42 total properties
Did you mean the neighborhood Winter Park?
View 927 FAIRWAY DRIVE Winter Park, FL MLS# TB8498515
$680,000
4

Beds

3.0

Baths

1,918

Sq.Ft.

927 FAIRWAY DRIVE

Winter Park, FL

Courtesy of FLAT FEE MLS REALTY
View 630 SAINT DUNSTAN WAY Winter Park, FL MLS# O6376860
$675,000
5

Beds

2.0

Baths

2,240

Sq.Ft.

630 SAINT DUNSTAN WAY

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1618 INDIANA AVENUE Winter Park, FL MLS# O6398673
$675,000
4

Beds

2.0

Baths

1,604

Sq.Ft.

1618 INDIANA AVENUE

Winter Park, FL

Courtesy of NATIONAL REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 505 CORNWALL ROAD Winter Park, FL MLS# O6408759
  • Recently Listed with Virtual Tour
1 of 42
OPEN HOUSE: Sunday 5/31 12:00 PM - 2:00 PM
$675,000
4

Beds

2.0

Baths

1,813

Sq.Ft.

505 CORNWALL ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
  • Recently Listed with Virtual Tour
1 of 37
$675,000
4

Beds

2.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 2713 EASTERN PARKWAY Winter Park, FL MLS# O6398076
$670,000
3

Beds

2.0

Baths

1,304

Sq.Ft.

2713 EASTERN PARKWAY

Winter Park, FL

Courtesy of RE/MAX SELECT GROUP
View 352 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6375545
$650,000
5

Beds

3.0

Baths

1,917

Sq.Ft.

352 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2330 COLDSTREAM DRIVE Winter Park, FL MLS# O6384436
$650,000
4

Beds

2.0

Baths

1,750

Sq.Ft.

2330 COLDSTREAM DRIVE

Winter Park, FL

Courtesy of DTB FLORIDA REALTY, INC.
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 1830 EDWIN BOULEVARD Winter Park, FL MLS# O6400055
    • Virtual Tour
    1 of 52
    OPEN HOUSE: Friday 5/29 3:00 PM - 5:00 PM
    $639,900
    3

    Beds

    2.0

    Baths

    1,287

    Sq.Ft.

    1830 EDWIN BOULEVARD

    Winter Park, FL

    Courtesy of ZEN LIVING HOMES LLC
    View 1926 NATALEN ROAD Winter Park, FL MLS# O6388308
    $638,900
    3

    Beds

    2.0

    Baths

    1,469

    Sq.Ft.

    1926 NATALEN ROAD

    Winter Park, FL

    Courtesy of JAMIESON PROPERTIES, INC.
    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 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 2600 EUSTON ROAD Winter Park, FL MLS# O6397890
    • Virtual Tour
    1 of 36
    $630,000
    6

    Beds

    3.0

    Baths

    3,145

    Sq.Ft.

    2600 EUSTON ROAD

    Winter Park, FL

    Courtesy of AROD PARTNERS REALTY
    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 1760 GREENWICH AVENUE Winter Park, FL MLS# O6392001
    $625,000
    3

    Beds

    2.0

    Baths

    1,610

    Sq.Ft.

    1760 GREENWICH AVENUE

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES
    View 2756 SHERIFF WAY Winter Park, FL MLS# O6402570
    • Recently Listed with Virtual Tour
    1 of 48
    $625,000
    3

    Beds

    2.0

    Baths

    1,812

    Sq.Ft.

    2756 SHERIFF WAY

    Winter Park, FL

    Courtesy of PALM CIRCLE REALTY
    View 1780 GOODRICH AVENUE Winter Park, FL MLS# O6403811
    $625,000
    3

    Beds

    2.0

    Baths

    1,283

    Sq.Ft.

    1780 GOODRICH AVENUE

    Winter Park, FL

    Courtesy of SUMMERPARK HOMES REALTY LLC
    View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
    $619,900
    3

    Beds

    2.0

    Baths

    1,785

    Sq.Ft.

    2708 LION HEART ROAD

    Winter Park, FL

    Courtesy of EQUITYPRO LLC
    View 259 E CANTON AVENUE 259 Winter Park, FL MLS# O6389246
    $619,000
    2

    Beds

    2.0

    Baths

    1,040

    Sq.Ft.

    259 E CANTON AVENUE 259

    Winter Park, FL

    Courtesy of FANNIE HILLMAN & ASSOCIATES

    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.

    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.