279 total properties
Did you mean the neighborhood Winter Park?
View 1225 SHARON PLACE Winter Park, FL MLS# O6443546
$1,749,000
5

Beds

3.1

Baths

3,097

Sq.Ft.

1225 SHARON PLACE

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 1250 S DENNING DRIVE 119 Winter Park, FL MLS# O6444618
$265,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 119

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1003 GOLFSIDE DRIVE Winter Park, FL MLS# O6444366
$759,900
3

Beds

3.0

Baths

2,145

Sq.Ft.

1003 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of QP HOMES REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2818 AMBERGATE ROAD Winter Park, FL MLS# O6444112
$429,900
3

Beds

2.0

Baths

1,398

Sq.Ft.

2818 AMBERGATE ROAD

Winter Park, FL

Courtesy of MARK SPAIN REAL ESTATE
View 1660 ORANGE AVENUE Winter Park, FL MLS# L4965340
$449,900
3

Beds

2.0

Baths

1,614

Sq.Ft.

1660 ORANGE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 450 N LAKEMONT AVE Winter Park, FL MLS# O6445021
$200,000

450 N LAKEMONT AVE

Winter Park, FL

Courtesy of DOVER INTERNATIONAL CO., INC.
View 173 SCOTTSDALE SQUARE 173 Winter Park, FL MLS# S5158339
$100,000
1

Beds

1.0

Baths

785

Sq.Ft.

173 SCOTTSDALE SQUARE 173

Winter Park, FL

Courtesy of AXEN REALTY LLC
View 3334 YOUNG STREET Winter Park, FL MLS# O6442952
$469,900
3

Beds

2.0

Baths

1,706

Sq.Ft.

3334 YOUNG STREET

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 2614 PARKLAND DRIVE Winter Park, FL MLS# O6444165
$1,890,000
4

Beds

3.1

Baths

3,307

Sq.Ft.

2614 PARKLAND DRIVE

Winter Park, FL

Courtesy of JW GASTON LLC
View 100 S VIRGINIA AVENUE 201 Winter Park, FL MLS# O6442678
$1,450,000
3

Beds

3.0

Baths

2,756

Sq.Ft.

100 S VIRGINIA AVENUE 201

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 192 BALFOUR DRIVE 2 Winter Park, FL MLS# O6443731
  • Adult Community with Virtual Tour
1 of 52
$319,000
2

Beds

2.0

Baths

1,287

Sq.Ft.

192 BALFOUR DRIVE 2

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 1695 LEE ROAD C206 Winter Park, FL MLS# TB8551269
$140,000
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD C206

Winter Park, FL

Courtesy of INVESTMENT REALTY
View 120 BROADVIEW AVENUE Winter Park, FL MLS# O6440960
$1,250,000
3

Beds

2.0

Baths

1,747

Sq.Ft.

120 BROADVIEW AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 533 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6440841
  • Virtual Tour
1 of 31
OPEN HOUSE: Friday 10/30 3:00 PM - 6:00 PM
$1,599,000
4

Beds

3.1

Baths

2,942

Sq.Ft.

533 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1602 ALABAMA DRIVE 107 Winter Park, FL MLS# O6442900
$1,150,000
2

Beds

2.0

Baths

993

Sq.Ft.

1602 ALABAMA DRIVE 107

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1306 S PENNSYLVANIA AVENUE 5 Winter Park, FL MLS# O6443013
    1 of 33
    OPEN HOUSE: Saturday 10/31 12:00 PM - 2:00 PM
    $347,500
    2

    Beds

    1.0

    Baths

    830

    Sq.Ft.

    1306 S PENNSYLVANIA AVENUE 5

    Winter Park, FL

    Courtesy of KELLER WILLIAMS WINTER PARK
    View 250 CAROLINA AVENUE 202 Winter Park, FL MLS# O6442686
    $649,000
    3

    Beds

    2.0

    Baths

    1,450

    Sq.Ft.

    250 CAROLINA AVENUE 202

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES
    View 1517 HARMON AVENUE Winter Park, FL MLS# O6443217
      1 of 48
      OPEN HOUSE: Saturday 10/31 11:00 AM - 2:00 PM
      $1,049,000
      4

      Beds

      3.1

      Baths

      2,135

      Sq.Ft.

      1517 HARMON AVENUE

      Winter Park, FL

      Courtesy of BEYCOME OF FLORIDA LLC
      View 2345 BROOKSHIRE AVENUE Winter Park, FL MLS# O6439369
      $825,000
      3

      Beds

      3.0

      Baths

      2,488

      Sq.Ft.

      2345 BROOKSHIRE AVENUE

      Winter Park, FL

      Courtesy of KELLER WILLIAMS WINTER PARK
      View 7302 SWALLOW RUN 7302 Winter Park, FL MLS# O6442345
      $134,900
      2

      Beds

      2.0

      Baths

      756

      Sq.Ft.

      7302 SWALLOW RUN 7302

      Winter Park, FL

      Courtesy of THE NAVY HOUSE

      About Winter Park

      Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

      Listings in Winter Park, FL

      355

      Estimated median home price

      $799,000
      Winter Park FL Homes for Sale & Properties

      Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

      Homes for Sale by Price in Winter Park, FL

      PriceCount
      $0 - 100K3
      $100K - 200K34
      $200K - 300K20
      $300K - 400K16
      $400K - 500K32
      $500K - 600K25
      $600K - 700K35
      $700K - 800K16
      $800K - 900K15
      $900K - 1M13
      $1M - Max146

      Homes for Sale by Type in Winter Park, FL

      Property TypeCount
      Single Family211
      Townhouse22
      Condo76
      Commercial15
      Rental87
      Lots and Land23
      Condo/Town/CoOp0
      CoOp0
      Multi Family6
      Mobile Home0
      Farms0

      (Data as of 10/29/2026)

      Information deemed reliable but not guaranteed.

      The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

      The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

      Data is updated as of 10/29/2026.

      Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

      Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

      Data is updated as of 10/29/2026.