325 total properties
Did you mean the neighborhood Winter Park?
View 1225 SHARON PLACE Winter Park, FL MLS# O6443546
$1,749,000
5

Beds

3.1

Baths

3,097

Sq.Ft.

1225 SHARON PLACE

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 1250 S DENNING DRIVE 119 Winter Park, FL MLS# O6444618
$265,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 119

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1003 GOLFSIDE DRIVE Winter Park, FL MLS# O6444366
$759,900
3

Beds

3.0

Baths

2,145

Sq.Ft.

1003 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of QP HOMES REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 555 E LAKE SUE AVENUE Winter Park, FL MLS# O6442775
  • Virtual Tour
1 of 96
OPEN HOUSE: Sunday 11/1 1:00 PM - 3:00 PM
$2,095,000
4

Beds

4.0

Baths

3,776

Sq.Ft.

555 E LAKE SUE AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2818 AMBERGATE ROAD Winter Park, FL MLS# O6444112
$429,900
3

Beds

2.0

Baths

1,398

Sq.Ft.

2818 AMBERGATE ROAD

Winter Park, FL

Courtesy of MARK SPAIN REAL ESTATE
View 1660 ORANGE AVENUE Winter Park, FL MLS# L4965340
$449,900
3

Beds

2.0

Baths

1,614

Sq.Ft.

1660 ORANGE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 450 N LAKEMONT AVE Winter Park, FL MLS# O6445021
$200,000

450 N LAKEMONT AVE

Winter Park, FL

Courtesy of DOVER INTERNATIONAL CO., INC.
View 173 SCOTTSDALE SQUARE 173 Winter Park, FL MLS# S5158339
$100,000
1

Beds

1.0

Baths

785

Sq.Ft.

173 SCOTTSDALE SQUARE 173

Winter Park, FL

Courtesy of AXEN REALTY LLC
View 3334 YOUNG STREET Winter Park, FL MLS# O6442952
$469,900
3

Beds

2.0

Baths

1,706

Sq.Ft.

3334 YOUNG STREET

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 2614 PARKLAND DRIVE Winter Park, FL MLS# O6444165
$1,890,000
4

Beds

3.1

Baths

3,307

Sq.Ft.

2614 PARKLAND DRIVE

Winter Park, FL

Courtesy of JW GASTON LLC
View 1951 WINTER PARK ROAD Winter Park, FL MLS# O6441816
$1,949,000
4

Beds

3.1

Baths

3,479

Sq.Ft.

1951 WINTER PARK ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 100 S VIRGINIA AVENUE 201 Winter Park, FL MLS# O6442678
$1,450,000
3

Beds

3.0

Baths

2,756

Sq.Ft.

100 S VIRGINIA AVENUE 201

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 532 LANGHOLM DRIVE Winter Park, FL MLS# O6442823
  • New Construction with Virtual Tour
1 of 18
$2,990,000
5

Beds

4.1

Baths

4,050

Sq.Ft.

532 LANGHOLM DRIVE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 192 BALFOUR DRIVE 2 Winter Park, FL MLS# O6443731
  • Adult Community with Virtual Tour
1 of 52
$319,000
2

Beds

2.0

Baths

1,287

Sq.Ft.

192 BALFOUR DRIVE 2

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 1695 LEE ROAD C206 Winter Park, FL MLS# TB8551269
$140,000
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD C206

Winter Park, FL

Courtesy of INVESTMENT REALTY
View 120 BROADVIEW AVENUE Winter Park, FL MLS# O6440960
$1,250,000
3

Beds

2.0

Baths

1,747

Sq.Ft.

120 BROADVIEW AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 120 BROADVIEW AVENUE Winter Park, FL MLS# O6440974
$2,400,000
0.0

Baths

120 BROADVIEW AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 533 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6440841
  • Virtual Tour
1 of 31
OPEN HOUSE: Sunday 11/1 1:00 PM - 4:00 PM
$1,599,000
4

Beds

3.1

Baths

2,942

Sq.Ft.

533 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1602 ALABAMA DRIVE 107 Winter Park, FL MLS# O6442900
$1,150,000
2

Beds

2.0

Baths

993

Sq.Ft.

1602 ALABAMA DRIVE 107

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1306 S PENNSYLVANIA AVENUE 5 Winter Park, FL MLS# O6443013
$347,500
2

Beds

1.0

Baths

830

Sq.Ft.

1306 S PENNSYLVANIA AVENUE 5

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK

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

365

Estimated median home price

$825,000
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

PriceCount
$0 - 100K4
$100K - 200K34
$200K - 300K21
$300K - 400K16
$400K - 500K31
$500K - 600K26
$600K - 700K33
$700K - 800K16
$800K - 900K17
$900K - 1M13
$1M - Max154

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family218
Townhouse23
Condo79
Commercial15
Rental90
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 11/1/2026)

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 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 11/1/2026.

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.

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 11/1/2026.