73 total properties
Did you mean the neighborhood Winter Park?
View 151 N ORLANDO AVENUE 261 Winter Park, FL MLS# O6435092
  • Recently Listed with Virtual Tour
1 of 26
$239,999
1

Beds

1.0

Baths

582

Sq.Ft.

151 N ORLANDO AVENUE 261

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 3019 ANTIQUE OAKS CIRCLE 127 Winter Park, FL MLS# O6434819
  • Recently Listed
1 of 16
OPEN HOUSE: Saturday 8/29 1:00 PM - 3:00 PM
$144,999
1

Beds

1.0

Baths

749

Sq.Ft.

3019 ANTIQUE OAKS CIRCLE 127

Winter Park, FL

View 623 GRENADINE COURT 623 Winter Park, FL MLS# O6434195
  • Recently Listed with Virtual Tour
1 of 36
$199,900
2

Beds

2.0

Baths

1,037

Sq.Ft.

623 GRENADINE COURT 623

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 7468 CANFORD COURT 24 Winter Park, FL MLS# O6433680
  • Recently Listed with Virtual Tour
1 of 32
$189,900
2

Beds

1.1

Baths

1,365

Sq.Ft.

7468 CANFORD COURT 24

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
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 3014 ANTIQUE OAKS CIRCLE 120 Winter Park, FL MLS# O6430885
$148,000
1

Beds

1.0

Baths

749

Sq.Ft.

3014 ANTIQUE OAKS CIRCLE 120

Winter Park, FL

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 Address not provided Winter Park, FL MLS# O6427974
$179,900
2

Beds

2.0

Baths

840

Sq.Ft.

Address not provided

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 3651 N GOLDENROD ROAD A103 Winter Park, FL MLS# O6432285
$164,900
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD A103

Winter Park, FL

View 283 SANDLEWOOD TRAIL 3 Winter Park, FL MLS# O6431475
  • Recently Listed with Virtual Tour
1 of 41
$285,000
2

Beds

2.1

Baths

960

Sq.Ft.

283 SANDLEWOOD TRAIL 3

Winter Park, FL

View 1695 LEE ROAD D107 Winter Park, FL MLS# O6425124
$180,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD D107

Winter Park, FL

Courtesy of PRIMESTATE REALTY, INC.
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 7413 BELLE RIVER COURT 3 Winter Park, FL MLS# O6430667
  • Recently Listed with Virtual Tour
1 of 11
$219,900
3

Beds

2.1

Baths

1,151

Sq.Ft.

7413 BELLE RIVER COURT 3

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 1695 LEE ROAD A101 Winter Park, FL MLS# O6429942
$154,900
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A101

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 305 Winter Park, FL MLS# O6428044
$115,000
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 305

Winter Park, FL

View 200 SAINT ANDREWS BOULEVARD 2904 Winter Park, FL MLS# O6427536
$230,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2904

Winter Park, FL

View 846 DRIVER AVENUE Winter Park, FL MLS# O6426024
$325,000
2

Beds

1.0

Baths

824

Sq.Ft.

846 DRIVER AVENUE

Winter Park, FL

View 145 SCOTTSDALE SQUARE Winter Park, FL MLS# O6424788
$99,900
2

Beds

2.0

Baths

1,020

Sq.Ft.

145 SCOTTSDALE SQUARE

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

379

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 - 500K35
$500K - 600K34
$600K - 700K39
$700K - 800K14
$800K - 900K11
$900K - 1M11
$1M - Max149

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family231
Townhouse22
Condo85
Commercial9
Rental80
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 8/24/2026)

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 8/24/2026.