Location: Windermere
Do Not Show Listings
8351 BOWDEN WAY, WINDERMERE, FL 34786
$1,149,00067 Days on yellowkey MLS ID: O6393659
REDUCED by $50,000 (4.2%) on 06/02/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2599 Built: 2001Monthly Fee: $283 Tax: $8,252 (2025)Community: Keenes PointeSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,252
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Reduced 50k in price! Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal dining, family room, and separate sitting area, all anchored by a gourmet chef’s kitchen featuring quartz countertops, premium stainless steel appliances, and custom cabinetry—effortlessly flowing into expansive living and dining spaces ideal for both everyday comfort and refined entertaining. The luxurious primary suite offers a tranquil retreat with a sitting area, a spa-inspired en-suite bath, and a spacious walk-in closet. 2 of the additional bedrooms are split from the main suite, providing comfort and flexibility with a jack-n-jill bathroom. While a separate 4th bedroom is set apart from the others and can be used as a guest suite or office, it's in a perfect space for remote work or study. Outside, your private oasis awaits—a covered lanai overlooks a sparkling pool and lushly landscaped backyard, creating a serene setting for alfresco dining or lounging under the Florida sun. This residence is also zoned for A-rated schools, within minutes of Windermere’s charming shops, fine dining, and world-renowned attractions. (Roof Replace 2026). This exceptional home invites you to experience the very best of Central Florida living. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Sharon Brandt (407-310-3623)
1118 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786
$2,200,00076 Days on yellowkey MLS ID: O6390567
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4230 Built: 2019Monthly Fee: $250 Tax: $23,873 (2025)Community: Estancia/WindermereSpa: NoSingle Family
Taxes:$23,873
Remarks: Nestled within the exclusive enclave of Estancia at Windermere, this exceptional custom pool residence offers the perfect blend of sophisticated design, luxury finishes, and timeless Florida living. Built in 2019 and situated on a professionally landscaped homesite, this stunning two-story estate spans over 4,230 square feet of thoughtfully designed living space with 5 bedrooms and 5 bathrooms. The elegant interior showcases soaring ceilings, expansive living spaces, and a bright open-concept floor plan designed for both everyday comfort and grand-scale entertaining. A gourmet chef's kitchen serves as the heart of the home, featuring an oversized center island, premium built-in appliances, wine refrigerator, custom cabinetry, and generous gathering areas. The luxurious first-floor primary suite offers a private retreat with a spacious bedroom, spa-inspired bath, and oversized walk-in closet. Additional highlights include a dedicated office/den, formal dining room, loft-style secondary living area, media/flex space, oversized laundry room, and abundant storage throughout. High ceilings, designer finishes, custom window treatments, and expansive sliding glass doors enhance the home's sophisticated ambiance. Outdoor living is equally impressive. The resort-style backyard was designed for entertaining and relaxation, featuring a covered lanai, brick-paver pool deck, sparkling heated pool, outdoor kitchen, grill station, and a fully fenced private backyard surrounded by mature landscaping. The three-car garage, concrete tile roof, and covered front porch further complement the home's exceptional curb appeal. Located just minutes from charming downtown Windermere, residents enjoy one of Central Florida's most desirable luxury communities known for its tree-lined streets, lakeside setting, upscale estates, highly rated schools, and proximity to world-class golf, dining, shopping, and entertainment. Convenient access to the Butler Chain of Lakes, premier private schools, major highways, and the attractions of the Orlando area make this location as desirable as the home itself. Estancia offers an intimate luxury neighborhood atmosphere with beautifully maintained grounds and estate-sized homesites that provide both privacy and prestige. This extraordinary residence delivers the ultimate Windermere lifestyle—where luxury, comfort, and convenient living come together in one remarkable home.
