Preston Square Homes for Sale in Windermere - 6 homes

Remarks: Under contract-accepting backup offers. 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. One or more photo(s) has been virtually staged. Save Big: 1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred lender. Ask for details! This expansive two-story residence offers beautifully connected gathering spaces, multiple private retreats, and flexible rooms that adapt to your lifestyle. As you arrive, a welcoming entry and foyer set the tone for the home’s inviting layout. Just off the entrance, a dedicated office provides the ideal work-from-home space, library, or quiet study. Beyond the foyer, the floor plan opens into a spacious formal living room that creates a warm first impression and offers a natural transition into the heart of the home. At the center of the first floor, the kitchen is perfectly positioned for both daily life and entertaining, complete with a walk-in pantry, a generously sized island for seating, and a seamless connection to a separate dining room, providing an elegant setting for holidays, celebrations, and dinner parties. Natural lighting streams through multiple windows in the breakfast nook, which overlooks the outdoor living area, offering the perfect spot for casual morning coffee or relaxed meals. The family room creates an open concept gathering space where conversation flows effortlessly and allows for easy entertaining. A thoughtfully placed half bath with access to the outdoor patio area adds easy accessibility for guests and family alike, and the attached garage offers convenient parking and direct entry into the living space, enhancing both functionality and comfort. Upstairs, the home continues to impress with a thoughtfully designed second floor. The private primary suite is a true retreat, featuring generous proportions, multiple closet spaces, and a spa-inspired bath designed for relaxation. Two bedrooms provide comfort and privacy for siblings and share a Jack and Jill bathroom. An additional bedroom is ideal for family or guests with access to a covered balcony, creating a private outdoor escape to enjoy Florida evenings. A spacious flex room offers endless possibilities to create a home theater, game room, fitness studio, second office, or guest retreat to fit your needs. Completing the upper level is a third full bathroom with a walk-in shower and a laundry room, adding everyday convenience right where you need it most. Step outside to one of the home’s standout features, an oversized covered lanai and expansive brick-paver patio designed for true Florida outdoor living. Ample space for multiple seating and dining areas, this private backyard retreat is ideal for entertaining, weekend gatherings, outdoor dining, or simply relaxing under the shade of mature trees. Lush landscaping, privacy fencing, and natural greenery create a peaceful setting with room to enjoy year-round outdoor living. Residents enjoy a beautifully designed central gathering area featuring the community’s amenity center, resort-style pool, basketball court, playground, expansive open green space, and connected sidewalks for walking. The location is convenient, with nearby shopping, dining, and everyday essentials just minutes away at Westside Shoppes, Lakeside Village, and Windermere Village, plus additional retail and dining options throughout the surrounding Windermere area.

Listing is courtesy of: EXP REALTY LLC (407-305-4300)

Listing Agent: Kathryn West (321-277-1999)

Remarks: Under contract-accepting backup offers. 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,New Roof, 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: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **MOVE IN READY** TWO PRIMARY SUITES** EASY OWNER FINANCING AVAILABLE** Your new home is a beautifully maintained townhome tucked inside the charming Preston Square community in the heart of Windermere. The inviting front porch, lush landscaping, and towering palms create the perfect first impression of Florida living at its finest. This two-story residence blends comfort, style, and convenience offering the ideal opportunity for first-time buyers, professionals, investors, or anyone looking to enjoy the Windermere lifestyle without sacrificing value. Inside, you’ll immediately notice the bright and airy layout enhanced by soaring ceilings, elegant crown molding, and an abundance of natural light pouring through oversized windows. The spacious living and dining areas flow seamlessly together, creating an open-concept design perfect for entertaining guests or enjoying relaxing evenings at home. The kitchen is designed to impress, featuring rich solid wood cabinetry, granite countertops, sleek black appliances, ample prep space, and a functional breakfast bar overlooking the main living area. Whether you’re preparing a quick morning coffee or hosting dinner with friends, this kitchen offers both style and practicality. Just beyond the sliding glass doors, a private oversized courtyard patio creates a peaceful outdoor retreat ideal for grilling, dining al fresco, gardening, or simply unwinding after a long day. Upstairs, the spacious primary suite offers a relaxing sanctuary complete with tray ceilings, beautiful wood flooring, a massive walk-in closet, and private balcony access where you can enjoy tranquil mornings. The en-suite bathroom features a large soaking tub, walk-in shower, and elegant finishes designed to create a spa-like experience at home. What truly sets this floor plan apart is the generously sized second bedroom, which also features its own private en-suite bathroom — making this home feel almost like it has two primary suites. This rare setup provides incredible flexibility for guests, roommates, multigenerational living, or anyone seeking additional privacy and comfort. Between the charming front porch, private courtyard patio, upstairs balcony, and attached two-car garage, this home delivers the space and functionality buyers are searching for. The thoughtful floor plan maximizes every square foot, creating a home that lives larger than expected while maintaining a cozy and manageable feel. Additional upgrades provide peace of mind and added value, including newer kitchen appliances along with a washer and dryer that convey with the home. Major system updates have already been completed for the new owner, featuring a new roof installed in 2023, AC replaced in 2022, and a water heater installed in 2024 — making this home truly move-in ready with big-ticket items already taken care of. Located within Preston Square, residents enjoy access to community amenities including a resort-style pool, playground, basketball court, green spaces, and beautifully maintained sidewalks throughout the neighborhood. The location is truly unbeatable — just minutes from Disney, Winter Garden Village, Horizon West, major highways, top-rated Windermere schools, shopping, dining, and entertainment. This community continues to attract buyers seeking the perfect balance between convenience, lifestyle, and long-term value. Schedule a private showing today!

Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)

Listing Agent: Daniel Rodriguez (407-934-0305)

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)

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)