41 total properties
Did you mean the neighborhood Winter Park?
View 2974 CHANTILLY AVENUE Winter Park, FL MLS# O6412851
$500,000
3

Beds

2.0

Baths

1,433

Sq.Ft.

2974 CHANTILLY AVENUE

Winter Park, FL

View 528 SAINT DUNSTAN WAY Winter Park, FL MLS# O6414677
$524,990
3

Beds

2.0

Baths

1,656

Sq.Ft.

528 SAINT DUNSTAN WAY

Winter Park, FL

View 316 BECKETT COURT Winter Park, FL MLS# O6411108
$450,000
4

Beds

2.0

Baths

1,651

Sq.Ft.

316 BECKETT COURT

Winter Park, FL

Courtesy of VINTAGE REALTY SOLUTIONS
The time to sell is now! THE TIME TO SELL IS NOW!
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 731 BONGART ROAD Winter Park, FL MLS# O6406004
$499,000
4

Beds

3.0

Baths

1,526

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
$535,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
    1 of 42
    OPEN HOUSE: Sunday 7/26 12:00 PM - 3:00 PM
    $495,900
    3

    Beds

    3.0

    Baths

    1,786

    Sq.Ft.

    525 OLOLU DRIVE

    Winter Park, FL

    View 814 DENSMORE DR Winter Park, FL MLS# O6399773
    • Virtual Tour
    1 of 24
    $425,000
    4

    Beds

    2.0

    Baths

    1,610

    Sq.Ft.

    814 DENSMORE DR

    Winter Park, FL

    View 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
      1 of 25
      OPEN HOUSE: Sunday 7/26 1:00 PM - 4:00 PM
      $460,000
      3

      Beds

      2.0

      Baths

      1,606

      Sq.Ft.

      950 HANOVER AVENUE

      Winter Park, FL

      Courtesy of COMPASS FLORIDA LLC
      View 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
      $444,900
      3

      Beds

      2.0

      Baths

      1,491

      Sq.Ft.

      405 LAKE FAIR LANE

      Winter Park, FL

      View 512 N LAKEMONT AVENUE Winter Park, FL MLS# O6392353
      $500,000
      3

      Beds

      2.0

      Baths

      1,413

      Sq.Ft.

      512 N LAKEMONT AVENUE

      Winter Park, FL

      Courtesy of COLDWELL BANKER REALTY
      View 1807 HAMMERLIN AVENUE G Winter Park, FL MLS# O6391277
        1 of 29
        OPEN HOUSE: Sunday 7/26 2:00 PM - 4:00 PM
        $515,000
        3

        Beds

        2.1

        Baths

        1,818

        Sq.Ft.

        1807 HAMMERLIN AVENUE G

        Winter Park, FL

        Courtesy of ALL REAL ESTATE & INVESTMENTS
        View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
        $458,000
        4

        Beds

        2.0

        Baths

        1,376

        Sq.Ft.

        501 HERITAGE BOULEVARD

        Winter Park, FL

        View Address not provided Winter Park, FL MLS# S5145631
        $430,000
        4

        Beds

        2.0

        Baths

        1,296

        Sq.Ft.

        Address not provided

        Winter Park, FL

        View 4033 YACHT COURT Winter Park, FL MLS# O6379135
        • Virtual Tour
        1 of 26
        $549,000
        3

        Beds

        2.0

        Baths

        2,268

        Sq.Ft.

        4033 YACHT COURT

        Winter Park, FL

        Courtesy of COLDWELL BANKER REALTY
        View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
        $475,000
        2

        Beds

        2.1

        Baths

        1,428

        Sq.Ft.

        630 KILLARNEY BAY COURT 3

        Winter Park, FL

        View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
        $544,900
        3

        Beds

        2.0

        Baths

        1,570

        Sq.Ft.

        330 ELKHORN COURT

        Winter Park, FL

        View 1809 HAMMERLIN AVENUE Winter Park, FL MLS# O6373616
        $549,000
        3

        Beds

        2.1

        Baths

        1,818

        Sq.Ft.

        1809 HAMMERLIN AVENUE

        Winter Park, FL

        View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
        $459,900
        Studio

        Beds

        0.0

        Baths

        3601 MIDIRON DRIVE

        Winter Park, FL

        Courtesy of EMPIRE NETWORK REALTY
        View 346 S RANGER BOULEVARD Winter Park, FL MLS# S5134662
        $475,000
        3

        Beds

        2.0

        Baths

        1,592

        Sq.Ft.

        346 S RANGER BOULEVARD

        Winter Park, FL

        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

        375

        Estimated median home price

        $759,000
        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 - 100K8
        $100K - 200K43
        $200K - 300K24
        $300K - 400K18
        $400K - 500K31
        $500K - 600K24
        $600K - 700K31
        $700K - 800K15
        $800K - 900K14
        $900K - 1M10
        $1M - Max157

        Homes for Sale by Type in Winter Park, FL

        Property TypeCount
        Single Family229
        Townhouse19
        Condo83
        Commercial11
        Rental66
        Lots and Land24
        Condo/Town/CoOp0
        CoOp0
        Multi Family4
        Mobile Home0
        Farms0

        (Data as of 7/25/2026)

        Information deemed reliable but not guaranteed.

        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 7/26/2026.