216 total properties
Did you mean the neighborhood Winter Park?
View 423 OLOLU DRIVE Winter Park, FL MLS# O6369976
  • Virtual Tour
1 of 51
$549,000
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
$549,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1809 HAMMERLIN AVENUE

Winter Park, FL

Courtesy of NICOLE-HUDSON REALTY CORP
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 1807 HAMMERLIN AVENUE G Winter Park, FL MLS# O6391277
    1 of 25
    OPEN HOUSE: Sunday 5/24 1:00 PM - 3:00 PM
    $525,000
    3

    Beds

    2.1

    Baths

    1,818

    Sq.Ft.

    1807 HAMMERLIN AVENUE G

    Winter Park, FL

    Courtesy of ALL REAL ESTATE & INVESTMENTS
    View 1745 INDIANA AVENUE J Winter Park, FL MLS# O6402920
    $524,000
    3

    Beds

    2.1

    Baths

    1,616

    Sq.Ft.

    1745 INDIANA AVENUE J

    Winter Park, FL

    Courtesy of COLDWELL BANKER REALTY
    View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
    $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 5/24 4:00 PM - 7:00 PM
    $500,000
    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
    View 2560 Franklin Ave. Winter Park, FL MLS# F10431070
    $499,000
    4

    Beds

    2.0

    Baths

    1,514

    Sq.Ft.

    2560 Franklin Ave.

    Winter Park, FL

    View 3718 N Goldenrod Road Winter Park, FL MLS# A11792799
    $499,000
    Studio

    Beds

    0.0

    Baths

    3718 N Goldenrod Road

    Winter Park, FL

    Courtesy of PROCLOSE REALTY, LLC.
    View 230 STRATHY LANE Winter Park, FL MLS# O6371054
    • Virtual Tour
    1 of 12
    $499,000
    2

    Beds

    1.0

    Baths

    920

    Sq.Ft.

    230 STRATHY LANE

    Winter Park, FL

    Courtesy of PARK TOWN REAL ESTATE LLC
    View 2231 NAIRN DRIVE Winter Park, FL MLS# O6369016
    • Virtual Tour
    1 of 19
    $499,000
    3

    Beds

    2.0

    Baths

    1,088

    Sq.Ft.

    2231 NAIRN DRIVE

    Winter Park, FL

    Courtesy of PARK TOWN REAL ESTATE LLC
    View 841 W SWOOPE AVENUE Winter Park, FL MLS# O6373287
    $499,000
    2

    Beds

    1.0

    Baths

    1,396

    Sq.Ft.

    841 W SWOOPE AVENUE

    Winter Park, FL

    Courtesy of EXP REALTY LLC
    View 2560 Franklin Avenue Winter Park, FL MLS# F10431070
    $499,000
    4

    Beds

    2.0

    Baths

    1,514

    Sq.Ft.

    2560 Franklin Avenue

    Winter Park, FL

    View 731 BONGART ROAD Winter Park, FL MLS# O6406004
    • Recently Listed
    1 of 44
    $499,000
    4

    Beds

    3.0

    Baths

    1,526

    Sq.Ft.

    731 BONGART ROAD

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES
    View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
    $495,000
    2

    Beds

    2.1

    Baths

    1,428

    Sq.Ft.

    630 KILLARNEY BAY COURT 3

    Winter Park, FL

    Courtesy of FLORIDA ONE REAL ESTATE 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

    390

    Estimated median home price

    $787,500
    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 - 100K2
    $100K - 200K49
    $200K - 300K23
    $300K - 400K24
    $400K - 500K29
    $500K - 600K22
    $600K - 700K29
    $700K - 800K20
    $800K - 900K16
    $900K - 1M10
    $1M - Max166

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family246
    Townhouse15
    Condo88
    Commercial7
    Rental73
    Lots and Land27
    Condo/Town/CoOp0
    CoOp0
    Multi Family4
    Mobile Home0
    Farms0

    (Data as of 5/23/2026)

    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 5/24/2026.

    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 5/24/2026.

    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 5/24/2026.

    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 5/24/2026.