Windermere Single Family Homes For Sale - 229 homes

Remarks: Under contract-accepting backup offers. This is it! Welcome home to this updated, showstopper in Windermere with an oversized pool. From the moment you walk in the door, you will be impressed with how open and expansive the home feels- the kitchen, dining, family and living areas are included in one great space. The family and living room share a double-sided wood burning fireplace and both overlook the pool area. The kitchen has been upgraded with stainless steel appliances, granite counters, solid wood cabinets and designer fixtures. This split plan has a very private primary suite with access to the pool area. The bathroom has a large walk in closet, tub with separate shower and large dual vanity. The 2nd bath has been updated and also has access to the pool area. No carpet here- Luxury Vinyl has been installed throughout the whole house. Enjoy relaxing nights by the outdoor firepit in the backyard or quiet mornings with coffee in the front porch. NEWER Double Pane Windows and Doors. (ROOF 2021)

Listing is courtesy of: IRON VALLEY REAL ESTATE CENTRAL FLORIDA (407-203-9595)

Listing Agent: Richard Alpizar (386-747-8532)

Remarks: Welcome to “The Sounding:” a captivating lakefront estate residence with inviting water views and a serene and peaceful setting offering the best of Florida living. Tucked inside this privately gated and intimate enclave of estate homes across the street from Windermere Prep, Sawyer Sound offers an escape from the ordinary and this showplace residence sets the standard for lakefront living. A welcoming entrance showcases style and elegance with a massive Great Room as the lake and massive saltwater pool beckons beyond. An impressive chef’s kitchen with island and stainless appliances are perfectly fitted for entertaining family and friends. Highlights include rich hardwood floors throughout plus Thermador appliances including 6-burner plus griddle stove and hood, custom-built cabinetry, hidden walk-in pantry, expansive built-in China cabinet, and an especially large dining room with picturesque window. Opposite is a primary retreat with sitting room, spa-like bath with soaking tub, walk-in shower, toilet closet, and separate den. Bathrooms just updated. Upstairs are four bedrooms, each with a private full bath, plus gathering room and separate gaming room. Distinct outdoor spaces are crafted for year-round enjoyment: covered cabana with bar and gas grill plus dining space, mammoth saltwater pool with hot tub, and outdoor family room with fireplace and disappearing screens. Boat house with boat lift puts your water toys within reach and offers easy access to Little Lake Sawyer. Also, enjoy nightly Disney World fireworks viewing from the dock. Boat, trailer, kayaks, and all furniture available for purchase separately. Home is fitted with automatic Generac generator plus 3-car garage (one single and one double). Home may be sold furnished if desired.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Rob Rahter (407-497-4526)

Remarks: One or more photo(s) has been virtually staged. Presenting a newly remodeled luxury estate ideally positioned along Isleworth’s renowned championship golf course, showcasing stunning views of the signature 3rd hole. This exceptional residence offers approximately 4739 square feet of refined living space with 4 bedrooms and 4 1/2 bathrooms, soaring ceilings, elegant formal living and dining rooms, a private office, and a spacious owner’s retreat. Designed for elevated living and effortless entertaining, the home features marble and luxury vinyl flooring throughout, as well as a beautifully upgraded chef's kitchen with a casual dining area. Enclosed sunroom provides additional flex space and is not included in the official living square footage. The fully reimagined front and rear grounds create a true estate setting, highlighted by a grand front fountain entrance, a resort-style pool, an expansive lanai, a pavilion, and a summer kitchen. The upper-level balcony offers breathtaking golf course vistas, while the fully fenced private grounds include an extended driveway and an impressive circular motor court. A rare opportunity to own a move-in-ready luxury residence in one of Isleworth’s, golf-front locations.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Winnie Tam (863-651-4687)

