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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
This "Investment Opportunity" duplex is centrally located on a quiet, tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Me...
- 4 Beds
- 4 Baths
- O6433576 MLS
Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’s rarest offerings. Tucked...
- O6434678 MLS
This "Investment Opportunity" Duplex is centrally located on a quiet tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Mea...
- 4 Beds
- 4 Baths
- O6435228 MLS
A wonderful opportunity to build your dream home on one of Winter Park’s most idyllic streets. Situated on a quaint, one-way brick street with a charming park at its cent...
- 3 Beds
- 3 Baths
- O6435809 MLS
Welcome to this charming 2 bedroom, 2 bath home, with light and bright open floor plan, spacious rooms and many updates and upgrades. Roof was replaced (2019), new A/C (...
- 2 Beds
- 2 Baths
- O6435708 MLS
An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer...
- O6434973 MLS
An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer...
- 3 Beds
- 1 Baths
- O6434966 MLS
Virtually Staged! Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location, 3 bedroom, 2.5 bathroom with features of spacious living an...
- 3 Beds
- 3 Baths
- O6435026 MLS
- 7605 Bldg.
Completely Remodeled 2026 | Single-Story | Prime Location | Dual Suites | The redesigned kitchen features 42" shaker cabinetry, Calcutta quartz countertops, and new stain...
- 3 Beds
- 3 Baths
- O6435435 MLS
New Construction! New photos coming soon! First photo is a rendering of the new home and the following photos are interiors of a similar model by the builder. Discover Mo...
- 5 Beds
- 5 Baths
- O6435328 MLS
Virtually Staged. LOCATION, CONVENIENCE, AND EASY LIVING IN WINTER PARK! This move-in-ready first-floor, 1-bedroom, 1-bath condo features an open living and dining area, ...
- 1 Beds
- 1 Baths
- O6435396 MLS
- Lewfield 285 Bldg.
Welcome to this fully renovated four-bedroom, two-bathroom pool home offering close to 2,000 square feet of beautifully updated living space on an expansive .36-acre pie-...
- 4 Beds
- 2 Baths
- O6417303 MLS
PRICE ADJUSTMENT! Welcome to this Desirable Winter Park Villas Condo FIRST FLOOR 2 BEDROOM, 2 FULL BATH, 1037 square feet, featuring NEW AIR CONDITIONING SYSTEM and BRAND...
- 2 Beds
- 2 Baths
- O6434195 MLS
- 623 Bldg.
!!!PRICE IMPROVEMENT!!! Welcome home to 2112 Eastbrook Blvd, a fully remodeled gem tucked into the sought-after Eastbrook neighborhood of Winter Park! This 3-bedroom, ...
- 3 Beds
- 2 Baths
- O6434703 MLS
Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $899,000, this single-story block home sit...
- 3 Beds
- 3 Baths
- O6435086 MLS
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