75 total properties
Did you mean the neighborhood Winter Park?
View 150 KILLARNEY BAY COURT 5 Winter Park, FL MLS# O6328063
$355,000
2

Beds

2.0

Baths

1,140

Sq.Ft.

150 KILLARNEY BAY COURT 5

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 3117 SHADY PINE AVENUE Winter Park, FL MLS# O6339255
$355,000
3

Beds

2.0

Baths

1,214

Sq.Ft.

3117 SHADY PINE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 520 KILLARNEY BAY COURT 2 Winter Park, FL MLS# O6361081
$339,000
2

Beds

2.0

Baths

1,160

Sq.Ft.

520 KILLARNEY BAY COURT 2

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 638 WARRENTON ROAD Winter Park, FL MLS# O6324688
  • Virtual Tour
1 of 43
$331,985
2

Beds

2.0

Baths

1,362

Sq.Ft.

638 WARRENTON ROAD

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 2417 PASSAMONTE DRIVE 1E Winter Park, FL MLS# TB8387465
$329,999
3

Beds

2.1

Baths

1,837

Sq.Ft.

2417 PASSAMONTE DRIVE 1E

Winter Park, FL

Courtesy of FLAT FEE MLS REALTY
View 311 E MORSE BOULEVARD 7-11 Winter Park, FL MLS# O6337061
$329,900
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 7-11

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 311 E MORSE BOULEVARD 6-3 Winter Park, FL MLS# O6362964
  • Adult Community with Virtual Tour
1 of 36
$329,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 6-3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 615 WARRENTON ROAD Winter Park, FL MLS# O6356439
  • Virtual Tour
1 of 27
$320,000
2

Beds

2.0

Baths

1,221

Sq.Ft.

615 WARRENTON ROAD

Winter Park, FL

Courtesy of RE/MAX DOWNTOWN
View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$298,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

Courtesy of CREEGAN GROUP
View 1250 S DENNING DRIVE 213 Winter Park, FL MLS# O6344353
$275,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 213

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1500 GAY ROAD 24B Winter Park, FL MLS# O6348568
  • Virtual Tour
1 of 17
OPEN HOUSE: Sunday 1/4 2:00 PM - 4:00 PM
$275,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 24B

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 609 GALLERY DRIVE B204 Winter Park, FL MLS# O6357629
$275,000
2

Beds

2.0

Baths

893

Sq.Ft.

609 GALLERY DRIVE B204

Winter Park, FL

Courtesy of A2Z REALTY GROUP
View 2009 CORNELL AVENUE Winter Park, FL MLS# O6353956
  • Virtual Tour
1 of 35
$269,000
2

Beds

1.0

Baths

762

Sq.Ft.

2009 CORNELL AVENUE

Winter Park, FL

Courtesy of ORLANDO HOME DEALER LLC
View 3580 WILDE AVENUE Winter Park, FL MLS# O6296776
  • Virtual Tour
1 of 8
$260,000
Studio

Beds

0.0

Baths

3580 WILDE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 151 N ORLANDO AVENUE 101 Winter Park, FL MLS# G5102278
$260,000
2

Beds

1.0

Baths

804

Sq.Ft.

151 N ORLANDO AVENUE 101

Winter Park, FL

Courtesy of THE FLORIDA PROPERTY SHOP SALE
View 1996 INDIANA AVENUE Winter Park, FL MLS# O6309850
$250,000
2

Beds

1.0

Baths

818

Sq.Ft.

1996 INDIANA AVENUE

Winter Park, FL

Courtesy of MARKET CONNECT REALTY LLC
View 2500 LEE ROAD 202 Winter Park, FL MLS# O6277579
  • Virtual Tour
1 of 39
$239,990
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 202

Winter Park, FL

Courtesy of THE ANDERSON GROUP & CO PL
View 200 Saint Andrews 3001 Winter Park, FL MLS# A11924851
  • Recently Listed with Virtual Tour
1 of 20
$237,000
2

Beds

1.1

Baths

1,085

Sq.Ft.

200 Saint Andrews 3001

Winter Park, FL

Courtesy of KLEROS REALTY
View 700 MELROSE AVENUE J 23 Winter Park, FL MLS# O6347944
  • Adult Community with Virtual Tour
1 of 26
$235,000
1

Beds

1.0

Baths

772

Sq.Ft.

700 MELROSE AVENUE J 23

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 151 N ORLANDO AVENUE 204 Winter Park, FL MLS# O6307468
$229,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 204

Winter Park, FL

Courtesy of MAINFRAME REAL ESTATE

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

300

Estimated median home price

$649,900
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 22
$300K - 400K 20
$400K - 500K 27
$500K - 600K 26
$600K - 700K 21
$700K - 800K 22
$800K - 900K 5
$900K - 1M 11
$1M - Max 100

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 174
Townhouse 19
Condo 78
Commercial 5
Rental 109
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 12/30/2025)

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 12/31/2025.