240 Homes For Sale in Winter Park, FL

  • Updated Private House
    $360,000New
    4 Beds2 Baths1,949 Sq. Ft.
    Winter Park, FL, 32792
    Tracy Salmons
    |
    KELLER WILLIAMS ADVANTAGE REALTY
  • Condo In Cedarwood Village
    $209,100New
    2 Beds2 Baths1,295 Sq. Ft.
    Winter Park, FL, 32792
    Veronica Figueroa
    |
    EXP REALTY LLC
  • Private Condo With Upgrades
    $849,000New
    3 Beds3 Baths1,683 Sq. Ft.
    Winter Park, FL, 32789
    Tiffany Pantozzi
    |
    Real Estate Agent
  • Upgraded Coastal House
    $1,099,000New
    4 Beds3 Baths2,855 Sq. Ft.
    Winter Park, FL, 32792
    Nick McKee
    |
    KELLER WILLIAMS WINTER PARK
  • Renovated 4-Bedroom House In Park North
    $1,375,000New
    4 Beds3 Baths2,882 Sq. Ft.
    Winter Park, FL, 32789
    Greg Lowe
    |
    BHHS RESULTS REALTY
  • Renovated 3-Bedroom House In Brookshire Heights
    $469,000New
    3 Beds2 Baths1,340 Sq. Ft.
    Winter Park, FL, 32792
    Tania Harmon
    |
    KELLER WILLIAMS REALTY AT THE PARKS
  • Private House With Balcony
    $1,607,700New
    3 Beds3 Baths2,812 Sq. Ft.
    Winter Park, FL, 32789
    Troy Stevens
    |
    FLORIDA PROPERTY LLC
  • Updated Private House
    $328,000New
    2 Beds1 Bath1,323 Sq. Ft.
    Winter Park, FL, 32789
    Timothy W Boon
    |
    CREEGAN GROUP
  • 4-Bedroom House In Fairview Shores
    $715,000New
    4 Beds3 Baths2,546 Sq. Ft.
    Winter Park, FL, 32789
    Kris Kennedy
    |
    COMPASS FLORIDA LLC
  • Condo In Winter Park Pointe
    $265,000New
    2 Beds2 Baths1,225 Sq. Ft.
    Winter Park, FL, 32792
    Kamile Okatar
    |
    LA ROSA REALTY PREMIER LLC
  • 1-Story House In Winter Park Estates
    $359,500New
    3 Beds2 Baths1,264 Sq. Ft.
    Winter Park, FL, 32792
    Dragana Todorovic
    |
    CHARLES RUTENBERG REALTY ORLANDO
  • Updated 3-Bedroom House In Albert Lee Ridge
    $329,000New
    3 Beds2 Baths1,248 Sq. Ft.
    Winter Park, FL, 32789
    Nicole Dege
    |
    REDFIN CORPORATION
  • Private Condo With Fireplace
    $339,000New
    2 Beds3 Baths1,536 Sq. Ft.
    Winter Park, FL, 32789
    Lisa Gould
    |
    KELLER WILLIAMS WINTER PARK
  • Remodeled 2-Bedroom Townhouse In Park Green
    $300,000New
    2 Beds2 Baths1,639 Sq. Ft.
    Winter Park, FL, 32789
    Sean Burke
    |
    THE WILKINS WAY LLC
  • Upgraded 3-Bedroom Townhouse In Villas Of Casselberry
    $250,000New
    3 Beds2 Baths1,266 Sq. Ft.
    Winter Park, FL, 32792
    Nikki Bateman
    |
    KELLER WILLIAMS ADVANTAGE REALTY
  • Private House With Garden
    $1,590,000New
    4 Beds4 Baths3,673 Sq. Ft.
    Winter Park, FL, 32789
    Jennifer Tyre
    |
    REALTY AND COMPANY INT., LLC
  • Luxurious 4-Bedroom House In Dommerich Forests
    $539,900New
    4 Beds2 Baths1,893 Sq. Ft.
    Winter Park, FL, 32789
    Caroline Moffitt
    |
    KELLER WILLIAMS HERITAGE REALTY
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Nearby Homes

Winter Park, Florida, is a paradise to vacationers and residents alike. Located adjacent and northeast to Orlando, this lush and lovely area boasts multiple parks, golf courses, and all the amenities that create a fine resort area. Home buyers looking for quaint styles on old-fashioned brick streets will be delighted by the offerings in the Olde Winter Park area, which are often punctuated by Spanish moss-draped trees. Canals and interconnected lakes provide water-loving residents recreational opportunities all year long.

Those who like warm weather and outdoor activities will find no end to the possibilities in Winter Park. Festivals abound, including the Winter Park Sidewalk Art Festival, one of the oldest and top-rated outdoor festivals in the United States. Music lovers will discover that this is the home of the Bach Festival Society of Winter Park, central Florida’s oldest performing arts organization. Combine love of the outdoors and the love of music to experience the Annual Winter Park Jazz Festival, which features multiple acts over a two-day period. Foodies will find a treasure trove of restaurant options representing popular regional flavors as well as international-themed cuisine. Parks such as Dinky Dock provide picnic facilities, swimming, and fishing.

Despite being a popular vacation spot, Winter Park is a reasonably-priced city. Housing and cost of living are considered by residents to be fair; accessibility to multiple activities and the city’s central location within Florida are two huge draws. Even though the state as a whole has a reputation for attracting a lot of retirees, Winter Park also has a number of working professionals and families making up its population, and the unemployment rate is lower than the national average. While its proximity to Walt Disney World creates a large tourist population for much of the year, employment in Winter Park is robust on its own: the Adventist Health System and Publix Super Markets, along with various educational systems, are responsible for several thousand jobs. For those worried about the severe weather that can pop up in coastal areas, Winter Park has less hurricane backlash because of its inland location. Most transportation is via car; however, there is train service in Winter Park served by Orlando’s SunRail and national passenger rail system Amtrak. To experience life in this award-winning central Florida city that has entertainment and activities to spare, browse home openings and discover just why Winter Park is a great place to live, work, and play.