View 16971 TRADEWIND POINT Winter Garden, FL MLS# O6426531
  • Recently Listed with Virtual Tour
1 of 51
$703,000
4

Beds

3.1

Baths

2,782

Sq.Ft.

16971 TRADEWIND POINT

Winter Garden, FL

View 1668 SCARLET OAK LOOP C Winter Garden, FL MLS# O6428398
$335,000
3

Beds

2.1

Baths

1,699

Sq.Ft.

1668 SCARLET OAK LOOP C

Winter Garden, FL

View 16124 AZURE KEY STREET Winter Garden, FL MLS# O6428748
$778,000
5

Beds

4.0

Baths

2,840

Sq.Ft.

16124 AZURE KEY STREET

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 7594 LAKE HANCOCK BOULEVARD Winter Garden, FL MLS# O6426625
  • Recently Listed with Virtual Tour
1 of 58
$859,000
4

Beds

2.1

Baths

2,990

Sq.Ft.

7594 LAKE HANCOCK BOULEVARD

Winter Garden, FL

View 14897 ELLINGSWORTH LANE Winter Garden, FL MLS# O6429007
$945,000
4

Beds

3.1

Baths

3,588

Sq.Ft.

14897 ELLINGSWORTH LANE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 227 W BAY STREET Winter Garden, FL MLS# S5154601
  • Recently Listed
1 of 74
$565,000
3

Beds

2.0

Baths

1,338

Sq.Ft.

227 W BAY STREET

Winter Garden, FL

View 15510 CAMPDEN STREET Winter Garden, FL MLS# S5154448
  • Recently Listed with Virtual Tour
1 of 14
$369,900
3

Beds

2.1

Baths

1,924

Sq.Ft.

15510 CAMPDEN STREET

Winter Garden, FL

View 484 W PLANT STREET Winter Garden, FL MLS# O6428419
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Saturday 8/1 10:00 AM - 12:00 PM
$915,000
3

Beds

3.1

Baths

2,242

Sq.Ft.

484 W PLANT STREET

Winter Garden, FL

View 7189 SUMMERLAKE GROVES STREET Winter Garden, FL MLS# O6428522
  • Recently Listed with Virtual Tour
1 of 36
$530,000
3

Beds

2.1

Baths

2,138

Sq.Ft.

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3406 Winter Garden, FL MLS# S5154450
  • Recently Listed with Virtual Tour
1 of 29
$179,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3406

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 2119 Winter Garden, FL MLS# S5154456
  • Recently Listed with Virtual Tour
1 of 28
$219,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 2119

Winter Garden, FL

View 10108 SALT POINT DRIVE Winter Garden, FL MLS# S5154452
  • Recently Listed with Virtual Tour
1 of 30
$425,000
3

Beds

2.1

Baths

1,505

Sq.Ft.

10108 SALT POINT DRIVE

Winter Garden, FL

View 13852 JOMATT LOOP Winter Garden, FL MLS# O6427925
  • Recently Listed with Virtual Tour
1 of 39
$1,030,000
4

Beds

3.1

Baths

4,000

Sq.Ft.

13852 JOMATT LOOP

Winter Garden, FL

View 637 GRASSY STONE DRIVE Winter Garden, FL MLS# O6427944
  • Recently Listed with Virtual Tour
1 of 67
OPEN HOUSE: Saturday 8/1 1:00 PM - 3:00 PM
$850,000
5

Beds

3.0

Baths

3,241

Sq.Ft.

637 GRASSY STONE DRIVE

Winter Garden, FL

View 6274 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5115512
$1,016,060
6

Beds

4.0

Baths

4,236

Sq.Ft.

6274 FLOWERING CHERRY BEND

Winter Garden, FL

View 17631 LAKE STAR ROAD Winter Garden, FL MLS# TB8532670
  • Recently Listed with Virtual Tour
1 of 41
$830,186
3

Beds

3.0

Baths

3,004

Sq.Ft.

17631 LAKE STAR ROAD

Winter Garden, FL

View 2031 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6428109
  • Recently Listed with Virtual Tour
1 of 29
OPEN HOUSE: Wednesday 7/29 11:00 AM - 2:00 PM
$589,000
4

Beds

2.0

Baths

2,048

Sq.Ft.

2031 WINTERMERE POINTE DRIVE

Winter Garden, FL

View 7052 ENCHANTED LAKE DRIVE Winter Garden, FL MLS# S5154077
  • Recently Listed with Virtual Tour
1 of 65
OPEN HOUSE: Saturday 8/1 12:00 PM - 3:00 PM
$775,000
5

Beds

4.0

Baths

3,264

Sq.Ft.

7052 ENCHANTED LAKE DRIVE

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View 9225 HOLLISTON CREEK PLACE Winter Garden, FL MLS# O6427589
  • Recently Listed with Virtual Tour
1 of 44
$1,150,000
5

Beds

4.0

Baths

3,897

Sq.Ft.

9225 HOLLISTON CREEK PLACE

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3231 Winter Garden, FL MLS# O6423511
  • Recently Listed with Virtual Tour
1 of 51
$190,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 3231

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

1,063

Estimated median home price

$615,000
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 - 200K24
$200K - 300K92
$300K - 400K68
$400K - 500K155
$500K - 600K181
$600K - 700K113
$700K - 800K129
$800K - 900K102
$900K - 1M67
$1M - Max131

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family750
Townhouse140
Condo139
Commercial10
Rental223
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/29/2026)

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.

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 7/29/2026.