Location: Windermere
Do Not Show Listings
2806 WINDSOR HILL DR, WINDERMERE, FL 34786
$1,150,0008 Days on yellowkey MLS ID: O6385977
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3181 Built: 1989Monthly Fee: $111 Tax: $13,057 (2024)Community: Windsor HillSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,057
Elementary School: Thornebrooke Elem
High School: Olympia High
Tax Year: 2024
Middle School: Gotha Middle
Remarks: Step into this stunning 4-bedroom, 3-bathroom pool home nestled on nearly half an acre in the highly desirable Windsor Hill community of Windermere. From the moment you enter, you’ll appreciate the bright, open floor plan designed for both comfort and effortless entertaining. At the heart of the home is a beautifully updated kitchen featuring rich walnut cabinetry, quartz countertops, a mosaic tile backsplash, touch faucet and a spacious island that seamlessly connects to the dining and living areas. Equipped with a gas range, stainless steel appliances, and ample counter space, this kitchen is perfect for gathering with family and friends. The expansive media room offers the ultimate entertainment experience, complete with a built-in media center, kitchenette, wine refrigerator, and full-size refrigerator—ideal for movie nights or hosting guests in style. Step outside to your private backyard oasis, where a sparkling heated pool and spa await. Enjoy modern features including a heater, LED lighting with remote control, and a newer pool pump. The covered outdoor living area, complete with a sink and cabinetry, creates the perfect setting for al fresco dining and relaxation. Inside, every bathroom has been thoughtfully renovated with updated vanities, mirrors, bidets, and sleek shower stalls. The luxurious primary suite boasts a spa-inspired bath with a 67-inch freestanding soaking tub, smart mirror with defog function, and dual vanities. Major system upgrades provide peace of mind, including a new roof and skylight (2021), whole-home re-plumbing (2022), water heater (2022), and pool pump (2023). Garage features an electric car charger. Combining the tranquility of suburban living with convenient access to major roadways, shopping, dining, and downtown Orlando, this move-in ready home truly has it all. Don’t miss your opportunity to own this exceptional property—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Candace Hebert (321-246-0068)
10870 BAYSHORE DR, WINDERMERE, FL 34786
$2,995,00077 Days on yellowkey MLS ID: O6371471
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4693 Built: 1999 Tax: $27,527 (2024)Community: Lake Down EstatesSpa: YesSingle Family
Taxes:$27,527
Elementary School: Windermere Elem
Remarks: Set against the shimmering waters of Little Lake Down, this extraordinary lakefront home offers an elevated expression of luxury living. Thoughtfully designed to maximize sweeping water views, the residence delivers a refined yet inviting atmosphere ideal for both intimate living and grand entertaining. As you step inside you are greeted by a spacious open floor plan, highlighted by a wood-burning fireplace, and captivating views of the pool, backyard, and lake. At the heart of the home, a chef’s kitchen stands as a true centerpiece, appointed with top-of-the-line appliances and two expansive center islands, it’s the perfect place for family gatherings. The kitchen opens to a large family room and breakfast nook providing effortless flow for daily living, enhanced by panoramic lake views that bring the outdoors in. The primary suite serves as a luxurious retreat, featuring peaceful water views and a spa-like bathroom with dual vanities, a walk-in shower, and an elegant soaking tub. Additional first floor amenities include a guest bedroom, a home office, and a pool bath. Upstairs, you will find two additional bedrooms, a spacious bonus room, and a private balcony overlooking the lake. Outdoor living rivals a private resort with a large, covered lanai, sparkling pool, spa, and an expansive backyard that leads to a private boat dock with a boat lift and jet ski parking. With direct access to the Butler Chain’s interconnected lakes there will be no shortage of things to do on the weekend. Enjoy being just minutes from Windermere A rated schools, the Friday farmers market, quaint eateries, and a short drive to world class shopping, fine dining, and the Disney and Universal theme parks. This is more than a home, it is a rare opportunity to own a private lakefront retreat on the Butler Chain of Lakes, where luxury, lifestyle, and location converge in one truly exceptional offering.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
