View 12664 CHARMED DRIVE Winter Garden, FL MLS# O6358668
  • New Construction
1 of 22
$2,500
3

Beds

2.1

Baths

1,568

Sq.Ft.

12664 CHARMED DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 13817 LUNA HARVEST AVENUE Winter Garden, FL MLS# O6364255
$3,200
4

Beds

3.0

Baths

2,163

Sq.Ft.

13817 LUNA HARVEST AVENUE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 981 VINELAND ROAD Winter Garden, FL MLS# O6364366
  • New Construction with Virtual Tour
1 of 6
$0
8,700

Sq.Ft.

981 VINELAND ROAD

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 399 WINTER NELLIS CIRCLE Winter Garden, FL MLS# O6364179
$2,300
3

Beds

2.1

Baths

1,592

Sq.Ft.

399 WINTER NELLIS CIRCLE

Winter Garden, FL

Courtesy of JAMIESON PROPERTIES, INC.
View 316 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6363602
$2,100
3

Beds

2.0

Baths

1,453

Sq.Ft.

316 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

Courtesy of MBA REALTY GROUP, INC
View 11834 SHINE VIEW LANE Winter Garden, FL MLS# O6361356
  • New Construction with Virtual Tour
1 of 22
$3,300
3

Beds

2.1

Baths

2,027

Sq.Ft.

11834 SHINE VIEW LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14340 BRAEMAR STREET Winter Garden, FL MLS# O6359366
$3,500
3

Beds

2.1

Baths

2,062

Sq.Ft.

14340 BRAEMAR STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 5304 LAKE VIRGINIA STREET Winter Garden, FL MLS# O6361988
$3,300
4

Beds

3.0

Baths

2,040

Sq.Ft.

5304 LAKE VIRGINIA STREET

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 7121 BLUE INDIGO CRESCENT Winter Garden, FL MLS# O6357690
$1,800
Studio

Beds

1.0

Baths

750

Sq.Ft.

7121 BLUE INDIGO CRESCENT

Winter Garden, FL

Courtesy of THE FLORIDA LOUNGE REALTY LLC
View 12536 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6360575
  • New Construction with Virtual Tour
1 of 24
$3,400
4

Beds

3.0

Baths

2,500

Sq.Ft.

12536 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
View 15002 WINDFLOWER ALLEY Winter Garden, FL MLS# O6360807
$2,350
3

Beds

2.1

Baths

1,536

Sq.Ft.

15002 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16119 SKYSAIL STREET Winter Garden, FL MLS# O6359902
$4,200
4

Beds

3.1

Baths

3,327

Sq.Ft.

16119 SKYSAIL STREET

Winter Garden, FL

Courtesy of AAA GLOBAL VENTURES PA
View 186 S MAIN STREET Winter Garden, FL MLS# O6359871
  • New Construction with Virtual Tour
1 of 7
$0
16,000

Sq.Ft.

186 S MAIN STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 16324 SILVER GROVE BOULEVARD Winter Garden, FL MLS# O6358862
$5,000
5

Beds

4.1

Baths

3,743

Sq.Ft.

16324 SILVER GROVE BOULEVARD

Winter Garden, FL

Courtesy of WINDERMERE INTERNATIONAL REALTY
View 17865 ADRIFT ROAD Winter Garden, FL MLS# O6359041
$3,300
4

Beds

3.1

Baths

2,484

Sq.Ft.

17865 ADRIFT ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 950 S DILLARD STREET Winter Garden, FL MLS# O6359585
  • New Construction with Virtual Tour
1 of 6
$0
4,909

Sq.Ft.

950 S DILLARD STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 505 VARSITY STREET Winter Garden, FL MLS# O6345049
$1,749
2

Beds

1.0

Baths

780

Sq.Ft.

505 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 316 SOUTHERN PECAN CIRCLE 207 Winter Garden, FL MLS# O6355632
$2,050
2

Beds

2.0

Baths

1,276

Sq.Ft.

316 SOUTHERN PECAN CIRCLE 207

Winter Garden, FL

Courtesy of MBA REALTY GROUP, INC
View 5229 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6357630
  • New Construction with Virtual Tour
1 of 69
$5,600
4

Beds

3.1

Baths

3,300

Sq.Ft.

5229 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 12172 PLUMPTON DRIVE Winter Garden, FL MLS# O6352193
$2,900
3

Beds

2.1

Baths

1,850

Sq.Ft.

12172 PLUMPTON DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE

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

947

Estimated median home price

$589,000
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 - 100K4
$100K - 200K14
$200K - 300K92
$300K - 400K79
$400K - 500K157
$500K - 600K156
$600K - 700K111
$700K - 800K90
$800K - 900K78
$900K - 1M58
$1M - Max108

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family641
Townhouse143
Condo126
Commercial12
Rental228
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/24/2026)

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 3/26/2026.