235 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 14180 TITLE WAY Winter Garden, FL MLS# O6444490
$589,990
4

Beds

3.1

Baths

2,481

Sq.Ft.

14180 TITLE WAY

Winter Garden, FL

Courtesy of SUNSTAR REALTY FL INC
View 12525 SCARLETT SAGE COURT Winter Garden, FL MLS# O6444687
$595,000
4

Beds

3.0

Baths

2,529

Sq.Ft.

12525 SCARLETT SAGE COURT

Winter Garden, FL

Courtesy of JWJ REALTY LLC
View 1809 DELAFIELD DRIVE Winter Garden, FL MLS# O6444401
$735,000
4

Beds

2.1

Baths

3,605

Sq.Ft.

1809 DELAFIELD DRIVE

Winter Garden, FL

Courtesy of DALTON WADE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2102 GREEN ASH COURT Winter Garden, FL MLS# O6443783
$699,000
5

Beds

3.0

Baths

3,766

Sq.Ft.

2102 GREEN ASH COURT

Winter Garden, FL

Courtesy of MARK SPAIN REAL ESTATE
View 776 ORANGE BELT LOOP Winter Garden, FL MLS# O6443830
$710,000
3

Beds

2.0

Baths

1,860

Sq.Ft.

776 ORANGE BELT LOOP

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 14371 SHOCKLACH DRIVE Winter Garden, FL MLS# O6443368
$695,000
3

Beds

2.0

Baths

2,066

Sq.Ft.

14371 SHOCKLACH DRIVE

Winter Garden, FL

Courtesy of SERHANT
View 16137 HAMPTON CROSSING DRIVE Winter Garden, FL MLS# G5117862
$600,000
3

Beds

3.0

Baths

2,040

Sq.Ft.

16137 HAMPTON CROSSING DRIVE

Winter Garden, FL

Courtesy of CHELSEA & COMPANY REALTY
View 8091 BOWERY DRIVE Winter Garden, FL MLS# S5157882
$585,000
4

Beds

3.0

Baths

2,095

Sq.Ft.

8091 BOWERY DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY OF VERO
View 8091 BOWERY Drive Winter Garden, FL MLS# B26077664
$585,000
3

Beds

3.0

Baths

2,095

Sq.Ft.

8091 BOWERY Drive

Winter Garden, FL

View 6158 MERIWETHER CRESCENT Winter Garden, FL MLS# O6443007
$710,000
4

Beds

3.1

Baths

2,877

Sq.Ft.

6158 MERIWETHER CRESCENT

Winter Garden, FL

Courtesy of TOP TIER RESORT REALTY
View 1631 CHARLEMAGNE COURT Winter Garden, FL MLS# O6442789
$589,000
3

Beds

2.0

Baths

2,035

Sq.Ft.

1631 CHARLEMAGNE COURT

Winter Garden, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 14354 ORCHARD HILLS BOULEVARD Winter Garden, FL MLS# TB8547558
$595,000
4

Beds

2.1

Baths

2,496

Sq.Ft.

14354 ORCHARD HILLS BOULEVARD

Winter Garden, FL

Courtesy of OFFERPAD BROKERAGE FL, LLC
View 15601 DAHOON HOLLY LANE Winter Garden, FL MLS# O6442755
$669,990
4

Beds

2.1

Baths

2,635

Sq.Ft.

15601 DAHOON HOLLY LANE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 2242 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# G5117774
$780,000
5

Beds

4.0

Baths

3,381

Sq.Ft.

2242 WINTERMERE POINTE DRIVE

Winter Garden, FL

Courtesy of NEXTHOME BEST RESULTS REAL ESTATE
View 8819 SONOMA COAST DRIVE Winter Garden, FL MLS# O6440859
$759,900
4

Beds

3.1

Baths

3,327

Sq.Ft.

8819 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 10750 PETRILLO WAY Winter Garden, FL MLS# O6441092
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OPEN HOUSE: Saturday 11/14 11:00 AM - 1:00 PM
$625,000
3

Beds

2.1

Baths

2,613

Sq.Ft.

10750 PETRILLO WAY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 3019 CHERRY ORCHARD LANE Winter Garden, FL MLS# O6441872
$659,990
4

Beds

2.0

Baths

2,115

Sq.Ft.

3019 CHERRY ORCHARD LANE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 5506 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6439560
$624,000
5

Beds

3.1

Baths

2,369

Sq.Ft.

5506 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 13184 DENDY WAY Winter Garden, FL MLS# O6440321
$634,900
4

Beds

2.1

Baths

2,211

Sq.Ft.

13184 DENDY WAY

Winter Garden, FL

Courtesy of VOSS REALTY INC
View 17108 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5117579
$712,735
4

Beds

3.0

Baths

3,038

Sq.Ft.

17108 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY 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

947

Estimated median home price

$615,000
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 - 100K1
$100K - 200K37
$200K - 300K73
$300K - 400K67
$400K - 500K143
$500K - 600K146
$600K - 700K115
$700K - 800K102
$800K - 900K103
$900K - 1M54
$1M - Max106

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family648
Townhouse142
Condo116
Commercial5
Rental249
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home1
Farms0

(Data as of 11/12/2026)

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.

The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 11/13/2026.