8520 GREENBANK BLVD, WINDERMERE, FL 34786
$549,9009 Days on yellowkey MLS ID: O6396673
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1726 Built: 2004Monthly Fee: $170 Tax: $6,960 (2025)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$6,960
Elementary School: Bay Lake Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: Beautiful and inviting home located in the heart of Windermere, nestled within a charming gated community. Enjoy the rare opportunity to watch Disney fireworks right from your own backyard. Designed for modern living, this home features an open-concept floor plan that flows seamlessly, perfect for both everyday comfort and entertaining. The fully fenced backyard offers privacy and the ideal space for family gatherings, barbecues, and outdoor enjoyment. Additional highlights include solar panels for enhanced energy efficiency, a spacious two-car garage, and a welcoming front porch perfect for relaxing. Residents enjoy access to community amenities including a sparkling swimming pool, playground, and beautifully maintained green spaces. Ideally located near top-rated A+ schools, as well as shopping, dining, and everyday conveniences, this home offers the perfect blend of comfort, efficiency, and location in one of Central Florida’s most desirable areas. Roof is 2024, Water Heater is 2025.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Umberto Da Cunha Neto (407-690-3539)
11162 LEDGEMENT LN, WINDERMERE, FL 34786
$995,000184 Days on yellowkey MLS ID: O6346461
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3248 Built: 2002Monthly Fee: $170 Tax: $7,747 (2024)Community: Glenmuir Ut 02 51 42Single Family
Taxes:$7,747
Middle School: Bridgewater Middle
Remarks: NEW TILE ROOF INSTALLED BEFORE CLOSING! Welcome to Glenmuir—one of Windermere’s most sought-after gated communities. This 4 bedroom, 3 full bath, plus 2 half bath home includes a dedicated office and an upstairs bonus room within a primarily single-story layout—a thoughtful blend of functionality and comfort. Double doors open to a bright foyer with immediate views of the custom 2021 saltwater pool and serene greenspace—no rear neighbors. A private office with French doors and a closet sits just off the foyer. The formal living and dining rooms open directly to the covered lanai and pool, offering seamless indoor–outdoor living. The kitchen provides abundant cabinetry, extensive counter space, a butler’s pantry, and a café area overlooking the pool and outdoor spaces. The kitchen and dining nook flow into a spacious family room—an ideal gathering place. The family room provides lots of windows for natural light. The primary suite is a true retreat with direct pool access and a spa-style bath featuring dual vanities, a soaking tub, a walk-in shower, and an oversized walk-in closet. On the opposite wing, three secondary bedrooms and two full baths— including one en suite—offer excellent flexibility for family or guests. Upstairs, a large bonus room with a half bath functions beautifully as a game room, media space, lounge, or studio. Outdoor living shines with the 2021 custom saltwater pool and generous patio space to enjoy evening views of the Disney fireworks. A dedicated exterior half bath for pool access adds convenient hospitality. The fully fenced yard offers privacy and ample room for pets, gardening, or play. A three-car garage and extended driveway provide generous parking. A new tile roof will be installed prior to closing. Recent updates include two new A/C units (Nov 2024), a new water heater (2025), a new irrigation timer and well pump, fresh exterior paint, and a newly painted garage floor. Glenmuir offers a park, playground, basketball court, and picnic pavilion. Zoned for Windermere Elementary, Bridgewater Middle, and Windermere High, and convenient to Windermere Prep. Prime location near the Lake Butler public boat ramp (Butler Chain of Lakes), SR-429, the Florida Turnpike, and nearby shopping, dining, and world-class attractions including Disney, Universal, and SeaWorld. Schedule your private tour today!
