View 456 SILVERDALE AVENUE Winter Garden, FL MLS# O6398638
$3,100
4

Beds

2.0

Baths

1,844

Sq.Ft.

456 SILVERDALE AVENUE

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 12506 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# S5148369
$1,600
1

Beds

1.0

Baths

2,900

Sq.Ft.

12506 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 2040 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6397668
$2,495
4

Beds

2.1

Baths

1,606

Sq.Ft.

2040 PORTCASTLE CIRCLE

Winter Garden, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 9906 SUNNY MEWS ALLEY Winter Garden, FL MLS# S5147715
$2,800
3

Beds

2.1

Baths

1,875

Sq.Ft.

9906 SUNNY MEWS ALLEY

Winter Garden, FL

Courtesy of MBT REALTY LLC
View 6148 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6398414
$3,500
5

Beds

3.1

Baths

3,468

Sq.Ft.

6148 WATERSIDE ISLAND LANE

Winter Garden, FL

Courtesy of JHY REALTY INVESTMENTS, LLC
View Address not provided Winter Garden, FL MLS# O6398448
$3,400
4

Beds

3.1

Baths

2,570

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of ORLANDO SUNSHINE REALTY
View 215 CENTER STREET 225/227 Winter Garden, FL MLS# O6398301
  • New Construction with Virtual Tour
1 of 19
$32,400
2,304

Sq.Ft.

215 CENTER STREET 225/227

Winter Garden, FL

Courtesy of PREICO REALTY SERVICES INC
View 7564 BISHOP SQUARE DRIVE Winter Garden, FL MLS# O6398382
$3,499
3

Beds

2.0

Baths

2,300

Sq.Ft.

7564 BISHOP SQUARE DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 595 9TH STREET Winter Garden, FL MLS# O6398340
  • Virtual Tour
1 of 17
$34,800
1,204

Sq.Ft.

595 9TH STREET

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 1221 PRIORY CIRCLE Winter Garden, FL MLS# O6397929
  • Virtual Tour
1 of 12
$2,800
3

Beds

2.1

Baths

1,675

Sq.Ft.

1221 PRIORY CIRCLE

Winter Garden, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 13323 PONTOON ROAD Winter Garden, FL MLS# S5147574
  • Virtual Tour
1 of 28
$2,550
3

Beds

2.1

Baths

1,451

Sq.Ft.

13323 PONTOON ROAD

Winter Garden, FL

Courtesy of LA ROSA REALTY INTERNACIONAL L
View 595 9TH STREET 115 Winter Garden, FL MLS# O6398346
$42,000
1,204

Sq.Ft.

595 9TH STREET 115

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 16743 HERONGATE DRIVE Winter Garden, FL MLS# O6397844
$2,800
3

Beds

2.0

Baths

1,705

Sq.Ft.

16743 HERONGATE DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 16374 TURNING TIDE WAY Winter Garden, FL MLS# O6397885
$2,500
3

Beds

2.1

Baths

1,568

Sq.Ft.

16374 TURNING TIDE WAY

Winter Garden, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 15713 SWEET LIMETTA DRIVE Winter Garden, FL MLS# O6397517
$4,500
4

Beds

4.1

Baths

3,377

Sq.Ft.

15713 SWEET LIMETTA DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 15367 GILLIGAN COURT Winter Garden, FL MLS# O6397119
$3,500
4

Beds

2.1

Baths

2,156

Sq.Ft.

15367 GILLIGAN COURT

Winter Garden, FL

Courtesy of PAK HOME REALTY
View 455 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6397196
  • New Construction with Virtual Tour
1 of 47
$5,000
5

Beds

3.1

Baths

2,631

Sq.Ft.

455 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 9240 WOODCRANE DRIVE Winter Garden, FL MLS# O6396748
$5,499
5

Beds

4.0

Baths

3,760

Sq.Ft.

9240 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of HAMPTON & HAMPTON MGMT LEASING
View 595 9TH STREET 116 Winter Garden, FL MLS# O6398351
$12,000
1,204

Sq.Ft.

595 9TH STREET 116

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 16085 SCARPETTA STREET Winter Garden, FL MLS# O6393325
  • New Construction with Virtual Tour
1 of 27
$2,850
3

Beds

2.0

Baths

1,689

Sq.Ft.

16085 SCARPETTA STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES

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

1,042

Estimated median home price

$609,945
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 2
$100K - 200K 21
$200K - 300K 98
$300K - 400K 83
$400K - 500K 138
$500K - 600K 170
$600K - 700K 126
$700K - 800K 118
$800K - 900K 87
$900K - 1M 74
$1M - Max 125

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 716
Townhouse 139
Condo 145
Commercial 10
Rental 212
Lots and Land 29
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 2
Farms 0

(Data as of 5/23/2026)

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 5/24/2026.