368 total properties
Did you mean the neighborhood Winter Park?
View 2929 ANTIQUE OAKS CIRCLE 53 Winter Park, FL MLS# O6393633
$168,000
1

Beds

1.0

Baths

749

Sq.Ft.

2929 ANTIQUE OAKS CIRCLE 53

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 700 MELROSE AVENUE J1 Winter Park, FL MLS# O6394372
  • Adult Community with Virtual Tour
1 of 20
$350,000
2

Beds

2.0

Baths

1,074

Sq.Ft.

700 MELROSE AVENUE J1

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2330 COLDSTREAM DRIVE Winter Park, FL MLS# O6384436
$650,000
4

Beds

2.0

Baths

1,750

Sq.Ft.

2330 COLDSTREAM DRIVE

Winter Park, FL

Courtesy of DTB FLORIDA REALTY, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 1570 PALMER AVENUE Winter Park, FL MLS# O6383529
  • Virtual Tour
1 of 39
OPEN HOUSE: Saturday 4/18 12:00 PM - 2:00 PM
$1,640,000
4

Beds

3.1

Baths

3,048

Sq.Ft.

1570 PALMER AVENUE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
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 518 SHOREVIEW AVENUE Winter Park, FL MLS# O6392797
  • Virtual Tour
1 of 35
$490,090
2

Beds

2.0

Baths

1,609

Sq.Ft.

518 SHOREVIEW AVENUE

Winter Park, FL

Courtesy of UNITED REAL ESTATE PREFERRED
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 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
  • Virtual Tour
1 of 45
OPEN HOUSE: Sunday 4/19 12:00 PM - 3:00 PM
$459,999
3

Beds

2.0

Baths

1,491

Sq.Ft.

405 LAKE FAIR LANE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1750 CAROLLEE LANE Winter Park, FL MLS# O6391179
$1,890,000
4

Beds

3.1

Baths

3,249

Sq.Ft.

1750 CAROLLEE LANE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1649 HARMON AVENUE Winter Park, FL MLS# O6392216
  • Virtual Tour
1 of 51
OPEN HOUSE: Sunday 4/19 2:00 PM - 4:00 PM
$1,399,000
4

Beds

3.1

Baths

3,223

Sq.Ft.

1649 HARMON AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 512 N LAKEMONT AVENUE Winter Park, FL MLS# O6392353
$500,000
3

Beds

2.0

Baths

1,413

Sq.Ft.

512 N LAKEMONT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1840 BRYAN AVENUE Winter Park, FL MLS# O6391922
  • Virtual Tour
1 of 46
$1,899,500
4

Beds

3.1

Baths

3,727

Sq.Ft.

1840 BRYAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1016 HOWELL BRANCH ROAD Winter Park, FL MLS# O6392409
$1,699,000
4

Beds

3.0

Baths

3,142

Sq.Ft.

1016 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of PLAID PROPERTIES, LLC
View 1117 KENWOOD AVENUE Winter Park, FL MLS# O6389970
  • Virtual Tour
1 of 67
$3,978,900
4

Beds

4.1

Baths

4,353

Sq.Ft.

1117 KENWOOD AVENUE

Winter Park, FL

Courtesy of ROYALTY R E BOUTIQUE INC
View 668 OVERSPIN DRIVE Winter Park, FL MLS# O6392301
  • Virtual Tour
1 of 33
$875,000
4

Beds

3.0

Baths

2,509

Sq.Ft.

668 OVERSPIN DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2919 BOWER ROAD Winter Park, FL MLS# O6391025
  • Virtual Tour
1 of 38
$779,000
3

Beds

2.0

Baths

2,325

Sq.Ft.

2919 BOWER ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 300 CAROLINA AVENUE 207 Winter Park, FL MLS# O6391523
$495,000
1

Beds

2.0

Baths

1,149

Sq.Ft.

300 CAROLINA AVENUE 207

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1760 GREENWICH AVENUE Winter Park, FL MLS# O6392001
  • Virtual Tour
1 of 18
OPEN HOUSE: Sunday 4/19 1:00 PM - 3:00 PM
$650,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

1760 GREENWICH AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
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

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

$779,000
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 51
$200K - 300K 22
$300K - 400K 19
$400K - 500K 32
$500K - 600K 19
$600K - 700K 24
$700K - 800K 16
$800K - 900K 13
$900K - 1M 10
$1M - Max 157

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 225
Townhouse 14
Condo 89
Commercial 3
Rental 94
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 4/18/2026)

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 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 4/18/2026.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 4/18/2026.

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 4/18/2026.

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 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 4/18/2026.