162 total properties
Did you mean the neighborhood Winter Park?
View 340 KILLARNEY BAY COURT 4-4 Winter Park, FL MLS# O6407259
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Sunday 5/31 12:00 PM - 3:00 PM
$395,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

340 KILLARNEY BAY COURT 4-4

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 616 FITZWALTER DRIVE Winter Park, FL MLS# O6403982
$595,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

616 FITZWALTER DRIVE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
$410,000
3

Beds

2.0

Baths

1,402

Sq.Ft.

7532 AZUREBROOK COURT

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2482 ROXBURY ROAD Winter Park, FL MLS# O6406443
$400,000
2

Beds

1.0

Baths

913

Sq.Ft.

2482 ROXBURY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
  • Recently Listed with Virtual Tour
1 of 33
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 731 BONGART ROAD Winter Park, FL MLS# O6406004
    1 of 44
    OPEN HOUSE: Sunday 5/31 12:00 PM - 2:00 PM
    $499,000
    4

    Beds

    3.0

    Baths

    1,526

    Sq.Ft.

    731 BONGART ROAD

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES
    View 819 DENSMORE DRIVE Winter Park, FL MLS# O6405658
    $375,000
    3

    Beds

    2.0

    Baths

    1,300

    Sq.Ft.

    819 DENSMORE DRIVE

    Winter Park, FL

    Courtesy of DON HARKINS REALTY LLC
    View 2500 LEE ROAD 232 Winter Park, FL MLS# O6404916
    $164,900
    1

    Beds

    1.0

    Baths

    645

    Sq.Ft.

    2500 LEE ROAD 232

    Winter Park, FL

    Courtesy of COLDWELL BANKER REALTY
    View 721 DUNBAR STREET Winter Park, FL MLS# O6405338
    $399,999
    2

    Beds

    2.0

    Baths

    1,018

    Sq.Ft.

    721 DUNBAR STREET

    Winter Park, FL

    Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
    View 1695 LEE ROAD E116 Winter Park, FL MLS# O6399346
    $125,000
    3

    Beds

    2.0

    Baths

    1,149

    Sq.Ft.

    1695 LEE ROAD E116

    Winter Park, FL

    Courtesy of ALL REAL ESTATE & INVESTMENTS
    View 4772 TANGERINE AVENUE 4772 Winter Park, FL MLS# O6405042
    $199,000
    2

    Beds

    2.0

    Baths

    1,058

    Sq.Ft.

    4772 TANGERINE AVENUE 4772

    Winter Park, FL

    Courtesy of THE WILKINS WAY LLC
    View 3371 RIVER VIEW WAY 46 Winter Park, FL MLS# O6403947
    $205,000
    3

    Beds

    2.1

    Baths

    1,151

    Sq.Ft.

    3371 RIVER VIEW WAY 46

    Winter Park, FL

    Courtesy of REALTY ONE GROUP EVOLVE
    View 2237 WOODCREST DRIVE Winter Park, FL MLS# O6404115
    $490,000
    3

    Beds

    2.0

    Baths

    1,492

    Sq.Ft.

    2237 WOODCREST DRIVE

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES
    View 7327 FOREST HILL COURT 223 Winter Park, FL MLS# O6403841
    $185,000
    2

    Beds

    2.1

    Baths

    1,031

    Sq.Ft.

    7327 FOREST HILL COURT 223

    Winter Park, FL

    Courtesy of M L VAZ REALTY INC
    View 3282 OAK LAKE PLACE 3282 Winter Park, FL MLS# O6403912
    $159,000
    2

    Beds

    1.1

    Baths

    990

    Sq.Ft.

    3282 OAK LAKE PLACE 3282

    Winter Park, FL

    Courtesy of BUSBY REALTY LLC
    View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
    $545,000
    1,088

    Sq.Ft.

    4947 N PALM AVENUE

    Winter Park, FL

    Courtesy of FLORIDA REALTY INVESTMENTS
    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 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 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
    $250,000
    3

    Beds

    2.1

    Baths

    1,578

    Sq.Ft.

    7484 CANFORD COURT 8

    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

    398

    Estimated median home price

    $797,500
    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 - 100K3
    $100K - 200K45
    $200K - 300K24
    $300K - 400K26
    $400K - 500K29
    $500K - 600K22
    $600K - 700K30
    $700K - 800K21
    $800K - 900K14
    $900K - 1M10
    $1M - Max174

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family260
    Townhouse13
    Condo86
    Commercial7
    Rental78
    Lots and Land26
    Condo/Town/CoOp0
    CoOp0
    Multi Family4
    Mobile Home0
    Farms0

    (Data as of 5/30/2026)

    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 5/31/2026.

    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 5/31/2026.

    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 5/31/2026.