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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

1000 S Semoran Boulevard Unit 408, Winter Park image
1000 S Semoran Boulevard Unit 408, Winter Park — 4 $138,000 ▼

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Gre...

  • 1 Beds
  • 1 Baths
  • R4911527 MLS
  • 4 Bldg.
1000 S Semoran Boulevard Unit 404, Winter Park image
1000 S Semoran Boulevard Unit 404, Winter Park — 3 $138,000 ▼

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Gre...

  • 1 Beds
  • 1 Baths
  • R4911526 MLS
  • 3 Bldg.
1000 S Semoran Boulevard Unit 306, Winter Park image
1000 S Semoran Boulevard Unit 306, Winter Park — 3 $138,000 ▼

Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in...

  • 1 Beds
  • 1 Baths
  • R4911525 MLS
  • 3 Bldg.
2041 Jewell Avenue, Winter Park image
2041 Jewell Avenue, Winter Park $439,900 ▼

Seller is highly motivated. Competitively priced for a quick sale. Don't miss your opportunity to own this beautiful home! First time on the market in over 60 years! Fill...

  • 3 Beds
  • 1 Baths
  • O6420660 MLS
644 N Knowles Avenue Unit 3, Winter Park image
644 N Knowles Avenue Unit 3, Winter Park — Knowles Manor $425,000 ▼

LOCATION! LOCATION! LOCATION! Welcome to Knowles Manor...a charming 11 unit condo perched on quiet brick street in the heart of Olde Winter Park...just steps from the Win...

  • 1 Beds
  • 1 Baths
  • O6420484 MLS
  • Knowles Manor Bldg.
1610 Gladiolas Drive, Winter Park image
1610 Gladiolas Drive, Winter Park $399,800 ▼

PRICE IMPROVEMENT! This 4-bedroom, 2-bath pool home in the heart of Winter Park is priced to sell and offers an incredible opportunity to make it your own. While the prop...

  • 4 Beds
  • 2 Baths
  • O6420292 MLS
2228 Azalea Place, Winter Park image
2228 Azalea Place, Winter Park $5,600,000

This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated cor...

  • 5 Beds
  • 6 Baths
  • O6416342 MLS
981 Aragon Avenue, Winter Park image
981 Aragon Avenue, Winter Park $499,000 ▼

Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of pot...

  • 2 Beds
  • 1 Baths
  • O6420093 MLS
1138 S Pennsylvania Avenue, Winter Park image
1138 S Pennsylvania Avenue, Winter Park — Virginia Heights $1,025,000 ▼

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, ...

  • 3 Beds
  • 3 Baths
  • O6420090 MLS
  • Virginia Heights Bldg.
3006 Northwood Boulevard, Winter Park image
3006 Northwood Boulevard, Winter Park $1,099,000 ▼

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character w...

  • 4 Beds
  • 3 Baths
  • O6419056 MLS
1003 Lake Bell Drive, Winter Park image
1003 Lake Bell Drive, Winter Park $579,900 ▼

Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell fo...

  • 3 Beds
  • 2 Baths
  • O6418278 MLS
259 Orange Terrace Drive, Winter Park image
259 Orange Terrace Drive, Winter Park $459,900 ▼

*SELLER IS OFFERING $5,000 TO USE TOWARD A RATE BUY DOWN OR BUYERS CLOSING COSTS! Beautifully renovated three-bedroom, two-bath home in desirable Winter Park 32789. Exten...

  • 3 Beds
  • 2 Baths
  • O6419225 MLS
4353 Steed Terrace, Winter Park image
4353 Steed Terrace, Winter Park $609,900 ▼

MOTIVATED SELLER – $10,000 BUYER CREDIT AT CLOSING! QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove commu...

  • 4 Beds
  • 2 Baths
  • TB8517548 MLS
660 W Morse Boulevard, Winter Park image
660 W Morse Boulevard, Winter Park — 660 $2,800,000

Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desira...

  • 3 Beds
  • 4 Baths
  • O6419377 MLS
  • 660 Bldg.
2521 Galliano Circle, Winter Park image
2521 Galliano Circle, Winter Park — Na $350,000 ▼

Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its clas...

  • 3 Beds
  • 3 Baths
  • O6419329 MLS
  • Na Bldg.

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