368 total properties
Did you mean the neighborhood Winter Park?
View 1477 W FAIRBANKS AVENUE Winter Park, FL MLS# O6422964
  • Recently Listed with Virtual Tour
1 of 70
$2,500,000
6,049

Sq.Ft.

1477 W FAIRBANKS AVENUE

Winter Park, FL

View 4965 ORANGE AVENUE Winter Park, FL MLS# O6423739
  • Recently Listed with Virtual Tour
1 of 29
$379,900
4

Beds

2.0

Baths

1,444

Sq.Ft.

4965 ORANGE AVENUE

Winter Park, FL

View 708 BALMORAL ROAD Winter Park, FL MLS# O6423883
$1,690,000
4

Beds

3.0

Baths

2,786

Sq.Ft.

708 BALMORAL ROAD

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 2803 RIDDLE DRIVE Winter Park, FL MLS# O6423829
  • Recently Listed
1 of 28
OPEN HOUSE: Sunday 7/26 1:00 PM - 2:00 PM
$569,000
3

Beds

2.1

Baths

1,709

Sq.Ft.

2803 RIDDLE DRIVE

Winter Park, FL

View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
  • Recently Listed with Virtual Tour
1 of 38
$375,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

View 1754 TAYLOR AVENUE Winter Park, FL MLS# O6421927
  • Recently Listed with Virtual Tour
1 of 17
$2,569,999
5

Beds

4.1

Baths

3,670

Sq.Ft.

1754 TAYLOR AVENUE

Winter Park, FL

View 3360 ROYAL STREET Winter Park, FL MLS# O6423106
  • Recently Listed with Virtual Tour
1 of 15
$179,900
2

Beds

1.1

Baths

981

Sq.Ft.

3360 ROYAL STREET

Winter Park, FL

View 2905 PARKLAND DRIVE Winter Park, FL MLS# O6422550
  • New Construction with Virtual Tour
1 of 98
$3,395,000
6

Beds

6.2

Baths

4,850

Sq.Ft.

2905 PARKLAND DRIVE

Winter Park, FL

View 1415 GROVE TERRACE Winter Park, FL MLS# O6423553
  • Recently Listed with Virtual Tour
1 of 20
$2,200,000
Studio

Beds

0.0

Baths

1415 GROVE TERRACE

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 1823 SUNSET DRIVE Winter Park, FL MLS# O6421690
  • Recently Listed with Virtual Tour
1 of 14
$2,549,000
5

Beds

4.1

Baths

3,479

Sq.Ft.

1823 SUNSET DRIVE

Winter Park, FL

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 2824 WOODSIDE AVENUE Winter Park, FL MLS# O6423146
  • Recently Listed with 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 250 KILLARNEY Winter Park, FL MLS# O6419382
  • Recently Listed with Virtual Tour
1 of 10
$1,600,000
4

Beds

3.1

Baths

2,568

Sq.Ft.

250 KILLARNEY

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View 1250 S DENNING DRIVE 109 Winter Park, FL MLS# R4911491
  • Recently Listed with Virtual Tour
1 of 27
$190,000
1

Beds

1.0

Baths

658

Sq.Ft.

1250 S DENNING DRIVE 109

Winter Park, FL

View 1500 GAY ROAD 18D Winter Park, FL MLS# O6422691
$275,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 18D

Winter Park, FL

View 1695 LEE ROAD B108 Winter Park, FL MLS# O6422568
  • Recently Listed with Virtual Tour
1 of 15
$89,999
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B108

Winter Park, FL

View 2611 LOTAFUN AVENUE Winter Park, FL MLS# O6422197
$449,000
3

Beds

2.0

Baths

1,838

Sq.Ft.

2611 LOTAFUN AVENUE

Winter Park, FL

View 7500 WAUNATTA COURT Winter Park, FL MLS# TB8525179
$299,900
3

Beds

2.0

Baths

1,998

Sq.Ft.

7500 WAUNATTA COURT

Winter Park, FL

View 777 HALIFAX AVENUE Winter Park, FL MLS# O6422901
$1,500,000
5

Beds

4.1

Baths

3,109

Sq.Ft.

777 HALIFAX 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.

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 7/23/2026.

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

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.

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 7/23/2026.