View 6007 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5105905
$674,475
4

Beds

2.1

Baths

2,235

Sq.Ft.

6007 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 18344 OLIVER TWIST WAY Winter Garden, FL MLS# S5140531
  • Recently Listed with Virtual Tour
1 of 34
$789,990
4

Beds

3.0

Baths

2,924

Sq.Ft.

18344 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 17309 MARSH ROAD Winter Garden, FL MLS# O6369686
  • Recently Listed with Virtual Tour
1 of 7
$800,000
Studio

Beds

0.0

Baths

17309 MARSH ROAD

Winter Garden, FL

Courtesy of UPSIDE REAL ESTATE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 17309 MARSH ROAD Winter Garden, FL MLS# O6369367
  • Recently Listed with Virtual Tour
1 of 24
$800,000
4

Beds

2.0

Baths

1,685

Sq.Ft.

17309 MARSH ROAD

Winter Garden, FL

Courtesy of UPSIDE REAL ESTATE INC
View 17305 BEACHGRASS ALLEY Winter Garden, FL MLS# O6365499
$665,935
4

Beds

3.0

Baths

2,543

Sq.Ft.

17305 BEACHGRASS ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View Address not provided Winter Garden, FL MLS# O6367937
  • Recently Listed with Virtual Tour
1 of 38
$810,000
3

Beds

2.1

Baths

2,278

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 11175 HOLLOW BAY WAY Winter Garden, FL MLS# O6367441
  • Recently Listed with Virtual Tour
1 of 30
$758,841
4

Beds

3.0

Baths

2,113

Sq.Ft.

11175 HOLLOW BAY WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 11876 SHINE VIEW LANE Winter Garden, FL MLS# O6367171
  • New Construction with Virtual Tour
1 of 18
$701,945
4

Beds

3.1

Baths

2,489

Sq.Ft.

11876 SHINE VIEW LANE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 17344 BAL HARBOUR DRIVE Winter Garden, FL MLS# O6367040
$685,000
4

Beds

3.0

Baths

2,817

Sq.Ft.

17344 BAL HARBOUR DRIVE

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 14505 BREAKWATER WAY Winter Garden, FL MLS# O6362926
$859,900
6

Beds

3.1

Baths

3,942

Sq.Ft.

14505 BREAKWATER WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16718 HARPER COVE DRIVE Winter Garden, FL MLS# O6364111
$699,900
5

Beds

4.0

Baths

2,866

Sq.Ft.

16718 HARPER COVE DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12626 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6365821
$660,000
4

Beds

3.0

Baths

2,500

Sq.Ft.

12626 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 9282 WOODCRANE DRIVE Winter Garden, FL MLS# TB8455422
  • Recently Listed with Virtual Tour
1 of 69
$789,000
4

Beds

3.1

Baths

2,650

Sq.Ft.

9282 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of DOUGLAS ELLIMAN
View 14517 BLACK LAKE PRESERVE STREET Winter Garden, FL MLS# A4674838
$690,000
4

Beds

2.1

Baths

2,569

Sq.Ft.

14517 BLACK LAKE PRESERVE STREET

Winter Garden, FL

Courtesy of DALTON WADE INC
View 15010 SAWGRASS BLUFF DRIVE Winter Garden, FL MLS# G5105276
$699,000
3

Beds

2.0

Baths

1,673

Sq.Ft.

15010 SAWGRASS BLUFF DRIVE

Winter Garden, FL

Courtesy of RE FLORIDA HOMES
View 1005 CHASE DRIVE Winter Garden, FL MLS# A4674195
  • Virtual Tour
1 of 30
OPEN HOUSE: Saturday 1/3 12:00 PM - 4:00 PM
$697,000
4

Beds

3.0

Baths

2,319

Sq.Ft.

1005 CHASE DRIVE

Winter Garden, FL

Courtesy of SAVVY AVENUE, LLC
View 17317 BEACHGRASS Winter Garden, FL MLS# O6365266
  • New Construction with Virtual Tour
1 of 23
$659,990
4

Beds

3.1

Baths

2,791

Sq.Ft.

17317 BEACHGRASS

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 15399 GILLIGAN COURT Winter Garden, FL MLS# O6365269
$699,000
4

Beds

3.1

Baths

2,758

Sq.Ft.

15399 GILLIGAN COURT

Winter Garden, FL

Courtesy of FCG REALTY
View 6152 MERIWETHER CRESCENT Winter Garden, FL MLS# O6365054
$814,900
5

Beds

3.1

Baths

3,367

Sq.Ft.

6152 MERIWETHER CRESCENT

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6364989
$849,000
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS

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

774

Estimated median home price

$585,000
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 - 100K7
$100K - 200K8
$200K - 300K65
$300K - 400K82
$400K - 500K134
$500K - 600K122
$600K - 700K85
$700K - 800K68
$800K - 900K62
$900K - 1M49
$1M - Max92

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family499
Townhouse118
Condo111
Commercial10
Rental225
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/1/2026)

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 1/2/2026.