210 total properties
Did you mean the neighborhood Winter Park?
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 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
$599,999
Studio

Beds

0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

View 1707 HARMON AVENUE Winter Park, FL MLS# O6409180
  • Virtual Tour
1 of 37
$599,000
3

Beds

2.0

Baths

1,669

Sq.Ft.

1707 HARMON AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
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
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 4026 TENITA DRIVE Winter Park, FL MLS# O6430278
  • Virtual Tour
1 of 26
$599,000
3

Beds

2.0

Baths

2,031

Sq.Ft.

4026 TENITA DRIVE

Winter Park, FL

View 1313 S DENNING DRIVE Winter Park, FL MLS# O6435470
  • Recently Listed with Virtual Tour
1 of 34
$589,900
3

Beds

2.0

Baths

1,700

Sq.Ft.

1313 S DENNING DRIVE

Winter Park, FL

View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
  • Virtual Tour
1 of 13
$589,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

View 1071 ARAGON AVENUE Winter Park, FL MLS# O6429215
  • Virtual Tour
1 of 34
$575,000
2

Beds

2.1

Baths

1,851

Sq.Ft.

1071 ARAGON AVENUE

Winter Park, FL

View 2881 TEMPLE TRAIL Winter Park, FL MLS# O6431955
  • Virtual Tour
1 of 58
$575,000
2

Beds

2.1

Baths

1,704

Sq.Ft.

2881 TEMPLE TRAIL

Winter Park, FL

View 2627 AMBERGATE ROAD Winter Park, FL MLS# O6433352
  • Recently Listed with Virtual Tour
1 of 16
$575,000
4

Beds

3.0

Baths

1,745

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

View 2641 CARVELL COURT Winter Park, FL MLS# O6430894
  • Recently Listed with Virtual Tour
1 of 38
$575,000
4

Beds

2.0

Baths

2,126

Sq.Ft.

2641 CARVELL COURT

Winter Park, FL

View 1259 INDIANA AVENUE Winter Park, FL MLS# O6434701
  • Recently Listed with Virtual Tour
1 of 67
$575,000
2

Beds

2.1

Baths

1,648

Sq.Ft.

1259 INDIANA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
  • Virtual Tour
1 of 39
$574,900
3

Beds

2.0

Baths

1,269

Sq.Ft.

1354 INDIANA AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 4033 TENITA DRIVE Winter Park, FL MLS# O6424621
$569,000
4

Beds

2.0

Baths

2,022

Sq.Ft.

4033 TENITA DRIVE

Winter Park, FL

View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
  • Virtual Tour
1 of 37
OPEN HOUSE: Friday 9/4 2:00 PM - 4:00 PM
$550,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
  • Virtual Tour
1 of 32
$549,900
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1003 LAKE BELL DRIVE Winter Park, FL MLS# O6418278
  • Virtual Tour
1 of 30
$549,900
3

Beds

2.0

Baths

1,837

Sq.Ft.

1003 LAKE BELL DRIVE

Winter Park, FL

View 2803 RIDDLE DRIVE Winter Park, FL MLS# O6423829
$549,900
3

Beds

2.1

Baths

1,709

Sq.Ft.

2803 RIDDLE DRIVE

Winter Park, FL

View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
$549,000
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. 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

380

Estimated median home price

$697,250
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 4
$100K - 200K 42
$200K - 300K 23
$300K - 400K 13
$400K - 500K 39
$500K - 600K 32
$600K - 700K 39
$700K - 800K 12
$800K - 900K 11
$900K - 1M 11
$1M - Max 154

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 232
Townhouse 23
Condo 81
Commercial 9
Rental 79
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 8/30/2026)

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 9/1/2026.