View 33 TIMBERCREEK PINES CIRCLE Winter Garden, FL MLS# O6408941
$535,000
3

Beds

2.0

Baths

1,584

Sq.Ft.

33 TIMBERCREEK PINES CIRCLE

Winter Garden, FL

View 1503 COLUSO DRIVE Winter Garden, FL MLS# O6410109
  • Virtual Tour
1 of 42
$443,000
3

Beds

2.0

Baths

2,187

Sq.Ft.

1503 COLUSO DRIVE

Winter Garden, FL

View 15568 BLACKBEAD STREET Winter Garden, FL MLS# O6408861
$435,000
4

Beds

3.0

Baths

1,861

Sq.Ft.

15568 BLACKBEAD STREET

Winter Garden, FL

Courtesy of MARK SPAIN REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 9606 WOODCRANE DRIVE Winter Garden, FL MLS# O6410113
$525,000
3

Beds

2.1

Baths

2,101

Sq.Ft.

9606 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 46 W VINING STREET Winter Garden, FL MLS# O6408720
  • Virtual Tour
1 of 40
$549,900
3

Beds

2.0

Baths

1,273

Sq.Ft.

46 W VINING STREET

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 9652 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6409704
$430,000
4

Beds

2.1

Baths

1,948

Sq.Ft.

9652 AMBER CHESTNUT WAY

Winter Garden, FL

View 17013 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112484
  • New Construction with Virtual Tour
1 of 5
$455,752
3

Beds

2.1

Baths

1,772

Sq.Ft.

17013 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 2200 ROMANUM DRIVE Winter Garden, FL MLS# O6408190
  • Virtual Tour
1 of 33
$550,000
4

Beds

4.0

Baths

2,561

Sq.Ft.

2200 ROMANUM DRIVE

Winter Garden, FL

View 17001 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112433
$485,705
3

Beds

2.1

Baths

1,644

Sq.Ft.

17001 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

View 17007 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112438
$491,490
3

Beds

2.1

Baths

1,764

Sq.Ft.

17007 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7280 WINDY WILLOW STREET Winter Garden, FL MLS# G5112439
  • New Construction with Virtual Tour
1 of 5
$493,583
3

Beds

2.1

Baths

1,772

Sq.Ft.

7280 WINDY WILLOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 9318 MCLAREN ALLEY Winter Garden, FL MLS# S5150019
  • Virtual Tour
1 of 34
$489,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

9318 MCLAREN ALLEY

Winter Garden, FL

View 12103 EASTMOOR DRIVE Winter Garden, FL MLS# O6409071
$440,000
3

Beds

2.0

Baths

1,604

Sq.Ft.

12103 EASTMOOR DRIVE

Winter Garden, FL

View 729 MEADOW GLADE DRIVE Winter Garden, FL MLS# O6407943
1 of 54
OPEN HOUSE: Saturday 7/18 11:00 AM - 1:00 PM
$525,000
3

Beds

2.0

Baths

2,070

Sq.Ft.

729 MEADOW GLADE DRIVE

Winter Garden, FL

View 15518 FOUNTAIN COVE COURT Winter Garden, FL MLS# O6407942
  • Virtual Tour
1 of 64
OPEN HOUSE: Sunday 7/19 1:00 PM - 4:00 PM
$550,000
3

Beds

3.0

Baths

2,040

Sq.Ft.

15518 FOUNTAIN COVE COURT

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14501 GROVE RESORT AVE 1535 1535 Winter Garden, FL MLS# S5150001
$410,990
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVE 1535 1535

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View 12597 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6407413
$475,000
3

Beds

2.0

Baths

2,322

Sq.Ft.

12597 ENCORE AT OVATION WAY

Winter Garden, FL

View 5545 BOWMAN DRIVE Winter Garden, FL MLS# O6407484
  • Virtual Tour
1 of 29
OPEN HOUSE: Saturday 7/18 9:00 AM - 7:00 PM
$465,000
2

Beds

2.1

Baths

1,998

Sq.Ft.

5545 BOWMAN DRIVE

Winter Garden, FL

View 6174 WHISPERING GLEN Winter Garden, FL MLS# O6407807
  • New Construction with Virtual Tour
1 of 20
$518,290
3

Beds

2.1

Baths

1,628

Sq.Ft.

6174 WHISPERING GLEN

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 11117 BOSTWICK ALLEY Winter Garden, FL MLS# O6407552
$507,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

11117 BOSTWICK ALLEY

Winter Garden, FL

About Winter Garden

The balance between reverence for yesterday and vibrant growth is reflected in the Winter Garden slogan, "A City with a Future…Preserving Its Past."  Walking down historic Plant Street or catching a glimpse of landmark buildings like Tanner Hall immediately creates an image of small-town life at its finest in the heart of this quaint Main Street community. At the same time, redevelopment and growth are evident at every turn.  Antique stores, ice cream shops, and charming cafés combine with dynamic new businesses and residential development.  Covering approximately 17 square miles, Winter Garden offers access to the West Orange Trail for biking or jogging in a naturally beautiful setting.  Other amenities include large parks, a public boat ramp on Lake Apopka, and recreational complexes for tennis, swimming, and sports play.  This vast area once covered by citrus groves is rapidly transforming into a suburban environment that preserves the friendly, intimate spirit of yesterday.  Residents enjoy easy access to Highway 50, the East West Expressway, and the Florida Turnpike.

Listings in Winter Garden, FL

918

Estimated median home price

$608,645
Winter Garden FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Garden, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Garden, FL.

Homes for Sale by Price in Winter Garden, FL

Price Count
$0 - 100K 1
$100K - 200K 22
$200K - 300K 93
$300K - 400K 62
$400K - 500K 130
$500K - 600K 148
$600K - 700K 97
$700K - 800K 105
$800K - 900K 86
$900K - 1M 59
$1M - Max 115

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 619
Townhouse 127
Condo 139
Commercial 11
Rental 209
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 7/18/2026)

Information deemed reliable but not guaranteed.

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 7/18/2026.