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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

946 Enclave Place, Winter Park image
946 Enclave Place, Winter Park $2,375,000 ▲

Pre-Construction. To be built. Welcome to Lot 22 at 946 Enclave Place, a beautifully designed 5-bedroom, 4.5-bath home with 3,989 square feet of living space, a 2-car gar...

  • 5 Beds
  • 5 Baths
  • O6411633 MLS
723 Symonds Avenue, Winter Park image
723 Symonds Avenue, Winter Park $1,700,000 ▼

Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-...

  • 4 Beds
  • 4 Baths
  • O6406823 MLS
2418 Euston Road, Winter Park image
2418 Euston Road, Winter Park $624,444 ▼

Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the highly sought-after Winter Park 32789 zip code, just moments from scenic Lake K...

  • 3 Beds
  • 3 Baths
  • O6409323 MLS
1448 Lake Florence Way, Winter Park image
1448 Lake Florence Way, Winter Park $1,049,900 ▼

Located in an intimate gated community of just 28 homes and minutes from Downtown Winter Park, this exceptional former K. Hovnanian model home features over $200,000 in b...

  • 5 Beds
  • 5 Baths
  • O6411164 MLS
1946 Strathaven Road, Winter Park image
1946 Strathaven Road, Winter Park $599,000 ▼

***FULLY REMODELED WINTER PARK HOME NEAR BALDWIN PARK! *** 1 YR HOME WARRANTY INCLUDED — a beautifully updated 4-bedroom, 3-bath home with a dedicated office, ideally ...

  • 4 Beds
  • 3 Baths
  • O6411329 MLS
125 S Interlachen Avenue Unit 2, Winter Park image
125 S Interlachen Avenue Unit 2, Winter Park — South Interlachen Place $3,150,000 ▲

Virtually Staged. Welcome to South Interlachen Place, an exceptional luxury townhome ideally positioned in the heart of downtown Winter Park. Just steps from Park Avenue,...

  • 3 Beds
  • 5 Baths
  • O6411134 MLS
  • South Interlachen Place Bldg.
1841 Lake Spier Drive, Winter Park image
1841 Lake Spier Drive, Winter Park $1,498,000 ▼

Water skiers welcome. A rare opportunity to own a thoughtfully renovated lakefront residence in Winter Park. This home is perfectly situated between Winter Park, Baldwin ...

  • 3 Beds
  • 4 Baths
  • O6407841 MLS
316 Beckett Court, Winter Park image
316 Beckett Court, Winter Park $450,000

Opportunity knocks in one of Central Florida’s most sought-after locations! This 4-bedroom, 2-bath home at 316 Beckett Court has been completely demoed and is ready for y...

  • 4 Beds
  • 2 Baths
  • O6411108 MLS
193 Lewfield Circle, Winter Park image
193 Lewfield Circle, Winter Park — N/A $248,900

Virtually Staged. Welcome to 193 Lewfield Cir, Winter Park, FL 32792, a spacious two-story end-unit townhome offering 2 bedrooms, 2.5 bathrooms, and 1,300 square feet of ...

  • 2 Beds
  • 3 Baths
  • O6409075 MLS
  • N/A Bldg.
7522 Aloma Pines Court, Winter Park image
7522 Aloma Pines Court, Winter Park — 1 $375,000

Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring a bright and functional open-concept floor plan. The first floor offers tile flooring throughout t...

  • 3 Beds
  • 3 Baths
  • S5150544 MLS
  • 1 Bldg.
700 Melrose Avenue Unit J24, Winter Park image
700 Melrose Avenue Unit J24, Winter Park — 700 $350,000 ▼

Fully updated ..Amazing modern Winter Park Lake Front location! This is a DELUXE corner unit fully remodeled and totally updated one bedroom unit has just been completed....

  • 1 Beds
  • 1 Baths
  • R4911307 MLS
  • 700 Bldg.
616 Brechin Drive, Winter Park image
616 Brechin Drive, Winter Park $999,000 ▼

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
300 Carolina Avenue Unit 402C, Winter Park image
300 Carolina Avenue Unit 402C, Winter Park — C $710,000 ▼

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.
269 E Canton Avenue Unit 269, Winter Park image
269 E Canton Avenue Unit 269, Winter Park — Villages Of Winterset $989,500

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.
2923 Antique Oaks Circle Unit 34, Winter Park image
2923 Antique Oaks Circle Unit 34, Winter Park — 34 $180,000 ▼

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.

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