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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
Culture, Convenience, Community! Discover refined living in the heart of Winter Park, where timeless luxury meets an unmatched lifestyle. This beautifully designed single...
- 3 Beds
- 2 Baths
- O6410059 MLS
Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completel...
- 4 Beds
- 5 Baths
- O6409911 MLS
Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from ...
- 3 Beds
- 2 Baths
- O6410016 MLS
- C Bldg.
Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A pla...
- 4 Beds
- 2 Baths
- O6409379 MLS
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings be...
- 1 Beds
- 2 Baths
- O6404706 MLS
- Villages Of Winterset Bldg.
Located just steps to the Golf Course and Park Avenue, in downtown Winter Park, 622 Penn Place is in the highly sought after Penn Place neighborhood. One of the few homes...
- 3 Beds
- 4 Baths
- TB8511228 MLS
PRICE IMPROVEMENT! TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a f...
- 2 Beds
- 2 Baths
- S5150301 MLS
- 34 Bldg.
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home located in highly desirable Seminole County! From the moment you arrive, you'll appreciate the inviting fr...
- 4 Beds
- 2 Baths
- O6409544 MLS
This charming one story condo is located in the desirable Cedarwood Village. This unique home boasts an open layout that is different from many others in the community. T...
- 2 Beds
- 2 Baths
- O6395130 MLS
- 2503 Bldg.
Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...
- 5 Beds
- 5 Baths
- O6408030 MLS
Pre-Construction. To be built. Welcome to The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 thoughtfully crafted residences by FG...
- 5 Beds
- 5 Baths
- O6408090 MLS
A timeless blend of historic charm and modern luxury awaits in this beautifully restored 1927 Florida bungalow, nestled in the highly sought-after and peaceful neighborho...
- 3 Beds
- 2 Baths
- O6409180 MLS
ANOTHER PRICE ADJUSTMENT! AMAZING VALUE!!! Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living...
- 2 Beds
- 2 Baths
- O6408516 MLS
- 17 Bldg.
One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly...
- 5 Beds
- 6 Baths
- O6406300 MLS
- Urban Perch-A Boutique Homes Bldg.
Welcome to Grayson Square at Winter Park by Pulte Homes. This interior Springdale II two-story townhome has no direct rear neighbors, features 3 bedrooms, 2 full bathroom...
- 3 Beds
- 3 Baths
- G5112476 MLS
- 7 Bldg.
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