52 total properties
Did you mean the neighborhood Winter Park?
View 432 W SWOOPE AVENUE Winter Park, FL MLS# O6375719
$695,000
4

Beds

3.1

Baths

2,317

Sq.Ft.

432 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 2612 ROXBURY ROAD Winter Park, FL MLS# S5139410
$630,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 676 DUNBLANE DRIVE Winter Park, FL MLS# O6365557
$699,000
3

Beds

2.0

Baths

1,827

Sq.Ft.

676 DUNBLANE DRIVE

Winter Park, FL

Courtesy of BALDWIN PARK REALTY LLC
View 763 Overspin Drive Winter Park, FL MLS# 256173
$699,000
Studio

Beds

0.0

Baths

763 Overspin Drive

Winter Park, FL

View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
$630,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 3018 NORTHWOOD BOULEVARD Winter Park, FL MLS# G5103499
    1 of 47
    OPEN HOUSE: Saturday 5/30 11:00 AM - 2:00 PM
    $649,000
    3

    Beds

    2.0

    Baths

    1,761

    Sq.Ft.

    3018 NORTHWOOD BOULEVARD

    Winter Park, FL

    Courtesy of ROCK SPRINGS REALTY, LLC
    View 661 SELKIRK DRIVE Winter Park, FL MLS# O6354700
    $625,000
    3

    Beds

    2.1

    Baths

    2,150

    Sq.Ft.

    661 SELKIRK DRIVE

    Winter Park, FL

    Courtesy of KELLER WILLIAMS HERITAGE REALTY
    View 1977 DUNDEE DRIVE Winter Park, FL MLS# O6341378
    $695,500
    1,656

    Sq.Ft.

    1977 DUNDEE DRIVE

    Winter Park, FL

    Courtesy of HOMEVEST REALTY
    View 744 CORNWALL ROAD Winter Park, FL MLS# O6332168
    $695,000
    4

    Beds

    2.0

    Baths

    1,968

    Sq.Ft.

    744 CORNWALL ROAD

    Winter Park, FL

    Courtesy of VERSALIS REALTY POWERED BY SELLSTATE

    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

    $812,500
    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 - 500K28
    $500K - 600K22
    $600K - 700K30
    $700K - 800K21
    $800K - 900K15
    $900K - 1M10
    $1M - Max174

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family257
    Townhouse14
    Condo86
    Commercial7
    Rental81
    Lots and Land28
    Condo/Town/CoOp0
    CoOp0
    Multi Family4
    Mobile Home0
    Farms0

    (Data as of 5/29/2026)

    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 5/29/2026.

    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 5/29/2026.