Preston Square Homes for Sale in Windermere - 7 homes

Remarks: Windermere Lake View Home with Disney Fireworks - Best Value in the Area! Recent price improvement - now one of the best opportunities in Windermere. Welcome to your dream home! This beautiful 4-bedroom, 3.5-bathroom residence offers the perfect blend of elegance, comfort, and convenience — ideally located in one of Windermere’s most sought-after communities with top-rated “A” schools. Enjoy breathtaking views of the lake and conservation area right from your spacious covered screened lanai, with a large backyard ready for your future pool. The open-concept kitchen flows seamlessly into the living and dining areas, creating an inviting space for family gatherings and entertainment. On the first floor, you’ll find a guest suite with a full bath, a private office, and a welcoming foyer. Upstairs features a massive loft — perfect as a media room, playroom, or second family room — along with the master suite and two additional bedrooms. The home also features a newer air conditioning system replaced just two years ago, offering added comfort and peace of mind. Enjoy the exclusive community amenities, including a clubhouse, pool, playground, and sports court. From your backyard, you can even watch the Disney fireworks at night! Conveniently located near shopping centers, dining, and entertainment, this home truly combines luxury, location, and lifestyle — the perfect place for your family in Windermere! Seller willing to consider offers.

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

Listing Agent: Maqueli Gewehr (863-258-5656)

Remarks: Stunning Preston Square Windermere home — 4 beds, 4 baths and approximately 3,400 sq. ft. of heated living space in a functional two-story floor plan featuring multiple living areas, an open kitchen with an eat-in nook and architectural detailing, tray ceilings, custom built-ins, spacious walk-in closets and a versatile bonus room (ceiling fans throughout) that adapts to your lifestyle. Entertain outdoors in your private saltwater pool with outdoor kitchen sink and exhaust fan for effortless barbecues, enjoy peaceful pond views in front and nightly Disney fireworks from your porch, all within a fully fenced yard. Updates include a pool pump replaced ~2.5 years ago, a pool safety door alarm, and fresh paint about six months ago — an exceptional offering in a premier Windermere community. Owner relocated .motivated seller. Additional features include all appliances, washer and dryer, and a surround sound system in the downstairs family room.

Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)

Listing Agent: Eleanor Desimone (845-796-6951)

Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome home to this beautifully appointed 3-bedroom, 2.5-bath corner townhome in the highly desirable Preston Square community of Windermere. Ideally positioned, this townhome conveniently faces the community amenities, offering easy access while maintaining a welcoming neighborhood feel. From the moment you step onto the charming front porch, you'll appreciate the warmth and character this home provides. Inside, natural light fills the space through wrap-around windows, highlighting the 10-foot ceilings and rich hardwood flooring. The thoughtfully designed floor plan blends comfort and functionality, making it ideal for both everyday living and entertaining. A standout feature of this home is the private courtyard, creating a peaceful outdoor retreat perfect for gatherings, grilling, or simply relaxing. The kitchen is well-equipped with 42" solid wood cabinetry, granite countertops, and stainless steel appliances, a space any home chef will appreciate. The main level features a spacious primary suite with a tray ceiling and a luxurious en-suite bath, complete with dual vanities, a garden tub, and a walk-in shower with dual shower heads. Upstairs, you’ll find a spacious, open-concept loft with two additional bedrooms, providing comfortable accommodations and privacy for family members or visitors. The laundry room includes a utility sink, and a window for added natural light. The rear-entry two-car garage features overhead storage racks and a long driveway for additional parking. Residents of Preston Square enjoy resort-style amenities, including a stunning swimming pool, lush landscaping, basketball court, playground, fitness stations, and a large park that hosts movie nights and food trucks. Conveniently located near top-rated schools, shopping, dining, golf courses, hospitals, and major roadways, with easy access to Orlando, Windermere, Winter Garden, and the area’s world-renowned theme parks. A fantastic opportunity to own a home in one of Windermere’s most desirable communities.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Nora Arenivas Llc (407-230-5487)