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Corey Cannon (407-615-0215)
13936 EDEN ISLE BLVD, WINDERMERE, FL 34786
$655,0001 Day on yellowkey MLS ID: S5150801
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2675 Built: 2004Monthly Fee: $116 Tax: $8,759 (2025)Community: West Point CommonsSingle Family
Taxes:$8,759
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to 13936 Eden Isle Blvd, where comfort, space, and modern updates come together in one of Windermere’s desirable and sought after gated communities - Eden Isle. Step into a fresh chapter of elevated living with this beautifully updated 4-bedroom, bonus room, 3.5-bathroom residence offering approximately 2,675 square feet of thoughtfully designed living space. The open and functional floor plan creates the perfect balance for both everyday living and effortless entertaining. The first floor features a seamless flow between the kitchen, dining, and living areas, all enhanced by a blend of vinyl and tile flooring. The sleek kitchen showcases stainless-steel appliances, generous counter space, and brand-new cabinetry with elegant granite countertops, creating a stylish and functional centerpiece of the home. Upstairs, three well-proportioned bedrooms, including a secondary suite, offer comfort, privacy, and a versatile layout ideal for family or guests. The upper level provides a bright and functional living arrangement designed for everyday convenience. The spacious primary suite is located on the main level and features dual vanities, a separate shower, and generous closet space, creating a relaxing private retreat. A versatile bonus room located near the entry adds exceptional flexibility—ideal as a home office, media room, playroom, or additional lounge space. A first-floor laundry room adds everyday convenience, while the attached two-car garage and extended driveway provide ample parking. Recent upgrades include a new roof (2021), downstairs A/C unit replacement (2021), new water heater (2024), new exterior paint (April – May 2026), new carpet fully replaced upstairs and in the downstairs primary suite creating a fresh and cohesive interior feel (April – May 2026), and full kitchen and bathroom cabinetry upgrades with granite countertops (April – May 2026), delivering both style and long-term peace of mind. Outdoor living is just as inviting, with front and back porches perfect for morning coffee or evening relaxation, all set within a well-maintained community environment. Perfectly positioned in Windermere, known for its A-rated schools. The residents from Eden Isle Community enjoy gated security, a private boat dock with canal access to Lake Speer, and a prime location just outside the Summerport shopping plaza and Publix. You’re also minutes from Winter Garden Village, top-rated schools, grocery stores, dining, and major conveniences. This move-in-ready Windermere home delivers the ideal combination of location, upgrades, and lifestyle—an opportunity not to be missed. Schedule your showing today.
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)
Listing Agent: Jacob Hara (407-933-5478)
8715 QUIET MEADOWS TRL, WINDERMERE, FL 34786
$840,0008 Days on yellowkey MLS ID: O6410762
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3388 Built: 2013Monthly Fee: $10 Tax: $11,511 (2025)Community: Windermere Trls Ph 1CSpa: YesSingle Family
Taxes:$11,511
Remarks: Experience 8715 Quiet Meadows Trl, a residence recently refreshed with fresh interior paint throughout. The kitchen is equipped with a central island and all stainless steel appliances. The primary bathroom features double sinks and a separate tub and shower, while the primary bedroom contains a walk in closet. Outside, a covered patio overlooks a ground pool and partially fenced. A perfect blend of modern updates and refreshing outdoor comfort. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
9508 WINDY RIDGE RD, WINDERMERE, FL 34786
$30,000,000Listed 06/02/2026 3:21PM MLS ID: O6411343
Bed: 7 Bath: 13.0 Gar: 12 Liv Area Sq Ft: 51000 Built: 2011 Tax: $162,563 (2024)Community: N/ASpa: YesSingle Family
Taxes:$162,563
Elementary School: Thornebrooke Elem
High School: Olympia High
Tax Year: 2024
Middle School: Gotha Middle
Remarks: Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multiple buildings spanning 51,000 square feet of space including an expansive 20,333 square-foot Georgian-style Plantation mansion that is a showplace residence with generous luxurious spaces, classic elegance, and the ultimate in security and serenity. The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery leads to a spacious living room featuring rich mahogany millwork and expansive lake vistas. Gourmet kitchen: salamander, dual double convection ovens, commercial icemaker, full-size refrigerator, and freezer. The main level includes one of two owners' suites, plus a library-lounge or a possible sixth bedroom. Dual staircases or a Thyssenkrupp elevator provide access to the upper level, which features four-bedroom suites, including the primary retreat. An 85-foot parlor with 20-foot ceilings, built-in bookshelves, and a wet bar provide a dramatic entertaining space. Screened porch captures southern lake views and Disney fireworks. Breezeway connects to a 5,600 SF rustic lodge with a bar, catering kitchen, entertainment hall, and locker facilities. Outdoor amenities: Junior Olympic pool, spa, decorative fountain, architectural lighting, direct lake access. The vast and open water location offers an ideal space for seaplane arrivals and departures. Additional structures include a 4,000 SF paneled garage with 20-foot ceilings, an office, and a guest apartment; a 3,800 SF storage building; three separate garages accommodating motor coach and car collection; and staff quarters with a private courtyard. A rare fusion of Southern grandeur, lakefront serenity, and equestrian potential—without any interference of an HOA. Truly a legacy compound crafted for those who demand the extraordinary.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
