96 total properties
Did you mean the neighborhood Winter Park?
View 1695 LEE ROAD E215 Winter Park, FL MLS# O6383089
$149,990
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E215

Winter Park, FL

Courtesy of FOWLKES REALTY CO
View 184 SANDLEWOOD TRAIL #2 Winter Park, FL MLS# O6380753
$312,000
2

Beds

2.1

Baths

1,133

Sq.Ft.

184 SANDLEWOOD TRAIL #2

Winter Park, FL

View 1500 GAY ROAD 5 Winter Park, FL MLS# S5143213
  • Virtual Tour
1 of 17
$170,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 5

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1695 LEE ROAD B210 Winter Park, FL MLS# O6375872
$99,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B210

Winter Park, FL

Courtesy of GM SUNSHINE REALTY LLC
View 3220 NETHERWOOD DRIVE Winter Park, FL MLS# O6374172
$269,000
2

Beds

2.0

Baths

1,036

Sq.Ft.

3220 NETHERWOOD DRIVE

Winter Park, FL

Courtesy of THE FIRM RE
View 7468 CANFORD COURT 24 Winter Park, FL MLS# O6373850
$189,999
2

Beds

1.1

Baths

1,365

Sq.Ft.

7468 CANFORD COURT 24

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 1695 LEE ROAD B204 Winter Park, FL MLS# O6375348
$130,000
2

Beds

1.0

Baths

1695 LEE ROAD B204

Winter Park, FL

View 958 DUPONT AVENUE Winter Park, FL MLS# O6371341
$375,000
3

Beds

2.0

Baths

1,572

Sq.Ft.

958 DUPONT AVENUE

Winter Park, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 7514 LAUREL SPRINGS DRIVE Winter Park, FL MLS# O6372653
  • Recently Listed with Virtual Tour
1 of 30
$400,000
4

Beds

2.0

Baths

1,677

Sq.Ft.

7514 LAUREL SPRINGS DRIVE

Winter Park, FL

View 2500 LEE ROAD 237 Winter Park, FL MLS# V4946519
$169,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 237

Winter Park, FL

Courtesy of LPT REALTY LLC (DB)
View 2002 INDIANA AVENUE Winter Park, FL MLS# GC536284
$358,000
Studio

Beds

0.0

Baths

2002 INDIANA AVENUE

Winter Park, FL

Courtesy of DAWN REALTY
View 2500 LEE RD. 222 Winter Park, FL MLS# O6368580
$189,500
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE RD. 222

Winter Park, FL

Courtesy of HOMESMART
View 311 E MORSE BOULEVARD 7-19 Winter Park, FL MLS# O6368912
  • Adult Community with Virtual Tour
1 of 34
$284,900
1

Beds

1.0

Baths

482

Sq.Ft.

311 E MORSE BOULEVARD 7-19

Winter Park, FL

Courtesy of TURN-KEY MOVES REALTY
View 851 MILES AVENUE 13 Winter Park, FL MLS# O6368234
$209,999
2

Beds

1.0

Baths

808

Sq.Ft.

851 MILES AVENUE 13

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1695 LEE ROAD E204 Winter Park, FL MLS# O6366205
$114,000
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD E204

Winter Park, FL

View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$298,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

Courtesy of CREEGAN GROUP
View 7470 CANFORD COURT 23 Winter Park, FL MLS# O6360198
$245,900
3

Beds

2.1

Baths

1,580

Sq.Ft.

7470 CANFORD COURT 23

Winter Park, FL

View 311 SCOTTSDALE SQUARE 311 Winter Park, FL MLS# O6355536
$109,900
1

Beds

1.0

Baths

785

Sq.Ft.

311 SCOTTSDALE SQUARE 311

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 7471 CANFORD COURT 19 Winter Park, FL MLS# G5103114
$199,000
2

Beds

1.1

Baths

1,393

Sq.Ft.

7471 CANFORD COURT 19

Winter Park, FL

Courtesy of IAD FLORIDA LLC
View 1500 GAY ROAD 24B Winter Park, FL MLS# O6348568
$259,500
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 24B

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC

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

399

Estimated median home price

$820,000
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 - 100K2
$100K - 200K42
$200K - 300K24
$300K - 400K22
$400K - 500K29
$500K - 600K31
$600K - 700K30
$700K - 800K19
$800K - 900K14
$900K - 1M9
$1M - Max177

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family263
Townhouse16
Condo85
Commercial7
Rental73
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 6/20/2026)

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 6/20/2026.