Top 25 Latest Winter Park Real Estate Listings

Welcome to this beautifully updated corner home in the Whisperwood community of Winter Park! Featuring 3 bedrooms and 2.5 bathrooms, this property offers an open-concept ...

New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This s...

Welcome home to this charming 1940's bungalow in Orwin Manor, one of Winter Park’s most sought-after neighborhoods. The single-story home has 3 bedrooms, 2 full baths and...

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live...

Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of estab...

Welcome to 603 Carnation Dr in Winter Park! This 4-bedroom, 2-bathroom home offers 1,427 square feet of living space with an updated kitchen and inviting living and dinin...

Investor or renovation opportunity in the Winter Park High school district! This solid block home features a great location for the buyer with vision. Opportunity await...

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigne...

Welcome to this charming Winter Park home, featuring classic terrazzo floors and wonderful natural light. This home boasts a cozy wood-burning fireplace that serves as a...

Welcome to 808 Densmore Drive, a beautifully updated 3-bedroom, 2-bathroom pool home tucked into the established Winter Park Estates neighborhood! Blending modern farmhou...

Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natu...

Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, ab...

Welcome to comfortable living in desirable East Winter Park. This beautifully maintained condominium offers a spacious and inviting floor plan in a quiet, established com...

1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed natural stone, a stately brick entry, and striking black-framed windows define its European-ins...

Discover comfort, style, and convenience in the heart of Winter Park! This beautifully updated 2-bedroom, 1.5-bathroom, two-story condominium offers approximately 1,281 s...

Welcome to 239 Orange Terrace Drive! This charming 4 bedroom, 2.5 bath home offers 1,866 square feet of living space in a convenient Winter Park location. Situated on a s...

Some homes stand out because of their finishes. Others because of their location. Rarely do you find one that brings both together so beautifully. Nestled alongside an 8...

Virtually Staged. Set within the guard-gated community of Hawk’s Crest, this inviting single-story residence offers a beautifully maintained open floor plan with more tha...

Welcome to this spacious end unit townhome in Winter Park’s Fernbrook Trails community! Featuring 3 bedrooms and 2.5 bathrooms, this home offers a convenient main floor p...

Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival e...

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a produc...

Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, th...

Solid 1949 bungalow on a usable 50 x 150 lot (approx. 7,553 sq ft) in unincorporated Orange County with a Winter Park mailing address, just blocks from Lake Killarney. A ...

Welcome to refined modern living in the heart of Winter Park. Meticulously crafted in 2020, this stunning two story residence showcases four bedrooms, three full baths, a...

Virtually Staged. Welcome to your dream estate inside the highly sought-after, gated enclave of Lakeside Estates in Winter Park! This magnificent 2-story residence, built...