252 total properties
Did you mean the neighborhood Winter Park?
View 1564 CAVENDISH ROAD Winter Park, FL MLS# O6380505
$470,000
2

Beds

1.0

Baths

1,140

Sq.Ft.

1564 CAVENDISH ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 100 S INTERLACHEN AVENUE 404 Winter Park, FL MLS# O6375851
    1 of 36
    OPEN HOUSE: Sunday 3/1 2:00 PM - 4:00 PM
    $1,165,000
    2

    Beds

    2.0

    Baths

    1,634

    Sq.Ft.

    100 S INTERLACHEN AVENUE 404

    Winter Park, FL

    Courtesy of COLDWELL BANKER RESIDENTIAL RE
    View 501 DARCEY DRIVE Winter Park, FL MLS# O6378578
    • Virtual Tour
    1 of 39
    $1,675,000
    5

    Beds

    4.1

    Baths

    3,033

    Sq.Ft.

    501 DARCEY DRIVE

    Winter Park, FL

    Courtesy of COLDWELL BANKER RESIDENTIAL RE
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 2600 EUSTON ROAD Winter Park, FL MLS# O6380534
    $650,000
    6

    Beds

    3.0

    Baths

    3,145

    Sq.Ft.

    2600 EUSTON ROAD

    Winter Park, FL

    Courtesy of YOUNG REAL ESTATE
    View 630 SAINT DUNSTAN WAY Winter Park, FL MLS# O6376860
    $675,000
    5

    Beds

    2.0

    Baths

    2,240

    Sq.Ft.

    630 SAINT DUNSTAN WAY

    Winter Park, FL

    Courtesy of EXP REALTY LLC
    View 2500 LEE ROAD 229 Winter Park, FL MLS# O6377616
    $255,000
    2

    Beds

    2.0

    Baths

    956

    Sq.Ft.

    2500 LEE ROAD 229

    Winter Park, FL

    Courtesy of REALCOM REAL ESTATE SERVICES INC
    View 1860 STAUNTON AVENUE Winter Park, FL MLS# O6378461
    $630,000
    Studio

    Beds

    0.0

    Baths

    1860 STAUNTON AVENUE

    Winter Park, FL

    Courtesy of COMPASS FLORIDA LLC
    View 1751 GOODRICH AVENUE Winter Park, FL MLS# O6377936
    $1,475,000
    4

    Beds

    3.1

    Baths

    2,170

    Sq.Ft.

    1751 GOODRICH AVENUE

    Winter Park, FL

    Courtesy of EXP REALTY LLC
    View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
    $549,900
    2

    Beds

    2.1

    Baths

    1,428

    Sq.Ft.

    630 KILLARNEY BAY COURT 3

    Winter Park, FL

    Courtesy of FLORIDA ONE REAL ESTATE LLC
    View 507 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6377844
    $1,550,000
    4

    Beds

    3.1

    Baths

    2,985

    Sq.Ft.

    507 COUNTRY CLUB DRIVE

    Winter Park, FL

    Courtesy of SOTERA LIVING
    View 620 DARCEY DRIVE Winter Park, FL MLS# O6378148
    $739,000
    4

    Beds

    2.0

    Baths

    2,075

    Sq.Ft.

    620 DARCEY DRIVE

    Winter Park, FL

    Courtesy of LPT REALTY, LLC
    View 1702 GLENRIDGE WAY Winter Park, FL MLS# A11954444
    • Virtual Tour
    1 of 21
    OPEN HOUSE: Sunday 3/1 1:00 PM - 3:00 PM
    $789,000
    2

    Beds

    2.0

    Baths

    1,832

    Sq.Ft.

    1702 GLENRIDGE WAY

    Winter Park, FL

    Courtesy of BHHS EWM REALTY
    View 841 W SWOOPE AVENUE Winter Park, FL MLS# O6373287
    $740,000
    2

    Beds

    1.0

    Baths

    1,396

    Sq.Ft.

    841 W SWOOPE AVENUE

    Winter Park, FL

    Courtesy of EXP REALTY LLC
    View 2249 MINNESOTA AVENUE Winter Park, FL MLS# O6377279
    $419,990
    4

    Beds

    2.0

    Baths

    1,536

    Sq.Ft.

    2249 MINNESOTA AVENUE

    Winter Park, FL

    Courtesy of MARKET CONNECT REALTY LLC
    View 3315 AMBER WOOD WAY 104 Winter Park, FL MLS# O6376997
    $165,000
    2

    Beds

    1.1

    Baths

    990

    Sq.Ft.

    3315 AMBER WOOD WAY 104

    Winter Park, FL

    Courtesy of 100% REAL ESTATE, INC
    View 508 DARCEY DRIVE Winter Park, FL MLS# O6377090
    $580,000
    3

    Beds

    1.1

    Baths

    1,295

    Sq.Ft.

    508 DARCEY DRIVE

    Winter Park, FL

    Courtesy of OLDE TOWN BROKERS INC
    View 2609 SUMMERFIELD ROAD Winter Park, FL MLS# O6377302
    $899,000
    5

    Beds

    2.0

    Baths

    2,554

    Sq.Ft.

    2609 SUMMERFIELD ROAD

    Winter Park, FL

    Courtesy of COLDWELL BANKER RESIDENTIAL RE
    View 1810 HOLLYWOOD AVENUE Winter Park, FL MLS# O6377320
    • New Construction with Virtual Tour
    1 of 10
    $1,689,000
    4

    Beds

    3.1

    Baths

    2,604

    Sq.Ft.

    1810 HOLLYWOOD AVENUE

    Winter Park, FL

    Courtesy of REAL BROKER, LLC
    View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
    $579,999
    3

    Beds

    2.0

    Baths

    1,570

    Sq.Ft.

    330 ELKHORN COURT

    Winter Park, FL

    Courtesy of LA ROSA REALTY CW PROPERTIES L
    View 3207 LOWNDES DRIVE Winter Park, FL MLS# O6362285
    $499,000
    3

    Beds

    2.0

    Baths

    2,028

    Sq.Ft.

    3207 LOWNDES DRIVE

    Winter Park, FL

    Courtesy of MILLER GRANT AND COMPANY

    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

    308

    Estimated median home price

    $697,250
    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 - 100K6
    $100K - 200K38
    $200K - 300K30
    $300K - 400K21
    $400K - 500K25
    $500K - 600K16
    $600K - 700K20
    $700K - 800K21
    $800K - 900K6
    $900K - 1M7
    $1M - Max118

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family174
    Townhouse15
    Condo84
    Commercial4
    Rental80
    Lots and Land22
    Condo/Town/CoOp0
    CoOp0
    Multi Family5
    Mobile Home0
    Farms0

    (Data as of 2/28/2026)

    Information deemed reliable but not guaranteed.

    The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

    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.

    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 3/1/2026.

    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 3/1/2026.

    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 3/1/2026.