View 16217 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6298248
$405,000
3

Beds

2.1

Baths

1,792

Sq.Ft.

16217 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View W ORANGE COUNTRY CLUB DRIVE Winter Garden, FL MLS# O6244629
$400,000
Studio

Beds

0.0

Baths

W ORANGE COUNTRY CLUB DRIVE

Winter Garden, FL

Courtesy of KELLY RIGHT REAL ESTATE
View 14501 Grove Resort Ave 3-3442 Winter Garden, FL MLS# A11770012
$400,000
3

Beds

3.0

Baths

14501 Grove Resort Ave 3-3442

Winter Garden, FL

Courtesy of FLORIDA REALTY OF MIAMI CORP
The time to sell is now! THE TIME TO SELL IS NOW!
View 11018 HANLON TERRACE ALLEY Winter Garden, FL MLS# TB8395071
$400,000
4

Beds

3.0

Baths

2,037

Sq.Ft.

11018 HANLON TERRACE ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS SUBURBAN TAMPA
View 282 E NEWELL STREET Winter Garden, FL MLS# O6339616
$400,000
Studio

Beds

0.0

Baths

282 E NEWELL STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 12325 & 12303 STAGG ROAD Winter Garden, FL MLS# O6358096
$400,000
Studio

Beds

0.0

Baths

12325 & 12303 STAGG ROAD

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 14501 GROVE RESORT AVENUE 1318 Winter Garden, FL MLS# S5094992
$399,900
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1318

Winter Garden, FL

Courtesy of PORTAL ORLANDO REALTY, 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 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 0 GROVE RESORT AVENUE 3209 Winter Garden, FL MLS# O6238165
$399,000
2

Beds

2.0

Baths

1,434

Sq.Ft.

0 GROVE RESORT AVENUE 3209

Winter Garden, FL

Courtesy of SUNNY 365 REALTY GROUP
View 14501 GROVE RESORT AVENUE 3632 Winter Garden, FL MLS# S5124117
$399,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3632

Winter Garden, FL

Courtesy of AMERICAN INTERNATIONAL REALTY
View 9591 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6318183
$399,000
3

Beds

2.1

Baths

1,789

Sq.Ft.

9591 AMBER CHESTNUT WAY

Winter Garden, FL

Courtesy of STANICA REALTY GROUP
View 13158 BOUNTY AVENUE Winter Garden, FL MLS# O6334532
$399,000
3

Beds

2.1

Baths

1,567

Sq.Ft.

13158 BOUNTY AVENUE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 12043 HOLYSTONE STREET Winter Garden, FL MLS# O6339950
$399,000
3

Beds

2.1

Baths

1,568

Sq.Ft.

12043 HOLYSTONE STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 329 W BAY STREET Winter Garden, FL MLS# O6349821
$399,000
2

Beds

1.0

Baths

1,004

Sq.Ft.

329 W BAY STREET

Winter Garden, FL

Courtesy of SHAHRAM SONDI + CO.
View 15511 CAMPDEN STREET Winter Garden, FL MLS# O6337720
$395,000
3

Beds

2.1

Baths

1,916

Sq.Ft.

15511 CAMPDEN STREET

Winter Garden, FL

Courtesy of SUSANA JORDAN STUTSMAN
View 14501 GROVE RESORT AVENUE 3327 Winter Garden, FL MLS# O6178930
$390,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 3327

Winter Garden, FL

Courtesy of FLORIDA CAPITAL REALTY
View 14501 GROVE RESORT AVENUE 3733 Winter Garden, FL MLS# O6281904
$390,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3733

Winter Garden, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 14501 GROVE RESORT AVENUE 2623 Winter Garden, FL MLS# O6329943
$390,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 2623

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 14501 GROVE RESORT AVENUE 3535 Winter Garden, FL MLS# S5138632
$389,990
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 3535

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, 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

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.

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 12/29/2025.

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.

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 12/29/2025.