View 13158 BOUNTY AVENUE Winter Garden, FL MLS# O6421321
$395,000
3

Beds

2.1

Baths

1,567

Sq.Ft.

13158 BOUNTY AVENUE

Winter Garden, FL

View 13349 HARBOR SHORE LANE Winter Garden, FL MLS# G5114466
  • Recently Listed with Virtual Tour
1 of 24
$316,000
2

Beds

2.1

Baths

1,236

Sq.Ft.

13349 HARBOR SHORE LANE

Winter Garden, FL

View 1300 EASTERN PECAN PLACE 208 Winter Garden, FL MLS# O6420493
  • Recently Listed with Virtual Tour
1 of 32
$295,000
3

Beds

2.0

Baths

1,453

Sq.Ft.

1300 EASTERN PECAN PLACE 208

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 15340 OAK APPLE COURT COURT 16B Winter Garden, FL MLS# O6419809
$350,000
3

Beds

2.1

Baths

1,544

Sq.Ft.

15340 OAK APPLE COURT COURT 16B

Winter Garden, FL

View 8019 JEREMY JOSEPH ALLEY Winter Garden, FL MLS# O6415530
$400,000
3

Beds

2.1

Baths

1,696

Sq.Ft.

8019 JEREMY JOSEPH ALLEY

Winter Garden, FL

Courtesy of SAUNDERS PLAKON
View 5863 CYPRESS HILL ROAD Winter Garden, FL MLS# TB8522840
  • Recently Listed with Virtual Tour
1 of 11
$390,000
2

Beds

2.1

Baths

1,594

Sq.Ft.

5863 CYPRESS HILL ROAD

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3227 Winter Garden, FL MLS# S5152479
  • Recently Listed with Virtual Tour
1 of 43
$365,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 3227

Winter Garden, FL

View 142 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6414551
$297,900
3

Beds

2.0

Baths

1,453

Sq.Ft.

142 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

View 1701 E BAY STREET Winter Garden, FL MLS# O6413973
$295,000
2

Beds

2.0

Baths

825

Sq.Ft.

1701 E BAY STREET

Winter Garden, FL

View 14903 DRIFTWATER DRIVE Winter Garden, FL MLS# S5151359
$380,000
3

Beds

2.1

Baths

1,745

Sq.Ft.

14903 DRIFTWATER DRIVE

Winter Garden, FL

View 5686 CYPRESS HILL ROAD Winter Garden, FL MLS# O6410760
$399,000
3

Beds

2.1

Baths

1,712

Sq.Ft.

5686 CYPRESS HILL ROAD

Winter Garden, FL

View 16461 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6414427
$400,000
4

Beds

2.1

Baths

1,768

Sq.Ft.

16461 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

View 15511 CAMPDEN STREET Winter Garden, FL MLS# O6413461
$395,000
3

Beds

2.1

Baths

1,916

Sq.Ft.

15511 CAMPDEN STREET

Winter Garden, FL

View 338 WINDFORD COURT Winter Garden, FL MLS# O6413058
$330,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

338 WINDFORD COURT

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 1437 SCARLET OAK LOOP Winter Garden, FL MLS# O6411620
$350,000
3

Beds

2.1

Baths

1,684

Sq.Ft.

1437 SCARLET OAK LOOP

Winter Garden, FL

View 13232 DANIELS LANDING CIRCLE Winter Garden, FL MLS# G5112999
$350,000
2

Beds

2.1

Baths

1,232

Sq.Ft.

13232 DANIELS LANDING CIRCLE

Winter Garden, FL

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 14501 GROVE RESORT AVENUE 3429 Winter Garden, FL MLS# O6401719
$317,900
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3429

Winter Garden, FL

View 330 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# S5150108
$300,000
3

Beds

2.0

Baths

1,453

Sq.Ft.

330 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

View 15625 BOGGY OAK CIRCLE 108B Winter Garden, FL MLS# G5112579
$340,000
3

Beds

2.1

Baths

1,419

Sq.Ft.

15625 BOGGY OAK CIRCLE 108B

Winter Garden, FL

Courtesy of SCATES REALTY & INVESTMENT PRO

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

1,058

Estimated median home price

$615,000
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 - 300K96
$300K - 400K71
$400K - 500K142
$500K - 600K186
$600K - 700K119
$700K - 800K115
$800K - 900K99
$900K - 1M70
$1M - Max137

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family746
Townhouse133
Condo143
Commercial11
Rental198
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/7/2026)

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

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties 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 7/8/2026.