Winter Park Homes with Duplex Property Style

Winter Park Homes with Duplex Property Style

Welcome to Winter Park, Florida – a charming city that beautifully blends the warmth of Southern hospitality with a vibrant cultural scene. Nestled just north of Orlando, Winter Park is renowned for its picturesque tree-lined streets, stunning lakes, and a rich history that dates back to the late 1800s. The city is home to a delightful array of boutiques, art galleries, and fine dining options, making it a perfect destination for both residents and visitors alike. With its acclaimed Rollins College and the renowned Morse Museum of American Art, Winter Park offers an enriching lifestyle that is both dynamic and serene.

Among the many housing options available in this enchanting city, duplex properties stand out as a unique investment opportunity. Homes with a duplex property style provide the perfect blend of comfort and practicality. Ideal for multi-generational living or as an income-generating rental, these properties offer two distinct living spaces under one roof. Imagine the convenience of sharing a home while still enjoying your own privacy – whether you’re hosting family or looking to rent out one side for additional income.

Duplex homes in Winter Park are often nestled in friendly neighborhoods, providing easy access to parks, schools, and the vibrant downtown area. With their spacious layouts and potential for customization, these properties allow you to create a living space that reflects your personal style while maximizing your investment. Experience the charm and opportunity that Winter Park offers, and discover why duplex living could be the perfect fit for you!

Newest Winter Park Homes with Duplex Property Style

$650,900
5 Beds ⋅ 4 Baths ⋅ Grand Pines SubDv. ⋅ 32792 Zip Code
Very nice duplex property. No HOA. Located on a cul-de-sac. This property has a 3 bedroom 2 bath with a 2 car garage on one side and a 2 bedroom 1 bath with a 1 car garage on the other side. Both currently rented and tenant occupied. The 3/2 tenant is on a month to month lease for $2,000 per month and the 2/1 is on a 1 year lease at $1,500 per month. There are many options for you with this purchase. You can keep both sides rented, you could live in one side and rent the other or you can even split the property into two separate parcels and sell one side, as has already been done in this neighborhood. Both units have granite counters and fenced in yards.

5427 Peaco Place, Winter Park
$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
$1,185,999
6 Beds ⋅ 4 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code
Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, and wood and tile flooring throughout, finishes that attract quality tenants while keeping maintenance straightforward. Private, fenced patios extend the living space outdoors, while in-unit laundry and ample parking add everyday convenience that renters actively prioritize. The location is the true driver, just steps from the Winter Park Golf Course and a short walk to Park Avenue’s dining, shopping, and lifestyle. This level of walkability continues to support strong tenant demand and long-term appreciation, particularly in the rapidly growing West End of Winter Park. As an added benefit, the property includes a membership to the Winter Park Country Club, further enhancing its appeal for both owners and tenants. For buyers looking to secure a property that offers immediate usability, consistent rental demand, and long-term upside in one of Central Florida’s most sought-after markets, this is a rare opportunity to check all three boxes in a single acquisition.

726/720 N Pennsylvania Avenue, Winter Park
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