Remarks: We present a luxury residence in Windermere, Florida, that combines modern design, spacious areas, and a prime location. Situated at 6208 Winter Garden Vineland Road, this property is strategically positioned in front of Windermere Preparatory School, one of the best private schools in Florida. With 5,441 sqft of climate-controlled living space and a total area of 8,091 sqft, this home impresses with its size and sophistication. It features 6 en-suite bedrooms, all with walk-in closets, plus a half bath and an additional full bathroom dedicated to the pool area, totaling 7.5 bathrooms. The modern architecture, a rare find in Orlando, stands out with its 12-foot ceilings, sliding doors in all bedrooms, and an open-concept social area that provides integration and elegance. The outdoor area is one of the highlights of this property. The swimming pool with a jacuzzi invites relaxation, while the spacious 880 sqft gourmet patio is perfect for entertaining friends and family. The property also features a tennis court. To ensure maximum privacy, the entire 1.29-acre lot will be enclosed with a fence. The house is equipped with modern, energy-efficient appliances, 100% LED lighting, and infrastructure ready for surveillance systems and smart home automation, compatible with the leading platforms on the market. Another great feature is the four-car garage, which includes two electric vehicle chargers, offering convenience and sustainability for its residents. This property offers the perfect balance of luxury, technology, and comfort. Additionally, its location provides easy access to key points in the city, being approximately 30 minutes from Orlando International Airport (MCO), 19 minutes from Magic Kingdom, 18 minutes from Universal Studios, and 20 minutes from downtown Orlando. An added benefit is the absence of HOA fees, allowing total freedom to personalize and use the space as desired. This is a unique opportunity for those seeking an exclusive home in one of Florida's most sought-after areas. Schedule a visit and discover what makes this house truly special!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Daniel Pavel (407-747-3408)

Remarks: Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense” remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble and wood flooring below, complemented by wood beams, stone gas fireplace with marble mantle, and shimmering chandeliers. An adjacent cocktail bar next to the dining room is fitted with Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The well-appointed chef’s kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. Family room and breakfast nook are perfectly sized for everyday entertaining with vaulted ceilings, reclaimed wood floors, and access to the pool patio and summer kitchen cabana. The dramatic first floor primary retreat features picturesque windows and a luxurious spa-like bath complete with chandelier, breakfast bar with Sub Zero fridge, dual vanities, garden tub, glass shower, and French doors to a walled outdoor space. The master closet provides access to a discrete room at the top of a spiral staircase that can be a gym, second study, or hidden Pilates room. Up the main staircase are three additional bedroom suites and a movie theater. An executive office is located on the first floor. Exterior living spaces feature a large covered lanai, heated saltwater pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, custom-built stacked stone outdoor fireplace, and nearly 300 feet of golf frontage. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. Home is built with concrete construction on both first and second floors. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Rob Rahter (407-497-4526)

Remarks: Back on market—buyer withdrew for personal reasons, not due to any home-related issues. Set on 1.3 acres in the Lake Buynak Estate community, this 4-bedroom, 3.5-bath home presents an outstanding opportunity for investors, builders, or buyers wanting space and a Windermere-area address with NO HOA. Offering over 2,600 square feet, two ensuite bedrooms, a split layout, multiple screened porches, and a wood-burning fireplace, the home provides a solid framework for renovation, rental use, multigenerational living, or a future custom build. Upgrades include energy-efficient double-paned windows and a dual septic system with an expanded drain field, enhancing functionality and long-term value. The expansive 1.3-acre lot allows for substantial expansion, an ADU, or complete redevelopment in an area surrounded by high-end homes near Lake Butler. With optional HOA membership and no Windermere city restrictions, the property offers freedom that is rarely available in this ZIP code. Located minutes from Disney, Universal, shopping, dining, and major roadways, it combines convenience with the space and privacy acreage buyers crave. Owner financing may be considered. Explore the potential this unique property provides and imagine the possibilities.

Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)

Listing Agent: Tania Matthews (407-497-9660)

Remarks: Welcome to this beautifully renovated home in highly desirable Windermere, where modern upgrades meet timeless comfort on a rare one-acre lot with NO HOA. Completely remodeled this home has been thoughtfully updated from top to bottom. Renovations include new flooring throughout, fresh interior paint, a fully redesigned kitchen, updated bathrooms, new windows, new interior doors and custom blinds. Every detail was carefully selected to create a cohesive, move-in-ready space. The kitchen shines with contemporary finishes and flows seamlessly into the main living areas — perfect for both everyday living and entertaining. Bathrooms have been stylishly updated, and custom master and coat closet provide elevated organization and storage. Enjoy true peace of mind with major system upgrades, including: • Whole-house water treatment system (2020), softener equipment updated in (2025) • Septic drain field in (2025) • Trane A/C installed (2026) • Well pump (2024) • Insulation (2021) • Balcony deck and railing (2025) Step outside to your private backyard retreat featuring a saltwater pool with electric heater, ideal for year-round enjoyment. The expansive one-acre property offers space, privacy, and endless possibilities — bring your boat, RV, or build your dream outdoor oasis. This home has been remodeled with tremendous care, offering confidence that the work has been done and done right. A rare opportunity in Windermere combining luxury updates, land, and freedom from HOA restrictions. Move-in ready. Fully upgraded. Peace of mind included.

Listing is courtesy of: KNIGHTS REALTY (407-252-7411)

Listing Agent: Frank Mediavilla (407-252-7411)

Remarks: Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large center island and ample space to prepare gourmet meals. Enjoy the Florida lifestyle year-round from the screened-in lanai overlooking the serene, tree-lined backyard. Additional highlights include a side-entry 2-car garage and a detached private workshop or storage building with electricity—perfect for hobbies, home projects, or extra storage. As a resident of the Town of Windermere, you'll enjoy exclusive access to two private boat ramps on the Butler Chain of Lakes, six lighted tennis courts, multiple parks and playgrounds, frisbee golf, and scenic lakefront beaches. The town also hosts vibrant community events including weekly farmers markets, monthly food truck nights, and seasonal festivals. Zoned for top-rated schools and just minutes from world-class golf, premier shopping and dining, hospitals, and Central Florida’s renowned theme parks, this home offers the best of both serenity and convenience. Schedule your private showing today and discover the charm and lifestyle that only Windermere can offer!

Listing is courtesy of: JULIAN PROPERTIES, INC. (407-291-4900)

Listing Agent: Bo Julian (407-694-5843)

Remarks: Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Craftsman Home overlooking a serene Wooded View, located in the community of Lakes of Windermere. Impeccably maintained and Move-in ready, this 4-bedroom, 2.5-bath home offers numerous Upgrades and Touches throughout. Such as all new kitchen appliances, newly painted interior, new A/C, Hardwood flooring, Water Softener, Built-Ins, and Newer Roof. Three stylish transom windows located in the Living Room allow lots of Natural Light. Granite counters and solid wood cabinetry in the kitchen. Butler's pantry off the Dining Room. A relaxing spa is located on the screened-in Lanai with custom pavers. This home has paid attention to detail, finish, form, and function. The Lakes of Windermere community is known for promoting a well-maintained, safe, and family-friendly environment with many acres of natural beauty amidst great live oaks, pine trees, and beautiful natural habitats. The oak tree-lined community and combination of outdoor amenities rival the best of Orlando’s communities. Our neighborhood features include: A picturesque pier located on Lake Sawyer is perfect for fishing, relaxing, or nightly star gazing. This community features a large pool and sun deck perfect for those hot summer days. There is also a kitchen available for use by reservation. Tennis. Volleyball. Basketball. Gazebo. 3 Playgrounds. Whatever your favorite activity is, the Lakes of Windermere will have a place for you to enjoy the beautiful sunshine of Central Florida. (Room measurements are approximate, Buyer to verify) Home Warranty to be provided by Seller.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Sean Flatley (609-208-8204)