Remarks: Welcome home to Preston Square in beautiful Windermere! This stunning corner-unit townhome with 4 bedroom, 3 bathrooms offers the perfect blend of comfort, style, and convenience, with a new roof and fresh exterior paint. Step onto the cozy front porch and into a bright, inviting two-story home filled with natural light. The main living areas feature tile flooring throughout; great room showcases a mirror accent wall along with board and batten in the dining area. Kitchen features granite countertops, breakfast bar, stainless steel appliances, and stone backsplash. Sliding glass door leads to a private paver patio, perfect for relaxing or entertaining. Downstairs bedroom with full bath, inside laundry room plus a utility sink leads to the attached two-car garage with long driveway for additional parking. Upstairs you will find 3 additional bedrooms, stunning primary suite with balcony views. Primary bath features dual sinks, large garden tub, and separate shower. Preston Square offers amenities including a stunning community pool, playground, mature landscaping, basketball court, green space for events, and fitness stations. Ideally located near local dining, shopping, top-rated schools, golf courses, hospitals, and major roadways and attractions.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Morgan Horsley (256-283-8747)

Remarks: Under contract-accepting backup offers. NEW ROOF! Welcome to 6846 Helmsley Circle in beautiful Windermere, FL! This stunning 5-bedroom, 3-bathroom home is situated on the largest lot in the neighborhood, offering over a quarter-acre of space with two expansive backyards. Imagine the possibilities—perhaps a pool or even a pickleball court! The home boasts two primary suites, one conveniently located on the main floor and another upstairs, catering to versatile living arrangements. Spanning 2,555 square feet, the interior is both spacious and inviting. The open kitchen, equipped with stainless steel appliances, seamlessly connects to a kitchenette opening up to a large family room, perfect for entertaining. In addition to the second primary suite upstairs you will find a spacious loft versatile for your needs. You won't find any carpet in this home, upgraded tile and LVP throughout. Outside, relax on the porch with peaceful views or take advantage of the community's amenities. Rear loaded attached garage! Located in Horizon West, this home offers pond and conservation views right from the front, all while being just a stone's throw away from Disney, retail, shopping, and dining. This listing is a must-see for anyone looking to embrace modern living with ample outdoor space! Come make this yours.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Nickolas Amburgey (407-864-7622)

Remarks: Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story home offers 5 bedrooms, 3.5 bathrooms, an office, and an attached 2-car garage in the highly desirable community of Preston Square in Windermere. Perfectly situated on a premium lot with no rear neighbors, the home features a charming front porch and covered balcony overlooking the serene, tree-lined neighborhood. The updated kitchen is a showstopper, featuring quartz countertops, all new stainless steel appliances, a huge island perfect for gatherings, a cozy breakfast nook, and a separate formal dining room (or flexible bonus space). The open floor plan offers immaculate interiors designed for both comfort and entertaining, complemented by beautiful new flooring throughout. Upstairs, you’ll find a spacious primary suite, laundry room, and four additional bedrooms, offering plenty of space for family and guests. A private fenced courtyard provides an inviting outdoor retreat. Residents of Preston Square enjoy outstanding amenities including a community swimming pool, sport court, playground, and lushly landscaped green spaces. Conveniently located near top-rated schools, restaurants, and shopping, this move-in ready home is truly a rare find in one of Windermere’s most sought-after communities.

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

Listing Agent: Angela Gann (407-212-8552)

Remarks: Immaculately maintained, MOVE IN READY family home in the highly sought after Preston Square neighborhood located in the heart of 34786 - a well established hidden gem with tree lined streets! Built in 2008 with NEW ROOF IN 2025, this gorgeous, 4 bedroom 3.5 bath home with fully FENCED-IN back yard, has a unique layout with a guest bedroom with ensuite bathroom and french doors leading onto front covered porch, ideal for rocking chair evenings under the shade of the canopy trees. A 2-story ceiling great room adds dramatic appeal and separation to the floor plan, leading back through a dining space to the kitchen and family room all overlooking the private backyard. The kitchen boasts all stainless appliances, new dishwasher in 2023 and new refrigerator in 2024. AC was replaced in 2019 and new coils fitted in 2022. Upstairs is a large loft space overlooking living room - a perfect space for an office desk or gym equipment. The large primary bedroom suite has tray ceiling, walk-in closet, his & her vanities with soaking tub and separate shower. Two additional bedrooms and full bathroom completes the upper floor. Preston square has a charming atmosphere and features its own community pool, park, playground and sport court, all located just minutes from shopping, dining, and theme parks. A short drive to historic Windermere Town with its weekly farmers market, monthly food carts, historic town hall and old school house. Don't miss the opportunity to live the Florida lifestyle in this gorgeous home located within a great school district!

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Sue Webb (407-361-6425)