579 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 8013 BOWERY DRIVE Winter Garden, FL MLS# O6372299
$700,000
4

Beds

2.0

Baths

2,115

Sq.Ft.

8013 BOWERY DRIVE

Winter Garden, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 2425 PRAIRIE VIEW DRIVE Winter Garden, FL MLS# O6376886
$700,000
5

Beds

3.0

Baths

3,524

Sq.Ft.

2425 PRAIRIE VIEW DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 14673 GLADE HILL PARK WAY Winter Garden, FL MLS# O6370598
$699,999
5

Beds

3.0

Baths

2,808

Sq.Ft.

14673 GLADE HILL PARK WAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 13398 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105139
  • New Construction with Virtual Tour
1 of 28
$699,990
4

Beds

2.1

Baths

2,235

Sq.Ft.

13398 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8018 BOWERY DRIVE Winter Garden, FL MLS# O6325853
$699,900
5

Beds

3.0

Baths

3,075

Sq.Ft.

8018 BOWERY DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 6399 WILD PERSIMMON WAY Winter Garden, FL MLS# G5108439
$699,520
5

Beds

4.0

Baths

2,704

Sq.Ft.

6399 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14673 Glade Hill Park WAY Winter Garden, FL MLS# O6194833
$699,000
5

Beds

3.0

Baths

2,808

Sq.Ft.

14673 Glade Hill Park WAY

Winter Garden, FL

Courtesy of SERHANT
View 15399 GILLIGAN COURT Winter Garden, FL MLS# O6365269
$699,000
4

Beds

3.1

Baths

2,758

Sq.Ft.

15399 GILLIGAN COURT

Winter Garden, FL

Courtesy of FCG REALTY
View 15010 SAWGRASS BLUFF DRIVE Winter Garden, FL MLS# G5105276
$699,000
3

Beds

2.0

Baths

1,673

Sq.Ft.

15010 SAWGRASS BLUFF DRIVE

Winter Garden, FL

Courtesy of RE FLORIDA HOMES
View 2394 BARONSMEDE COURT Winter Garden, FL MLS# O6373715
$699,000
3

Beds

2.0

Baths

2,310

Sq.Ft.

2394 BARONSMEDE COURT

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 14872 WINKFIELD COURT Winter Garden, FL MLS# O6381769
  • Recently Listed with Virtual Tour
1 of 66
$699,000
4

Beds

3.0

Baths

2,554

Sq.Ft.

14872 WINKFIELD COURT

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 15087 TEA TREE DRIVE Winter Garden, FL MLS# G5107020
$698,466
4

Beds

2.1

Baths

2,235

Sq.Ft.

15087 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1421 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# S5135740
$698,000
6

Beds

4.0

Baths

4,204

Sq.Ft.

1421 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
View 13900 FOX GLOVE STREET Winter Garden, FL MLS# S5143671
$689,900
5

Beds

3.0

Baths

3,887

Sq.Ft.

13900 FOX GLOVE STREET

Winter Garden, FL

Courtesy of SELECT ESTATES, LLC
View 15133 SUMMER HARVEST STREET Winter Garden, FL MLS# TB8477249
$689,900
4

Beds

4.1

Baths

2,908

Sq.Ft.

15133 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of COMMUNITY REALTY ASSOCIATES
View 17404 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5108715
$685,645
4

Beds

2.1

Baths

2,235

Sq.Ft.

17404 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5685 SURPRISE LILY DRIVE Winter Garden, FL MLS# O6353593
$685,000
5

Beds

2.1

Baths

2,902

Sq.Ft.

5685 SURPRISE LILY DRIVE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 14518 BLACK QUILL DR DRIVE 14518 Winter Garden, FL MLS# O6354129
$685,000
4

Beds

2.1

Baths

2,490

Sq.Ft.

14518 BLACK QUILL DR DRIVE 14518

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 16256 MISTY HILLS AVENUE Winter Garden, FL MLS# O6369818
$685,000
4

Beds

3.0

Baths

2,240

Sq.Ft.

16256 MISTY HILLS AVENUE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 16055 SILVER BROOK WAY Winter Garden, FL MLS# O6381599
$685,000
3

Beds

2.1

Baths

2,072

Sq.Ft.

16055 SILVER BROOK WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE

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

903

Estimated median home price

$594,990
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 - 100K6
$100K - 200K13
$200K - 300K88
$300K - 400K78
$400K - 500K151
$500K - 600K135
$600K - 700K108
$700K - 800K89
$800K - 900K68
$900K - 1M64
$1M - Max103

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family606
Townhouse130
Condo127
Commercial9
Rental233
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 3/1/2026)

Information deemed reliable but not guaranteed.

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.

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© Copyright 2026 New Smyrna Beach Board 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 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 3/2/2026.

Copyright 2026 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 3/2/2026.

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

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.

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 3/2/2026.