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Discover the refined charm of Winter Park, FL, a picturesque city just north of Orlando where oak-lined streets, scenic lakes, and elegant architecture create an atmosphere of timeless beauty. Stroll across Park Avenue — Winter Park’s cultural and culinary heart — filled with boutique shops, sidewalk cafés, and lush Central Park hosting seasonal festivals. Immerse yourself in the arts at gems like the Charles Hosmer Morse Museum of American Art or the Rollins Museum of Art, tour historic Casa Feliz, or unwind in the green tranquility of Mead Botanical Garden or Kraft Azalea Park. Whether you love lakeside walks, weekend farmers’ markets, or exploring unique museums, there’s always something delightful here — and plenty of opportunity when you explore homes for sale Winter Park FL to call this sophisticated oasis home.
Homes for Sale in Winter Park
Exceptional opportunity to build on beautiful Bonita Drive, one of Winter Park’s most picturesque brick-lined streets, with this 0.18-acre (approximately 8,014-square-foo...
- O6452330 MLS
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...
- 3 Beds
- 2 Baths
- O6451977 MLS
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...
- 3 Beds
- 2 Baths
- O6450978 MLS
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...
- 5 Beds
- 6 Baths
- O6443872 MLS
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...
- 2 Beds
- 2 Baths
- O6451613 MLS
- 4832 Tangerine Ave Bldg.
1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed stone, a stately brick entry, and striking black-framed windows define its European-inspired ar...
- 4 Beds
- 6 Baths
- O6450811 MLS
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...
- 2 Beds
- 2 Baths
- S5159925 MLS
- 4786 Bldg.
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...
- 2 Beds
- 3 Baths
- O6450536 MLS
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...
- 3 Beds
- 3 Baths
- A4710176 MLS
- Na Bldg.
LAKE KILLARNEY • WINTER PARK • CONDO DUES JUST $455 MONTHLY! • Enjoy exceptional value in Killarney Bay, a private lakefront community offering an oasis in the city...
- 2 Beds
- 2 Baths
- O6450663 MLS
- Killarney Bay Condo Bldg.
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...
- 11 Beds
- 8 Baths
- R4912183 MLS
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...
- 5 Beds
- 6 Baths
- O6450869 MLS
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...
- 5 Beds
- 5 Baths
- O6449440 MLS
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 ...
- 3 Beds
- 1 Baths
- TB8559088 MLS
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...
- 4 Beds
- 4 Baths
- O6449666 MLS
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