View 188 MARY STREET Winter Garden, FL MLS# O6352643
$119,000
Studio

Beds

0.0

Baths

188 MARY STREET

Winter Garden, FL

Courtesy of TOP ORLANDO REALTY
View 651 J W JONES ROAD Winter Garden, FL MLS# G5103151
$252,000
3

Beds

2.0

Baths

1,747

Sq.Ft.

651 J W JONES ROAD

Winter Garden, FL

View 844 KLONDIKE STREET Winter Garden, FL MLS# O6350424
$225,000
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 68 WINDTREE LANE 201 Winter Garden, FL MLS# O6351273
$214,000
2

Beds

2.0

Baths

918

Sq.Ft.

68 WINDTREE LANE 201

Winter Garden, FL

Courtesy of KEY CLASSIC REALTY LLC
View 14501 GROVE RESORT AVENUE 1440 Winter Garden, FL MLS# O6348465
$245,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1440

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 15695 GROVE RESORT AVENUE 4417 Winter Garden, FL MLS# O6346254
$150,000
Studio

Beds

1.0

Baths

350

Sq.Ft.

15695 GROVE RESORT AVENUE 4417

Winter Garden, FL

Courtesy of CONDOMINIUM MARKETING LLC
View 14501 GROVE RESORT AVENUE 2119 Winter Garden, FL MLS# G5100002
$224,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 2119

Winter Garden, FL

Courtesy of WATSON REALTY CORP., REALTORS
View 14501 GROVE RESORT AVENUE 2436 Winter Garden, FL MLS# O6323858
$268,500
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 2436

Winter Garden, FL

Courtesy of NOVALUX REALTY, LLC.
View 14501 GROVE RESORT AVENUE 3406 Winter Garden, FL MLS# G5098127
$204,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3406

Winter Garden, FL

Courtesy of WATSON REALTY CORP., REALTORS
View 14501 GROVE RESORT AVENUE 2103 Winter Garden, FL MLS# O6300605
$265,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 2103

Winter Garden, FL

Courtesy of RE/MAX DOWNTOWN
View 14501 GROVE RESORT AVENUE 2232 Winter Garden, FL MLS# O6300606
$265,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 2232

Winter Garden, FL

Courtesy of RE/MAX DOWNTOWN
View 120 S DILLARD STREET Winter Garden, FL MLS# O6280408
$160,000
2,638

Sq.Ft.

120 S DILLARD STREET

Winter Garden, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
View 14501 GROVE RESORT AVENUE 1237 Winter Garden, FL MLS# O6279915
$210,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1237

Winter Garden, FL

Courtesy of KARDOSH REALTY
View 764 KLONDIKE STREET Winter Garden, FL MLS# O6255583
$59,000
Studio

Beds

0.0

Baths

764 KLONDIKE STREET

Winter Garden, FL

View 14577 SIPLIN ROAD Winter Garden, FL MLS# O6233008
$129,900
Studio

Beds

0.0

Baths

14577 SIPLIN ROAD

Winter Garden, FL

Courtesy of KEL REALTY INC
View 14501 GROVE RESORT AVENUE 1637 Winter Garden, FL MLS# S5095151
$240,100
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1637

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

978

Estimated median home price

$602,728
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 - 200K21
$200K - 300K91
$300K - 400K65
$400K - 500K141
$500K - 600K170
$600K - 700K106
$700K - 800K105
$800K - 900K91
$900K - 1M63
$1M - Max124

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family672
Townhouse136
Condo135
Commercial11
Rental200
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/14/2026)

Information deemed reliable but not guaranteed.

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 7/14/2026.