Location: Preston Square, Windermere
Do Not Show Listings
6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786
$469,00069 Days on yellowkey MLS ID: O6392752
0 Days Off yellowkey (back on 5/31/2026)
REDUCED by $10,000 (2.1%) on 04/23/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1980 Built: 2008Monthly Fee: $315 Tax: $3,248 (2025)Community: Preston SquareTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,248
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
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)
6528 HELMSLEY CIR, WINDERMERE, FL 34786
$325,00014 Days on yellowkey MLS ID: O6408661
0 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1411 Built: 2008Monthly Fee: $315 Tax: $3,641 (2025)Community: Preston SquareTownhouse
Taxes:$3,641
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)
11401 EVESHAM DR, WINDERMERE, FL 34786
$440,00010 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
Tax Year: 2024
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)
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