Listing is courtesy of: INFINITY REALTY GROUP LLC (407-234-2256)
Listing Agent: Deb Schroeder (407-234-2256)
13243 CHARFIELD ST, WINDERMERE, FL 34786
$699,00050 Days on yellowkey MLS ID: O6385405
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2794 Built: 2010Monthly Fee: $81 Tax: $6,403 (2024)Community: Lake Sawyer South Ph 02Single Family
Taxes:$6,403
Elementary School: None
High School: None
Middle School: None
Remarks: A Windermere pool home under $700K like this is hard to come by, especially on one of the best tree-lined streets in the community. As soon as you walk in, you’re greeted by a two-story entrance and open living area that brings in great natural light and gives the home a larger, more elevated feel. The layout includes a formal dining room and hardwood floors throughout the main living areas, complemented by tile in all the right spaces. This home is set up perfectly for both everyday living and entertaining, with multiple living and dining spaces, a powder bath, and a spacious kitchen featuring wood cabinetry, newer appliances, and direct access to the outdoor area. The primary suite is on the first floor and includes a custom walk-in closet with built-ins, along with a spacious bathroom featuring a double sink vanity, garden tub, and walk-in shower. Upstairs, you’ll find a large loft that works great as an office, game room, or second living space, along with three additional bedrooms. One bedroom has its own en-suite, giving you a second primary-style setup. The backyard is the highlight. A fully screen-enclosed pool with sun deck, waterfalls, brick pavers, multiple seating areas, and a summer kitchen creates a true indoor-outdoor lifestyle. There’s even a large projector screen for movie nights. The yard is fully fenced with plenty of green space left over. Additional features include a 3-car garage, a driveway that fits up to six cars, a welcoming front porch, a large laundry room, and a newer upgraded AC unit. Located in a highly desirable Windermere community with A-rated schools, you’ll also have access to great amenities including a community pool, covered playgrounds, walking trails, a golf putting green, and courts for basketball, tennis, and pickleball, all close to shopping, dining, and everyday convenience. Minutes from Disney and all the fun, you don't want to miss out on this truly incredible home! Schedule your showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
6857 VALHALLA WAY, WINDERMERE, FL 34786
$3,700,0003 Days on yellowkey MLS ID: S5147781
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 7153 Built: 2006Monthly Fee: $298 Tax: $35,537 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$35,537
Remarks: Perfection has an address along with comfortable Florida living. Located on the 17th fairway of Jack Nicklaus-designed Golden Bear Club's golf course, this stunning home offers 5 bedrooms with the master on the 1st floor, 5 full baths, 2 half baths, home theatre, game room, office, and 2nd floor gathering room overlooking a stunning balcony. Invest in quality in this Rick Watson built masterpiece offering a detailed office with coffered ceiling and built-ins, gourmet kitchen with Wolf appliances, and an abundance of custom features. Come experience the peaceful setting of this lovely home with a beautiful view of the golf course and the perfect floor plan for entertainment with its integrated sound system all over the house. An expansive master suite offers lanai access, two spacious walk-in closets with custom organization system, a spa-like bath with stone-top jetted tub, a travertine-covered wrap around walk-in shower with multiple shower heads, and separate vanities. Year-round outdoor activity is possible on the lanai with a summer kitchen and generous outdoor living space that includes covered seating areas, a gas fireplace, space for an outdoor TV, and a gorgeous pool and spa. Watch cinematic masterpieces in your very own home theater, or host game nights in your very own game room with a wet bar diso style. Additional Features include but are not limited to: 5 A/C units with an upgraded air filtration system, a stone-paver driveway, an over-sized 3-car garage, elegant landscaping, and a hand crafted wood and iron front door. Located within 24-HR guard gated Keene’s Pointe and zoned for top-rated schools, this home is a true pleasure to experience.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Mely Carrero (786-717-1121)
1002 OAKDALE ST, WINDERMERE, FL 34786
$975,0003 Days on yellowkey MLS ID: TB8495717
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: 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)
13609 ANCILLA BLVD, WINDERMERE, FL 34786
$749,99963 Days on yellowkey MLS ID: O6381542
REDUCED by $39,001 (4.9%) on 04/14/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3360 Built: 2005Monthly Fee: $130 Tax: $9,521 (2024)Community: Summerport Ph 03Single Family
Taxes:$9,521
Elementary School: Keene Crossing Elementary
Remarks: Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor includes a private primary suite with its own balcony, providing a serene retreat, as well as a dedicated home office perfect for remote work or study. Generous living areas are filled with natural light and create a seamless connection between indoor and outdoor living. Step outside to enjoy the covered patio and expansive backyard, offering ample space for entertaining, relaxing, or future customization. The property sits on a well-sized lot and is part of a community that features amenities such as a pool, park, playground, and sidewalks. Conveniently located near top-rated schools, shopping, dining, and major roadways, this home delivers an exceptional combination of location, space, and lifestyle. A rare opportunity to own a lake-view property in one of Windermere’s most desirable areas. Schedule your private showing today.
