225 total properties
Did you mean the neighborhood Winter Park?
View 1780 GOODRICH AVENUE Winter Park, FL MLS# O6403811
$625,000
3

Beds

2.0

Baths

1,283

Sq.Ft.

1780 GOODRICH AVENUE

Winter Park, FL

Courtesy of SUMMERPARK HOMES REALTY LLC
View 1407 MILLER AVENUE Winter Park, FL MLS# O6406408
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1407 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 2940 DE BROCY WAY Winter Park, FL MLS# O6408085
$785,000
3

Beds

2.0

Baths

2,679

Sq.Ft.

2940 DE BROCY WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 505 CORNWALL ROAD Winter Park, FL MLS# O6408759
  • Recently Listed with Virtual Tour
1 of 42
OPEN HOUSE: Saturday 6/6 12:00 PM - 2:00 PM
$675,000
4

Beds

2.0

Baths

1,813

Sq.Ft.

505 CORNWALL ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
  • Recently Listed with Virtual Tour
1 of 23
$399,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

Courtesy of JC FLORIDA REALTY LLC
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6407540
    1 of 39
    OPEN HOUSE: Saturday 6/6 12:00 PM - 3:00 PM
    $719,000
    4

    Beds

    2.0

    Baths

    1,688

    Sq.Ft.

    2215 WOODCREST DRIVE

    Winter Park, FL

    Courtesy of ADAIR REALTY INC
    View 340 KILLARNEY BAY COURT 4-4 Winter Park, FL MLS# O6407259
    $395,000
    2

    Beds

    2.1

    Baths

    1,428

    Sq.Ft.

    340 KILLARNEY BAY COURT 4-4

    Winter Park, FL

    Courtesy of KELLER WILLIAMS WINTER PARK
    View 616 FITZWALTER DRIVE Winter Park, FL MLS# O6403982
    $595,000
    3

    Beds

    2.0

    Baths

    1,396

    Sq.Ft.

    616 FITZWALTER DRIVE

    Winter Park, FL

    Courtesy of EXP REALTY LLC
    View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
    • Virtual Tour
    1 of 34
    $745,000
    2

    Beds

    3.0

    Baths

    1,440

    Sq.Ft.

    408 HOLT AVENUE

    Winter Park, FL

    Courtesy of THE REAL ESTATE PRINCIPLE, INC
    View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
    $410,000
    3

    Beds

    2.0

    Baths

    1,402

    Sq.Ft.

    7532 AZUREBROOK COURT

    Winter Park, FL

    Courtesy of RE/MAX TOWN & COUNTRY REALTY
    View 2482 ROXBURY ROAD Winter Park, FL MLS# O6406443
    $375,000
    2

    Beds

    1.0

    Baths

    913

    Sq.Ft.

    2482 ROXBURY ROAD

    Winter Park, FL

    Courtesy of COLDWELL BANKER REALTY
    View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
    $425,000
    940

    Sq.Ft.

    157 E NEW ENGLAND AVENUE 302

    Winter Park, FL

    Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
    View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
    $380,000
    2

    Beds

    1.0

    Baths

    988

    Sq.Ft.

    440 CAMBRIDGE BOULEVARD

    Winter Park, FL

    Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
    View 731 BONGART ROAD Winter Park, FL MLS# O6406004
      1 of 44
      OPEN HOUSE: Sunday 6/7 12:00 PM - 2:00 PM
      $499,000
      4

      Beds

      3.0

      Baths

      1,526

      Sq.Ft.

      731 BONGART ROAD

      Winter Park, FL

      Courtesy of FANNIE HILLMAN & ASSOCIATES
      View 819 DENSMORE DRIVE Winter Park, FL MLS# O6405658
      $375,000
      3

      Beds

      2.0

      Baths

      1,300

      Sq.Ft.

      819 DENSMORE DRIVE

      Winter Park, FL

      Courtesy of DON HARKINS REALTY LLC
      View 1960 WINTER PARK ROAD Winter Park, FL MLS# O6406091
      $899,000
      3

      Beds

      3.0

      Baths

      1,864

      Sq.Ft.

      1960 WINTER PARK ROAD

      Winter Park, FL

      Courtesy of FANNIE HILLMAN & ASSOCIATES
      View 2500 LEE ROAD 232 Winter Park, FL MLS# O6404916
      $164,900
      1

      Beds

      1.0

      Baths

      645

      Sq.Ft.

      2500 LEE ROAD 232

      Winter Park, FL

      Courtesy of COLDWELL BANKER REALTY
      View 721 DUNBAR STREET Winter Park, FL MLS# O6405338
      $399,999
      2

      Beds

      2.0

      Baths

      1,018

      Sq.Ft.

      721 DUNBAR STREET

      Winter Park, FL

      Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
      View 1695 LEE ROAD E116 Winter Park, FL MLS# O6399346
      $110,000
      3

      Beds

      2.0

      Baths

      1,149

      Sq.Ft.

      1695 LEE ROAD E116

      Winter Park, FL

      Courtesy of ALL REAL ESTATE & INVESTMENTS
      View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6404545
      $800,000
      5

      Beds

      3.0

      Baths

      2,194

      Sq.Ft.

      739 ROUGHBEARD ROAD

      Winter Park, FL

      Courtesy of SERHANT

      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

      397

      Estimated median home price

      $795,000
      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 - 200K41
      $200K - 300K25
      $300K - 400K24
      $400K - 500K28
      $500K - 600K27
      $600K - 700K31
      $700K - 800K21
      $800K - 900K15
      $900K - 1M9
      $1M - Max173

      Homes for Sale by Type in Winter Park, FL

      Property TypeCount
      Single Family261
      Townhouse15
      Condo84
      Commercial7
      Rental68
      Lots and Land24
      Condo/Town/CoOp0
      CoOp0
      Multi Family4
      Mobile Home0
      Farms0

      (Data as of 6/6/2026)

      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 Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes 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 6/6/2026.

      The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

      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 6/6/2026.

      The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

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

      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 6/6/2026.