141 total properties
Did you mean the neighborhood Winter Park?
View 218 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6388723
$600,000
3

Beds

2.0

Baths

1,618

Sq.Ft.

218 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 1951 STAUNTON AVENUE Winter Park, FL MLS# O6379543
$599,000
3

Beds

2.0

Baths

2,556

Sq.Ft.

1951 STAUNTON AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
$595,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

Courtesy of GALLOWAY REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
$589,900
3

Beds

2.0

Baths

1,269

Sq.Ft.

1354 INDIANA AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 423 OLOLU DRIVE Winter Park, FL MLS# O6369976
  • Virtual Tour
1 of 51
$589,000
3

Beds

3.0

Baths

1,920

Sq.Ft.

423 OLOLU DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1809 HAMMERLIN AVENUE Winter Park, FL MLS# O6373616
$585,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1809 HAMMERLIN AVENUE

Winter Park, FL

Courtesy of NICOLE-HUDSON REALTY CORP
View 2829 ALOMA Winter Park, FL MLS# O6404107
  • Recently Listed with Virtual Tour
1 of 36
OPEN HOUSE: Sunday 5/3 12:00 PM - 4:00 PM
$579,000
4

Beds

2.0

Baths

1,821

Sq.Ft.

2829 ALOMA

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 517 ROUGHBEARD ROAD Winter Park, FL MLS# O6399029
  • Recently Listed with Virtual Tour
1 of 53
$565,000
3

Beds

2.0

Baths

1,873

Sq.Ft.

517 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
$554,900
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 1807 HAMMERLIN AVENUE G Winter Park, FL MLS# O6391277
    1 of 25
    OPEN HOUSE: Sunday 5/3 2:00 PM - 4:00 PM
    $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 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
    • Recently Listed with Virtual Tour
    1 of 27
    $550,000
    1,088

    Sq.Ft.

    4947 N PALM AVENUE

    Winter Park, FL

    Courtesy of FLORIDA REALTY INVESTMENTS
    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 1210 FAIRWAY DR Winter Park, FL MLS# O6398533
    $549,000
    3

    Beds

    2.0

    Baths

    1,737

    Sq.Ft.

    1210 FAIRWAY DR

    Winter Park, FL

    Courtesy of CENTRAL FLORIDA PRIME REAL ESTATE LLC
    View 1781 INDIANA AVENUE A Winter Park, FL MLS# O6381195
    $545,000
    3

    Beds

    2.1

    Baths

    1,616

    Sq.Ft.

    1781 INDIANA AVENUE A

    Winter Park, FL

    Courtesy of CARLISLE REALTY, LLC
    View 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
    $539,000
    3

    Beds

    2.1

    Baths

    1,660

    Sq.Ft.

    1261 INDIANA AVENUE

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES
    View 720 W WEBSTER AVENUE Winter Park, FL MLS# G5108643
    $525,000
    3

    Beds

    2.0

    Baths

    1,356

    Sq.Ft.

    720 W WEBSTER AVENUE

    Winter Park, FL

    Courtesy of SERHANT
    View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
    • Recently Listed
    1 of 42
    $515,000
    3

    Beds

    3.0

    Baths

    1,786

    Sq.Ft.

    525 OLOLU DRIVE

    Winter Park, FL

    Courtesy of CAISSA REALTY INVESTMENT INC
    View 2627 AMBERGATE ROAD Winter Park, FL MLS# O6093816
    $510,000
    4

    Beds

    3.0

    Baths

    1,805

    Sq.Ft.

    2627 AMBERGATE ROAD

    Winter Park, FL

    Courtesy of COLDWELL BANKER REALTY
    View 1036 ARAGON AVENUE Winter Park, FL MLS# O6382491
    • Virtual Tour
    1 of 41
    OPEN HOUSE: Sunday 5/3 5:00 PM - 7:30 PM
    $510,000
    2

    Beds

    1.0

    Baths

    1,073

    Sq.Ft.

    1036 ARAGON AVENUE

    Winter Park, FL

    Courtesy of WATSON REALTY CORP
    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

    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

    $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 - 100K4
    $100K - 200K50
    $200K - 300K22
    $300K - 400K18
    $400K - 500K28
    $500K - 600K19
    $600K - 700K27
    $700K - 800K20
    $800K - 900K10
    $900K - 1M10
    $1M - Max167

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family233
    Townhouse14
    Condo88
    Commercial5
    Rental92
    Lots and Land27
    Condo/Town/CoOp0
    CoOp0
    Multi Family4
    Mobile Home0
    Farms0

    (Data as of 5/2/2026)

    Information deemed reliable but not guaranteed.

    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.