Winter Park Homes with Fence Exterior Features

Welcome to Winter Park, Florida—a picturesque city that perfectly blends small-town charm with vibrant cultural offerings. Nestled just north of Orlando, Winter Park is renowned for its stunning tree-lined streets, beautiful lakes, and a rich history that dates back to the late 19th century. The city is a haven for art enthusiasts, boasting a plethora of galleries, museums, and the renowned Charles Hosmer Morse Museum of American Art, home to an impressive collection of Tiffany glass.

Winter Park is also famous for its outdoor spaces, with the enchanting Central Park serving as a community hub for events and relaxation. The city’s delightful shopping district along Park Avenue features boutique shops, gourmet restaurants, and cozy cafes, making it a perfect spot for leisurely afternoons. Plus, with its proximity to the scenic Chain of Lakes, residents enjoy endless opportunities for boating, fishing, and enjoying the great outdoors.

When it comes to housing, Winter Park offers a diverse selection of homes, many of which come with the added benefit of fenced exteriors. These charming properties not only provide a sense of privacy and security, but they also create a perfect environment for families and pets to play freely. Imagine hosting summer barbecues in your backyard oasis or enjoying peaceful evenings under the stars—homes with fenced exterior features in Winter Park truly enhance the quality of life.

Whether you’re drawn to its artistic spirit, lush landscapes, or family-friendly atmosphere, Winter Park is a place where dreams of homeownership can become a reality. Come explore the enchantment of Winter Park and find your perfect fenced sanctuary today!

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

Start Your Search