Listing Agent: Fernanda Soares Santos De Oliveira (407-840-0734)
4301 DOWN POINT LN, WINDERMERE, FL 34786
$2,950,0006 Days on yellowkey MLS ID: O6398366
Bed: 5 Bath: 4.0 Gar: 6 Liv Area Sq Ft: 7153 Built: 1983 Tax: $19,012 (2025)Community: Down Point SubSingle Family
Taxes:$19,012
Middle School: Chain of Lakes Middle
Remarks: Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly, creating strong value for buyers seeking premier waterfront frontage, square footage, and long-term upside in one of Windermere’s most desirable locations. Main level includes kitchen, dining area, secondary bedrooms, full baths, oversized laundry room, and sliding doors opening to covered outdoor living and lake views. A few steps down, the sunken living room features a bar, fireplace, storage, and direct water views. Upstairs, the primary suite includes a fireplace, large walk-in closet, dual vanities, tub, separate shower, and screened balcony overlooking the lake. This level also includes a private office. The lower level is a standout feature, offering a full basement living space with its own kitchen, living room, bedroom, full bath, and direct pool access, ideal for extended family, guests, or multigenerational living. An additional reinforced interior room provides flexible use as a secure safe room, storm shelter, private storage room, or secluded flex space. Outdoor features include a screened pool, covered entertaining area, fenced yard, and private dock with space for two boats and two jet skis. Garage space accommodates up to 6 cars, plus a 2-car carport and a large circular driveway that provides additional parking for guests, larger households, or recreational vehicles. Additional storage areas and the lower-level garage create excellent space for boat gear, kayaks, paddle boards, trailers, and lakefront equipment. Home is priced in line with its recent appraisal, with the value reflecting both its current condition and the renovation investment a future owner may choose to make. For buyers seeking a large lakefront footprint, multigenerational layout, extensive parking, and the ability to modernize to today’s standards, this property offers a rare value on the Butler Chain. Located minutes from downtown Windermere, Restaurant Row, golf, shopping, and major attractions.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Phil Mariani (407-257-3609)
8411 WOBURN CT, WINDERMERE, FL 34786
$1,260,00022 Days on yellowkey MLS ID: O6391980
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2582 Built: 1999Monthly Fee: $222 Tax: $12,964 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$12,964
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Welcome to this beautifully reimagined luxury residence in the highly sought-after Keene’s Pointe, ideally positioned on a quiet cul-de-sac and backing onto the serene natural beauty of the Tibet Butler Preserve. This exceptional 4 bedroom, 3 bathroom home with a dedicated office has been extensively renovated to an outstanding standard, offering a perfect blend of modern design, comfort, and privacy in one of Windermere’s premier guard-gated communities. From the moment you arrive, the custom iron front door sets the tone for the quality found throughout. Inside, the entire home has been thoughtfully updated with smooth finished walls and ceilings, elegant crown molding in every room, and wood-look ceramic flooring that flows seamlessly throughout. Every space has been freshly painted, creating a light, bright, and cohesive feel, while feature walls, custom trim detailing, and designer touches elevate the overall aesthetic. The heart of the home is the fully remodeled kitchen, showcasing custom cabinetry, granite countertops, and WiFi-enabled LG appliances, perfectly designed for both everyday living and entertaining. The open layout connects effortlessly to the main living areas, enhanced by upgraded LED lighting and stylish ceiling fans throughout. The primary suite offers a true retreat, featuring a beautifully redesigned bathroom with custom cabinetry, upgraded finishes, and a luxurious soaking tub. Guest bathrooms have also been fully renovated with new flooring, showers, and modern fixtures. Additional highlights include custom closet systems with integrated lighting, a redesigned pantry with barn-style doors, and upgraded ceilings in both the dining room and sunroom. Step outside to your private outdoor oasis, where the oversized screened lanai, pool, and spa create the perfect setting for relaxation or entertaining. The pool has been enhanced with an acid wash, updated tile, and a resurfaced pool deck, complemented by a new spa heater, WiFi-enabled pool controls, and thoughtfully designed landscaping with ambient lighting that adds to the home’s tranquil atmosphere. This home is as smart as it is stylish, featuring a comprehensive ADT security system with cameras, glass break sensors, water detection, CO2, and fire monitoring, along with an air purification system integrated into the HVAC for added comfort and peace of mind. Additional upgrades include new garage door openers, updated exterior lighting, and professionally enhanced landscaping. Located toward the front of Keene’s Pointe, the home also benefits from convenient access to CR 535 and I-4, offering a meaningful time-saving advantage compared to properties deeper within the community. With its private setting, extensive high-end upgrades, and prime location, this is a rare opportunity to own a truly turnkey luxury home in one of Windermere’s most desirable communities.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Andy Neal (407-619-3517)
6310 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786
$490,000115 Days on yellowkey MLS ID: O6368983
5 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1977 Built: 2012Monthly Fee: $125 Tax: $7,927 (2024)Community: Windermere Lndgs Ph 02Single Family
Taxes:$7,927
Remarks: Under contract-accepting backup offers. Windermere Landings, Highly desirable community, only five minutes from downtown Windermere, and great school district. Beautiful two story home, Three bedroom Two and half bath with upstairs loft space for a home office. The Kitchen has overlooking the great family room and dining room.wood cabinets, granite countertops, an island, and counter height bar seating. A/C unit was replaced in 2019 with an inverter that helps save on energy and utility expenses. The community has a pool, playground, dog park and a huge land area.
