88 total properties
Did you mean the neighborhood Winter Park?
View 3939 FORSYTH ROAD Winter Park, FL MLS# O6451794
  • Recently Listed with Virtual Tour
1 of 11
$240,000
50,585

Sq.Ft.

3939 FORSYTH ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 328 W MORSE BLVD 105 Winter Park, FL MLS# O6443023
  • Recently Listed with Virtual Tour
1 of 24
$102,410
1,862

Sq.Ft.

328 W MORSE BLVD 105

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 330 W MORSE BLVD 104 Winter Park, FL MLS# O6416951
  • Virtual Tour
1 of 21
$98,450
1,790

Sq.Ft.

330 W MORSE BLVD 104

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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.
View 2250 LEE ROAD 200 Winter Park, FL MLS# O6452334
  • Recently Listed
1 of 25
$76,500
17,600

Sq.Ft.

2250 LEE ROAD 200

Winter Park, FL

Courtesy of INNOVATIVE REALTY, LLC
View 931 S SEMORAN BOULEVARD 208 Winter Park, FL MLS# O6442791
$41,886
2,327

Sq.Ft.

931 S SEMORAN BOULEVARD 208

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 663 HAROLD AVENUE Winter Park, FL MLS# O6387903
  • Virtual Tour
1 of 6
$38,400
10,429

Sq.Ft.

663 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
View 2306 LEE ROAD Winter Park, FL MLS# O6390092
  • Virtual Tour
1 of 30
$29,150
550

Sq.Ft.

2306 LEE ROAD

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 541 W CANTON AVENUE Winter Park, FL MLS# O6442825
  • New Construction with Virtual Tour
1 of 50
$12,000
4

Beds

3.1

Baths

3,553

Sq.Ft.

541 W CANTON AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1442 PALM AVENUE Winter Park, FL MLS# O6421394
  • Virtual Tour
1 of 33
$9,900
5

Beds

6.0

Baths

2,735

Sq.Ft.

1442 PALM AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 660 OSCEOLA AVENUE 101 Winter Park, FL MLS# O6439850
$8,500
3

Beds

3.1

Baths

2,714

Sq.Ft.

660 OSCEOLA AVENUE 101

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 440 CLARENDON AVENUE Winter Park, FL MLS# O6444115
  • Virtual Tour
1 of 47
$7,995
4

Beds

3.1

Baths

3,184

Sq.Ft.

440 CLARENDON AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1368 HIBISCUS AVENUE Winter Park, FL MLS# O6429182
  • Virtual Tour
1 of 46
$7,250
4

Beds

2.1

Baths

2,394

Sq.Ft.

1368 HIBISCUS AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1981 BLUE RIDGE ROAD Winter Park, FL MLS# O6446473
  • Virtual Tour
1 of 57
$6,495
5

Beds

2.0

Baths

2,750

Sq.Ft.

1981 BLUE RIDGE ROAD

Winter Park, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
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 17
$6,000
2

Beds

2.1

Baths

1,500

Sq.Ft.

301 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of THE SYDGAN CORP
View 860 N DENNING DRIVE Winter Park, FL MLS# O6450630
  • Recently Listed with Virtual Tour
1 of 7
$6,000
3

Beds

2.1

Baths

1,411

Sq.Ft.

860 N DENNING DRIVE

Winter Park, FL

Courtesy of OUTLET REALTY
View 98 S VIRGINIA AVENUE 111 Winter Park, FL MLS# O6451012
  • Recently Listed with Virtual Tour
1 of 68
$5,700
3

Beds

3.1

Baths

2,860

Sq.Ft.

98 S VIRGINIA AVENUE 111

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 1136 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6430077
$5,600
3

Beds

3.0

Baths

2,434

Sq.Ft.

1136 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of CENTRAL FLORIDA PRIME REAL ESTATE LLC
View 350 N PHELPS AVENUE Winter Park, FL MLS# O6440072
  • Virtual Tour
1 of 50
$4,677
4

Beds

3.0

Baths

2,267

Sq.Ft.

350 N PHELPS AVENUE

Winter Park, FL

Courtesy of GOYAL & DECOSTER REALTY

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

353

Estimated median home price

$775,000
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 3
$100K - 200K 34
$200K - 300K 20
$300K - 400K 16
$400K - 500K 33
$500K - 600K 24
$600K - 700K 35
$700K - 800K 16
$800K - 900K 14
$900K - 1M 15
$1M - Max 143

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 208
Townhouse 22
Condo 76
Commercial 15
Rental 86
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/26/2026)

Information deemed reliable but not guaranteed.

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 10/26/2026.