233 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 622 SIGLER DRIVE Winter Garden, FL MLS# O6447381
  • New Construction with Virtual Tour
1 of 15
$604,580
3

Beds

2.1

Baths

1,634

Sq.Ft.

622 SIGLER DRIVE

Winter Garden, FL

Courtesy of DAVILA HOMES
View 618 SIGLER DRIVE Winter Garden, FL MLS# O6447410
  • New Construction with Virtual Tour
1 of 13
$685,240
3

Beds

2.1

Baths

1,852

Sq.Ft.

618 SIGLER DRIVE

Winter Garden, FL

Courtesy of DAVILA HOMES
View 13160 DENDY WAY Winter Garden, FL MLS# O6450625
$635,000
3

Beds

2.1

Baths

2,207

Sq.Ft.

13160 DENDY WAY

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
The time to sell is now! THE TIME TO SELL IS NOW!
View 12934 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6450081
  • New Construction with Virtual Tour
1 of 52
$750,000
3

Beds

3.1

Baths

2,858

Sq.Ft.

12934 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 17055 SEVILLE ORANGE ROAD Winter Garden, FL MLS# O6449811
$649,000
3

Beds

2.1

Baths

2,134

Sq.Ft.

17055 SEVILLE ORANGE ROAD

Winter Garden, FL

Courtesy of PREMIUM PROPERTIES R.E SERVICE
View 14743 FIELD DAISY DRIVE Winter Garden, FL MLS# O6450084
  • New Construction with Virtual Tour
1 of 32
$654,718
3

Beds

4.1

Baths

2,618

Sq.Ft.

14743 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 16012 MICELLI DRIVE Winter Garden, FL MLS# O6450178
$599,000
4

Beds

3.0

Baths

2,428

Sq.Ft.

16012 MICELLI DRIVE

Winter Garden, FL

Courtesy of ALVES AND HOWELL REALTY
View 725 TRANQUIL TRAIL Winter Garden, FL MLS# O6449702
$669,000
5

Beds

2.1

Baths

2,834

Sq.Ft.

725 TRANQUIL TRAIL

Winter Garden, FL

Courtesy of MANSION REALTY, INC
View 1818 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# S5159396
$730,000
6

Beds

4.0

Baths

4,204

Sq.Ft.

1818 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
View 1349 CASTLEPORT ROAD Winter Garden, FL MLS# O6449173
$749,000
5

Beds

3.1

Baths

3,673

Sq.Ft.

1349 CASTLEPORT ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 14779 FIELD DAISY DRIVE Winter Garden, FL MLS# O6449273
  • New Construction with Virtual Tour
1 of 42
$625,000
4

Beds

4.1

Baths

2,149

Sq.Ft.

14779 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14775 FIELD DAISY DRIVE Winter Garden, FL MLS# O6449282
  • New Construction with Virtual Tour
1 of 31
$635,572
4

Beds

4.1

Baths

2,618

Sq.Ft.

14775 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14795 FIELD DAISY DRIVE Winter Garden, FL MLS# O6449311
  • New Construction with Virtual Tour
1 of 50
$609,481
3

Beds

3.1

Baths

1,992

Sq.Ft.

14795 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 1481 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# S5158890
$718,000
6

Beds

4.0

Baths

4,194

Sq.Ft.

1481 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
View 251 N PLANT STREET Winter Garden, FL MLS# G5118540
$650,000
4

Beds

4.0

Baths

2,080

Sq.Ft.

251 N PLANT STREET

Winter Garden, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 7186 WILD STRAWBERRY RUN Winter Garden, FL MLS# S5159215
$750,000
4

Beds

3.1

Baths

3,049

Sq.Ft.

7186 WILD STRAWBERRY RUN

Winter Garden, FL

Courtesy of SHANI BUILDERS & REALTY LLC
View 14825 PORTER ROAD Winter Garden, FL MLS# O6448723
$609,998
3

Beds

2.1

Baths

2,732

Sq.Ft.

14825 PORTER ROAD

Winter Garden, FL

Courtesy of NEXTHOME HORIZON REALTY
View 190 ROPER DRIVE Winter Garden, FL MLS# O6447968
$750,000
3

Beds

2.0

Baths

1,755

Sq.Ft.

190 ROPER DRIVE

Winter Garden, FL

Courtesy of NEXTDWELL
View 24 W GARDEN AVENUE Winter Garden, FL MLS# O6446518
$698,800
4

Beds

4.0

Baths

2,110

Sq.Ft.

24 W GARDEN AVENUE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 17326 WILD DAISY DRIVE Winter Garden, FL MLS# G5118742
  • New Construction with Virtual Tour
1 of 22
$722,222
4

Beds

2.1

Baths

2,235

Sq.Ft.

17326 WILD DAISY 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 11/12/2026.