13019 LANGSTAFF DR, WINDERMERE, FL 34786
$360,0005 Days on yellowkey MLS ID: O6411551
0 Days Off yellowkey (back on 6/2/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1375 Built: 2005Monthly Fee: $200 Tax: $5,303 (2025)Community: Lakes/Windermere-Lk Reams TwnhSpa: NoTownhouse
Taxes:$5,303
Elementary School: Bay Lake Elementary
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. Tucked away in the peaceful Lake Reams Townhome community, this charming home offers the perfect balance of excitement and relaxation — just minutes from Disney, shopping, dining, and top-rated schools, yet surrounded by the quiet comfort you’ll love coming home to after a day at the parks. Located at the end of a cul-de-sac with no rear neighbors and serene conservation views, this townhome feels like a private retreat in the heart of it all. Inside, you’ll find a bright eat-in kitchen featuring granite countertops and stainless steel appliances, opening into a spacious living and dining area designed for easy everyday living and entertaining. Outside you’ll find your private courtyard — the ideal spot for morning coffee before heading to Disney or winding down in the evening. The courtyard also leads to the detached 2-car garage for added convenience. Upstairs, the spacious primary suite creates a relaxing escape with double sinks, granite countertops, a garden tub, separate shower, and walk-in closet. The second bedroom includes its own private bathroom as well. The laundry closet is upstairs which makes laundry a breeze and the washer and dryer convey! Additional updates and features include a new AC (2025), newer roof (2022), downstairs half bath, ceiling fans, and generous storage throughout. The HOA takes care of lawn maintenance, exterior pest control, and provides access to the community pool — giving you more time to enjoy everything Central Florida has to offer while still coming home to peace and privacy.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Tennille Biggers (850-628-4455)
11401 EVESHAM DR, WINDERMERE, FL 34786
$440,00011 Days on yellowkey MLS ID: O6410182
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1847 Built: 2008Monthly Fee: $315 Tax: $3,077 (2024)Community: Preston SquareTownhouse
Taxes:$3,077
Elementary School: Sunset Park Elem
Remarks: One or more photo(s) has been virtually staged. Brand New Roof just installed a couple of weeks ago! Welcome to this stunning corner unit townhome in the highly sought after Preston Square community in Windermere. Offering 3 bedrooms, 2.5 baths, and an exceptional layout.This beautifully maintained home perfectly combines elegance, comfort, and convenience. Ideally situated directly across from the community amenities, you’ll enjoy easy access to everything Preston Square has to offer while still enjoying the charm and privacy of a welcoming neighborhood setting. From the inviting front porch to the light filled interior, every detail of this home has been thoughtfully designed. Expansive wrap around windows flood the space with natural light, accentuating the soaring 10 foot ceilings and rich hardwood flooring throughout the main living areas. The open and functional floor plan is ideal for both everyday living and effortless entertaining. One of the home’s standout features is the private courtyard, a tranquil outdoor oasis perfect for hosting gatherings, grilling with friends, or simply unwinding after a long day. Inside, the gourmet kitchen is sure to impress with 42 inch solid wood cabinetry, granite countertops, stainless steel appliances, and ample prep and storage space for any home chef. The spacious first floor primary suite offers a peaceful retreat with a tray ceiling and a luxurious ensuite bath featuring dual vanities, a relaxing garden tub, and a walk in shower with dual shower heads. Upstairs, an oversized open concept loft provides flexible living space along with two additional bedrooms, creating ideal separation and privacy for family members or guests. Additional highlights include a laundry room with a utility sink and natural light, plus a rear entry two car garage complete with overhead storage racks and an extended driveway for extra parking. Residents of Preston Square enjoy resort style amenities including a sparkling community pool, beautifully landscaped grounds, basketball court, playground, fitness stations, and a large community park that regularly hosts movie nights and food truck events. Conveniently located near top rated schools, shopping, dining, golf courses, hospitals, and major roadways, this home offers easy access to Orlando, Winter Garden, and Central Florida’s world famous theme parks. This is an incredible opportunity to own a stylish and move in ready home in one of Windermere’s most desirable communities.
