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Winter Park Real Estate

Winter Park is a very upscale city located just three miles northeast of downtown Orlando.  Known for its beautiful chain of lakes, brick streets with massive oaks, high-end shopping, and old world charm, Winter Park is considered by many to be the finest urban village in the state of Florida.  Once a 19th century resort destination, Winter Park is now home to Central Florida's highest priced real estate.  Residents and visitors enjoy art galleries and museums, including the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass in the world.  Winter Park Homes For Sale MapClick the blue button to view all Winter Park homes for sale.

Rollins College, a highly-rated private liberal arts school, sits in the middle of Winter Park on the shores of Lake Virginia.  The Winter Park chain of lakes are connected by small navigable canals, giving the community an old world Venetian charm.  Winter Park's Park Avenue shopping and dining district is a popular area destination and is Central Florida's version of Rodeo Drive.  In March, Park Ave. and Central Park in downtown Winter Park host the annual, Winter Park Sidewalk Art Festival, one of the largest art festivals in the southeast.  With more than 70 parks, Winter Park is a nature lover's paradise.

Homes for sale in Winter Park range from $250,000 cottages to multi-million dollar lakefront estates.

Latest Winter Park Listings

532 Darcey Drive, Winter Park image
532 Darcey Drive, Winter Park $575,000

Expect to be impressed! This 3 bedroom/1.5 bathroom CORNER lot home has been completely renovated and is located in the desirable Brookshire Heights neighborhood. The hom...

  • 3 Beds
  • 1.5 Baths
  • Brookshire Heights SubDv.
  • 32792 Zip Code
417 Saint Dunstan Way, Winter Park image
417 Saint Dunstan Way, Winter Park $534,900

She. Is. A. Prize. So who is gonna win the prize? Living it up in the stylish Winter Park Pines, you'll find her in one of the nicest neighborhoods in ALL of Central Flor...

  • 4 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
625 Brechin Drive, Winter Park image
625 Brechin Drive, Winter Park $749,900

A timeless home awaits among the tree canopies of Kenilworth Shores, a tried-and-true Winter Park neighborhood steeped in history. A pristine property and beautifully app...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 04 SubDv.
  • 32792 Zip Code
428 S Phelps Avenue, Winter Park image
428 S Phelps Avenue, Winter Park $895,000

Located in the quaint, desirable Kenilworth Shores of Winter Park is where you will find this UPDATED traditional home that features over 2100 sq. ft., boasting 3 bedroom...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 02 SubDv.
  • 32789 Zip Code
1460 Sunset Drive, Winter Park image
1460 Sunset Drive, Winter Park $2,299,000

Welcome to Old Winter Park's coveted Tree Streets - a place where your dream home is waiting for you! This truly remarkable 5/3 property rests in a neighborhood teeming w...

  • 5 Beds
  • 2.5 Baths
  • Lake Knowles Terrace SubDv.
  • 32789 Zip Code

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