Listing is courtesy of: JOY ESTATE ENTERPRISE INC (321-754-9131)
Listing Agent: Mengshi Lu (407-800-3900)
11608 CLAYMONT CIRCLE, WINDERMERE, FL 34786
$1,299,00036 Days on yellowkey MLS ID: O6390072
0 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2614 Built: 2004Monthly Fee: $298 Tax: $7,193 (2025)Community: Keenes Pointe Ut 04 Sec 31 48 82Spa: YesSingle Family
Taxes:$7,193
Remarks: Under contract-accepting backup offers. Keene's Pointe - 24-hour gated/attended golf community in Windermere, Florida. Experience refined living in this beautifully updated 4-bedroom, 3-bathroom residence. Designed for both comfort and elegance, this home features thoughtful upgrades throughout and exceptional indoor-outdoor living. Enter through the custom iron doors to discover porcelain flooring throughout the home and gorgeous quartz countertops that elevate the kitchen and bathrooms. Natural light pours in through new windows installed in 2023. There is a formal living and dining room, kitchen with stainless appliances overlooking the great room with access to the lanai. The primary suite is located privately on one side of the home with spacious bedroom, walk-in closet with built-in shelving, bathroom with dual vanities, large walk-in shower and freestanding tub. Out back, enjoy your own private resort-style retreat. The large swimming pool and spa are complemented by a rock waterfall, creating a tranquil ambiance. The paver pool deck and gazebo provide the perfect space for entertaining, relaxing, or enjoying Florida’s sunshine year-round.Additional highlights include a new roof in 2019, new double pane windows in 2023, spacious three-car garage with extra storage, large paver driveway offering ample parking and upgraded finishes throughout the house.In close proximity to shopping, dining, tourist attractions, major expressways and top-rated public and private schools, Keene's Pointe is home to The Golden Bear Club, a members only club featuring golf, tennis, fitness, dining and swimming, combines luxury, privacy, and lifestyle—perfect for those seeking upscale living with access to premier amenities.Schedule your private showing today and discover everything this exceptional home has to offer.
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
5018 RIVER GEM AVE, WINDERMERE, FL 34786
$775,00079 Days on yellowkey MLS ID: TB8469061
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2379 Built: 2005Monthly Fee: $130 Tax: $8,026 (2025)Community: Summerport Ph 03Spa: YesSingle Family
Taxes:$8,026
Remarks: Welcome to 5018 River Gem Avenue, an exceptional one-story pool estate with serene pond views in the prestigious Summerport community of Windermere, perfectly positioned for luxury living, convenience, and resort-style enjoyment — only 20 minutes from the Disney Theme Parks, Disney Springs, premier shopping, dining, and major roadways. This 3-bedroom, 2.5-bath, 2,379 sq ft showpiece features a refined split floor plan with 10- and 12-foot ceilings, abundant natural light, and new tile and marble flooring throughout (no carpet). Custom interior finishes elevate the living spaces, while tranquil water views grace multiple rooms. Recent high-end improvements include a new pool screen enclosure (Jan 2025), vinyl/iron fencing (2023), roof (2018), tankless water heater (2017), HVAC (2017), and Kinetico water softener & reverse osmosis system (2023). A natural gas line is in place for future chef-ready upgrades. The gourmet kitchen boasts granite countertops, stainless steel appliances, wood cabinetry, a raised breakfast bar, and a cozy nook overlooking the great room and pool. Designed for effortless entertaining, the interior flows to the travertine-finished, screen-enclosed lanai, extended patio, and solar-heated saltwater pool with a new pool pump (2025) and salt cell (2024, with warranty) — all framed by calming pond vistas. The primary suite is a private sanctuary with a tray ceiling, dual walk-in closets, garden tub, electronic window treatments, and direct access to outdoor living. Additional highlights include a pool-access half bath, oversized split garage with high ceilings and deep storage, and impeccably landscaped, low-maintenance grounds with mature fruit trees (lemon, lime, avocado, guava and papaya). Living in Summerport means enjoying an unparalleled lifestyle. Residents have access to the community’s exclusive clubhouse