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Chris Courtney (407-406-0506)
5067 SAWYER COVE WAY, WINDERMERE, FL 34786
$2,100,000Listed 06/02/2026 12:09PM MLS ID: O6409382
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3461 Built: 2018Monthly Fee: $287 Tax: $21,824 (2025)Community: Sawyer SoundSingle Family
Taxes:$21,824
Remarks: Rare opportunity to be one of the 20 custom homes of Gated Sawyer Sound. Each one a stunning architectural masterpiece after another as you drive thru the enclave community. This stunning one-story custom home will leave you saying "wow" at every turn. Situated on an oversized cul-de-sac lot , this one-of-a-kind residence offers unparalleled curb appeal and fully embraces the Florida lifestyle with thoughtful flowing design in and out, creating the perfect blend of form and function. Pass double entry metal doors to soaring 18-foot ceilings accented by genuine wood beams that create an atmosphere of grandeur and warmth. Expertly laid marble tile flooring gleams throughout, guiding you into the expansive great room anchored by two spa-inspired primary suites on opposite wings for ultimate privacy. The heart of the home features a show-stopping kitchen adorned with hand-selected Cristallo Quartzite countertops featuring integrated uplighting that delivers a dramatic, one-of-a-kind glow. Top-of-the-line Thermador appliances powered by the community's natural gas lines, custom cabinetry, and a massive walk-in pantry—engineered as a FEMA-grade safe room—provide both gourmet functionality and exceptional storage. A dramatic wall of pocketing sliding glass doors seamlessly blends indoor and outdoor living, perfect for effortless entertaining. This opens to a sprawling covered lanai with tongue-and-groove ceilings and a cozy gas fireplace, overlooking a large saltwater heated pool with extensive travertine decking and a cabana-style summer kitchen that remains with the home. The generous lot—one of the largest in this intimate 20-home community—offers ample space for a private backyard oasis despite the impressive pool footprint. Additional premium features include a whole-home water filtration system, a Briggs & Stratton whole-home natural gas generator, spray foam insulation, a tile roof, and energy-efficient windows for comfort and efficiency. The oversized CLIMATE CONTROLLED three-car garage boasts soaring ceilings (ideal for lifts), epoxy flooring, built-in storage cabinets, and an EV charger. Located in a highly sought-after K-12 school district, this property sits directly across from Windermere Preparatory School with Foundation Academy just minutes away. Residents enjoy convenient access to world-class shopping, dining, and entertainment in every direction, plus quick commutes via the 429 expressway and proximity to Disney's front gates. This Architectural Digest-worthy masterpiece was thoughtfully crafted as a personal vacation home by a professional interior designer who spared no detail. Custom silk draperies convey with the sale, and all like-new furniture is negotiable. Opportunities like this rarely arise in Sawyer Sound—don't miss your chance to own a true Florida luxury retreat that combines elegance, functionality, and resort-style living at its finest.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Ronald Ziolkowski (407-592-7653)
12812 JACOB GRACE CT, WINDERMERE, FL 34786
$3,699,888326 Days on yellowkey MLS ID: V4943735
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6054 Built: 2007Monthly Fee: $317 Tax: $25,596 (2024)Community: Tildens Grove Ph 01 47/65Spa: YesSingle Family
Taxes:$25,596
Remarks: Under contract-accepting backup offers. Experience Unmatched Lakeside Luxury in a Custom-Built Masterpiece Discover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend of relaxation, recreation, and refined living. Step inside to a beautifully designed open-concept living space where the family room and gourmet kitchen seamlessly connect. The kitchen is a chef’s dream, featuring top-of-the-line appliances, a breakfast bar, an inviting eat-in nook, and a spacious butler’s pantry. A custom wine closet nearby provides a perfect display for your finest vintages. Adjacent to the kitchen, a well-appointed guest suite and a large laundry room enhance the home's convenience. The formal dining and living rooms, centered around a