Winter Park Homes with Fence Exterior Features

Welcome to Winter Park, Florida, a picturesque city nestled in Orange County that seamlessly blends small-town charm with vibrant cultural experiences. Known for its beautiful tree-lined streets, stunning lakes, and historic architecture, Winter Park is a haven for those seeking a serene lifestyle with easy access to urban amenities. With an array of boutique shops, art galleries, and delightful dining options, residents enjoy a rich community atmosphere that celebrates creativity and connection.

One of the standout features of homes in Winter Park is their enchanting outdoor spaces, particularly those with fenced exteriors. These properties offer a perfect blend of privacy and security, making them ideal for families, pet owners, and anyone who cherishes their outdoor moments. Imagine sipping your morning coffee on a sun-drenched patio, surrounded by a beautifully landscaped yard, or hosting lively gatherings with friends and family in a safe, enclosed environment.

Fenced homes in Winter Park not only provide peace of mind but also enhance the overall aesthetic of the property, contributing to the charming streetscape that the city is known for. Whether you're looking for a cozy bungalow or a more spacious family home, the options are plentiful, each with its unique character and charm.

With its rich history, vibrant community, and beautiful homes with fenced exteriors, Winter Park is more than just a place to live—it's a lifestyle. Discover your dream home in this enchanting city and experience all the warmth and beauty it has to offer!

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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