253 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 16933 OAKBORO STREET Winter Garden, FL MLS# R4910916
  • Recently Listed with Virtual Tour
1 of 31
$560,000
3

Beds

2.1

Baths

2,014

Sq.Ft.

16933 OAKBORO STREET

Winter Garden, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 13617 SALAMANDER STREET Winter Garden, FL MLS# O6391534
$549,900
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
  • Recently Listed with Virtual Tour
1 of 52
$470,000
3

Beds

3.0

Baths

2,032

Sq.Ft.

7078 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 337 SUNSET OAKS RD Winter Garden, FL MLS# O6391526
$599,900
4

Beds

3.0

Baths

2,186

Sq.Ft.

337 SUNSET OAKS RD

Winter Garden, FL

Courtesy of REAL LIVING R E SOLUTIONS
View 16736 OAKBORO STREET Winter Garden, FL MLS# O6388784
  • Recently Listed with Virtual Tour
1 of 65
$585,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

16736 OAKBORO STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 7532 SPRING VALLEY STREET Winter Garden, FL MLS# G5109790
$615,990
4

Beds

3.1

Baths

2,520

Sq.Ft.

7532 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17156 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5109791
$606,440
4

Beds

3.0

Baths

2,102

Sq.Ft.

17156 INGRAM BLUFF DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 503 FIRST CAPE CORAL DRIVE Winter Garden, FL MLS# O6381166
$564,000
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
  • Recently Listed with Virtual Tour
1 of 42
$559,900
3

Beds

2.1

Baths

2,082

Sq.Ft.

9972 PALLIDA HICKORY WAY

Winter Garden, FL

Courtesy of VESTI LLC
View 14748 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391410
  • Recently Listed with Virtual Tour
1 of 44
$614,000
4

Beds

4.1

Baths

2,149

Sq.Ft.

14748 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14736 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391435
  • Recently Listed with Virtual Tour
1 of 43
$596,832
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 107 TRADITIONS DRIVE Winter Garden, FL MLS# S5145650
  • Recently Listed with Virtual Tour
1 of 30
$524,975
3

Beds

2.0

Baths

1,582

Sq.Ft.

107 TRADITIONS DRIVE

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View 1836 WINGED ELM PLACE Winter Garden, FL MLS# O6390771
  • Recently Listed with Virtual Tour
1 of 32
$475,000
4

Beds

2.0

Baths

1,712

Sq.Ft.

1836 WINGED ELM PLACE

Winter Garden, FL

Courtesy of MARK SPAIN REAL ESTATE
View 6072 GLORY BOWER DRIVE Winter Garden, FL MLS# O6389207
  • Recently Listed with Virtual Tour
1 of 37
$479,000
3

Beds

2.1

Baths

2,128

Sq.Ft.

6072 GLORY BOWER DRIVE

Winter Garden, FL

Courtesy of INTOP REALTY LLC
View 6530 PASTURELANDS PLACE Winter Garden, FL MLS# O6390459
  • Recently Listed with Virtual Tour
1 of 53
$515,000
3

Beds

2.1

Baths

2,067

Sq.Ft.

6530 PASTURELANDS PLACE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 17055 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109480
  • Recently Listed
1 of 1
OPEN HOUSE: Saturday 3/28 1:00 PM - 4:00 PM
$580,682
4

Beds

3.0

Baths

2,102

Sq.Ft.

17055 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1419 HUNTERMAN LANE Winter Garden, FL MLS# O6390064
$479,900
5

Beds

4.1

Baths

2,840

Sq.Ft.

1419 HUNTERMAN LANE

Winter Garden, FL

Courtesy of ENTERA REALTY LLC
View 17144 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5109520
$605,455
4

Beds

3.1

Baths

2,520

Sq.Ft.

17144 INGRAM BLUFF DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 16149 WIND VIEW LANE Winter Garden, FL MLS# O6389892
$505,000
3

Beds

2.1

Baths

2,036

Sq.Ft.

16149 WIND VIEW LANE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 1531 HAWKESBURY COURT Winter Garden, FL MLS# O6388237
$575,000
4

Beds

2.0

Baths

2,141

Sq.Ft.

1531 HAWKESBURY COURT

Winter Garden, FL

Courtesy of SERHANT

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

941

Estimated median home price

$588,900
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

PriceCount
$0 - 100K4
$100K - 200K12
$200K - 300K92
$300K - 400K79
$400K - 500K153
$500K - 600K160
$600K - 700K111
$700K - 800K91
$800K - 900K74
$900K - 1M60
$1M - Max105

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family644
Townhouse135
Condo126
Commercial11
Rental229
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/18/2026)

Information deemed reliable but not guaranteed.

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 3/23/2026.

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.

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Data is updated as of 3/23/2026.

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.

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 3/23/2026.