cozy shared fireplace, has stunning views of the lake—creating a warm and relaxed setting for entertaining. The first floor also features a private office, a full pool bathroom, and a luxurious primary suite. This expansive retreat includes a dedicated exercise room, while the spa-inspired en-suite bath boasts double vanities, dual walk-in closets, a garden tub, and a walk-through shower. A beautifully crafted wood and iron staircase leads to the second floor, where you'll find two spacious bedrooms, each with its own private bathroom. The expansive game room opens to a lake-view balcony, perfect for taking in serene sunsets. Movie nights are elevated in the state-of-the-art home theater, complemented by a convenient half bath. Step outside to your own private paradise—an entertainer’s dream. The large covered lanai includes a fireplace and a fully equipped summer kitchen. A sparkling pool and spa, along with a generous open patio, set the stage for unforgettable gatherings or peaceful evenings under the stars—complete with views of the nightly fireworks. Rounding out this extraordinary residence is a three-car garage, offering ample room for vehicles and recreational equipment. This is more than a home—it’s a lifestyle. Luxury, privacy, and breathtaking views await. Schedule your private tour today and experience the ultimate in lakeside living.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ali Partovi (386-295-5115)
7719 ANSELMO LN, WINDERMERE, FL 34786
$375,00070 Days on yellowkey MLS ID: O6392007
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $7,000 (1.8%) on 04/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2008Monthly Fee: $375 Tax: $5,537 (2025)Community: Lake Sawyer South Ph 03Townhouse
Taxes:$5,537
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Move-in ready townhome offering a clean, functional layout with abundant natural light throughout. Upon entry, you’re welcomed into a spacious living room that provides a comfortable and defined gathering space separate from the kitchen and dining areas. Toward the rear of the home, the kitchen and dining area are thoughtfully positioned for everyday functionality and ease of use. The kitchen features granite counters, stainless steel appliances, ample cabinetry, and a breakfast bar that offers additional seating and prep space. The adjacent dining area provides direct access to a private, fenced paver patio, creating a low-maintenance outdoor space ideal for relaxing or entertaining. Recent updates include new interior paint, new carpet, and a new water heater, enhancing both comfort and long-term value. A/C unit was replaced with a brand new unit in 2021. Upstairs, all bedrooms feature fresh carpet flooring and generous closet space. The primary suite offers a spacious layout with an en suite bathroom that includes dual sinks and a walk-in shower. Additional bedrooms are well-sized and versatile for guests, office space, or hobbies. A convenient upstairs laundry area and a main-level half bath add to the home’s practical appeal. With neutral finishes, thoughtful updates, and a well-maintained interior, this property is a strong option for buyers seeking low-maintenance living with functional space and modern touches.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Stephanie Pitts (407-353-6132)
11861 VERMILLION AVE, WINDERMERE, FL 34786
$475,000Listed 06/02/2026 10:24AM MLS ID: O6410430
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1600 Built: 2015Monthly Fee: $363 Tax: $6,340 (2025)Community: Windermere Trls Prcl 3Single Family
Taxes:$6,340
Remarks: MUST SEE. TOP RATED SCHOOLS. Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Windermere Trails community! This spacious two-story home features an open-concept layout with a modern kitchen offering stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas — perfect for entertaining. Upstairs, the spacious primary suite includes a walk-in closet and private en-suite bathroom. Enjoy the convenience of a rear-entry 2-car garage and low-maintenance living in one of Windermere’s most desirable locations. Community amenities include a resort-style pool, playgrounds, walking trails, dog park, and scenic green spaces. Ideally located near top-rated schools, shopping, dining, major highways, and Disney attractions. Don’t miss this incredible opportunity!
