60 total properties
Did you mean the neighborhood Winter Park?
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 1562 ARBOR PARK DRIVE Winter Park, FL MLS# O6425628
$775,000
4

Beds

2.1

Baths

1,899

Sq.Ft.

1562 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 901 HARMON AVENUE Winter Park, FL MLS# O6425358
  • Virtual Tour
1 of 20
$650,000
2

Beds

2.0

Baths

1,277

Sq.Ft.

901 HARMON AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 786 MCINTYRE AVENUE Winter Park, FL MLS# O6424399
  • Virtual Tour
1 of 28
$625,000
3

Beds

2.1

Baths

1,934

Sq.Ft.

786 MCINTYRE AVENUE

Winter Park, FL

View 436 W SWOOPE AVENUE Winter Park, FL MLS# O6423105
  • Virtual Tour
1 of 59
$699,000
4

Beds

3.1

Baths

2,602

Sq.Ft.

436 W SWOOPE AVENUE

Winter Park, FL

View 943 FAIRWAY DRIVE Winter Park, FL MLS# O6426672
  • Recently Listed with Virtual Tour
1 of 47
$689,900
4

Beds

3.0

Baths

2,067

Sq.Ft.

943 FAIRWAY DRIVE

Winter Park, FL

View 2824 WOODSIDE AVENUE Winter Park, FL MLS# O6423146
  • Virtual Tour
1 of 17
$600,000
2

Beds

2.0

Baths

912

Sq.Ft.

2824 WOODSIDE AVENUE

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, LLC
View 722 S RANGER BOULEVARD Winter Park, FL MLS# O6421873
$795,000
4

Beds

3.0

Baths

2,164

Sq.Ft.

722 S RANGER BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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 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
View 2361 ROXBURY ROAD Winter Park, FL MLS# O6418164
  • Virtual Tour
1 of 34
$599,000
3

Beds

2.0

Baths

1,723

Sq.Ft.

2361 ROXBURY ROAD

Winter Park, FL

View 1278 S PENNSYLVANIA AVENUE 13 Winter Park, FL MLS# O6417455
  • Recently Listed with Virtual Tour
1 of 16
$799,000
3

Beds

2.1

Baths

1,957

Sq.Ft.

1278 S PENNSYLVANIA AVENUE 13

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 7525 LODGE POLE TRAIL Winter Park, FL MLS# O6417303
  • Recently Listed with Virtual Tour
1 of 38
$600,000
4

Beds

2.0

Baths

1,936

Sq.Ft.

7525 LODGE POLE TRAIL

Winter Park, FL

View 275 N RANGER BOULEVARD Winter Park, FL MLS# O6415904
$759,000
4

Beds

3.0

Baths

1,950

Sq.Ft.

275 N RANGER BOULEVARD

Winter Park, FL

View 2831 MULFORD AVENUE Winter Park, FL MLS# O6414319
  • Virtual Tour
1 of 28
$635,000
4

Beds

2.1

Baths

1,647

Sq.Ft.

2831 MULFORD AVENUE

Winter Park, FL

View 860 N DENNING DRIVE Winter Park, FL MLS# O6412589
  • Virtual Tour
1 of 52
$699,900
3

Beds

2.1

Baths

1,411

Sq.Ft.

860 N DENNING DRIVE

Winter Park, FL

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 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 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
  • Virtual Tour
1 of 37
$599,000
4

Beds

3.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

Courtesy of LPT REALTY, 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

379

Estimated median home price

$695,000
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 41
$200K - 300K 23
$300K - 400K 15
$400K - 500K 35
$500K - 600K 34
$600K - 700K 39
$700K - 800K 14
$800K - 900K 11
$900K - 1M 11
$1M - Max 149

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 231
Townhouse 22
Condo 85
Commercial 9
Rental 80
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 8/24/2026)

Information deemed reliable but not guaranteed.

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 8/25/2026.