195 total properties
Did you mean the neighborhood Winter Park?
View 2600 EUSTON ROAD Winter Park, FL MLS# O6397890
  • Virtual Tour
1 of 36
$630,000
6

Beds

3.0

Baths

3,145

Sq.Ft.

2600 EUSTON ROAD

Winter Park, FL

View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
$629,900
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

View 2612 ROXBURY ROAD Winter Park, FL MLS# S5139410
$629,900
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

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

Beds

2.1

Baths

1,934

Sq.Ft.

786 MCINTYRE AVENUE

Winter Park, FL

View 1871 BRYAN AVENUE Winter Park, FL MLS# O6424945
$625,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

1871 BRYAN AVENUE

Winter Park, FL

View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
$614,500
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

View 2824 WOODSIDE AVENUE Winter Park, FL MLS# O6423146
$600,000
2

Beds

2.0

Baths

912

Sq.Ft.

2824 WOODSIDE AVENUE

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, LLC
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
$599,000
3

Beds

2.0

Baths

1,669

Sq.Ft.

1707 HARMON AVENUE

Winter Park, FL

View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
$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
$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
$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
$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
$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
$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
$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

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

374

Estimated median home price

$705,000
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

PriceCount
$0 - 100K4
$100K - 200K41
$200K - 300K22
$300K - 400K13
$400K - 500K38
$500K - 600K32
$600K - 700K37
$700K - 800K10
$800K - 900K11
$900K - 1M9
$1M - Max157

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family229
Townhouse24
Condo79
Commercial9
Rental79
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 9/2/2026)

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 9/2/2026.