Listing is courtesy of: KARDOSH REALTY (407-499-4466)
Listing Agent: Frederico Hexsel (407-745-8841)
2931 SUNBITTERN CT, WINDERMERE, FL 34786
$1,199,000116 Days on yellowkey MLS ID: O6378100
2 Days Off yellowkey (back on 2/26/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 4018 Built: 1985Monthly Fee: $215 Tax: $8,710 (2024)Community: Butler BaySpa: YesSingle Family
Taxes:$8,710
Remarks: Under contract-accepting backup offers. Discover the charm of the Town of Windermere, Tree City USA, where the sparkling lakes, mature tree canopies, and a quaint ambiance create an exceptional place to call home. Deeply committed to preserving its character while embracing thoughtful cultural progress, Windermere offers a vibrant community filled with playful events. Nestled within the town proper and the gates of Lake Crescent Reserve, this freshly painted, custom 4018 sf home rests on pristine a 1.06 acre lot, showcasing an outdoor oasis. Designed for seamless indoor-outdoor living, this home also features an impressive 1100 sf flex suite with a private entrance, full kitchen, sliding doors to the pool. This area is ideal for a pool party or game area, multigenerational living, private office and work area, fitness center, or other creative space that best suits your needs. From the moment you enter, you’re welcomed into the family room featuring the vaulted ceilings, a wondrous wood-burning fireplace and wet bar conveniently located by the sliding pocket doors to the pool and outdoor entertaining spaces. Overlooking a privately landscaped yard with a new firepit, this home invites you to the perfect balance of year-round entertaining and peaceful retreat, where indoor comfort meets outdoor beauty in effortless harmony. Thoughtful home design is exhibited by a split floor plan, providing flexible spaces for separate conversations, play areas, multigenerational living, or large, scale entertaining. The spacious, well-appointed kitchen features a large eat-in area, SubZero refrigerator, quartz and granite countertops, wood cabinetry, and a center island with a cooktop and countertop eating. The owner’s suite offers a luxurious, recently updated en-suite and generous walk-in closet. Take advantage of the flex-space opportunities, which include the 1100 sf private entrance suite and the expansive second-floor loft with natural light from skylights. Notable upgrades include a Gerard stone-coated metal roof, resurfaced pool, re-sealed patio deck, and oversized septic leach field. Additional features include two water heaters, three-zone HVAC, vaulted family room ceiling, a large, covered lanai with retractable sunscreens on those days you prefer a little shade, and two outdoor kitchen plumbing access points for future expansion of the outdoor living space. Located within the Town of Windermere, residents enjoy exclusive amenities, including access to tennis courts, boat ramps to the various lakes, events, food truck night, farmers market, art and holiday special events, and other exclusive Town of Windermere residents-only events, to mention a few. The recently approved project to enhance the already meaningful community, involves the development of the Windermere Ward Trail and pedestrian bridge to provide safe and convenient access for pedestrians, bicyclists, and golf carts, to safely connect to local recreational areas, businesses, and government.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Christa Dinallo (561-702-2112)
9072 WOODBREEZE BLVD, WINDERMERE, FL 34786
$549,90027 Days on yellowkey MLS ID: O6403789
REDUCED by $12,600 (2.2%) on 05/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1721 Built: 1985Monthly Fee: $30 Tax: $3,899 (2025)Community: Silver WoodsSpa: NoSingle Family
Taxes:$3,899
Middle School: Chain of Lakes Middle
Remarks: Best price Improvement.. Welcome to 9072 Woodbreeze Blvd, a beautifully maintained and thoughtfully updated home nestled in the highly desirable Silver Woods community of Windermere. This charming single-story residence offers 3 bedrooms, 2 bathrooms, and 1,728 square feet of comfortable living space, perfectly blending classic character with modern improvements. Set on a spacious quarter-acre lot, the property showcases mature landscaping and a serene pond view that creates a peaceful backyard retreat. Inside, the home is filled with natural light and designed for both relaxation and everyday living. The kitchen and family room flow seamlessly together, offering inviting spaces to gather while enjoying picturesque views of the lush yard and water beyond. A standout feature is the added Florida room—an ideal spot to unwind, entertain, or simply take in the tranquil surroundings year-round. This home has been lovingly cared for, with key updates already completed for peace of mind. Recent improvements include a newer A/C system, newer hot water heater, updated exterior lighting and door hardware, and consistent professional grounds maintenance. Major systems have also been addressed, with the septic system replaced in 2019 and the roof replaced in 2020. The kitchen, updated in 2010, features full-sized cabinetry and durable Corian countertops, offering both functionality and timeless appeal. Silver Woods is known for its welcoming, family-friendly atmosphere and remarkably low HOA dues of just $364 annually. Residents enjoy access to community amenities including tennis and pickleball courts, all while being conveniently located within walking distance to local middle and high schools, as well as the Grove Publix shopping center with its variety of restaurants, shops, and fitness options. The location is truly exceptional—just minutes from Sand Lake Road’s renowned dining and entertainment, with easy access to major highways including I-4, the Turnpike, 528, and the 408. Downtown Orlando is only about 20 minutes away, and Orlando International Airport is approximately a 25-minute drive. This home offers a rare combination of comfort, updates, location, and community charm. It’s a place where you can truly settle in and enjoy the best of Central Florida living!
