253 total properties
Did you mean the neighborhood Winter Park?
View 3207 LOWNDES DRIVE Winter Park, FL MLS# O6362285
  • Virtual Tour
1 of 31
$499,000
3

Beds

2.0

Baths

2,028

Sq.Ft.

3207 LOWNDES DRIVE

Winter Park, FL

Courtesy of MILLER GRANT AND COMPANY
View 535 N INTERLACHEN AVENUE 106 Winter Park, FL MLS# O6376040
$595,000
2

Beds

2.0

Baths

970

Sq.Ft.

535 N INTERLACHEN AVENUE 106

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 681 OVERSPIN DRIVE Winter Park, FL MLS# O6376464
  • Virtual Tour
1 of 64
$669,000
4

Beds

2.1

Baths

2,220

Sq.Ft.

681 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RE/MAX SELECT GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 1861 TAYLOR AVENUE Winter Park, FL MLS# O6375732
  • Virtual Tour
1 of 50
$1,775,000
5

Beds

5.2

Baths

3,116

Sq.Ft.

1861 TAYLOR AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 352 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6375545
$650,000
5

Beds

3.0

Baths

1,917

Sq.Ft.

352 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 2500 LEE ROAD 110 Winter Park, FL MLS# O6375907
  • Virtual Tour
1 of 27
$159,900
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 110

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1500 GAY ROAD 18A Winter Park, FL MLS# O6376215
  • Virtual Tour
1 of 21
$259,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 18A

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 352 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6377540
$650,000
5

Beds

3.0

Baths

1,917

Sq.Ft.

352 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 7618 WAUNATTA COURT Winter Park, FL MLS# V4946886
  • Virtual Tour
1 of 31
$460,000
3

Beds

3.0

Baths

1,970

Sq.Ft.

7618 WAUNATTA COURT

Winter Park, FL

Courtesy of PHOENIX REALTY ADVISORS LLC
View 2500 LEE ROAD 228 Winter Park, FL MLS# O6375288
  • Virtual Tour
1 of 35
$249,900
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 228

Winter Park, FL

Courtesy of HOMEVEST REALTY
View 1541 WESTCHESTER AVENUE Winter Park, FL MLS# O6374409
$1,144,000
3

Beds

2.1

Baths

2,578

Sq.Ft.

1541 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1541 WESTCHESTER AVENUE Winter Park, FL MLS# O6374414
$1,144,000
Studio

Beds

0.0

Baths

1541 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 640 ARJAY WAY Winter Park, FL MLS# O6372947
  • Virtual Tour
1 of 46
$2,000,000
5

Beds

3.2

Baths

3,860

Sq.Ft.

640 ARJAY WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1500 BERKSHIRE AVENUE Winter Park, FL MLS# O6374856
$625,000
3

Beds

1.1

Baths

1,485

Sq.Ft.

1500 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of SOTERA LIVING
View 3220 NETHERWOOD DRIVE Winter Park, FL MLS# O6374172
$285,000
2

Beds

2.0

Baths

1,036

Sq.Ft.

3220 NETHERWOOD DRIVE

Winter Park, FL

Courtesy of THE FIRM RE
View 1840 ANZLE AVENUE Winter Park, FL MLS# O6374102
  • New Construction with Virtual Tour
1 of 12
$1,750,000
4

Beds

2.1

Baths

2,350

Sq.Ft.

1840 ANZLE AVENUE

Winter Park, FL

Courtesy of B LIVE COMMERCIAL AND RESIDENT
View 432 W SWOOPE AVENUE Winter Park, FL MLS# O6375719
  • Virtual Tour
1 of 20
$750,000
4

Beds

3.1

Baths

2,317

Sq.Ft.

432 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1500 GAY ROAD 21-C Winter Park, FL MLS# O6373517
  • Virtual Tour
1 of 27
$265,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 21-C

Winter Park, FL

Courtesy of REDFIN CORPORATION
View 6980 ALOMA AVENUE 32 Winter Park, FL MLS# O6373864
  • Virtual Tour
1 of 12
$250,000
900

Sq.Ft.

6980 ALOMA AVENUE 32

Winter Park, FL

Courtesy of APPLE REALTY
View 7468 CANFORD COURT 24 Winter Park, FL MLS# O6373850
$205,000
2

Beds

1.1

Baths

1,365

Sq.Ft.

7468 CANFORD COURT 24

Winter Park, FL

Courtesy of EMPIRE NETWORK 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

306

Estimated median home price

$699,400
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 5
$100K - 200K 38
$200K - 300K 30
$300K - 400K 21
$400K - 500K 25
$500K - 600K 16
$600K - 700K 19
$700K - 800K 21
$800K - 900K 6
$900K - 1M 7
$1M - Max 118

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 173
Townhouse 15
Condo 83
Commercial 4
Rental 78
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 3/1/2026)

Information deemed reliable but not guaranteed.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes 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 3/2/2026.

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 3/2/2026.

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 3/2/2026.