71 total properties
Did you mean the neighborhood Winter Park?
View 3053 GEORGE MASON AVENUE 8A Winter Park, FL MLS# O6402957
  • Recently Listed with Virtual Tour
1 of 29
$75,000
1

Beds

1.0

Baths

809

Sq.Ft.

3053 GEORGE MASON AVENUE 8A

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
  • Recently Listed with Virtual Tour
1 of 25
$250,000
3

Beds

2.1

Baths

1,578

Sq.Ft.

7484 CANFORD COURT 8

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 639 SAINT JOHNS COURT 639 Winter Park, FL MLS# O6402025
  • Recently Listed with Virtual Tour
1 of 42
$199,900
2

Beds

2.0

Baths

1,120

Sq.Ft.

639 SAINT JOHNS COURT 639

Winter Park, FL

Courtesy of PLATINUM REALTY GROUP FLORIDA INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1250 S DENNING DRIVE 117 Winter Park, FL MLS# O6401802
  • Recently Listed with Virtual Tour
1 of 28
$240,000
2

Beds

1.1

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 117

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3651 N GOLDENROD ROAD D102 Winter Park, FL MLS# O6401114
  • Recently Listed with Virtual Tour
1 of 14
$159,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D102

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3028 GEORGE MASON AVENUE J-7E Winter Park, FL MLS# O6398380
$105,000
2

Beds

2.0

Baths

1,088

Sq.Ft.

3028 GEORGE MASON AVENUE J-7E

Winter Park, FL

Courtesy of EXP REALTY LLC
View 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6386578
  • Recently Listed with Virtual Tour
1 of 29
$229,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE REALTY
View 7429 DANIEL WEBSTER DRIVE 14 (#C) Winter Park, FL MLS# O6400425
  • Recently Listed with Virtual Tour
1 of 17
$133,000
2

Beds

2.0

Baths

1,036

Sq.Ft.

7429 DANIEL WEBSTER DRIVE 14 (#C)

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 3021 AARON BURR AVENUE 3 Winter Park, FL MLS# S5147382
  • Recently Listed with Virtual Tour
1 of 21
$140,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3021 AARON BURR AVENUE 3

Winter Park, FL

Courtesy of NAIM REAL ESTATE LLC
View 7301 CEDAR CREEK COURT 66 Winter Park, FL MLS# O6397477
  • Recently Listed
1 of 44
$187,500
2

Beds

2.1

Baths

1,031

Sq.Ft.

7301 CEDAR CREEK COURT 66

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 1695 LEE ROAD D211 Winter Park, FL MLS# O6396190
  • Recently Listed with Virtual Tour
1 of 28
$115,000
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD D211

Winter Park, FL

Courtesy of LOKATION
View 200 SAINT ANDREWS BOULEVARD 2901 Winter Park, FL MLS# O6395720
$225,000
2

Beds

1.1

Baths

1,266

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2901

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1500 GAY ROAD 8D Winter Park, FL MLS# O6392693
$267,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 8D

Winter Park, FL

Courtesy of SOLID OAK REAL ESTATE LLC
View Address not provided Winter Park, FL MLS# O6393932
  • Virtual Tour
1 of 30
$257,000
2

Beds

2.1

Baths

959

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of DERENTHAL REALTY
View 1695 LEE ROAD E103 Winter Park, FL MLS# S5146352
  • Virtual Tour
1 of 23
$139,990
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD E103

Winter Park, FL

Courtesy of RE/MAX SELECT GROUP
View 1000 S SEMORAN BOULEVARD 805 Winter Park, FL MLS# O6392099
$174,700
2

Beds

2.0

Baths

1,003

Sq.Ft.

1000 S SEMORAN BOULEVARD 805

Winter Park, FL

Courtesy of SHAWFIELD REALTY GROUP
View 7300 DANIEL WEBSTER DRIVE M7 Winter Park, FL MLS# O6388668
$165,000
2

Beds

2.1

Baths

1,108

Sq.Ft.

7300 DANIEL WEBSTER DRIVE M7

Winter Park, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
View 3027 AARON BURR AVENUE L1 Winter Park, FL MLS# O6390662
$165,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3027 AARON BURR AVENUE L1

Winter Park, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
View 3651 N GOLDENROD ROAD D101 Winter Park, FL MLS# O6391256
$179,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D101

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 3217 OAK LAWN PLACE 211 Winter Park, FL MLS# O6390713
$179,000
3

Beds

2.0

Baths

1,117

Sq.Ft.

3217 OAK LAWN PLACE 211

Winter Park, FL

Courtesy of SHORES REAL ESTATE

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

367

Estimated median home price

$795,000
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

Price Count
$0 - 100K 4
$100K - 200K 49
$200K - 300K 23
$300K - 400K 19
$400K - 500K 29
$500K - 600K 18
$600K - 700K 27
$700K - 800K 16
$800K - 900K 11
$900K - 1M 10
$1M - Max 161

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 224
Townhouse 16
Condo 87
Commercial 4
Rental 97
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 4/29/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 4/29/2026.

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 4/29/2026.