Listing Agent: Charles Kohlinger (407-421-9188)
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
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)
4474 BEGONIA CT, WINDERMERE, FL 34786
$1,170,00038 Days on yellowkey MLS ID: O6402227
REDUCED by $100,000 (7.9%) on 05/13/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4380 Built: 1998Monthly Fee: $133 Tax: $7,670 (2025)Community: Magnolia Park WindermereSingle Family
Taxes:$7,670
Remarks: Beautifully maintained estate in a small, private gated community in Windermere, zoned for some of the area's best school- you can even walk to Windermere High School. Situated on a quiet cul-de-sac with no rear neighbors, the property offers exceptional privacy along with generously sized lots compared to many surrounding Windermere communities. Master bedroom and one additional room are located on the first floor, ideal for guests or multigenerational living. No carpet throughout the entire home! This 5-bedroom, 4.5 bath home offers a screened pool, extensive system upgrades and efficient well and septic utilities- meaning no water or sewer bills. Recent improvements include a new roof and water heater (2026), a new chlorine injection pump (2026), and two main A/C units replaced in 2020. Additional comfort is provided by two mini-split A/C and heating systems, installed in the master bedroom (2024) and an extra room (2025). Ideally located just minutes from SR-429, SR-535, and just minutes from Publix, Walmart, Target and nearby hospitals. This home offers the perfect blend of comfort, convenience, and luxury. If this home interests you, schedule your showing today!
Listing is courtesy of: SOGO REAL ESTATE SERVICES LLC (407-730-3100)
Listing Agent: Ranah Nam (321-277-3482)
13755 BRAVANTE ALY, WINDERMERE, FL 34786
$480,00076 Days on yellowkey MLS ID: O6389321
REDUCED by $9,999 (2.0%) on 05/28/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1996 Built: 2017Monthly Fee: $254 Tax: $5,646 (2025)Community: Vineyards/Horizons West Ph 2BTownhouse
Taxes:$5,646
Elementary School: Independence Elementary
Remarks: **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 13755 Bravante Aly, Windermere, FL 34786, a charming two story home featuring 3 bedrooms and 2 bathrooms located in a desirable Windermere community. This home offers a bright open floor plan with comfortable living and dining areas that flow seamlessly into the kitchen, creating a welcoming space for everyday living and entertaining. The thoughtful layout provides both functionality and comfort, making it ideal for a variety of lifestyles. Upstairs, the bedrooms offer privacy and relaxation, along with a versatile second floor loft area that can be used as a home office, media space, or additional living area. The overall design maximizes space and natural light throughout the home. The property also features a covered patio on the side of the home complete with retractable screens, providing a comfortable outdoor space to relax, enjoy your morning coffee, or entertain guests year round. Residents enjoy access to community amenities including a pool and park, offering great opportunities for recreation and outdoor enjoyment. Conveniently located near shopping, dining, schools, and major roadways, this home offers comfort and convenience in the heart of Windermere.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
33 MAIN ST, WINDERMERE, FL 34786
$1,575,00022 Days on yellowkey MLS ID: O6406887
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2130 Built: 1961 Tax: $9,485 (2025)Community: Davis ShoresSpa: NoSingle Family
Taxes:$9,485
Remarks: BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere residents can access Fernwood Park and boat ramp 8/10 mile away. Drive your Golf Cart to downtown Windermere. Multiple possibilities for this property in the prime location of Windermere. Home needs major renovation or demolish and rebuild. Sold AS IS.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Bruce Higgins (407-883-2728)
7644 RIPPLEPOINTE WAY, WINDERMERE, FL 34786
$435,00061 Days on yellowkey MLS ID: O6395582
2 Days Off yellowkey (back on 6/2/2026)
REDUCED by $10,000 (2.2%) on 05/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1881 Built: 2015Monthly Fee: $240 Tax: $6,847 (2025)Community: Lake Burden South Ph 2 #35 36Townhouse
Taxes:$6,847
