Winter Park Homes with Fence Exterior Features

Welcome to Winter Park, Florida—a charming city nestled in Orange County that beautifully blends small-town warmth with urban sophistication. Known for its picturesque tree-lined streets, vibrant arts scene, and stunning lakes, Winter Park is a haven for those seeking a tranquil yet dynamic lifestyle.

As you explore this delightful city, you’ll discover a rich tapestry of cultural experiences, from the renowned Charles Hosmer Morse Museum of American Art to the enchanting scenic boat tours that glide through the area's serene waterways. With its delightful boutiques, gourmet restaurants, and lively farmers' market, Winter Park offers a unique blend of leisure and luxury that captivates both residents and visitors alike.

For those considering a move to this idyllic locale, homes with fenced exterior features are a popular choice. These properties not only provide an added layer of privacy and security but also create a perfect space for families and pets to enjoy the outdoors. Imagine hosting summer barbecues or letting your children play freely in a safe, enclosed yard while you relax on the patio, soaking up the Florida sunshine.

Whether you’re drawn to the historic charm of Park Avenue or the lush landscapes of the city’s many parks, Winter Park offers a diverse range of homes to suit every taste and lifestyle. With its welcoming community, rich history, and beautiful surroundings, it’s no wonder that Winter Park is considered one of Florida’s most desirable places to live. Come and discover the perfect home for you in this enchanting city!

Newest Winter Park Homes with Fence Exterior Features

$650,000

2 Beds ⋅ 2 Baths ⋅ Mack Peter Rev SubDv. ⋅ 32789 Zip Code

Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Located walking distance to Mead gardens and Orange Ave, and less than a mile from Park Ave. shopping and dining, this incredible investment is positioned for convenience and enjoyment! Across the street is a community garden. Whether you are looking for an investment property to add to your portfolio or a primary residence with income generating capabilities, this property has it all! New roof in 2024, and new windows and exterior paint in 2026. AC's updated in 2024 & 2025. Schedule a tour to secure this incredible investment today!

901 Harmon Avenue, Winter Park

$745,000

2 Beds ⋅ 3 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code

Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns. The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood. The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses. This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.

408 Holt Avenue, Winter Park

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