33 total properties
Did you mean the neighborhood Winter Park?
View 1927 S LAKEMONT AVENUE Winter Park, FL MLS# O6426102
$925,000
3

Beds

3.1

Baths

2,093

Sq.Ft.

1927 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of IAD REAL ESTATE
View 938 GOLFSIDE DRIVE Winter Park, FL MLS# O6425467
$820,000
4

Beds

3.0

Baths

2,366

Sq.Ft.

938 GOLFSIDE DRIVE

Winter Park, FL

View 1562 ARBOR PARK DRIVE Winter Park, FL MLS# O6425628
  • Recently Listed with Virtual Tour
1 of 49
$775,000
4

Beds

2.1

Baths

1,899

Sq.Ft.

1562 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1871 BARKER DRIVE Winter Park, FL MLS# O6425831
  • Recently Listed with Virtual Tour
1 of 36
$779,000
3

Beds

3.0

Baths

2,231

Sq.Ft.

1871 BARKER DRIVE

Winter Park, FL

View 724 MONMOUTH WAY Winter Park, FL MLS# O6424409
$849,999
5

Beds

3.1

Baths

2,832

Sq.Ft.

724 MONMOUTH WAY

Winter Park, FL

View 1310 FAIRVIEW AVENUE Winter Park, FL MLS# O6424108
  • Recently Listed with Virtual Tour
1 of 14
$925,000
4

Beds

2.1

Baths

2,552

Sq.Ft.

1310 FAIRVIEW AVENUE

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View 439 N CAPEN AVENUE Winter Park, FL MLS# O6422949
$849,000
3

Beds

2.1

Baths

1,861

Sq.Ft.

439 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 729 MONMOUTH WAY Winter Park, FL MLS# O6422168
$799,000
4

Beds

3.0

Baths

2,332

Sq.Ft.

729 MONMOUTH WAY

Winter Park, FL

View 722 S RANGER BOULEVARD Winter Park, FL MLS# O6421873
$825,000
4

Beds

3.0

Baths

2,164

Sq.Ft.

722 S RANGER BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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 1411 MILLER AVENUE Winter Park, FL MLS# O6416926
$899,000
3

Beds

3.1

Baths

1,824

Sq.Ft.

1411 MILLER AVENUE

Winter Park, FL

View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
$849,900
3

Beds

3.1

Baths

2,030

Sq.Ft.

1265 ARLINGTON PL

Winter Park, FL

View 437 N CAPEN AVENUE Winter Park, FL MLS# O6414283
$849,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

437 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 275 N RANGER BOULEVARD Winter Park, FL MLS# O6415904
  • Virtual Tour
1 of 32
OPEN HOUSE: Saturday 7/25 2:00 PM - 4:30 PM
$759,000
4

Beds

3.0

Baths

1,950

Sq.Ft.

275 N RANGER BOULEVARD

Winter Park, FL

View 241 W LAKE SUE AVENUE Winter Park, FL MLS# O6411621
$995,000
3

Beds

2.1

Baths

2,304

Sq.Ft.

241 W LAKE SUE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 338 BLUE HERON DRIVE Winter Park, FL MLS# O6410174
$865,000
3

Beds

3.0

Baths

2,017

Sq.Ft.

338 BLUE HERON DRIVE

Winter Park, FL

View 300 CAROLINA AVENUE 402C Winter Park, FL MLS# O6410016
$750,000
3

Beds

2.0

Baths

1,350

Sq.Ft.

300 CAROLINA AVENUE 402C

Winter Park, FL

View 269 E CANTON AVENUE 269 Winter Park, FL MLS# O6404706
$989,500
1

Beds

1.1

Baths

1,109

Sq.Ft.

269 E CANTON AVENUE 269

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2324 LEE ROAD Winter Park, FL MLS# O6403791
  • Virtual Tour
1 of 36
$750,000
2,124

Sq.Ft.

2324 LEE ROAD

Winter Park, FL

View 1780 BRYAN AVENUE Winter Park, FL MLS# O6402643
$850,000
Studio

Beds

0.0

Baths

1780 BRYAN AVENUE

Winter Park, FL

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

381

Estimated median home price

$799,000
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 - 100K7
$100K - 200K43
$200K - 300K24
$300K - 400K18
$400K - 500K29
$500K - 600K24
$600K - 700K33
$700K - 800K14
$800K - 900K15
$900K - 1M9
$1M - Max165

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family233
Townhouse20
Condo84
Commercial11
Rental68
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 7/23/2026)

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 7/24/2026.