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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
PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this ...
- 5 Beds
- 4 Baths
- O6384756 MLS
Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated fr...
- 3 Beds
- 2 Baths
- O6387685 MLS
Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent mas...
- 6 Beds
- 7 Baths
- O6387200 MLS
LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA....
- 2 Beds
- 2 Baths
- O6385626 MLS
- Building 20 Bldg.
Stunning renovated 1-bedroom in Winter Park! Enjoy all-new flooring, fresh paint, knockdown ceilings, and a sleek bath and kitchen with new cabinets and stainless applian...
- 1 Beds
- 1 Baths
- S5144503 MLS
- 1 Bldg.
One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto ...
- 1 Beds
- 1 Baths
- O6382547 MLS
- 291 Bldg.
*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead e...
- 5 Beds
- 3 Baths
- O6381009 MLS
Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer repr...
- 5 Beds
- 6 Baths
- O6380444 MLS
Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides im...
- 4 Beds
- 2 Baths
- O6379884 MLS
Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. ...
- 3 Beds
- 2 Baths
- O6379697 MLS
Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open ...
- 2 Beds
- 3 Baths
- O6375307 MLS
- 1 Bldg.
Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture w...
- 4 Beds
- 4 Baths
- O6377936 MLS
330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and...
- 3 Beds
- 2 Baths
- O6376757 MLS
PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre l...
- 3 Beds
- 2 Baths
- O6376260 MLS
Looking for the next location of your current or future business? There is no better place than this! Located in the heart of Winter Park and zoned for C-3, this space is...
- S5142219 MLS
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