223 total properties
Did you mean the neighborhood Winter Park?
View JESSICA COURT Winter Park, FL MLS# O6419256
  • Recently Listed with Virtual Tour
1 of 11
$449,000
Studio

Beds

0.0

Baths

JESSICA COURT

Winter Park, FL

View 751 WARRENTON ROAD Winter Park, FL MLS# TB8522073
  • Recently Listed with Virtual Tour
1 of 16
$319,900
3

Beds

2.0

Baths

1,196

Sq.Ft.

751 WARRENTON ROAD

Winter Park, FL

View 1826 BANCHORY ROAD Winter Park, FL MLS# O6419474
$779,000
4

Beds

2.1

Baths

2,391

Sq.Ft.

1826 BANCHORY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View Address not provided Winter Park, FL MLS# O6419422
  • Recently Listed
1 of 34
$229,900
2

Beds

1.1

Baths

1,219

Sq.Ft.

Address not provided

Winter Park, FL

View 2652 ABBEY ROAD Winter Park, FL MLS# O6419026
  • Virtual Tour
1 of 44
$625,000
5

Beds

2.0

Baths

1,938

Sq.Ft.

2652 ABBEY ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 7488 WHISPERWOOD DRIVE 28 Winter Park, FL MLS# O6419151
  • Recently Listed with Virtual Tour
1 of 63
$230,000
2

Beds

2.1

Baths

1,578

Sq.Ft.

7488 WHISPERWOOD DRIVE 28

Winter Park, FL

View 2344 WOODCREST DRIVE Winter Park, FL MLS# O6418782
  • Recently Listed with Virtual Tour
1 of 22
$729,900
4

Beds

2.0

Baths

1,764

Sq.Ft.

2344 WOODCREST DRIVE

Winter Park, FL

View 332 FLEET ROAD Winter Park, FL MLS# O6414829
  • Virtual Tour
1 of 35
$595,000
4

Beds

2.0

Baths

2,355

Sq.Ft.

332 FLEET ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Recently Listed with Virtual Tour
1 of 26
$250,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

View 4053 COOL WATER COURT Winter Park, FL MLS# O6419831
$549,000
3

Beds

2.0

Baths

1,930

Sq.Ft.

4053 COOL WATER COURT

Winter Park, FL

View 2361 ROXBURY ROAD Winter Park, FL MLS# O6418164
  • Recently Listed with Virtual Tour
1 of 34
$599,000
3

Beds

2.0

Baths

1,723

Sq.Ft.

2361 ROXBURY ROAD

Winter Park, FL

View 4756 TANGERINE AVENUE 4756 Winter Park, FL MLS# R4911483
  • Recently Listed with Virtual Tour
1 of 5
$195,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4756 TANGERINE AVENUE 4756

Winter Park, FL

View 1411 MILLER AVENUE Winter Park, FL MLS# O6416926
  • Recently Listed
1 of 37
$899,000
3

Beds

3.1

Baths

1,824

Sq.Ft.

1411 MILLER AVENUE

Winter Park, FL

View 200 SAINT ANDREWS BLVD 3206 Winter Park, FL MLS# O6416143
$230,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BLVD 3206

Winter Park, FL

View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
  • Recently Listed with Virtual Tour
1 of 38
$879,000
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
  • Recently Listed with Virtual Tour
1 of 36
$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
  • Recently Listed with Virtual Tour
1 of 32
$775,000
4

Beds

3.0

Baths

1,950

Sq.Ft.

275 N RANGER BOULEVARD

Winter Park, FL

View 1521 CAVENDISH RD Winter Park, FL MLS# O6415985
  • Recently Listed with Virtual Tour
1 of 22
$470,000
2

Beds

1.0

Baths

1,036

Sq.Ft.

1521 CAVENDISH RD

Winter Park, FL

View 700 MELROSE AVENUE K25 Winter Park, FL MLS# O6414821
  • Adult Community with Virtual Tour
1 of 30
$245,000
1

Beds

1.0

Baths

787

Sq.Ft.

700 MELROSE AVENUE K25

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Recently Listed with Virtual Tour
1 of 24
$259,999
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

Winter Park, FL

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

400

Estimated median home price

$747,500
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 - 200K49
$200K - 300K26
$300K - 400K19
$400K - 500K31
$500K - 600K30
$600K - 700K33
$700K - 800K18
$800K - 900K13
$900K - 1M9
$1M - Max169

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family254
Townhouse16
Condo95
Commercial7
Rental71
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 7/1/2026)

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 7/1/2026.

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 7/1/2026.