258 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 17061 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5110436
$565,990
4

Beds

3.1

Baths

2,515

Sq.Ft.

17061 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5778 LAUREL CHERRY AVENUE Winter Garden, FL MLS# O6395452
$540,000
4

Beds

3.1

Baths

2,524

Sq.Ft.

5778 LAUREL CHERRY AVENUE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 7655 SILVER MEADOW STREET Winter Garden, FL MLS# G5110445
$511,705
3

Beds

2.0

Baths

1,772

Sq.Ft.

7655 SILVER MEADOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View Address not provided Winter Garden, FL MLS# G5110456
  • New Construction
1 of 2
$510,880
3

Beds

2.0

Baths

1,772

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14542 GOLDEN HARBOR LANE Winter Garden, FL MLS# O6395116
$500,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

14542 GOLDEN HARBOR LANE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 6020 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5110387
$573,990
4

Beds

3.0

Baths

2,102

Sq.Ft.

6020 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5413 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# S5146601
$488,000
4

Beds

2.1

Baths

2,131

Sq.Ft.

5413 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of MD3 HOMES LLC
View 10089 SALT POINT DRIVE Winter Garden, FL MLS# O6392385
$475,000
3

Beds

2.1

Baths

1,654

Sq.Ft.

10089 SALT POINT DRIVE

Winter Garden, FL

Courtesy of AUTHENTIC REAL ESTATE TEAM
View 9355 TYRELLA PINE TRAIL Winter Garden, FL MLS# O6391856
$467,000
3

Beds

2.1

Baths

1,670

Sq.Ft.

9355 TYRELLA PINE TRAIL

Winter Garden, FL

Courtesy of REDFIN CORPORATION
View 16385 ADMIRALS COVE LANE Winter Garden, FL MLS# O6393056
$469,900
3

Beds

2.0

Baths

1,705

Sq.Ft.

16385 ADMIRALS COVE LANE

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
View 16933 OAKBORO STREET Winter Garden, FL MLS# R4910916
$560,000
3

Beds

2.1

Baths

2,027

Sq.Ft.

16933 OAKBORO STREET

Winter Garden, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 15659 JUNGLE ALLEY Winter Garden, FL MLS# S5143684
  • Virtual Tour
1 of 16
$435,000
3

Beds

2.1

Baths

1,732

Sq.Ft.

15659 JUNGLE ALLEY

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 13617 SALAMANDER STREET Winter Garden, FL MLS# O6391534
$530,000
3

Beds

2.1

Baths

2,216

Sq.Ft.

13617 SALAMANDER STREET

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7078 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6391631
$462,500
3

Beds

3.0

Baths

2,032

Sq.Ft.

7078 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16736 OAKBORO STREET Winter Garden, FL MLS# O6388784
$563,900
4

Beds

3.1

Baths

2,477

Sq.Ft.

16736 OAKBORO STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 503 FIRST CAPE CORAL DRIVE Winter Garden, FL MLS# O6381166
$556,000
4

Beds

2.0

Baths

2,365

Sq.Ft.

503 FIRST CAPE CORAL DRIVE

Winter Garden, FL

Courtesy of REGENCY REAL ESTATE LLC
View 9972 PALLIDA HICKORY WAY Winter Garden, FL MLS# O6391384
$559,900
3

Beds

2.1

Baths

2,082

Sq.Ft.

9972 PALLIDA HICKORY WAY

Winter Garden, FL

Courtesy of VESTI LLC
View 14736 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391435
  • New Construction with Virtual Tour
1 of 43
$550,000
3

Beds

3.1

Baths

2,149

Sq.Ft.

14736 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 9107 GRAND ISLAND WAY Winter Garden, FL MLS# O6391117
$499,900
3

Beds

2.1

Baths

2,082

Sq.Ft.

9107 GRAND ISLAND WAY

Winter Garden, FL

Courtesy of FHG REALTY, LLC
View 107 TRADITIONS DRIVE Winter Garden, FL MLS# S5145650
$474,975
3

Beds

2.0

Baths

1,582

Sq.Ft.

107 TRADITIONS DRIVE

Winter Garden, FL

Courtesy of WATSON REALTY CORP

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

1,041

Estimated median home price

$609,900
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 2
$100K - 200K 22
$200K - 300K 96
$300K - 400K 83
$400K - 500K 142
$500K - 600K 168
$600K - 700K 124
$700K - 800K 119
$800K - 900K 87
$900K - 1M 73
$1M - Max 125

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 715
Townhouse 141
Condo 143
Commercial 10
Rental 214
Lots and Land 29
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 2
Farms 0

(Data as of 5/26/2026)

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 5/26/2026.

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.

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 5/26/2026.

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 5/26/2026.