24 total properties
Did you mean the neighborhood Winter Park?
View 938 GOLFSIDE DRIVE Winter Park, FL MLS# O6425467
  • Recently Listed
1 of 48
OPEN HOUSE: Saturday 7/18 12:00 PM - 3:00 PM
$820,000
4

Beds

3.0

Baths

2,366

Sq.Ft.

938 GOLFSIDE DRIVE

Winter Park, FL

View 1562 ARBOR PARK DRIVE Winter Park, FL MLS# O6425628
  • Recently Listed with Virtual Tour
1 of 49
OPEN HOUSE: Sunday 7/19 1:30 PM - 3:30 PM
$775,000
4

Beds

2.1

Baths

1,899

Sq.Ft.

1562 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1871 BARKER DRIVE Winter Park, FL MLS# O6425831
  • Recently Listed with Virtual Tour
1 of 36
OPEN HOUSE: Saturday 7/18 1:00 PM - 3:00 PM
$779,000
3

Beds

3.0

Baths

2,231

Sq.Ft.

1871 BARKER DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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
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 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 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 275 N RANGER BOULEVARD Winter Park, FL MLS# O6415904
    $775,000
    4

    Beds

    3.0

    Baths

    1,950

    Sq.Ft.

    275 N RANGER BOULEVARD

    Winter Park, FL

    View 338 BLUE HERON DRIVE Winter Park, FL MLS# O6410174
    • Virtual Tour
    1 of 44
    OPEN HOUSE: Saturday 7/18 1:00 PM - 3:00 PM
    $865,000
    3

    Beds

    3.0

    Baths

    2,017

    Sq.Ft.

    338 BLUE HERON DRIVE

    Winter Park, FL

    View 300 CAROLINA AVENUE 402C Winter Park, FL MLS# O6410016
    $750,000
    3

    Beds

    2.0

    Baths

    1,350

    Sq.Ft.

    300 CAROLINA AVENUE 402C

    Winter Park, FL

    View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
    • Virtual Tour
    1 of 34
    $745,000
    2

    Beds

    3.0

    Baths

    1,440

    Sq.Ft.

    408 HOLT AVENUE

    Winter Park, FL

    Courtesy of THE REAL ESTATE PRINCIPLE, INC
    View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6404545
    $780,000
    5

    Beds

    3.0

    Baths

    2,194

    Sq.Ft.

    739 ROUGHBEARD ROAD

    Winter Park, FL

    Courtesy of SERHANT
    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 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 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 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 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

    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

    289

    Estimated median home price

    $725,000
    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 - 100K7
    $100K - 200K39
    $200K - 300K16
    $300K - 400K14
    $400K - 500K19
    $500K - 600K22
    $600K - 700K23
    $700K - 800K11
    $800K - 900K10
    $900K - 1M7
    $1M - Max121

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family171
    Townhouse12
    Condo72
    Commercial7
    Rental67
    Lots and Land20
    Condo/Town/CoOp0
    CoOp0
    Multi Family3
    Mobile Home0
    Farms0

    (Data as of 7/17/2026)

    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 7/18/2026.