View 14835 OLD THICKET TRACE Winter Garden, FL MLS# O6375317
  • Recently Listed with Virtual Tour
1 of 32
$3,800
4

Beds

3.1

Baths

2,630

Sq.Ft.

14835 OLD THICKET TRACE

Winter Garden, FL

Courtesy of THE AGENCY FL
View 418 CHARLES STREET Winter Garden, FL MLS# O6375338
  • Recently Listed with Virtual Tour
1 of 27
$2,600
3

Beds

2.0

Baths

1,439

Sq.Ft.

418 CHARLES STREET

Winter Garden, FL

Courtesy of CANI PROPERTY MANAGEMENT
View 16560 WINGSPREAD LOOP Winter Garden, FL MLS# O6375137
$2,800
3

Beds

2.0

Baths

1,676

Sq.Ft.

16560 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
The time to sell is now! THE TIME TO SELL IS NOW!
View 9129 PINCH SHOT DRIVE Winter Garden, FL MLS# O6374872
  • Recently Listed with Virtual Tour
1 of 21
$3,150
5

Beds

3.0

Baths

2,638

Sq.Ft.

9129 PINCH SHOT DRIVE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 13890 TITLE WAY Winter Garden, FL MLS# O6372589
  • Recently Listed with Virtual Tour
1 of 31
$2,950
3

Beds

2.1

Baths

1,717

Sq.Ft.

13890 TITLE WAY

Winter Garden, FL

Courtesy of PRISTINE INTERNATIONAL REALTY LLC
View 319 GRAND ROYAL CIRCLE Winter Garden, FL MLS# G5106960
  • Recently Listed
1 of 29
$2,600
3

Beds

2.0

Baths

1,612

Sq.Ft.

319 GRAND ROYAL CIRCLE

Winter Garden, FL

Courtesy of ENGEL & VOLKERS CLERMONT
View 11425 PIXIE MANDARIN CT Winter Garden, FL MLS# S5142077
  • Recently Listed
1 of 26
$3,200
3

Beds

2.0

Baths

1,791

Sq.Ft.

11425 PIXIE MANDARIN CT

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15375 BURGTHEATER DRIVE Winter Garden, FL MLS# S5142163
  • Recently Listed with Virtual Tour
1 of 15
$2,900
3

Beds

2.1

Baths

1,563

Sq.Ft.

15375 BURGTHEATER DRIVE

Winter Garden, FL

Courtesy of MBT REALTY LLC
View 233 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# S5142016
  • Recently Listed with Virtual Tour
1 of 10
$1,795
2

Beds

1.0

Baths

966

Sq.Ft.

233 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of HOMESMART
View 11007 BOOKMARK LANE Winter Garden, FL MLS# O6375276
  • Recently Listed with Virtual Tour
1 of 16
$2,600
3

Beds

2.1

Baths

1,599

Sq.Ft.

11007 BOOKMARK LANE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 16332 HAMLIN VIEW STREET Winter Garden, FL MLS# O6374681
  • Recently Listed with Virtual Tour
1 of 60
$2,800
4

Beds

3.0

Baths

1,725

Sq.Ft.

16332 HAMLIN VIEW STREET

Winter Garden, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 1446 WAVERUNNER LANE Winter Garden, FL MLS# O6372952
  • Recently Listed with Virtual Tour
1 of 35
$2,990
4

Beds

3.0

Baths

2,030

Sq.Ft.

1446 WAVERUNNER LANE

Winter Garden, FL

Courtesy of HONEST REAL ESTATE COMPANY
View 16430 TANGERINE MESA DRIVE Winter Garden, FL MLS# O6374204
  • Recently Listed with Virtual Tour
1 of 26
$2,850
4

Beds

3.0

Baths

1,715

Sq.Ft.

16430 TANGERINE MESA DRIVE

Winter Garden, FL

Courtesy of KARDOSH REALTY
View 12063 HOLYSTONE STREET Winter Garden, FL MLS# O6374014
  • Recently Listed with Virtual Tour
1 of 48
$2,690
3

Beds

2.1

Baths

1,451

Sq.Ft.

12063 HOLYSTONE STREET

Winter Garden, FL

Courtesy of ALLUX REAL ESTATE LLC
View 13139 TOLLCROSS WAY Winter Garden, FL MLS# O6374230
  • Recently Listed
1 of 42
$3,200
3

Beds

2.1

Baths

2,062

Sq.Ft.

13139 TOLLCROSS WAY

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 15663 PELICAN CAY DRIVE Winter Garden, FL MLS# O6374627
  • Recently Listed with Virtual Tour
1 of 26
$3,750
4

Beds

3.1

Baths

2,489

Sq.Ft.

15663 PELICAN CAY DRIVE

Winter Garden, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 5755 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6374324
  • Recently Listed with Virtual Tour
1 of 21
$3,100
4

Beds

2.1

Baths

2,061

Sq.Ft.

5755 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
View 1440 SCARLET OAK LOOP Winter Garden, FL MLS# O6374115
  • Recently Listed with Virtual Tour
1 of 25
$2,550
3

Beds

2.1

Baths

1,638

Sq.Ft.

1440 SCARLET OAK LOOP

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 13121 BOUNTY AVENUE Winter Garden, FL MLS# O6374687
  • Recently Listed with Virtual Tour
1 of 38
$2,600
3

Beds

2.1

Baths

1,568

Sq.Ft.

13121 BOUNTY AVENUE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15506 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6373188
  • Recently Listed with Virtual Tour
1 of 47
$3,400
4

Beds

2.1

Baths

2,071

Sq.Ft.

15506 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of DELUX MIAMI GROUP, 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

821

Estimated median home price

$590,700
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 7
$100K - 200K 11
$200K - 300K 74
$300K - 400K 80
$400K - 500K 144
$500K - 600K 115
$600K - 700K 103
$700K - 800K 76
$800K - 900K 70
$900K - 1M 49
$1M - Max 92

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 539
Townhouse 126
Condo 115
Commercial 7
Rental 243
Lots and Land 32
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 1/27/2026)

Information deemed reliable but not guaranteed.

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 1/27/2026.