Remarks: Welcome to Lake Burden, one of Windermere’s most desirable and well-established communities! This corner-lot townhome offers 3 bedrooms, 2.5 bathrooms plus office. This open-concept floor plan that flows seamlessly with a well-appointed kitchen with granite countertops and backsplash, and a walk-in pantry. Large living room features high ceilings and tons of windows for natural light. French doors open to your own private paved garden courtyard, an ideal spot for morning coffee, weekend gatherings, or evening relaxation. The courtyard also provides direct access to a two-car garage via a tranquil rear alley. Upstairs laundry room has built-ins with a full-size front load washer and dryer. Enjoy a vibrant lifestyle with resort-style amenities — a sparkling community pool, shaded picnic tables, two tennis courts, a playground, and scenic walking paths around the lake ideal for peaceful evening strolls. This is a full-of-life neighborhood where pride of ownership shows everywhere. Residents enjoy wonderful community amenities such as a clubhouse, resort-style swimming pool, tennis courts, and scenic walking paths, perfect for relaxing or staying active. Ideally situated just minutes from Walt Disney World, major highways, top-rated A schools, shopping centers, Publix, restaurants, and everyday conveniences. This property offers the perfect combination of location, lifestyle, and value, ideal as a primary residence, vacation home, or investment opportunity in one of Central Florida’s most sought-after areas.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Kelly Zannini (407-970-6298)
13525 GORGONA ISLE DR, WINDERMERE, FL 34786
$1,115,000106 Days on yellowkey MLS ID: O6377789
REDUCED by $5,000 (0.4%) on 05/22/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4625 Built: 2018Monthly Fee: $268 Tax: $9,351 (2025)Community: Windermere IsleSpa: NoSingle Family
Taxes:$9,351
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless entertaining. A dramatic two-story foyer creates a striking first impression, highlighted by a custom hardwood staircase with decorative iron balusters. Architectural details continue throughout with 9.5-foot ceilings, 8-foot doors, coffered ceilings, porcelain tile on the main level, and hardwood flooring upstairs. Custom Disney-inspired stained-glass window inserts throughout the home offer a subtle and charming nod to the nearby magic. The expansive open-concept living area is anchored by a chef-level gourmet kitchen featuring a natural gas cooktop, dual convection ovens, quartz countertops and backsplash, oversized island, 42-inch cabinetry, café dining area, and walk-in butler’s pantry—perfect for entertaining and daily convenience alike. The main-level primary suite serves as a tranquil retreat with a spa-style bathroom, soaking tub, glass-enclosed walk-in shower, and generous custom closet. Upstairs, five additional bedrooms include a private guest suite and well-designed shared layouts, along with a spacious upper-level great room and reading nook ideal for a media room, game space, or lounge. Significant upgrades include a 27kW commercial-grade whole-house generator, tankless water heater, gas dryer, advanced humidification and UV air filtration, and a garage with custom cabinetry, overhead storage, and durable polyaspartic flooring. Energy-efficient systems and abundant natural light enhance comfort throughout. The lot to the right of the home is Protected Green Space in perpetuity and cannot be developed so you will always have that space. Seller is providing a credit towards a 2-1 RATE BUY DOWN with full price offer. Inquire for more details.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Roo Klaers (407-493-5615)
1002 OAKDALE ST, WINDERMERE, FL 34786
$975,00049 Days on yellowkey MLS ID: TB8495717
1 Days Off yellowkey (back on 4/22/2026)
Bed: 4 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 3516 Built: 1973 Tax: $8,799 (2025)Community: Windermere TownSingle Family
Taxes:$8,799
Remarks: Under contract-accepting backup offers. Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by. Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining. The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations. A rare offering in this location, the property features an impressive 3 bay, 30' long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs. Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home. Seller is offering up to a $25,000 closing cost credit, providing added flexibility and value for buyers. A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Frank Smith (401-644-4762)
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