View 446 REGAL DOWNS CIRCLE Winter Garden, FL MLS# O6360436
$328,800
2

Beds

2.0

Baths

1,508

Sq.Ft.

446 REGAL DOWNS CIRCLE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 10097 MEMOIR AVENUE Winter Garden, FL MLS# O6360629
$399,500
3

Beds

2.1

Baths

1,636

Sq.Ft.

10097 MEMOIR AVENUE

Winter Garden, FL

Courtesy of FLORIDA HOME TEAM REALTY LLC
View 14801 EVERGREEN OAK LOOP Winter Garden, FL MLS# O6360967
$415,000
3

Beds

2.1

Baths

1,741

Sq.Ft.

14801 EVERGREEN OAK LOOP

Winter Garden, FL

Courtesy of VYLLA HOME
The time to sell is now! THE TIME TO SELL IS NOW!
View 14501 GROVE RESORT AVENUE 1535 Winter Garden, FL MLS# TB8447837
$435,999
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 1535

Winter Garden, FL

Courtesy of BY OWNER.COM
View 8105 RED STOPPER LANE Winter Garden, FL MLS# O6360454
$425,000
3

Beds

2.1

Baths

1,725

Sq.Ft.

8105 RED STOPPER LANE

Winter Garden, FL

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
View 15693 KINNOW MANDARIN LANE Winter Garden, FL MLS# O6357939
$449,000
4

Beds

3.0

Baths

2,033

Sq.Ft.

15693 KINNOW MANDARIN LANE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14501 GROVE RESORT AVENUE 3716 Winter Garden, FL MLS# O6360135
$399,900
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3716

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 15825 GEM VIEW STREET Winter Garden, FL MLS# O6360246
  • Adult Community with Virtual Tour
1 of 30
$440,080
2

Beds

2.0

Baths

1,579

Sq.Ft.

15825 GEM VIEW STREET

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 15831 GEM VIEW STREET Winter Garden, FL MLS# O6360251
  • Adult Community with Virtual Tour
1 of 30
$442,090
3

Beds

2.0

Baths

1,579

Sq.Ft.

15831 GEM VIEW STREET

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 15843 GEM VIEW STREET Winter Garden, FL MLS# O6360258
  • Adult Community with Virtual Tour
1 of 25
$451,090
2

Beds

2.0

Baths

1,579

Sq.Ft.

15843 GEM VIEW STREET

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 15873 GEM VIEW STREET Winter Garden, FL MLS# O6360259
  • Adult Community with Virtual Tour
1 of 25
$448,970
2

Beds

2.0

Baths

1,579

Sq.Ft.

15873 GEM VIEW STREET

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 6355 GLORY BOWER DRIVE Winter Garden, FL MLS# O6361074
$440,000
3

Beds

2.1

Baths

1,714

Sq.Ft.

6355 GLORY BOWER DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 18153 CIDER MILL LANE Winter Garden, FL MLS# O6359765
  • New Construction with Virtual Tour
1 of 14
$419,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

18153 CIDER MILL LANE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 14501 GROVE RESORT AVENUE 3712 Winter Garden, FL MLS# O6359458
$325,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3712

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 1166 WESTSIDE DRIVE Winter Garden, FL MLS# O6359545
$229,000
3

Beds

2.0

Baths

846

Sq.Ft.

1166 WESTSIDE DRIVE

Winter Garden, FL

Courtesy of MILLENIUM REALTY GROUP
View 1428 SCARLET OAK LOOP Winter Garden, FL MLS# O6359131
$359,900
3

Beds

2.1

Baths

1,592

Sq.Ft.

1428 SCARLET OAK LOOP

Winter Garden, FL

Courtesy of ERIC BRESS REAL ESTATE LLC
View 1286 WINTER GREEN WAY Winter Garden, FL MLS# G5104510
$255,000
2

Beds

1.1

Baths

1,144

Sq.Ft.

1286 WINTER GREEN WAY

Winter Garden, FL

Courtesy of EXIT REALTY TRI-COUNTY
View 14501 GROVE RESORT AVENUE 1545 Winter Garden, FL MLS# O6357793
$213,900
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1545

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 14501 GROVE RESORT AVENUE 3215 Winter Garden, FL MLS# S5138120
$259,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3215

Winter Garden, FL

Courtesy of TEAM DONOVAN
View 10061 BEDTIME STORY DRIVE Winter Garden, FL MLS# O6358280
$450,000
3

Beds

2.1

Baths

1,770

Sq.Ft.

10061 BEDTIME STORY DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY

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

794

Estimated median home price

$589,990
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 - 200K7
$200K - 300K66
$300K - 400K81
$400K - 500K138
$500K - 600K125
$600K - 700K90
$700K - 800K67
$800K - 900K67
$900K - 1M49
$1M - Max97

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family516
Townhouse123
Condo110
Commercial10
Rental232
Lots and Land31
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 12/28/2025)

Information deemed reliable but not guaranteed.

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.

Copyright 2025 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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.

Data is updated as of 12/28/2025.

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 12/28/2025.