199 total properties
Did you mean the neighborhood Winter Park?
View 250 CAROLINA AVENUE 205 Winter Park, FL MLS# O6433913
  • Recently Listed with Virtual Tour
1 of 86
$739,000
2

Beds

2.0

Baths

1,311

Sq.Ft.

250 CAROLINA AVENUE 205

Winter Park, FL

View 1409 SUNSET DRIVE Winter Park, FL MLS# O6433393
  • Recently Listed with Virtual Tour
1 of 33
$649,000
2

Beds

1.1

Baths

1,107

Sq.Ft.

1409 SUNSET DRIVE

Winter Park, FL

View 2183 CRANDON AVENUE Winter Park, FL MLS# O6433521
  • Recently Listed
1 of 28
$499,000
4

Beds

2.0

Baths

1,200

Sq.Ft.

2183 CRANDON AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
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 1652 BERKSHIRE AVENUE Winter Park, FL MLS# O6432617
  • Recently Listed with Virtual Tour
1 of 29
$499,000
3

Beds

2.0

Baths

1,498

Sq.Ft.

1652 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER 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 2627 AMBERGATE ROAD Winter Park, FL MLS# O6433352
  • Recently Listed with Virtual Tour
1 of 16
$575,000
4

Beds

3.0

Baths

1,745

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

View 1955 ELAND AVENUE Winter Park, FL MLS# O6433345
  • Recently Listed with Virtual Tour
1 of 19
$425,000
3

Beds

2.0

Baths

1,494

Sq.Ft.

1955 ELAND AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 2641 CARVELL COURT Winter Park, FL MLS# O6430894
  • Recently Listed with Virtual Tour
1 of 38
$575,000
4

Beds

2.0

Baths

2,126

Sq.Ft.

2641 CARVELL COURT

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 2881 TEMPLE TRAIL Winter Park, FL MLS# O6431955
  • Virtual Tour
1 of 58
$575,000
2

Beds

2.1

Baths

1,704

Sq.Ft.

2881 TEMPLE TRAIL

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 950 S KENTUCKY AVENUE Winter Park, FL MLS# O6432779
$799,000
4

Beds

3.0

Baths

2,155

Sq.Ft.

950 S KENTUCKY AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2015 TAYLOR AVENUE Winter Park, FL MLS# O6436061
  • Recently Listed with Virtual Tour
1 of 22
$430,000
3

Beds

2.0

Baths

1,439

Sq.Ft.

2015 TAYLOR AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS CLASSIC
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 4033 TENITA DRIVE Winter Park, FL MLS# O6424621
$569,000
4

Beds

2.0

Baths

2,022

Sq.Ft.

4033 TENITA DRIVE

Winter Park, FL

View 913 CAMELLIA AVENUE Winter Park, FL MLS# O6430229
  • Virtual Tour
1 of 50
$655,000
3

Beds

2.1

Baths

1,389

Sq.Ft.

913 CAMELLIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 310 GRANADA DRIVE Winter Park, FL MLS# TB8536242
  • Virtual Tour
1 of 6
$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.

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

$697,250
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 41
$200K - 300K 23
$300K - 400K 13
$400K - 500K 39
$500K - 600K 31
$600K - 700K 37
$700K - 800K 11
$800K - 900K 11
$900K - 1M 9
$1M - Max 155

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 229
Townhouse 24
Condo 80
Commercial 9
Rental 78
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 9/1/2026)

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 9/1/2026.