View Address not provided Winter Garden, FL MLS# O6403450
$320,000
2

Beds

2.0

Baths

1,434

Sq.Ft.

Address not provided

Winter Garden, FL

View 342 WINDFORD COURT Winter Garden, FL MLS# O6407632
$319,900
3

Beds

2.0

Baths

1,194

Sq.Ft.

342 WINDFORD COURT

Winter Garden, FL

View 15357 OAK APPLE COURT 4C Winter Garden, FL MLS# O6401625
$319,500
3

Beds

2.1

Baths

1,699

Sq.Ft.

15357 OAK APPLE COURT 4C

Winter Garden, FL

Courtesy of THE SIMON SIMAAN GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 14501 GROVE RESORT AVENUE 2536 Winter Garden, FL MLS# O6364192
$314,900
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 2536

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 1518 Winter Garden, FL MLS# O6380808
$310,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1518

Winter Garden, FL

Courtesy of FLORIDA CAPITAL REALTY
View 15316 OAK APPLE COURT B Winter Garden, FL MLS# O6397688
$310,000
3

Beds

2.1

Baths

1,544

Sq.Ft.

15316 OAK APPLE COURT B

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3134 Winter Garden, FL MLS# O6235590
$309,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3134

Winter Garden, FL

Courtesy of RE/MAX SOLUTIONS
View 14501 GROVE RESORT AVENUE 3137 Winter Garden, FL MLS# O6236595
$309,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3137

Winter Garden, FL

Courtesy of RE/MAX SOLUTIONS
View 14501 GROVE RESORT AVENUE 3229 Winter Garden, FL MLS# O6236600
$309,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3229

Winter Garden, FL

Courtesy of RE/MAX SOLUTIONS
View 14501 GROVE RESORT AVENUE 3329 Winter Garden, FL MLS# O6236603
$309,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3329

Winter Garden, FL

Courtesy of RE/MAX SOLUTIONS
View 13759 GOLDEN RUSSET DRIVE Winter Garden, FL MLS# O6409757
$309,000
3

Beds

2.1

Baths

1,647

Sq.Ft.

13759 GOLDEN RUSSET DRIVE

Winter Garden, FL

View 241 DEEPCOVE ROAD Winter Garden, FL MLS# O6429690
$309,000
2

Beds

2.1

Baths

1,234

Sq.Ft.

241 DEEPCOVE ROAD

Winter Garden, FL

View 13349 HARBOR SHORE LANE Winter Garden, FL MLS# G5114466
$307,000
2

Beds

2.1

Baths

1,236

Sq.Ft.

13349 HARBOR SHORE LANE

Winter Garden, FL

View 441 E CYPRESS STREET Winter Garden, FL MLS# O6407560
$305,000
Studio

Beds

0.0

Baths

441 E CYPRESS STREET

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 1105 Winter Garden, FL MLS# O6365470
$304,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1105

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3109 Winter Garden, FL MLS# O6386655
$299,900
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 3109

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3429 Winter Garden, FL MLS# O6401719
$299,900
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3429

Winter Garden, FL

View ARROWHEAD BOULEVARD Winter Garden, FL MLS# S5155609
$299,900
Studio

Beds

0.0

Baths

ARROWHEAD BOULEVARD

Winter Garden, FL

Courtesy of FLORIDA REALTY RESULTS LLC
View 14501 GROVE RESORT AVENUE 1612 Winter Garden, FL MLS# S5136940
$299,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1612

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View 14501 GROVE RESORT AVENUE 1703 Winter Garden, FL MLS# O6394100
$299,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 1703

Winter Garden, FL

Courtesy of REALTY ONE GROUP INSPIRATION

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

1,023

Estimated median home price

$605,000
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 - 100K1
$100K - 200K22
$200K - 300K90
$300K - 400K78
$400K - 500K153
$500K - 600K167
$600K - 700K109
$700K - 800K113
$800K - 900K110
$900K - 1M62
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family709
Townhouse145
Condo133
Commercial9
Rental189
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/30/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 8/31/2026.