View 14843 DRIFTWATER DRIVE Winter Garden, FL MLS# S5143055
$3,000
4

Beds

2.1

Baths

1,997

Sq.Ft.

14843 DRIFTWATER DRIVE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 8125 GRAYCLIFF AVENUE Winter Garden, FL MLS# O6379515
$2,750
3

Beds

2.0

Baths

1,676

Sq.Ft.

8125 GRAYCLIFF AVENUE

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 12012 HOLYSTONE STREET Winter Garden, FL MLS# O6379118
$2,495
3

Beds

2.1

Baths

1,451

Sq.Ft.

12012 HOLYSTONE STREET

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 483 SETTING SUN DRIVE Winter Garden, FL MLS# O6379134
$2,800
4

Beds

2.0

Baths

1,960

Sq.Ft.

483 SETTING SUN DRIVE

Winter Garden, FL

Courtesy of SANCHEZ PROPERTIES GROUP LLC
View Address not provided Winter Garden, FL MLS# O6378945
$2,100
2

Beds

2.0

Baths

1,152

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of MARTI PURDY PROPERTIES INC
View 15487 BAY BRIDGE STREET Winter Garden, FL MLS# O6378648
  • New Construction with Virtual Tour
1 of 26
$2,700
3

Beds

2.1

Baths

1,691

Sq.Ft.

15487 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of SOGO REAL ESTATE SERVICES LLC
View 15274 GROVESIDE ROAD Winter Garden, FL MLS# S5142597
  • New Construction with Virtual Tour
1 of 12
$2,800
3

Beds

2.1

Baths

1,846

Sq.Ft.

15274 GROVESIDE ROAD

Winter Garden, FL

Courtesy of FRONTLINE FLORIDA REALTY, INC.
View 233 WOODFALL LANE Winter Garden, FL MLS# O6378843
  • New Construction with Virtual Tour
1 of 47
$4,365
5

Beds

3.1

Baths

2,681

Sq.Ft.

233 WOODFALL LANE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 14531 CRESTED PLUME DRIVE Winter Garden, FL MLS# S5142754
$2,900
4

Beds

2.1

Baths

1,868

Sq.Ft.

14531 CRESTED PLUME DRIVE

Winter Garden, FL

Courtesy of K REALTY
View 2262 ROMANUM DRIVE Winter Garden, FL MLS# O6378310
$3,800
6

Beds

3.1

Baths

3,862

Sq.Ft.

2262 ROMANUM DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 1276 PRIORY CIRCLE Winter Garden, FL MLS# O6377534
$2,600
3

Beds

2.1

Baths

1,793

Sq.Ft.

1276 PRIORY CIRCLE

Winter Garden, FL

Courtesy of BELLA VIEW REALTY LLC
View 4812 LIME RICKEY ALLEY Winter Garden, FL MLS# O6377477
  • New Construction with Virtual Tour
1 of 19
$3,500
4

Beds

2.1

Baths

2,084

Sq.Ft.

4812 LIME RICKEY ALLEY

Winter Garden, FL

Courtesy of ON ME REALTY
View 15523 BAY BRIDGE STREET Winter Garden, FL MLS# O6376958
  • New Construction with Virtual Tour
1 of 20
$2,800
3

Beds

2.1

Baths

1,691

Sq.Ft.

15523 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 16147 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6376967
$2,850
4

Beds

3.1

Baths

2,042

Sq.Ft.

16147 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 9249 GRAN TEATRO DRIVE Winter Garden, FL MLS# S5142467
$2,900
3

Beds

2.1

Baths

1,684

Sq.Ft.

9249 GRAN TEATRO DRIVE

Winter Garden, FL

Courtesy of PRIMUS CRE GROUP
View 14843 ASTROLYN STREET Winter Garden, FL MLS# O6374084
$1,799
3

Beds

2.0

Baths

1,260

Sq.Ft.

14843 ASTROLYN STREET

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 15532 SWEET ORANGE AVENUE Winter Garden, FL MLS# O6376556
$3,950
3

Beds

2.1

Baths

2,571

Sq.Ft.

15532 SWEET ORANGE AVENUE

Winter Garden, FL

Courtesy of BEST ORLANDO PROPERTY MANAGEMENT LLC
View 4306 OLD SYCAMORE LOOP Winter Garden, FL MLS# O6376530
$6,600
5

Beds

3.1

Baths

4,050

Sq.Ft.

4306 OLD SYCAMORE LOOP

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6376599
$5,400
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 14464 WHITTRIDGE DRIVE Winter Garden, FL MLS# G5106944
$3,400
5

Beds

3.1

Baths

2,835

Sq.Ft.

14464 WHITTRIDGE DRIVE

Winter Garden, FL

Courtesy of OPTIMA ONE REALTY, INC.

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

941

Estimated median home price

$588,900
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 - 200K12
$200K - 300K92
$300K - 400K79
$400K - 500K153
$500K - 600K160
$600K - 700K111
$700K - 800K91
$800K - 900K74
$900K - 1M60
$1M - Max105

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family644
Townhouse135
Condo126
Commercial11
Rental229
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/18/2026)

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 3/20/2026.