Windward Square Sec 3 Real Estate

Welcome to Windward Square Sec 3, a charming subdivision nestled in the heart of Winter Park, Florida. Known for its picturesque landscapes and friendly atmosphere, this community offers the perfect blend of suburban tranquility and urban convenience. With its lush greenery and beautifully maintained homes, Windward Square Sec 3 is a hidden gem that captures the essence of Florida living.

Located in Seminole County, this subdivision boasts a prime location just minutes away from the vibrant downtown area of Winter Park. Residents enjoy easy access to a variety of shops, restaurants, and cultural attractions, including the renowned Charles Hosmer Morse Museum of American Art and the scenic Winter Park Chain of Lakes. Whether you’re strolling through the historic Park Avenue or indulging in a delightful meal at one of the local eateries, there’s always something to explore.

Windward Square Sec 3 is perfect for families and individuals alike, offering a warm sense of community and a safe environment. The neighborhood features spacious homes with modern amenities, many of which are designed with outdoor living in mind—ideal for enjoying the sunny Florida weather. Additionally, the area is served by highly-rated schools, making it an attractive choice for families seeking quality education for their children.

If you’re looking for a place that combines the charm of small-town living with the conveniences of urban life, Windward Square Sec 3 in Winter Park is the perfect destination. Come discover your dream home in this delightful community, where every day feels like a vacation!

Newest Listings in Windward Square Sec 3

$295,000

2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code

Welcome to Windward Square, a desirable Winter Park community conveniently located near shopping, dining, entertainment and major roadways. This spacious end-unit home offers 2 bedrooms, 2 full bathrooms with 1,544 square feet of living space. The home adds fabulous sun room with French doors to a private rear space. Originally designed as a 3-bedroom home, the third bedroom has been converted into a versatile flex room—ideal for a home office, den, hobby room or additional living space. The primary suite features a spacious walk-in closet with custom built-ins. Recent updates include a new roof in 2023, new flooring, fresh interior paint and more. As an end unit, the home provides additional privacy and a more open feel than interior units. The enclosed sunroom offers additional space for relaxing, entertaining or enjoying your morning coffee. Windward Square residents enjoy community amenities including a swimming pool and tennis courts. The convenient location provides easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this move-in-ready home offers space, flexibility and an excellent Winter Park location.

2302 Barbados Drive, Winter Park

$299,990

3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code

Great opportunity in the established Windward Square community of Winter Park! This END-UNIT home offers 3 bedrooms, 2 full bathrooms and approximately 1,467 square feet of living space, with added privacy and plenty of potential. ROOF REPLACED IN 2017! 10K seller contribution for the floor. The home is ready for some TLC and personal updates, giving the next owner the opportunity to renovate and make it their own. The spacious living and dining areas gives a functional layout, while the large screened porch provides additional space to relax, entertain, and enjoy Florida living. Being located at the end provides additional privacy and a more open feel compared with interior units. The community offers amenities including a swimming pool and tennis courts. Conveniently located near shopping, dining and major roadways, with easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this property offers great potential and an excellent opportunity to add value through your own improvements. Bring your vision and make this home your own!

2275 Island Run, Winter Park

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