980 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
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
The time to sell is now! THE TIME TO SELL IS NOW!
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
View 72 N PARK AVENUE 8 Winter Garden, FL MLS# O6441100
  • Virtual Tour
1 of 47
$1,149,000
3

Beds

4.0

Baths

2,040

Sq.Ft.

72 N PARK AVENUE 8

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 10750 PETRILLO WAY Winter Garden, FL MLS# O6441092
  • Virtual Tour
1 of 32
$649,900
4

Beds

2.1

Baths

2,613

Sq.Ft.

10750 PETRILLO WAY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 16614 WINGSPREAD LOOP Winter Garden, FL MLS# O6441370
$579,000
3

Beds

2.1

Baths

2,372

Sq.Ft.

16614 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 17336 LAKE STAR ROAD Winter Garden, FL MLS# O6435581
$1,075,000
4

Beds

3.1

Baths

3,101

Sq.Ft.

17336 LAKE STAR ROAD

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
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 8174 BLUEJACK OAK DRIVE Winter Garden, FL MLS# O6441119
$465,900
4

Beds

3.0

Baths

1,853

Sq.Ft.

8174 BLUEJACK OAK DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 988 STUCKI TERRACE Winter Garden, FL MLS# TB8539994
$230,000
3

Beds

2.1

Baths

1,216

Sq.Ft.

988 STUCKI TERRACE

Winter Garden, FL

Courtesy of BEACHFRONT REALTY INC
View 5506 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6439560
$629,000
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
  • Virtual Tour
1 of 48
$649,900
4

Beds

2.1

Baths

2,211

Sq.Ft.

13184 DENDY WAY

Winter Garden, FL

Courtesy of VOSS REALTY INC
View 8819 SONOMA COAST DRIVE Winter Garden, FL MLS# O6440859
$779,900
4

Beds

3.1

Baths

3,327

Sq.Ft.

8819 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 15279 HARROWGATE WAY Winter Garden, FL MLS# O6440200
$359,900
3

Beds

2.1

Baths

1,845

Sq.Ft.

15279 HARROWGATE WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1707 FULLERS OAK LOOP Winter Garden, FL MLS# S5157229
$839,000
6

Beds

4.0

Baths

4,181

Sq.Ft.

1707 FULLERS OAK LOOP

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
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
View 285 CRYSTAL WOOD DRIVE Winter Garden, FL MLS# O6440648
  • New Construction with Virtual Tour
1 of 34
$871,620
5

Beds

4.0

Baths

3,202

Sq.Ft.

285 CRYSTAL WOOD DRIVE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 1720 LAKE ROBERTS LANDING DRIVE Winter Garden, FL MLS# O6436608
$1,399,999
5

Beds

4.1

Baths

4,919

Sq.Ft.

1720 LAKE ROBERTS LANDING DRIVE

Winter Garden, FL

Courtesy of ACCORD REAL ESTATE SERVICES
View 11367 GREAT ROCK STREET Winter Garden, FL MLS# O6440807
  • New Construction with Virtual Tour
1 of 34
$430,000
3

Beds

2.1

Baths

1,717

Sq.Ft.

11367 GREAT ROCK STREET

Winter Garden, FL

Courtesy of FLORIDA 360 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

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

Price Count
$0 - 100K 1
$100K - 200K 34
$200K - 300K 69
$300K - 400K 77
$400K - 500K 158
$500K - 600K 161
$600K - 700K 105
$700K - 800K 109
$800K - 900K 102
$900K - 1M 60
$1M - Max 103

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 670
Townhouse 152
Condo 119
Commercial 6
Rental 226
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(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.