and pool complex with fitness center and social spaces at Summerport Residential POA Clubhouse. Meandering walking and biking trails, parks, and green spaces provide daily opportunities for outdoor recreation just steps from home. The nearby Summerport Neighborhood Park offers playgrounds, picnic areas, and scenic paths for all ages. For everyday convenience, Cornerstone at Summerport village-style shopping is just around the corner, providing groceries, cafés, services, and more. Downtown Windermere and Winter Garden’s vibrant boutiques, specialty dining, and lifestyle retail are also moments away, with premier destinations like Winter Garden Village and The Grove reachable in under 15–20 minutes. This remarkable home blends luxury, comfort, and lifestyle — ideal as a primary residence, second home, or Florida retreat with everything you want just minutes away.
Listing is courtesy of: KELLER WILLIAMS SOUTH TAMPA (813-875-3700)
Listing Agent: Anastasia Fischer (813-597-4791)
6752 TRELLIS VINE LOOP, WINDERMERE, FL 34786
$1,000,00084 Days on yellowkey MLS ID: O6376318
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3820 Built: 2018Monthly Fee: $200 Tax: $10,983 (2024)Community: WindstoneSingle Family
Taxes:$10,983
Elementary School: Sunset Park Elem
Remarks: ONLY APPROXIMATELY 7 YEARS NEW, THIS HOME OFFERS MODERN DESIGN AND PEACE OF MIND. MAJOR PRICE DROP - $50,000 OFF! Designed for those who crave space, privacy, and elevated living, this exceptional newer home offers 5 BEDROOMS PLUS TWO BONUS ROOMS, including ALL 4 MAIN BEDROOMS with WALK-IN CLOSETS and a private guest suite featuring an EN-SUITE and WALK-IN CLOSET—all complemented by NO REAR NEIGHBORS and NO FRONT NEIGHBORS, creating extraordinary flexibility for refined living, entertaining, and everyday comfort. Have you ever dreamt of living close to Disney in an upscale neighborhood—where modern luxury meets peaceful surroundings? This is where that dream becomes reality. At the heart of the home, a gourmet kitchen that chefs will love anchors the OPEN-CONCEPT design. A Gas line is available for the stove. flowing effortlessly into the main living areas. Whether hosting celebrations or enjoying quiet evenings at home, the thoughtfully designed layout includes a living room, a family room, and expansive, light-filled spaces designed for connection. One of the large bonus rooms is currently being used as a MOVIE ROOM, offering a private, theater-style retreat ideal for entertaining or cozy nights in. The bedroom layout is equally impressive, offering space and privacy for everyone. ALL 4 MAIN BEDROOMS include WALK-IN CLOSETS, while the guest bedroom’s EN-SUITE and WALK-IN CLOSET create the perfect setup for visitors, multi-generational living, or a luxurious secondary retreat. Step outside to a truly rare outdoor setting—AN OVERSIZED BACKYARD with NO REAR NEIGHBORS and NO FRONT NEIGHBORS, where privacy and tranquility take center stage. This expansive space is ready to become your personal oasis, whether that includes a resort-style pool, outdoor kitchen, or serene garden escape. When the day winds down, retreat to the MASTER SUITE, an impressively spacious sanctuary designed for rest, relaxation, and renewal. Every detail throughout the home reflects thoughtful design, modern elegance, and effortless functionality. Ideally located VERY, VERY CLOSE TO DISNEY and ALL ATTRACTIONS in CENTRAL FLORIDA, this home offers the rare balance of privacy, space, and proximity—placing world-class entertainment, dining, and lifestyle experiences just minutes away. This is more than a home—it’s a lifestyle defined by luxury, location, and possibility.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Candice Liceaga (407-861-7303)
11226 MACAW CT, WINDERMERE, FL 34786
$1,825,0004 Days on yellowkey MLS ID: O6393210
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4549 Built: 2004Monthly Fee: $283 Tax: $19,332 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$19,332
