Winter Park Homes with Fence Exterior Features

Welcome to Winter Park, Florida—a picturesque gem nestled in Orange County that blends small-town charm with vibrant cultural experiences. Known for its stunning lakes, lush parks, and historic architecture, Winter Park offers a unique lifestyle that attracts residents from all walks of life. With its tree-lined streets and a thriving arts scene, this city is perfect for those seeking both tranquility and excitement.

One of the standout features of homes in Winter Park is the availability of properties with fenced exteriors. These homes provide not only privacy but also a secure space for children and pets to play freely. Imagine enjoying your morning coffee on the patio while your furry friends romp around in the backyard, all within the safety of your own fenced oasis. Many of these homes boast beautifully landscaped yards, perfect for hosting gatherings or simply unwinding after a long day.

Winter Park is also home to a variety of amenities, including boutique shops, gourmet restaurants, and renowned cultural institutions like the Charles Hosmer Morse Museum of American Art. The city is well-connected to downtown Orlando, making it an ideal location for commuters who appreciate a quieter lifestyle without sacrificing convenience.

Whether you’re drawn to Winter Park for its scenic beauty, community spirit, or the allure of homes with fenced exteriors, you’ll find that this charming city offers a perfect balance of comfort and sophistication. Explore the possibilities of making Winter Park your new home 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