951 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 16137 HAMPTON CROSSING DRIVE Winter Garden, FL MLS# G5117862
  • Recently Listed with Virtual Tour
1 of 58
$600,000
3

Beds

3.0

Baths

2,040

Sq.Ft.

16137 HAMPTON CROSSING DRIVE

Winter Garden, FL

Courtesy of CHELSEA & COMPANY REALTY
View 15601 DAHOON HOLLY LANE Winter Garden, FL MLS# O6442755
  • Recently Listed with Virtual Tour
1 of 45
$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 14058 FRASIER STREET Winter Garden, FL MLS# O6443674
$450,000
4

Beds

2.1

Baths

1,996

Sq.Ft.

14058 FRASIER STREET

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 16513 SILVER BROOK WAY Winter Garden, FL MLS# O6443784
  • Recently Listed with Virtual Tour
1 of 44
$879,000
4

Beds

3.1

Baths

3,424

Sq.Ft.

16513 SILVER BROOK WAY

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 16570 BARBOURS CREEK WAY Winter Garden, FL MLS# O6442156
  • New Construction with Virtual Tour
1 of 93
$452,000
3

Beds

2.1

Baths

1,567

Sq.Ft.

16570 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 325 W NEWELL STREET Winter Garden, FL MLS# O6441955
$585,000
2

Beds

2.0

Baths

1,051

Sq.Ft.

325 W NEWELL STREET

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 8091 BOWERY Drive Winter Garden, FL MLS# B26077664
$585,000
3

Beds

2.0

Baths

2,095

Sq.Ft.

8091 BOWERY Drive

Winter Garden, FL

View 5074 BREEZY ACRES STREET Winter Garden, FL MLS# O6442063
$1,159,900
7

Beds

4.1

Baths

4,720

Sq.Ft.

5074 BREEZY ACRES STREET

Winter Garden, FL

Courtesy of CREEGAN GROUP
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 263 DEER ISLE DRIVE Winter Garden, FL MLS# O6440044
$1,495,000
3

Beds

2.1

Baths

2,735

Sq.Ft.

263 DEER ISLE DRIVE

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY
View 2242 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# G5117774
$790,000
5

Beds

4.0

Baths

3,381

Sq.Ft.

2242 WINTERMERE POINTE DRIVE

Winter Garden, FL

Courtesy of NEXTHOME BEST RESULTS REAL ESTATE
View 14501 GROVE RESORT AVENUE 2608 Winter Garden, FL MLS# O6441962
$255,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 2608

Winter Garden, FL

Courtesy of BP REALTY
View 1118 MAIDENMOOR ROAD Winter Garden, FL MLS# O6440167
$460,000
4

Beds

2.0

Baths

2,009

Sq.Ft.

1118 MAIDENMOOR ROAD

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 14501 GROVE RESORT AVENUE 3201 Winter Garden, FL MLS# O6442533
$245,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 3201

Winter Garden, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 330 LAKE AMBERLEIGH DRIVE Winter Garden, FL MLS# O6441793
  • Virtual Tour
1 of 42
OPEN HOUSE: Sunday 10/11 11:00 AM - 1:00 PM
$529,900
4

Beds

2.0

Baths

2,138

Sq.Ft.

330 LAKE AMBERLEIGH DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14961 LEBEAU LOOP Winter Garden, FL MLS# O6441782
  • Recently Listed with Virtual Tour
1 of 79
$899,000
4

Beds

3.1

Baths

3,042

Sq.Ft.

14961 LEBEAU LOOP

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 17206 RED BIRD ROAD Winter Garden, FL MLS# O6441311
$824,900
0.0

Baths

17206 RED BIRD ROAD

Winter Garden, FL

Courtesy of CREEGAN GROUP
View 9845 EMERALD BERRY DRIVE Winter Garden, FL MLS# O6441968
$1,050,000
5

Beds

4.1

Baths

3,878

Sq.Ft.

9845 EMERALD BERRY DRIVE

Winter Garden, FL

Courtesy of ON ME REALTY
View 16773 WINGSPREAD LOOP Winter Garden, FL MLS# O6440424
$950,000
5

Beds

4.0

Baths

3,752

Sq.Ft.

16773 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 14766 PEEKSKILL DRIVE Winter Garden, FL MLS# O6440912
$332,500
2

Beds

2.1

Baths

1,406

Sq.Ft.

14766 PEEKSKILL DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY

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

979

Estimated median home price

$595,000
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 - 200K34
$200K - 300K69
$300K - 400K77
$400K - 500K158
$500K - 600K161
$600K - 700K105
$700K - 800K109
$800K - 900K102
$900K - 1M60
$1M - Max103

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family670
Townhouse152
Condo119
Commercial6
Rental226
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 10/9/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

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 10/11/2026.

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Weichert Realtors are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. 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.

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Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Copyright © 2026 Midwest Real Estate Data LLC.

Data is updated as of 10/11/2026.

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 real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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 10/11/2026.