165 total properties
Did you mean the neighborhood Winter Park?
View 3334 YOUNG STREET Winter Park, FL MLS# O6442952
  • Virtual Tour
1 of 22
$459,900
3

Beds

2.0

Baths

1,706

Sq.Ft.

3334 YOUNG STREET

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 192 BALFOUR DRIVE 2 Winter Park, FL MLS# O6443731
  • Adult Community with Virtual Tour
1 of 52
$319,000
2

Beds

2.0

Baths

1,287

Sq.Ft.

192 BALFOUR DRIVE 2

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 1695 LEE ROAD C206 Winter Park, FL MLS# TB8551269
  • Virtual Tour
1 of 24
$140,000
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD C206

Winter Park, FL

Courtesy of INVESTMENT REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1306 S PENNSYLVANIA AVENUE 5 Winter Park, FL MLS# O6443013
$347,500
2

Beds

1.0

Baths

830

Sq.Ft.

1306 S PENNSYLVANIA AVENUE 5

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 250 CAROLINA AVENUE 202 Winter Park, FL MLS# O6442686
$649,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

250 CAROLINA AVENUE 202

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6442348
  • Virtual Tour
1 of 41
OPEN HOUSE: Saturday 11/14 12:00 PM - 2:00 PM
$637,500
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 3209 HEARTWOOD AVENUE Winter Park, FL MLS# O6442556
$439,900
4

Beds

2.0

Baths

1,627

Sq.Ft.

3209 HEARTWOOD AVENUE

Winter Park, FL

Courtesy of LEDGE REAL ESTATE SOLUTIONS LLC
View 7453 DANIEL WEBSTER DRIVE A5 Winter Park, FL MLS# O6442597
$150,000
2

Beds

2.0

Baths

1,063

Sq.Ft.

7453 DANIEL WEBSTER DRIVE A5

Winter Park, FL

Courtesy of LA ROSA REALTY PREMIER LLC
View 786 W CANTON AVENUE Winter Park, FL MLS# O6441522
  • Virtual Tour
1 of 20
$450,000
0.0

Baths

786 W CANTON AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7476 WOODBURN COURT 38 Winter Park, FL MLS# O6434437
$170,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7476 WOODBURN COURT 38

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 822 SYMONDS AVENUE Winter Park, FL MLS# O6441180
$599,999
0.0

Baths

822 SYMONDS AVENUE

Winter Park, FL

Courtesy of NEWBERRY REALTY & DEV GRP INC.
View 1211 SCHULTZ AVENUE Winter Park, FL MLS# O6442460
  • Virtual Tour
1 of 35
$475,000
3

Beds

2.0

Baths

1,085

Sq.Ft.

1211 SCHULTZ AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2626 AMBERGATE ROAD Winter Park, FL MLS# O6439689
  • Virtual Tour
1 of 20
$380,000
3

Beds

1.0

Baths

1,143

Sq.Ft.

2626 AMBERGATE ROAD

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
View 2260 COLDSTREAM DRIVE Winter Park, FL MLS# O6437438
$675,000
4

Beds

2.0

Baths

1,509

Sq.Ft.

2260 COLDSTREAM DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 3651 N GOLDENROD ROAD C109 Winter Park, FL MLS# O6439897
$165,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD C109

Winter Park, FL

Courtesy of REAL ESTATE PROFESSIONALS SE
View 1250 S DENNING DRIVE 127 Winter Park, FL MLS# O6439854
$245,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 127

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 508 BRECHIN DRIVE Winter Park, FL MLS# O6439220
  • Virtual Tour
1 of 34
$579,000
3

Beds

2.0

Baths

1,783

Sq.Ft.

508 BRECHIN DRIVE

Winter Park, FL

Courtesy of MTL REALTY LLC
View 3020 ANTIQUE OAKS CIRCLE 129 Winter Park, FL MLS# O6438679
$135,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

3020 ANTIQUE OAKS CIRCLE 129

Winter Park, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 500 N PENNSYLVANIA AVENUE G Winter Park, FL MLS# G5117377
$349,500
2

Beds

1.0

Baths

709

Sq.Ft.

500 N PENNSYLVANIA AVENUE G

Winter Park, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1850 BRYAN AVENUE Winter Park, FL MLS# O6438184
  • Virtual Tour
1 of 31
$699,000
3

Beds

2.0

Baths

1,563

Sq.Ft.

1850 BRYAN AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER 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

357

Estimated median home price

$825,000
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 32
$200K - 300K 23
$300K - 400K 18
$400K - 500K 32
$500K - 600K 24
$600K - 700K 26
$700K - 800K 18
$800K - 900K 17
$900K - 1M 12
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 210
Townhouse 25
Condo 80
Commercial 15
Rental 96
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 11/11/2026)

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 11/12/2026.