176 total properties
Did you mean the neighborhood Winter Park?
View 1725 CAROLLEE LANE Winter Park, FL MLS# O6402656
$1,005,000
3

Beds

2.0

Baths

2,335

Sq.Ft.

1725 CAROLLEE LANE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 241 W LAKE SUE AVENUE Winter Park, FL MLS# O6411621
$999,000
3

Beds

2.1

Baths

2,304

Sq.Ft.

241 W LAKE SUE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1800 MAGNOLIA AVENUE Winter Park, FL MLS# NS1087637
$994,000
4

Beds

2.1

Baths

2,431

Sq.Ft.

1800 MAGNOLIA AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 269 E CANTON AVENUE 269 Winter Park, FL MLS# O6404706
$989,500
1

Beds

1.1

Baths

1,109

Sq.Ft.

269 E CANTON AVENUE 269

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • New Construction with Virtual Tour
1 of 9
$944,890
4

Beds

3.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 29
$925,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1310 FAIRVIEW AVENUE Winter Park, FL MLS# O6424108
  • Recently Listed with Virtual Tour
1 of 14
$925,000
4

Beds

2.1

Baths

2,552

Sq.Ft.

1310 FAIRVIEW AVENUE

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6390670
$899,900
3

Beds

2.0

Baths

1,536

Sq.Ft.

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6398302
$899,900
Studio

Beds

0.0

Baths

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View 1411 MILLER AVENUE Winter Park, FL MLS# O6416926
    1 of 37
    OPEN HOUSE: Saturday 7/18 12:00 PM - 2:00 PM
    $899,000
    3

    Beds

    3.1

    Baths

    1,824

    Sq.Ft.

    1411 MILLER AVENUE

    Winter Park, FL

    View 338 BLUE HERON DRIVE Winter Park, FL MLS# O6410174
    $865,000
    3

    Beds

    3.0

    Baths

    2,017

    Sq.Ft.

    338 BLUE HERON DRIVE

    Winter Park, FL

    View 1507 GOLFSIDE DRIVE Winter Park, FL MLS# O6395355
    • Virtual Tour
    1 of 44
    OPEN HOUSE: Sunday 7/19 1:00 PM - 4:00 PM
    $850,000
    3

    Beds

    2.0

    Baths

    2,003

    Sq.Ft.

    1507 GOLFSIDE DRIVE

    Winter Park, FL

    View 724 MONMOUTH WAY Winter Park, FL MLS# O6424409
    $849,999
    5

    Beds

    3.1

    Baths

    2,832

    Sq.Ft.

    724 MONMOUTH WAY

    Winter Park, FL

    View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
    $849,900
    3

    Beds

    3.1

    Baths

    2,030

    Sq.Ft.

    1265 ARLINGTON PL

    Winter Park, FL

    View 1780 BRYAN AVENUE Winter Park, FL MLS# O6365369
    $849,000
    4

    Beds

    2.0

    Baths

    1,617

    Sq.Ft.

    1780 BRYAN AVENUE

    Winter Park, FL

    Courtesy of KELLER WILLIAMS WINTER PARK
    View 1780 BRYAN AVENUE Winter Park, FL MLS# O6402643
    $849,000
    Studio

    Beds

    0.0

    Baths

    1780 BRYAN AVENUE

    Winter Park, FL

    Courtesy of KELLER WILLIAMS WINTER PARK
    View 437 N CAPEN AVENUE Winter Park, FL MLS# O6414283
    $849,000
    3

    Beds

    2.1

    Baths

    1,904

    Sq.Ft.

    437 N CAPEN AVENUE

    Winter Park, FL

    Courtesy of COMPASS FLORIDA LLC
    View 730 W SWOOPE AVENUE Winter Park, FL MLS# S5152493
    • Recently Listed with Virtual Tour
    1 of 35
    $839,000
    5

    Beds

    3.0

    Baths

    2,132

    Sq.Ft.

    730 W SWOOPE AVENUE

    Winter Park, FL

    View 722 S RANGER BOULEVARD Winter Park, FL MLS# O6421873
    • Recently Listed with Virtual Tour
    1 of 67
    $825,000
    4

    Beds

    3.0

    Baths

    2,164

    Sq.Ft.

    722 S RANGER BOULEVARD

    Winter Park, FL

    Courtesy of CHARLES RUTENBERG REALTY ORLANDO

    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

    315

    Estimated median home price

    $825,000
    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 - 100K6
    $100K - 200K39
    $200K - 300K17
    $300K - 400K14
    $400K - 500K23
    $500K - 600K23
    $600K - 700K23
    $700K - 800K11
    $800K - 900K13
    $900K - 1M7
    $1M - Max139

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family194
    Townhouse16
    Condo71
    Commercial7
    Rental71
    Lots and Land21
    Condo/Town/CoOp0
    CoOp0
    Multi Family3
    Mobile Home0
    Farms0

    (Data as of 7/15/2026)

    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 7/16/2026.

    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 7/16/2026.