205 total properties
Did you mean the neighborhood Winter Park?
View 418 GILBERT ROAD Winter Park, FL MLS# O6385950
    1 of 30
    OPEN HOUSE: Sunday 5/3 2:00 PM - 4:00 PM
    $729,000
    3

    Beds

    3.0

    Baths

    1,680

    Sq.Ft.

    418 GILBERT ROAD

    Winter Park, FL

    Courtesy of SOTERA LIVING
    View 1500 GAY ROAD 8D Winter Park, FL MLS# O6392693
    $267,000
    2

    Beds

    2.0

    Baths

    1,026

    Sq.Ft.

    1500 GAY ROAD 8D

    Winter Park, FL

    Courtesy of SOLID OAK REAL ESTATE LLC
    View Address not provided Winter Park, FL MLS# O6393932
    $257,000
    2

    Beds

    2.1

    Baths

    959

    Sq.Ft.

    Address not provided

    Winter Park, FL

    Courtesy of DERENTHAL REALTY
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 2330 COLDSTREAM DRIVE Winter Park, FL MLS# O6384436
    $650,000
    4

    Beds

    2.0

    Baths

    1,750

    Sq.Ft.

    2330 COLDSTREAM DRIVE

    Winter Park, FL

    Courtesy of DTB FLORIDA REALTY, INC.
    View 1695 LEE ROAD E103 Winter Park, FL MLS# S5146352
    $139,990
    2

    Beds

    1.0

    Baths

    881

    Sq.Ft.

    1695 LEE ROAD E103

    Winter Park, FL

    Courtesy of RE/MAX SELECT GROUP
    View 518 SHOREVIEW AVENUE Winter Park, FL MLS# O6392797
    $490,090
    2

    Beds

    2.0

    Baths

    1,609

    Sq.Ft.

    518 SHOREVIEW AVENUE

    Winter Park, FL

    Courtesy of UNITED REAL ESTATE PREFERRED
    View 1000 S SEMORAN BOULEVARD 805 Winter Park, FL MLS# O6392099
    $174,700
    2

    Beds

    2.0

    Baths

    1,003

    Sq.Ft.

    1000 S SEMORAN BOULEVARD 805

    Winter Park, FL

    Courtesy of SHAWFIELD REALTY GROUP
    View 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
    • Virtual Tour
    1 of 45
    OPEN HOUSE: Saturday 5/2 12:00 PM - 3:00 PM
    $459,000
    3

    Beds

    2.0

    Baths

    1,491

    Sq.Ft.

    405 LAKE FAIR LANE

    Winter Park, FL

    Courtesy of EXP REALTY LLC
    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 2919 BOWER ROAD Winter Park, FL MLS# O6391025
    • Virtual Tour
    1 of 38
    $779,000
    3

    Beds

    2.0

    Baths

    2,325

    Sq.Ft.

    2919 BOWER ROAD

    Winter Park, FL

    Courtesy of KELLER WILLIAMS WINTER PARK
    View 300 CAROLINA AVENUE 207 Winter Park, FL MLS# O6391523
    $495,000
    1

    Beds

    2.0

    Baths

    1,149

    Sq.Ft.

    300 CAROLINA AVENUE 207

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES
    View 1760 GREENWICH AVENUE Winter Park, FL MLS# O6392001
    $650,000
    3

    Beds

    2.0

    Baths

    1,610

    Sq.Ft.

    1760 GREENWICH AVENUE

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES
    View 7300 DANIEL WEBSTER DRIVE M7 Winter Park, FL MLS# O6388668
    $165,000
    2

    Beds

    2.1

    Baths

    1,108

    Sq.Ft.

    7300 DANIEL WEBSTER DRIVE M7

    Winter Park, FL

    Courtesy of STIRLING INTERNATIONAL REAL ES
    View 3027 AARON BURR AVENUE L1 Winter Park, FL MLS# O6390662
    $165,000
    2

    Beds

    2.1

    Baths

    1,090

    Sq.Ft.

    3027 AARON BURR AVENUE L1

    Winter Park, FL

    Courtesy of STIRLING INTERNATIONAL REAL ES
    View 2119 HOWARD DRIVE Winter Park, FL MLS# O6390345
    $850,000
    4

    Beds

    2.0

    Baths

    2,479

    Sq.Ft.

    2119 HOWARD DRIVE

    Winter Park, FL

    Courtesy of KELLER WILLIAMS WINTER PARK
    View 1807 HAMMERLIN AVENUE G Winter Park, FL MLS# O6391277
    $550,000
    3

    Beds

    2.1

    Baths

    1,818

    Sq.Ft.

    1807 HAMMERLIN AVENUE G

    Winter Park, FL

    Courtesy of ALL REAL ESTATE & INVESTMENTS
    View 3651 N GOLDENROD ROAD D101 Winter Park, FL MLS# O6391256
    $179,000
    2

    Beds

    2.0

    Baths

    840

    Sq.Ft.

    3651 N GOLDENROD ROAD D101

    Winter Park, FL

    Courtesy of ANNE ROGERS REALTY GROUP INC
    View 2779 SANBINA STREET Winter Park, FL MLS# O6388746
    $449,000
    3

    Beds

    2.0

    Baths

    1,405

    Sq.Ft.

    2779 SANBINA STREET

    Winter Park, FL

    Courtesy of MAINFRAME REAL ESTATE
    View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6390670
    $929,900
    3

    Beds

    2.0

    Baths

    1,536

    Sq.Ft.

    2823 WRIGHT AVENUE

    Winter Park, FL

    Courtesy of TAL BUSIDAN PA
    View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
    $489,990
    4

    Beds

    2.0

    Baths

    1,376

    Sq.Ft.

    501 HERITAGE BOULEVARD

    Winter Park, FL

    Courtesy of EXP REALTY LLC

    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

    370

    Estimated median home price

    $784,500
    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 - 100K4
    $100K - 200K49
    $200K - 300K22
    $300K - 400K19
    $400K - 500K28
    $500K - 600K19
    $600K - 700K27
    $700K - 800K20
    $800K - 900K10
    $900K - 1M10
    $1M - Max162

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family227
    Townhouse16
    Condo87
    Commercial5
    Rental96
    Lots and Land27
    Condo/Town/CoOp0
    CoOp0
    Multi Family4
    Mobile Home0
    Farms0

    (Data as of 5/1/2026)

    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 5/2/2026.

    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 5/2/2026.

    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 5/2/2026.

    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 5/2/2026.