80 total properties
Did you mean the neighborhood Winter Park?
View 3302 ROYAL STREET Winter Park, FL MLS# O6437344
  • Recently Listed with Virtual Tour
1 of 17
$289,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

3302 ROYAL STREET

Winter Park, FL

View 151 N ORLANDO AVENUE 242 Winter Park, FL MLS# O6437574
  • Recently Listed with Virtual Tour
1 of 25
$269,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 242

Winter Park, FL

View 7530 CRANES CREEK COURT Winter Park, FL MLS# O6436269
  • Recently Listed with Virtual Tour
1 of 24
$309,900
3

Beds

2.1

Baths

1,545

Sq.Ft.

7530 CRANES CREEK COURT

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1941 OGLESBY AVENUE Winter Park, FL MLS# N6145448
  • Recently Listed with Virtual Tour
1 of 30
$340,000
2

Beds

1.0

Baths

780

Sq.Ft.

1941 OGLESBY AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
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
$144,500
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

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
  • Recently Listed with Virtual Tour
1 of 31
$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 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
$249,900
4

Beds

3.0

Baths

1,611

Sq.Ft.

7487 CANFORD COURT 5

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 310 GRANADA DRIVE Winter Park, FL MLS# TB8536242
$354,999
3

Beds

2.0

Baths

1,344

Sq.Ft.

310 GRANADA DRIVE

Winter Park, FL

Courtesy of A-WARD WINNING REALTY LLC
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
$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

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

374

Estimated median home price

$705,000
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 - 100K4
$100K - 200K41
$200K - 300K22
$300K - 400K13
$400K - 500K38
$500K - 600K32
$600K - 700K37
$700K - 800K10
$800K - 900K11
$900K - 1M9
$1M - Max157

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family229
Townhouse24
Condo79
Commercial9
Rental79
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 9/2/2026)

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 9/2/2026.