144 total properties
Did you mean the neighborhood Winter Park?
View 640 KILLARNEY BAY COURT 4 Winter Park, FL MLS# O6300075
$599,000
2

Beds

2.1

Baths

1,718

Sq.Ft.

640 KILLARNEY BAY COURT 4

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1835 JESSICA COURT Winter Park, FL MLS# O6364599
  • Virtual Tour
1 of 26
$599,000
2

Beds

2.0

Baths

1,637

Sq.Ft.

1835 JESSICA COURT

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2758 BANCHORY ROAD Winter Park, FL MLS# O6329628
  • Virtual Tour
1 of 37
$598,000
3

Beds

2.0

Baths

1,539

Sq.Ft.

2758 BANCHORY ROAD

Winter Park, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6328855
  • Virtual Tour
1 of 34
$590,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 1740 ANZLE AVENUE Winter Park, FL MLS# O6339726
$580,000
4

Beds

2.0

Baths

1,808

Sq.Ft.

1740 ANZLE AVENUE

Winter Park, FL

Courtesy of GOYAL & DECOSTER REALTY
View 720 W WEBSTER AVENUE Winter Park, FL MLS# O6338765
  • Virtual Tour
1 of 22
$575,000
3

Beds

2.0

Baths

1,356

Sq.Ft.

720 W WEBSTER AVENUE

Winter Park, FL

Courtesy of THE AGENCY ORLANDO
View 2350 CADY WAY Winter Park, FL MLS# O6367536
  • Recently Listed with Virtual Tour
1 of 31
OPEN HOUSE: Sunday 12/28 2:00 PM - 4:00 PM
$575,000
4

Beds

2.0

Baths

1,854

Sq.Ft.

2350 CADY WAY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 640 PARK AVENUE N 26 Winter Park, FL MLS# O6343212
  • Virtual Tour
1 of 26
$572,500
2

Beds

2.0

Baths

858

Sq.Ft.

640 PARK AVENUE N 26

Winter Park, FL

Courtesy of MICHAEL O'SHAUGHNESSY, INC.
View 151 N ORLANDO AVENUE 212 Winter Park, FL MLS# O6314915
$570,000
3

Beds

2.0

Baths

1,875

Sq.Ft.

151 N ORLANDO AVENUE 212

Winter Park, FL

Courtesy of THE AGENCY ORLANDO
View 7502 WAUNAQUA DRIVE Winter Park, FL MLS# O6355169
  • Virtual Tour
1 of 7
$567,000
5

Beds

3.0

Baths

2,615

Sq.Ft.

7502 WAUNAQUA DRIVE

Winter Park, FL

Courtesy of REALTY TECH INC
View 701 DENTON ROAD Winter Park, FL MLS# O6295021
  • Virtual Tour
1 of 32
$565,000
3

Beds

2.0

Baths

2,268

Sq.Ft.

701 DENTON ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 212 BLOSSOM LANE Winter Park, FL MLS# G5098632
$565,000
3

Beds

2.0

Baths

1,771

Sq.Ft.

212 BLOSSOM LANE

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 1875 STAUNTON AVENUE Winter Park, FL MLS# O6342876
  • Virtual Tour
1 of 16
$560,000
4

Beds

2.0

Baths

2,036

Sq.Ft.

1875 STAUNTON AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2758 SANDWELL DRIVE Winter Park, FL MLS# O6350252
  • Virtual Tour
1 of 14
$560,000
4

Beds

2.0

Baths

2,303

Sq.Ft.

2758 SANDWELL DRIVE

Winter Park, FL

Courtesy of CALL IT CLOSED INTL REALTY
View 720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6281659
$550,000
3

Beds

2.0

Baths

1,115

Sq.Ft.

720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6344260
  • Virtual Tour
1 of 45
$549,900
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

Courtesy of PRESTIGE PROPERTY SHOP LLC
View 100 S INTERLACHEN AVENUE 410F Winter Park, FL MLS# O6303353
$549,000
2

Beds

1.0

Baths

901

Sq.Ft.

100 S INTERLACHEN AVENUE 410F

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2412 MIDDLETON AVENUE Winter Park, FL MLS# O6356193
$549,000
3

Beds

2.0

Baths

1,340

Sq.Ft.

2412 MIDDLETON AVENUE

Winter Park, FL

Courtesy of REAL ESTATE INVESTMENTS BY BOR
View Address not provided Winter Park, FL MLS# O6352582
  • Virtual Tour
1 of 27
$540,000
4

Beds

3.0

Baths

2,878

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of MID-STATE PROPERTIES PSL LLC
View 240 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6312795
$525,000
3

Beds

2.0

Baths

1,630

Sq.Ft.

240 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of REAL BROKER, LLC

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

301

Estimated median home price

$639,000
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 6
$100K - 200K 40
$200K - 300K 21
$300K - 400K 19
$400K - 500K 32
$500K - 600K 26
$600K - 700K 21
$700K - 800K 22
$800K - 900K 5
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 176
Townhouse 19
Condo 77
Commercial 5
Rental 108
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 12/28/2025)

Information deemed reliable but not guaranteed.

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 12/28/2025.

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 12/28/2025.