View 2010 BOSS HEWETT STREET Winter Garden, FL MLS# O6423216
  • Recently Listed with Virtual Tour
1 of 94
$1,500,000
5

Beds

4.0

Baths

3,781

Sq.Ft.

2010 BOSS HEWETT STREET

Winter Garden, FL

Courtesy of RE/MAX ASSURED
View 14067 JOMATT LOOP Winter Garden, FL MLS# O6422734
  • Recently Listed with Virtual Tour
1 of 55
$1,099,000
6

Beds

5.0

Baths

4,741

Sq.Ft.

14067 JOMATT LOOP

Winter Garden, FL

View 10750 PETRILLO WAY Winter Garden, FL MLS# O6423067
  • Recently Listed with Virtual Tour
1 of 43
$749,000
3

Beds

2.1

Baths

2,613

Sq.Ft.

10750 PETRILLO WAY

Winter Garden, FL

Courtesy of SUNSHINE LIFE REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 13551 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6423265
  • Recently Listed with Virtual Tour
1 of 53
$299,500
2

Beds

2.1

Baths

1,293

Sq.Ft.

13551 DANIELS LANDING CIRCLE

Winter Garden, FL

View 346 CRYSTAL WOOD DRIVE Winter Garden, FL MLS# O6423640
  • Recently Listed with Virtual Tour
1 of 28
$899,000
4

Beds

3.0

Baths

3,147

Sq.Ft.

346 CRYSTAL WOOD DRIVE

Winter Garden, FL

View 443 WRANGLER ROAD Winter Garden, FL MLS# O6423892
  • Recently Listed with Virtual Tour
1 of 57
$795,000
4

Beds

3.1

Baths

2,877

Sq.Ft.

443 WRANGLER ROAD

Winter Garden, FL

Courtesy of PREFERRED RE BROKERS III
View 8150 RED STOPPER LANE Winter Garden, FL MLS# O6416867
  • Recently Listed with Virtual Tour
1 of 47
$439,900
3

Beds

2.1

Baths

1,738

Sq.Ft.

8150 RED STOPPER LANE

Winter Garden, FL

View 15081 GROVESIDE ROAD Winter Garden, FL MLS# O6422882
  • Recently Listed with Virtual Tour
1 of 5
$510,580
3

Beds

2.1

Baths

1,846

Sq.Ft.

15081 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 14543 WHITTRIDGE DRIVE Winter Garden, FL MLS# G5114561
  • Recently Listed with Virtual Tour
1 of 37
$574,900
3

Beds

2.0

Baths

2,224

Sq.Ft.

14543 WHITTRIDGE DRIVE

Winter Garden, FL

View 14816 PORTER RD Winter Garden, FL MLS# O6423001
  • Recently Listed with Virtual Tour
1 of 61
$545,000
5

Beds

3.0

Baths

2,790

Sq.Ft.

14816 PORTER RD

Winter Garden, FL

View 15619 GIANT FOXTAIL COURT Winter Garden, FL MLS# O6422589
  • Recently Listed with Virtual Tour
1 of 69
$1,450,000
4

Beds

3.1

Baths

3,086

Sq.Ft.

15619 GIANT FOXTAIL COURT

Winter Garden, FL

View 2025 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6422627
  • Recently Listed with Virtual Tour
1 of 60
$715,000
5

Beds

4.0

Baths

2,655

Sq.Ft.

2025 WINTERMERE POINTE DRIVE

Winter Garden, FL

View 16625 POINT ROCK DRIVE Winter Garden, FL MLS# O6423042
  • Recently Listed with Virtual Tour
1 of 53
$569,900
3

Beds

2.1

Baths

2,216

Sq.Ft.

16625 POINT ROCK DRIVE

Winter Garden, FL

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 16936 TRADEWIND POINT Winter Garden, FL MLS# O6424578
  • Recently Listed with Virtual Tour
1 of 54
$645,000
4

Beds

3.1

Baths

2,930

Sq.Ft.

16936 TRADEWIND POINT

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 427 EGRET PLACE DRIVE Winter Garden, FL MLS# O6422411
  • Recently Listed with Virtual Tour
1 of 64
$1,095,000
6

Beds

5.0

Baths

4,693

Sq.Ft.

427 EGRET PLACE DRIVE

Winter Garden, FL

View 16161 MANGROVE ROAD Winter Garden, FL MLS# O6420311
  • Recently Listed with Virtual Tour
1 of 48
$499,900
3

Beds

2.1

Baths

2,200

Sq.Ft.

16161 MANGROVE ROAD

Winter Garden, FL

View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6422754
  • Recently Listed with Virtual Tour
1 of 87
$799,000
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

View 9567 MEADOW HUNT WAY Winter Garden, FL MLS# O6422408
  • Recently Listed with Virtual Tour
1 of 69
$965,000
4

Beds

3.2

Baths

4,305

Sq.Ft.

9567 MEADOW HUNT WAY

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

989

Estimated median home price

$610,000
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 - 200K20
$200K - 300K93
$300K - 400K62
$400K - 500K141
$500K - 600K170
$600K - 700K104
$700K - 800K115
$800K - 900K100
$900K - 1M63
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family688
Townhouse131
Condo136
Commercial11
Rental215
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/22/2026)

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 7/22/2026.