrounds, and recreation parks.Windermere is known for its strong sense of community, highlighted by the beloved weekly farmers market and a variety of town-sponsored events held throughout the year.This is a rare opportunity to enjoy lake views, generous space, and the lifestyle that makes Windermere one of Central Florida’s most desirable communities.
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Kathie Glass (407-902-9238)
13263 STRODE LN, WINDERMERE, FL 34786
$798,90068 Days on yellowkey MLS ID: O6383141
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2559 Built: 2008Monthly Fee: $86 Tax: $8,367 (2024)Community: Berkshire ParkSingle Family
Taxes:$8,367
Remarks: This beautifully maintained residence showcases rich engineered oak wood flooring throughout, a designer kitchen featuring quartz countertops with a full-height quartz backsplash, and newer stainless steel appliances. Step into your private backyard retreat with a solar-heated screened pool, propane-heated spa, elegant pavers, and wireless app-controlled access to all pool features. Additional highlights include a Google camera system and full alarm security system for added peace of mind. The spacious primary suite offers a large bedroom, custom walk-in closet, dual under-mount sinks, and a relaxing soaking tub. All bedrooms are conveniently located upstairs, along with a generously sized laundry room complete with cabinetry. A rare 3-car garage features custom built-in storage and an epoxy-finished floor. Enjoy resort-style community amenities including a pool, covered playground, walking trails, golf putting green, basketball, tennis, and pickleball court. Zoned for top-rated Windermere schools and offering views of Disney fireworks. Located on one of the most desirable streets in the community, this is a rare opportunity to own a truly exceptional home in a neighborhood known for its festive Halloween and Christmas decorations.
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Pedro Garcia Ponce (786-238-2207)
5074 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786
$7,595,000102 Days on yellowkey MLS ID: O6373191
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 6937 Built: 1988Monthly Fee: $1,043 Tax: $21,279 (2024)Community: IsleworthSingle Family
Taxes:$21,279
Remarks: Luxury living perfectly positioned along the 6th fairway in the world-renowned guard-gated community of Isleworth. This exceptional estate offers over 6,900 square feet of completely remodeled space which includes over 2,400 square foot addition upstairs thoughtfully reimagined by acclaimed architect Mark Nasrallah. Featuring 5 bedrooms and 6.5 bathrooms, the home sits on over half an acre and seamlessly blends timeless modern design with resort-style comfort. From the striking 10-foot custom pivot door to the expansive light-filled interior, the home is truly an entertainer’s dream. The main living areas showcase elegant European porcelain tile creating a bright and inviting ambiance throughout. Expansive sliding glass doors deliver a seamless indoor-outdoor lifestyle and open to a stunning backyard that can be fully screened at the touch of a remote. The open living space flows effortlessly into the chef’s kitchen appointed with top-of-the-line appliances, custom European cabinetry, designer countertops, and an oversized island. A hidden chef’s pantry and temperature-controlled wine cellar provide both functionality and refined style for entertaining. The downstairs primary suite is a private retreat designed to feel like a luxury resort. Highlights include a striking custom walk-in closet, a versatile bonus room for fitness, yoga, or massage, and a dedicated spa room connected to the suite that brings the full salon experience into the comfort of your home. The spa-inspired primary bathroom features a soaking tub, expansive walk-in shower, and tropical outdoor shower creating a true island-like escape. Upstairs, the newly built addition offers a secondary primary suite with a luxurious bath and walk-in closet, additional en-suite bedrooms, a spacious game room opening to a grand balcony with panoramic golf course views, and a refined home theater for elevated entertainment. Outdoor living is equally impressive with a sleek pool and heated spa, outdoor kitchen, wet bar, surround sound, and lush landscaping. The home is fully integrated with a Crestron smart home system controlling lighting, audio, climate, and security, and is equipped with a brand-new Generac generator for uninterrupted comfort. Every aspect of the property has been fully remodeled, renovated, and upgraded making it ready for its first owner. Contact today for a private showing!
Listing is courtesy of: MEMARPOURI REALTY LLC (407-/58-3702)
Listing Agent: Armaan Memarpouri (407-583-7028)
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