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 3305 Winter Garden, FL MLS# O6300378
$250,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3305

Winter Garden, FL

Courtesy of THE FLORIDA LOUNGE REALTY LLC
View 844 KLONDIKE STREET Winter Garden, FL MLS# O6350424
$250,000
1,300

Sq.Ft.

844 KLONDIKE STREET

Winter Garden, FL

Courtesy of ALVARENGA REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1125 LINCOLN TERRACE Winter Garden, FL MLS# O6345921
$249,900
3

Beds

1.0

Baths

814

Sq.Ft.

1125 LINCOLN TERRACE

Winter Garden, FL

Courtesy of IHOME REALTY FL LLC
View 14501 GROVE RESORT AVENUE 1332 Winter Garden, FL MLS# S5132222
$249,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1332

Winter Garden, FL

Courtesy of FLARE PROPERTIES LLC
View 14200 AVALON ROAD 426 Winter Garden, FL MLS# O6353582
$249,000
2

Beds

2.0

Baths

1,203

Sq.Ft.

14200 AVALON ROAD 426

Winter Garden, FL

Courtesy of BLUE CHIP INTERNATIONAL REALTY LLC
View 1040 MAXEY DRIVE Winter Garden, FL MLS# O6276848
$235,000
3

Beds

2.0

Baths

1,184

Sq.Ft.

1040 MAXEY DRIVE

Winter Garden, FL

Courtesy of ALLIANCE REAL ESTATE GROUP
View 14501 GROVE RESORT AVENUE 3230 Winter Garden, FL MLS# S5140628
  • Recently Listed with Virtual Tour
1 of 34
$235,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3230

Winter Garden, FL

Courtesy of FLARE PROPERTIES LLC
View 14200 AVALON ROAD 409 Winter Garden, FL MLS# O6307611
$233,000
2

Beds

2.0

Baths

1,253

Sq.Ft.

14200 AVALON ROAD 409

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 14501 GROVE RESORT AVENUE 2522 Winter Garden, FL MLS# O6285998
  • New Construction with Virtual Tour
1 of 36
$232,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 2522

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14501 GROVE RESORT AVENUE 2231 Winter Garden, FL MLS# O6304520
$230,500
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 2231

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 1009 WESTSIDE DRIVE Winter Garden, FL MLS# S5136485
$230,000
3

Beds

2.0

Baths

1,120

Sq.Ft.

1009 WESTSIDE DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 14501 GROVE RESORT AVE 2138 Winter Garden, FL MLS# S5123245
$229,990
3

Beds

2.0

Baths

1,395

Sq.Ft.

14501 GROVE RESORT AVE 2138

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
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 428 SAND LIME ROAD Winter Garden, FL MLS# S5119829
$225,000
3

Beds

1.1

Baths

1,234

Sq.Ft.

428 SAND LIME ROAD

Winter Garden, FL

Courtesy of VYLLA HOME
View 14200 AVALON ROAD 406 Winter Garden, FL MLS# O6335697
$225,000
3

Beds

2.0

Baths

1,288

Sq.Ft.

14200 AVALON ROAD 406

Winter Garden, FL

Courtesy of MAINFRAME REAL ESTATE
View 14501 GROVE RESORT 3540 Winter Garden, FL MLS# O6347617
$225,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT 3540

Winter Garden, FL

Courtesy of REALTY ONE GROUP INSPIRATION
View 304 ERON WAY 2 Winter Garden, FL MLS# O6366946
  • Recently Listed
1 of 3
$225,000
2

Beds

2.0

Baths

840

Sq.Ft.

304 ERON WAY 2

Winter Garden, FL

Courtesy of WINDERMERE REALTY GROUP
View 14501 GROVE RESORT AVENUE 2709 Winter Garden, FL MLS# O6197673
$220,000
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 2709

Winter Garden, FL

Courtesy of IRM INVEST., REAL EST.& MGMT.
View 22 WINDTREE LANE 203 Winter Garden, FL MLS# S5139914
$220,000
2

Beds

2.0

Baths

918

Sq.Ft.

22 WINDTREE LANE 203

Winter Garden, FL

Courtesy of EXP REALTY LLC

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.

Copyright 2026 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 1/2/2026.

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 1/2/2026.