18 total properties
Did you mean the neighborhood Winter Park?
View 758 WARRENTON ROAD Winter Park, FL MLS# O6395298
$318,985
3

Beds

2.0

Baths

1,196

Sq.Ft.

758 WARRENTON ROAD

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 642 WARRENTON ROAD Winter Park, FL MLS# O6431914
$300,000
2

Beds

2.0

Baths

1,362

Sq.Ft.

642 WARRENTON ROAD

Winter Park, FL

View 151 N ORLANDO AVENUE 118 Winter Park, FL MLS# O6311340
$299,999
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 118

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1333 S DENNING DRIVE Winter Park, FL MLS# O6431370
$299,000
2

Beds

1.0

Baths

702

Sq.Ft.

1333 S DENNING DRIVE

Winter Park, FL

View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$285,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

View 283 SANDLEWOOD TRAIL 3 Winter Park, FL MLS# O6431475
$285,000
2

Beds

2.1

Baths

960

Sq.Ft.

283 SANDLEWOOD TRAIL 3

Winter Park, FL

View 311 E MORSE BOULEVARD 7-11 Winter Park, FL MLS# O6337061
  • Virtual Tour
1 of 25
OPEN HOUSE: Sunday 8/23 12:00 PM - 2:00 PM
$279,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 7-11

Winter Park, FL

View 311 E MORSE BOULEVARD 6-12 Winter Park, FL MLS# O6413554
$275,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 6-12

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 3220 NETHERWOOD DRIVE Winter Park, FL MLS# O6374172
$268,950
2

Beds

2.0

Baths

1,036

Sq.Ft.

3220 NETHERWOOD DRIVE

Winter Park, FL

Courtesy of THE FIRM RE
View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Adult Community with Virtual Tour
1 of 23
$249,900
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

Winter Park, FL

View 7487 CANFORD COURT 5 Winter Park, FL MLS# TB8537513
  • Recently Listed with Virtual Tour
1 of 20
$249,900
4

Beds

3.0

Baths

1,611

Sq.Ft.

7487 CANFORD COURT 5

Winter Park, FL

View 669 W COMSTOCK AVENUE Winter Park, FL MLS# TB8535201
$249,000
Studio

Beds

0.0

Baths

669 W COMSTOCK AVENUE

Winter Park, FL

View 1500 GAY ROAD 20D Winter Park, FL MLS# O6385626
$245,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 20D

Winter Park, FL

View 1250 S DENNING DR Unit 233 Winter Park, FL MLS# O6430611
$245,000
2

Beds

2.0

Baths

913

Sq.Ft.

1250 S DENNING DR Unit 233

Winter Park, FL

View 151 N ORLANDO AVENUE 261 Winter Park, FL MLS# O6435092
  • Recently Listed with Virtual Tour
1 of 25
$239,999
1

Beds

1.0

Baths

582

Sq.Ft.

151 N ORLANDO AVENUE 261

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Virtual Tour
1 of 26
$238,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

View 1500 GAY ROAD 17D Winter Park, FL MLS# O6408516
  • Virtual Tour
1 of 47
OPEN HOUSE: Sunday 8/23 1:00 PM - 4:00 PM
$234,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 17D

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

376

Estimated median home price

$695,000
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 - 200K41
$200K - 300K23
$300K - 400K15
$400K - 500K34
$500K - 600K34
$600K - 700K38
$700K - 800K14
$800K - 900K11
$900K - 1M11
$1M - Max148

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family229
Townhouse22
Condo85
Commercial9
Rental80
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 8/23/2026)

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 8/23/2026.