Remarks: The Ultimate Entertainer’s Dream Home. Welcome to this exceptional custom-built courtyard estate by Bill Sauerwine, offering 4 bedrooms, 4.5 bathrooms, and 4,549 square feet of luxurious living in the highly sought-after Windermere area. Designed for both grand entertaining and everyday comfort, this stunning residence centers around a private courtyard pool, creating a true indoor-outdoor lifestyle. The expansive outdoor patio overlooks the sparkling pool, providing the perfect setting for hosting guests or enjoying peaceful Florida evenings in your own private retreat. Inside, the home showcases spacious, thoughtfully designed living areas, including a dedicated movie theater for an elevated at-home experience and a versatile separate living space complete with a full bathroom—ideal for guests, in-laws, or multi-generational living. A generously sized loft adds flexibility for a home office, game room, or additional lounge space. At the heart of the home, the gourmet kitchen is a true chef’s delight. Featuring a premium Sub-Zero refrigerator, gas cooktop, and built-in oven and microwave, this space blends high-end functionality with timeless design. Abundant counter space, a spacious breakfast bar, and soaring two-story ceilings create an open and inviting atmosphere perfect for both entertaining and everyday living. The luxurious primary suite serves as a private sanctuary, offering ample space and a spa-like bathroom designed for ultimate relaxation and comfort. Combining custom craftsmanship, elegant design, and resort-style amenities, this one-of-a-kind home delivers an unparalleled lifestyle in Windermere, just moments from premier dining, shopping, and convenient access to major roadways. Opportunity awaits in the highly coveted guard-gate community of Keenes Pointe. Expansive W.J. Sauerwine custom home offering the best value in the community.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Sean Hooke (603-481-3377)
12411 MONTALCINO CIR, WINDERMERE, FL 34786
$1,550,0004 Days on yellowkey MLS ID: O6398677
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: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Mauro Costa (321-231-6800)
825 OAKDALE ST, WINDERMERE, FL 34786
$792,50010 Days on yellowkey MLS ID: O6396351
2 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1664 Built: 1935 Tax: $9,799 (2025)Community: Windermere TownSingle Family
Taxes:$9,799
Remarks: THE ONLY HOME ON WINDERMERE’S ICONIC SANDY STREETS UNDER $800,000 — DON’T MISS YOUR CHANCE. Back on the market and better than ever, this charming traditional cottage now features thoughtful exterior enhancements that further showcase its incredible homesite and future potential. Nestled along one of Windermere’s signature sandy streets, this property offers the perfect blend of nostalgia, community, and convenience—just steps from the Farmers Market, Town Hall, Windermere Library, the new Ace Hardware plaza, and beloved town events. Set on an expansive .38-acre lot beneath beautiful mature trees, this 3-bedroom, 2-bath home now features a freshly cleared and improved backyard. Select trees and brush have been professionally trimmed and removed, creating a more open, usable space ideal for recreation, entertaining, or future expansion. Whether you envision a pool, home addition, or simply the ultimate setting for flag football and weekend gatherings, the groundwork has been laid. Inside, the home welcomes you with a vaulted-ceiling great room and kitchen featuring newly refinished REAL wood floors, exposed beams, and abundant natural light. A cozy adjacent living room offers built-in shelving and a double closet. The quaint kitchen blends character and function with tile and wood countertops, vintage-style paneled appliances, and nearby laundry. A separate dining room with REAL wood floors comfortably seats eight and opens through French doors to a refreshed screened rear porch—perfect for relaxing evenings overlooking your newly enhanced backyard. From here, updated wood steps lead directly into the fully fenced yard. The bedroom wing includes two secondary bedrooms with a shared hall bath, while the private primary suite features its own en-suite bath and French doors opening to a secluded outdoor porch. Major updates provide peace of mind: Brand-New Roof & Skylights (11/2025), HVAC (May 2024), Natural Gas Water Heater (Oct 2021), Exterior Paint (Jan 2024), Wired for High Speed Fiber by ATT and more. The home also includes a transferable annual termite bond, recent septic service (June 2025), and ongoing maintenance including tree care and exterior improvements. An oversized carport with a large enclosed storage/workshop space completes this exceptional Windermere opportunity. BACK ON MARKET BY CHOICE — NOT CONDITION. YOUR SECOND CHANCE IS HERE.
