289 total properties
Did you mean the neighborhood Winter Park?
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 2228 AZALEA PLACE Winter Park, FL MLS# O6416342
  • Recently Listed with Virtual Tour
1 of 72
$5,600,000
5

Beds

5.1

Baths

5,152

Sq.Ft.

2228 AZALEA PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 229 ALEXANDER PLACE Winter Park, FL MLS# O6412911
  • Recently Listed with Virtual Tour
1 of 53
$4,250,000
4

Beds

4.2

Baths

4,431

Sq.Ft.

229 ALEXANDER PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2504 FORFARSHIRE DRIVE Winter Park, FL MLS# O6424656
$630,000
3

Beds

2.0

Baths

1,915

Sq.Ft.

2504 FORFARSHIRE DRIVE

Winter Park, FL

Courtesy of RE/MAX CENTRAL REALTY
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 708 BALMORAL ROAD Winter Park, FL MLS# O6423883
$1,690,000
4

Beds

3.0

Baths

2,786

Sq.Ft.

708 BALMORAL ROAD

Winter Park, FL

View 3360 ROYAL STREET Winter Park, FL MLS# O6423106
$179,900
2

Beds

2.0

Baths

981

Sq.Ft.

3360 ROYAL STREET

Winter Park, FL

View 2905 PARKLAND DRIVE Winter Park, FL MLS# O6422550
  • New Construction with Virtual Tour
1 of 98
$3,395,000
6

Beds

6.2

Baths

4,850

Sq.Ft.

2905 PARKLAND DRIVE

Winter Park, FL

View 2824 WOODSIDE AVENUE Winter Park, FL MLS# O6423146
$600,000
2

Beds

2.0

Baths

912

Sq.Ft.

2824 WOODSIDE AVENUE

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, LLC
View 7500 WAUNATTA COURT Winter Park, FL MLS# TB8525179
$299,900
3

Beds

2.0

Baths

1,998

Sq.Ft.

7500 WAUNATTA COURT

Winter Park, FL

View 777 HALIFAX AVENUE Winter Park, FL MLS# O6422901
$1,500,000
5

Beds

4.1

Baths

3,109

Sq.Ft.

777 HALIFAX AVENUE

Winter Park, FL

View 7509 GLENMOOR LANE Winter Park, FL MLS# O6421887
$499,500
3

Beds

2.0

Baths

2,067

Sq.Ft.

7509 GLENMOOR LANE

Winter Park, FL

View 1622 ARBOR PARK DRIVE Winter Park, FL MLS# O6420937
$695,000
Studio

Beds

0.0

Baths

1622 ARBOR PARK DRIVE

Winter Park, FL

View 1622 ARBOR PARK DRIVE Winter Park, FL MLS# O6420928
$695,000
3

Beds

1.1

Baths

1,351

Sq.Ft.

1622 ARBOR PARK DRIVE

Winter Park, FL

View 1037 N VIRGINIA AVENUE Winter Park, FL MLS# O6419694
$649,000
3

Beds

1.0

Baths

1,101

Sq.Ft.

1037 N VIRGINIA AVENUE

Winter Park, FL

View 1037 N VIRGINIA AVENUE Winter Park, FL MLS# O6419696
$649,000
Studio

Beds

0.0

Baths

1037 N VIRGINIA AVENUE

Winter Park, FL

View 3381 CEDAR SPRINGS PLACE 151 Winter Park, FL MLS# O6419959
$179,900
2

Beds

2.1

Baths

1,031

Sq.Ft.

3381 CEDAR SPRINGS PLACE 151

Winter Park, FL

View JESSICA COURT Winter Park, FL MLS# O6419256
  • 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
$319,900
3

Beds

2.0

Baths

1,196

Sq.Ft.

751 WARRENTON ROAD

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6419422
$229,900
2

Beds

1.1

Baths

1,219

Sq.Ft.

Address not provided

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

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.

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 7/17/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 7/17/2026.