75 total properties
Did you mean the neighborhood Winter Park?
View 1199 CLAY STREET Winter Park, FL MLS# O6393872
  • Virtual Tour
1 of 50
$170,124
184,510

Sq.Ft.

1199 CLAY STREET

Winter Park, FL

Courtesy of BUCKEYE REALTY LLC
View 2306 LEE ROAD Winter Park, FL MLS# O6390092
  • Virtual Tour
1 of 7
$119,568
2,289

Sq.Ft.

2306 LEE ROAD

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 687 HAROLD AVENUE Winter Park, FL MLS# O6387921
  • New Construction
1 of 3
$84,000
4,500

Sq.Ft.

687 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 4550 PALMETTO AVENUE Winter Park, FL MLS# O6388575
$78,750
4,206

Sq.Ft.

4550 PALMETTO AVENUE

Winter Park, FL

Courtesy of SOLANTIS LLC
View 2035 GLENWOOD DRIVE Winter Park, FL MLS# O6403420
  • Recently Listed with Virtual Tour
1 of 23
$47,400
3,718

Sq.Ft.

2035 GLENWOOD DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3029 FORSYTH ROAD Winter Park, FL MLS# O6348919
$42,000
1,500

Sq.Ft.

3029 FORSYTH ROAD

Winter Park, FL

Courtesy of C BRENNER INC
View 663 HAROLD AVENUE Winter Park, FL MLS# O6387903
$42,000
10,429

Sq.Ft.

663 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
View 7307 SANDSCOVE COURT 5 Winter Park, FL MLS# O6392725
$42,000
23,760

Sq.Ft.

7307 SANDSCOVE COURT 5

Winter Park, FL

Courtesy of FUSILIER MANAGEMENT GROUP
View 7507 ALOMA AVENUE 3B Winter Park, FL MLS# O6353856
$28,800
1,444

Sq.Ft.

7507 ALOMA AVENUE 3B

Winter Park, FL

Courtesy of MUSA REALTY COMPANY INC
View 1742 TEMPLE DRIVE Winter Park, FL MLS# O6378161
  • New Construction with Virtual Tour
1 of 27
$17,000
4

Beds

5.0

Baths

3,658

Sq.Ft.

1742 TEMPLE DRIVE

Winter Park, FL

Courtesy of ROI AVE LLC
View 2024 LAKE DRIVE Winter Park, FL MLS# O6409405
  • Recently Listed
1 of 40
$14,000
3

Beds

4.2

Baths

4,027

Sq.Ft.

2024 LAKE DRIVE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 4775 SEMINOLE AVENUE Winter Park, FL MLS# O6393586
$13,200
960

Sq.Ft.

4775 SEMINOLE AVENUE

Winter Park, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 1041 TUSCANY PLACE Winter Park, FL MLS# O6401030
$12,000
4

Beds

3.1

Baths

3,064

Sq.Ft.

1041 TUSCANY PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1814 BARKER DRIVE Winter Park, FL MLS# O6395037
$10,000
5

Beds

4.0

Baths

4,200

Sq.Ft.

1814 BARKER DRIVE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1760 LEGION DRIVE Winter Park, FL MLS# O6406982
  • Recently Listed
1 of 53
$9,700
4

Beds

5.1

Baths

4,392

Sq.Ft.

1760 LEGION DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 300 KILLARNEY DRIVE Winter Park, FL MLS# O6361584
$7,900
4

Beds

3.0

Baths

2,476

Sq.Ft.

300 KILLARNEY DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1701 WALNUT AVENUE Winter Park, FL MLS# O6397097
$7,800
4

Beds

4.1

Baths

3,819

Sq.Ft.

1701 WALNUT AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1077 MINNESOTA AVENUE Winter Park, FL MLS# O6409477
$7,500
4

Beds

4.0

Baths

3,046

Sq.Ft.

1077 MINNESOTA AVENUE

Winter Park, FL

Courtesy of SHAHRAM SONDI + CO.
View 2075 JEWELL AVENUE Winter Park, FL MLS# O6386721
$6,995
5

Beds

4.0

Baths

2,918

Sq.Ft.

2075 JEWELL AVENUE

Winter Park, FL

Courtesy of URBANISTA BROKERS
View 527 LANGHOLM DRIVE Winter Park, FL MLS# O6387427
$6,750
4

Beds

3.1

Baths

3,276

Sq.Ft.

527 LANGHOLM DRIVE

Winter Park, FL

Courtesy of WOODRUFF REALTY, INC.

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

387

Estimated median home price

$785,000
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 - 100K3
$100K - 200K50
$200K - 300K22
$300K - 400K22
$400K - 500K29
$500K - 600K23
$600K - 700K28
$700K - 800K20
$800K - 900K16
$900K - 1M8
$1M - Max166

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family242
Townhouse16
Condo88
Commercial7
Rental72
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 5/20/2026)

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

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 5/20/2026.