68 total properties
Did you mean the neighborhood Winter Park?
View 1199 CLAY STREET Winter Park, FL MLS# O6393872
  • Virtual Tour
1 of 50
$170,124
184,510

Sq.Ft.

1199 CLAY STREET

Winter Park, FL

Courtesy of BUCKEYE REALTY LLC
View 2306 LEE ROAD Winter Park, FL MLS# O6390092
  • Virtual Tour
1 of 7
$119,568
2,289

Sq.Ft.

2306 LEE ROAD

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 687 HAROLD AVENUE Winter Park, FL MLS# O6387921
  • New Construction
1 of 3
$84,000
4,500

Sq.Ft.

687 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 4550 PALMETTO AVENUE Winter Park, FL MLS# O6388575
  • Virtual Tour
1 of 28
$78,750
4,206

Sq.Ft.

4550 PALMETTO AVENUE

Winter Park, FL

Courtesy of SOLANTIS LLC
View 2035 GLENWOOD DRIVE Winter Park, FL MLS# O6403420
  • Virtual Tour
1 of 23
$47,400
3,718

Sq.Ft.

2035 GLENWOOD DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3029 FORSYTH ROAD Winter Park, FL MLS# O6348919
  • Virtual Tour
1 of 10
$42,000
1,500

Sq.Ft.

3029 FORSYTH ROAD

Winter Park, FL

Courtesy of C BRENNER INC
View 663 HAROLD AVENUE Winter Park, FL MLS# O6387903
  • Virtual Tour
1 of 6
$42,000
10,429

Sq.Ft.

663 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
View 7307 SANDSCOVE COURT 5 Winter Park, FL MLS# O6392725
$42,000
23,760

Sq.Ft.

7307 SANDSCOVE COURT 5

Winter Park, FL

Courtesy of FUSILIER MANAGEMENT GROUP
View 7507 ALOMA AVENUE 3B Winter Park, FL MLS# O6353856
$28,800
1,444

Sq.Ft.

7507 ALOMA AVENUE 3B

Winter Park, FL

Courtesy of MUSA REALTY COMPANY INC
View 2024 LAKE DRIVE Winter Park, FL MLS# O6409405
  • Virtual Tour
1 of 40
$14,000
3

Beds

4.2

Baths

4,027

Sq.Ft.

2024 LAKE DRIVE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1041 TUSCANY PLACE Winter Park, FL MLS# O6401030
  • Virtual Tour
1 of 39
$12,000
4

Beds

3.1

Baths

3,064

Sq.Ft.

1041 TUSCANY PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1760 ALABAMA DRIVE Winter Park, FL MLS# O6413560
  • Recently Listed
1 of 48
$10,900
3

Beds

2.1

Baths

2,841

Sq.Ft.

1760 ALABAMA DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1814 BARKER DRIVE Winter Park, FL MLS# O6395037
  • Virtual Tour
1 of 78
$10,000
5

Beds

4.0

Baths

4,200

Sq.Ft.

1814 BARKER DRIVE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1760 LEGION DRIVE Winter Park, FL MLS# O6406982
$9,700
4

Beds

5.1

Baths

4,392

Sq.Ft.

1760 LEGION DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2075 JEWELL AVENUE Winter Park, FL MLS# O6386721
  • Virtual Tour
1 of 65
$6,795
5

Beds

4.0

Baths

2,918

Sq.Ft.

2075 JEWELL AVENUE

Winter Park, FL

Courtesy of URBANISTA BROKERS
View 527 LANGHOLM DRIVE Winter Park, FL MLS# O6387427
  • Virtual Tour
1 of 18
$6,750
4

Beds

3.1

Baths

3,276

Sq.Ft.

527 LANGHOLM DRIVE

Winter Park, FL

Courtesy of WOODRUFF REALTY, INC.
View 1049 N KENTUCKY AVENUE Winter Park, FL MLS# O6373029
$6,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

1049 N KENTUCKY AVENUE

Winter Park, FL

Courtesy of THE AGENCY FL
View 301 W COMSTOCK AVENUE Winter Park, FL MLS# O6385827
  • New Construction with Virtual Tour
1 of 12
$6,000
2

Beds

2.1

Baths

1,500

Sq.Ft.

301 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of THE SYDGAN CORP
View 1235 VIA ESTRELLA Winter Park, FL MLS# O6388913
  • Virtual Tour
1 of 14
$5,895
4

Beds

3.0

Baths

2,207

Sq.Ft.

1235 VIA ESTRELLA

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 784 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6408937
  • Recently Listed with Virtual Tour
1 of 29
$5,500
3

Beds

2.1

Baths

1,940

Sq.Ft.

784 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of BEYCOME OF 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

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

Price Count
$0 - 100K 2
$100K - 200K 41
$200K - 300K 24
$300K - 400K 24
$400K - 500K 28
$500K - 600K 28
$600K - 700K 31
$700K - 800K 21
$800K - 900K 15
$900K - 1M 9
$1M - Max 175

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 263
Townhouse 16
Condo 82
Commercial 7
Rental 67
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/7/2026)

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.

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 6/8/2026.