View 14268 BRAEMAR STREET Winter Garden, FL MLS# S5153509
  • Recently Listed with Virtual Tour
1 of 40
$485,000
4

Beds

2.1

Baths

2,070

Sq.Ft.

14268 BRAEMAR STREET

Winter Garden, FL

View 15075 GROVESIDE ROAD Winter Garden, FL MLS# O6422529
  • Recently Listed with Virtual Tour
1 of 51
$491,080
3

Beds

2.1

Baths

1,881

Sq.Ft.

15075 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 15680 Orange Harvest Loop Winter Garden, FL MLS# 1081686
  • Recently Listed with Virtual Tour
1 of 38
$530,000
3

Beds

2.1

Baths

1,911

Sq.Ft.

15680 Orange Harvest Loop

Winter Garden, FL

Brevard
The time to sell is now! THE TIME TO SELL IS NOW!
View 15680 ORANGE HARVEST LOOP Winter Garden, FL MLS# O6422130
$530,000
3

Beds

2.1

Baths

2,011

Sq.Ft.

15680 ORANGE HARVEST LOOP

Winter Garden, FL

Courtesy of MARK SPAIN REAL ESTATE
View 16645 SILVER BROOK WAY Winter Garden, FL MLS# O6420565
$573,090
3

Beds

2.1

Baths

1,913

Sq.Ft.

16645 SILVER BROOK WAY

Winter Garden, FL

View 14629 BAHAMA SWALLOW BOULEVARD Winter Garden, FL MLS# O6421797
  • Recently Listed with Virtual Tour
1 of 25
$492,900
3

Beds

2.0

Baths

2,223

Sq.Ft.

14629 BAHAMA SWALLOW BOULEVARD

Winter Garden, FL

View 8873 FOUNTAIN PALM ALLEY Winter Garden, FL MLS# O6423477
  • Recently Listed with Virtual Tour
1 of 45
$565,000
3

Beds

2.1

Baths

2,162

Sq.Ft.

8873 FOUNTAIN PALM ALLEY

Winter Garden, FL

View 7840 WINTER WREN STREET Winter Garden, FL MLS# O6421167
$533,900
3

Beds

2.1

Baths

2,004

Sq.Ft.

7840 WINTER WREN STREET

Winter Garden, FL

View 6207 SUNNY TIME AVENUE Winter Garden, FL MLS# O6421162
  • New Construction with Virtual Tour
1 of 23
$547,190
3

Beds

2.1

Baths

1,628

Sq.Ft.

6207 SUNNY TIME AVENUE

Winter Garden, FL

View 6137 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6418786
  • Recently Listed with Virtual Tour
1 of 34
$599,900
4

Beds

3.1

Baths

2,607

Sq.Ft.

6137 WATERSIDE ISLAND LANE

Winter Garden, FL

View 15063 GROVESIDE ROAD Winter Garden, FL MLS# O6420626
  • New Construction with Virtual Tour
1 of 19
$516,430
3

Beds

2.1

Baths

1,846

Sq.Ft.

15063 GROVESIDE ROAD

Winter Garden, FL

View 12632 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# S5152652
  • Recently Listed with Virtual Tour
1 of 20
$575,000
4

Beds

2.1

Baths

2,148

Sq.Ft.

12632 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

View 14543 GOLDEN HARBOR LANE Winter Garden, FL MLS# O6420711
$525,000
3

Beds

2.1

Baths

2,039

Sq.Ft.

14543 GOLDEN HARBOR LANE

Winter Garden, FL

View 17059 HARBOR OAK PARKWAY Winter Garden, FL MLS# G5114379
  • Recently Listed with Virtual Tour
1 of 67
$620,000
4

Beds

3.0

Baths

2,692

Sq.Ft.

17059 HARBOR OAK PARKWAY

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 8937 LAKESHORE POINTE DRIVE Winter Garden, FL MLS# O6420679
  • Recently Listed with Virtual Tour
1 of 39
$585,000
3

Beds

2.1

Baths

2,052

Sq.Ft.

8937 LAKESHORE POINTE DRIVE

Winter Garden, FL

View 9166 CUT SHOT DRIVE Winter Garden, FL MLS# O6417611
$568,000
5

Beds

3.0

Baths

2,638

Sq.Ft.

9166 CUT SHOT DRIVE

Winter Garden, FL

View 6587 OLD CARRIAGE ROAD Winter Garden, FL MLS# O6421933
$645,000
3

Beds

2.0

Baths

2,224

Sq.Ft.

6587 OLD CARRIAGE ROAD

Winter Garden, FL

View 15411 GILLIGAN COURT Winter Garden, FL MLS# O6418437
$569,900
4

Beds

2.1

Baths

2,152

Sq.Ft.

15411 GILLIGAN COURT

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16681 SILVER BROOK WAY Winter Garden, FL MLS# O6419693
$539,790
4

Beds

2.1

Baths

1,896

Sq.Ft.

16681 SILVER BROOK WAY

Winter Garden, FL

View 13023 TRANQUIL WATER ALLEY Winter Garden, FL MLS# O6419366
  • New Construction with Virtual Tour
1 of 51
$539,990
3

Beds

2.1

Baths

2,078

Sq.Ft.

13023 TRANQUIL WATER ALLEY

Winter Garden, FL

Courtesy of LPT REALTY LLC

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

942

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

PriceCount
$0 - 100K1
$100K - 200K21
$200K - 300K91
$300K - 400K65
$400K - 500K135
$500K - 600K155
$600K - 700K102
$700K - 800K101
$800K - 900K89
$900K - 1M62
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family642
Townhouse132
Condo135
Commercial11
Rental203
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/16/2026)

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 7/17/2026.