373 total properties
Did you mean the neighborhood Winter Park?
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 29
$925,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • New Construction with Virtual Tour
1 of 9
$918,000
4

Beds

2.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6390670
$899,900
3

Beds

2.0

Baths

1,536

Sq.Ft.

2823 WRIGHT AVENUE

Winter Park, FL

View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6398302
$899,900
Studio

Beds

0.0

Baths

2823 WRIGHT AVENUE

Winter Park, FL

View 1405 MILLER AVENUE Winter Park, FL MLS# O6386405
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1405 MILLER AVENUE

Winter Park, FL

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 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 1507 GOLFSIDE DRIVE Winter Park, FL MLS# O6395355
  • Virtual Tour
1 of 44
OPEN HOUSE: Sunday 7/26 1:00 PM - 3:00 PM
$850,000
3

Beds

2.0

Baths

2,003

Sq.Ft.

1507 GOLFSIDE DRIVE

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

View 724 MONMOUTH WAY Winter Park, FL MLS# O6424409
  • Recently Listed with Virtual Tour
1 of 38
$849,949
5

Beds

3.1

Baths

2,832

Sq.Ft.

724 MONMOUTH WAY

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 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 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 1927 ELAND AVENUE Winter Park, FL MLS# O6381009
$820,000
5

Beds

3.0

Baths

2,242

Sq.Ft.

1927 ELAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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 1900 WINTER PARK ROAD Winter Park, FL MLS# O6402566
$799,000
4

Beds

2.0

Baths

1,511

Sq.Ft.

1900 WINTER PARK ROAD

Winter Park, FL

Courtesy of RE/MAX ASSURED

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

375

Estimated median home price

$759,000
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 - 100K8
$100K - 200K43
$200K - 300K24
$300K - 400K18
$400K - 500K31
$500K - 600K24
$600K - 700K31
$700K - 800K15
$800K - 900K14
$900K - 1M10
$1M - Max157

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family229
Townhouse19
Condo83
Commercial11
Rental66
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 7/25/2026)

Information deemed reliable but not guaranteed.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 7/26/2026.

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 7/26/2026.