View 1500 E BAY STREET Winter Garden, FL MLS# O6288408
$95,000
Studio

Beds

0.0

Baths

1500 E BAY STREET

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 142 Windtree Lane # 202 Winter Garden, FL MLS# RX11065560
$218,900
2

Beds

2.0

Baths

918

Sq.Ft.

142 Windtree Lane # 202

Winter Garden, FL

BeachesMLS
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 14501 GROVE RESORT AVENUE 1237 Winter Garden, FL MLS# O6279915
$229,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1237

Winter Garden, FL

Courtesy of KARDOSH REALTY
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 14718 MICAH STREET Winter Garden, FL MLS# O6268724
$165,000
Studio

Beds

0.0

Baths

14718 MICAH STREET

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 764 KLONDIKE STREET Winter Garden, FL MLS# O6255583
$59,000
Studio

Beds

0.0

Baths

764 KLONDIKE STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View W ORANGE COUNTRY CLUB DRIVE Winter Garden, FL MLS# O6244638
$100,000
Studio

Beds

0.0

Baths

W ORANGE COUNTRY CLUB DRIVE

Winter Garden, FL

Courtesy of KELLY RIGHT REAL ESTATE
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 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 KILLARNEY COVE DRIVE Winter Garden, FL MLS# O6099204
$69,999
Studio

Beds

0.0

Baths

KILLARNEY COVE DRIVE

Winter Garden, FL

Courtesy of REAL ESTATE FIRM OF ORLANDO
View KILLARNEY COVE DRIVE Winter Garden, FL MLS# O6099226
$69,999
Studio

Beds

0.0

Baths

KILLARNEY COVE DRIVE

Winter Garden, FL

Courtesy of REAL ESTATE FIRM OF ORLANDO
View KILLARNEY COVE DRIVE Winter Garden, FL MLS# O6099254
$69,999
Studio

Beds

0.0

Baths

KILLARNEY COVE DRIVE

Winter Garden, FL

Courtesy of REAL ESTATE FIRM OF ORLANDO

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 - 600K124
$600K - 700K91
$700K - 800K67
$800K - 900K67
$900K - 1M49
$1M - Max97

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family516
Townhouse123
Condo110
Commercial10
Rental235
Lots and Land31
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 12/27/2025)

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 12/28/2025.

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.