Listing Agent: Mildred Hershiser (407-758-5263)
10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786
$3,500,00080 Days on yellowkey MLS ID: O6377244
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 5273 Built: 1986Monthly Fee: $103 Tax: $28,092 (2025)Community: LakesSpa: YesSingle Family
Taxes:$28,092
Remarks: Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with artisan leaded glass. Inside, the great room makes an immediate statement with soaring 23’ cathedral ceilings and a striking Tennessee river rock fireplace. Entertain in the showstopping formal dining room, where oversized picture windows perfectly frame the lake. Designed for everyday comfort, the majority of the living space including all bedrooms is located on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a sunlit breakfast area with spectacular water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-inspired bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Generous secondary bedrooms offer ample closet space and well appointed baths, including a steam shower. Outdoors is where this home truly shines. Enjoy mature landscaping and colorful gardens, plus a motorized screened lanai with a chef-worthy summer kitchen pizza oven, prep area, grill, refrigerator, and TV alongside the pool, heated spa, and gas firepit. The desirable southern exposure delivers refreshing lake breezes and comfortable outdoor living without harsh afternoon sun. The custom floor plan maximizes lake views throughout, and the partially enclosed dock is a rare find grandfathered in, with a boat lift and side jet-ski lift. Additional highlights include newer doors and windows and a tile roof. The Lakes neighborhood also offers a community boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes from major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you. Be sure to explore the virtual tours.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
8648 POWDER RIDGE TRL, WINDERMERE, FL 34786
$499,00087 Days on yellowkey MLS ID: O6373065
REDUCED by $17,000 (3.3%) on 04/13/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1876 Built: 2014Monthly Fee: $81 Tax: $6,733 (2025)Community: Windermere Trls Ph 1CSingle Family
Taxes:$6,733
Remarks: LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door. Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a spacious loft, and 1,876 square feet of thoughtfully designed living space. The open-concept kitchen and living area create a warm, inviting flow—perfect for everyday living and entertaining. Upstairs, you’ll find a versatile loft, a spacious primary suite, and two additional bedrooms with a full bathroom conveniently located between them. Wood flooring throughout the main living areas and a wooden staircase. Step outside and enjoy Florida living at its finest. From the large front porch, take in breathtaking sunsets and the Magic Kingdom nightly fireworks, while the extra-wide private balcony offers peaceful sunrise views. The rear-entry 2-car attached garage and low-maintenance yard provide both functionality and ease of ownership. *** Owned solar panel system (paid in full—no lease) designed to offset most or all of your monthly electric bill.*** The location is truly unbeatable. The home is walking distance to Bay Lake Elementary, as well as top-rated daycare and middle schools—offering unmatched peace of mind for families. Everyday conveniences such as grocery stores, dining, gyms, and shopping are also just steps away, including the newly opened Lakeside Village shopping plaza. Windermere Trails residents enjoy resort-style amenities including a large community pool, playground, dog park, scenic lakes and preserves, and miles of biking and jogging trails surrounded by beautiful retention ponds and local wildlife—perfect for morning walks and outdoor living.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Renan Serretiello (407-415-7317)
6957 NORTHWICH DR, WINDERMERE, FL 34786
$585,000108 Days on yellowkey MLS ID: A4676454
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2667 Built: 2007Monthly Fee: $100 Tax: $8,184 (2024)Community: Lakes/Windermere Ph 04Single Family
Taxes:$8,184
Remarks: Beautiful two-story, 4-bedroom, 3.5-bathroom home in the highly desirable Lakes of Windermere Phase 4 community. Built in 2007, this well-maintained residence offers 2,667 sqft of living space on a 6,006 sqft lot. The home features a bright, open floor plan, spacious bedrooms, and a functional layout perfect for families and entertaining. Enjoy a serene backyard with privacy, while being conveniently located near top-rated schools, shopping, dining, and major roadways. With a shingle roof, two-car garage, and access to community amenities, this property combines comfort, style, and location in one of Central Florida’s most sought-after neighborhoods. Schedule your showing today!
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
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