85 total properties
Did you mean the neighborhood Winter Park?
View 3027 AARON BURR AVENUE L1 Winter Park, FL MLS# TB8559215
$1,795
2

Beds

2.1

Baths

1,090

Sq.Ft.

3027 AARON BURR AVENUE L1

Winter Park, FL

Courtesy of HOMESMART
View 98 S VIRGINIA AVENUE 111 Winter Park, FL MLS# O6451012
  • Recently Listed with Virtual Tour
1 of 68
$5,700
3

Beds

3.1

Baths

2,860

Sq.Ft.

98 S VIRGINIA AVENUE 111

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 7797 BROKEN ARROW TRAIL Winter Park, FL MLS# O6450524
  • Recently Listed with Virtual Tour
1 of 54
$3,900
4

Beds

2.0

Baths

2,548

Sq.Ft.

7797 BROKEN ARROW TRAIL

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
The time to sell is now! THE TIME TO SELL IS NOW!
View 860 N DENNING DRIVE Winter Park, FL MLS# O6450630
  • Recently Listed with Virtual Tour
1 of 7
$6,000
3

Beds

2.1

Baths

1,411

Sq.Ft.

860 N DENNING DRIVE

Winter Park, FL

Courtesy of OUTLET REALTY
View 1695 LEE ROAD E213 Winter Park, FL MLS# S5159591
  • Recently Listed with Virtual Tour
1 of 8
$1,600
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD E213

Winter Park, FL

Courtesy of LOKATION
View 1357 INDIANA AVENUE Winter Park, FL MLS# O6449179
  • Recently Listed with Virtual Tour
1 of 15
$1,850
2

Beds

2.0

Baths

1,090

Sq.Ft.

1357 INDIANA AVENUE

Winter Park, FL

Courtesy of ROMAN REALTY GROUP, LLC
View 1824 HOWELL BRANCH ROAD Winter Park, FL MLS# O6448658
  • Recently Listed with Virtual Tour
1 of 16
$2,000
2

Beds

1.0

Baths

1,100

Sq.Ft.

1824 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of AAA GLOBAL VENTURES PA
View 1695 LEE ROAD E103 Winter Park, FL MLS# S5159126
  • Recently Listed with Virtual Tour
1 of 15
$1,600
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD E103

Winter Park, FL

Courtesy of RE/MAX SELECT GROUP
View 2612 ROXBURY ROAD Winter Park, FL MLS# O6448814
  • Recently Listed with Virtual Tour
1 of 10
$2,500
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of HOMEPRIDE PROPERTY MANAGEMENT GROUP LLC
View 1111 WASHINGTON AVENUE 3 Winter Park, FL MLS# O6448230
$1,550
2

Beds

2.0

Baths

1,084

Sq.Ft.

1111 WASHINGTON AVENUE 3

Winter Park, FL

Courtesy of WILSON MANAGEMENT GROUP
View 2500 LEE ROAD 145 Winter Park, FL MLS# O6446265
  • Recently Listed with Virtual Tour
1 of 12
$1,099
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 145

Winter Park, FL

Courtesy of THE REALTY MEDICS
View 1415 HARMON AVENUE Winter Park, FL MLS# O6448198
  • Recently Listed with Virtual Tour
1 of 34
$3,600
3

Beds

2.1

Baths

1,753

Sq.Ft.

1415 HARMON AVENUE

Winter Park, FL

Courtesy of HOST MANAGEMENT GROUP LLC
View 300 N Knowles Ave 214 Winter Park, FL MLS# A12100777
  • Recently Listed with Virtual Tour
1 of 8
$1,750
2

Beds

1.0

Baths

1,100

Sq.Ft.

300 N Knowles Ave 214

Winter Park, FL

Courtesy of PROPERTY PROFESSIONALS, INC.
View 7444 WOODBURN COURT 29 Winter Park, FL MLS# S5158825
  • Recently Listed with Virtual Tour
1 of 8
$1,585
2

Beds

2.1

Baths

1,031

Sq.Ft.

7444 WOODBURN COURT 29

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1981 BLUE RIDGE ROAD Winter Park, FL MLS# O6446473
  • Recently Listed with Virtual Tour
1 of 57
$6,495
5

Beds

2.0

Baths

2,750

Sq.Ft.

1981 BLUE RIDGE ROAD

Winter Park, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 7262 SWALLOW RUN 7262 Winter Park, FL MLS# O6446527
$1,600
2

Beds

2.0

Baths

756

Sq.Ft.

7262 SWALLOW RUN 7262

Winter Park, FL

Courtesy of LUMINA PROPERTY MANAGEMENT LLC
View 735 MINNESOTA AVENUE Winter Park, FL MLS# O6446889
  • Recently Listed with Virtual Tour
1 of 10
$3,995
3

Beds

3.1

Baths

1,810

Sq.Ft.

735 MINNESOTA AVENUE

Winter Park, FL

Courtesy of FLORIDA HOMES SALES & MANAGEMENT LLC
View 737 MINNESOTA AVENUE Winter Park, FL MLS# O6446900
  • Recently Listed with Virtual Tour
1 of 10
$3,995
3

Beds

3.1

Baths

1,810

Sq.Ft.

737 MINNESOTA AVENUE

Winter Park, FL

Courtesy of FLORIDA HOMES SALES & MANAGEMENT LLC
View 690 OSCEOLA AVENUE 407 Winter Park, FL MLS# O6446888
$2,200
1

Beds

1.1

Baths

915

Sq.Ft.

690 OSCEOLA AVENUE 407

Winter Park, FL

Courtesy of CREEGAN GROUP
View 307 SANDLEWOOD TRAIL Winter Park, FL MLS# O6444878
  • Recently Listed with Virtual Tour
1 of 15
$1,895
2

Beds

2.1

Baths

960

Sq.Ft.

307 SANDLEWOOD TRAIL

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY

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

361

Estimated median home price

$769,000
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 - 100K3
$100K - 200K34
$200K - 300K22
$300K - 400K21
$400K - 500K30
$500K - 600K28
$600K - 700K34
$700K - 800K17
$800K - 900K14
$900K - 1M14
$1M - Max144

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family214
Townhouse20
Condo78
Commercial15
Rental85
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 10/20/2026)

Information deemed reliable but not guaranteed.

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

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 10/20/2026.