380 total properties
Did you mean the neighborhood Winter Park?
View 1591 Cardinal Court Winter Park, FL MLS# 1078693
  • New Construction
1 of 44
$2,995,000
5

Beds

3.0

Baths

3,523

Sq.Ft.

1591 Cardinal Court

Winter Park, FL

Brevard
View 2157 LAKE DRIVE Winter Park, FL MLS# O6412258
  • Virtual Tour
1 of 45
$689,000
3

Beds

3.0

Baths

2,124

Sq.Ft.

2157 LAKE DRIVE

Winter Park, FL

View 649 N PARK AVENUE Winter Park, FL MLS# O6411141
  • Virtual Tour
1 of 44
$3,500,000
3

Beds

3.2

Baths

3,180

Sq.Ft.

649 N PARK AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1571 WOODLAND AVENUE Winter Park, FL MLS# O6411706
  • Virtual Tour
1 of 75
$6,000,000
5

Beds

6.2

Baths

7,397

Sq.Ft.

1571 WOODLAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2261 MULBRY DRIVE Winter Park, FL MLS# O6410979
  • Virtual Tour
1 of 77
$1,995,000
4

Beds

3.0

Baths

3,696

Sq.Ft.

2261 MULBRY DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 723 SYMONDS AVENUE Winter Park, FL MLS# O6406823
  • Virtual Tour
1 of 50
OPEN HOUSE: Saturday 7/25 1:00 PM - 4:00 PM
$1,800,000
4

Beds

4.0

Baths

3,065

Sq.Ft.

723 SYMONDS AVENUE

Winter Park, FL

View 942 ENCLAVE PLACE Winter Park, FL MLS# O6411550
  • New Construction
1 of 4
$2,195,000
5

Beds

5.0

Baths

3,831

Sq.Ft.

942 ENCLAVE PLACE

Winter Park, FL

View 950 ENCLAVE PLACE Winter Park, FL MLS# O6410963
  • New Construction
1 of 3
$2,125,000
5

Beds

4.1

Baths

3,797

Sq.Ft.

950 ENCLAVE PLACE

Winter Park, FL

View 946 ENCLAVE PLACE Winter Park, FL MLS# O6411633
  • New Construction
1 of 3
$2,175,000
5

Beds

4.1

Baths

3,989

Sq.Ft.

946 ENCLAVE PLACE

Winter Park, FL

View 1404 BORDER DRIVE Winter Park, FL MLS# O6412140
  • Virtual Tour
1 of 38
$1,150,000
4

Beds

4.0

Baths

2,469

Sq.Ft.

1404 BORDER DRIVE

Winter Park, FL

View 241 W LAKE SUE AVENUE Winter Park, FL MLS# O6411621
$995,000
3

Beds

2.1

Baths

2,304

Sq.Ft.

241 W LAKE SUE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 840 W CANTON AVENUE Winter Park, FL MLS# O6412754
$649,900
3

Beds

2.0

Baths

1,370

Sq.Ft.

840 W CANTON AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1841 LAKE SPIER DRIVE Winter Park, FL MLS# O6407841
$1,595,000
3

Beds

4.0

Baths

2,467

Sq.Ft.

1841 LAKE SPIER DRIVE

Winter Park, FL

View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
  • Virtual Tour
1 of 37
$625,000
4

Beds

2.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

View 2500 LEE ROAD 220 Winter Park, FL MLS# O6411927
  • Virtual Tour
1 of 28
$199,900
2

Beds

1.0

Baths

851

Sq.Ft.

2500 LEE ROAD 220

Winter Park, FL

View 1120 WISCONSIN AVENUE Winter Park, FL MLS# O6406800
$1,095,000
3

Beds

3.1

Baths

2,213

Sq.Ft.

1120 WISCONSIN AVENUE

Winter Park, FL

View 316 BECKETT COURT Winter Park, FL MLS# O6411108
  • Virtual Tour
1 of 33
$450,000
4

Beds

2.0

Baths

1,651

Sq.Ft.

316 BECKETT COURT

Winter Park, FL

Courtesy of VINTAGE REALTY SOLUTIONS
View 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
$599,999
Studio

Beds

0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

View 338 BLUE HERON DRIVE Winter Park, FL MLS# O6410174
  • Virtual Tour
1 of 44
$865,000
3

Beds

3.0

Baths

2,017

Sq.Ft.

338 BLUE HERON DRIVE

Winter Park, FL

View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
  • Virtual Tour
1 of 32
$579,000
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

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

381

Estimated median home price

$799,000
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

Price Count
$0 - 100K 7
$100K - 200K 43
$200K - 300K 24
$300K - 400K 18
$400K - 500K 29
$500K - 600K 24
$600K - 700K 33
$700K - 800K 14
$800K - 900K 15
$900K - 1M 9
$1M - Max 165

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 233
Townhouse 20
Condo 84
Commercial 11
Rental 68
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 7/23/2026)

Information deemed reliable but not guaranteed.

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.

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 7/23/2026.

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 7/23/2026.