985 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 15411 GILLIGAN COURT Winter Garden, FL MLS# O6446141
  • Recently Listed with Virtual Tour
1 of 27
$539,900
4

Beds

2.1

Baths

2,152

Sq.Ft.

15411 GILLIGAN COURT

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 204 HARBOR DRIVE Winter Garden, FL MLS# O6445377
  • Recently Listed with Virtual Tour
1 of 28
$579,000
3

Beds

2.0

Baths

1,522

Sq.Ft.

204 HARBOR DRIVE

Winter Garden, FL

Courtesy of METROPOLIS R.E. SOLUTIONS, LLC
View 14501 GROVE RESORT AVENUE 3636 Winter Garden, FL MLS# O6446580
  • Recently Listed with Virtual Tour
1 of 45
$175,000
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 3636

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 16513 SILVER BROOK WAY Winter Garden, FL MLS# O6443784
  • Recently Listed with Virtual Tour
1 of 44
$879,000
4

Beds

3.1

Baths

3,424

Sq.Ft.

16513 SILVER BROOK WAY

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 721 FOSTER AVENUE Winter Garden, FL MLS# O6451848
$699,000
7

Beds

3.0

Baths

2,245

Sq.Ft.

721 FOSTER AVENUE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 6427 Argent Wood Dr DR Winter Garden, FL MLS# O6450528
  • New Construction with Virtual Tour
1 of 33
$3,000
4

Beds

3.0

Baths

1,847

Sq.Ft.

6427 Argent Wood Dr DR

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1069 GLENHARBOR CIRCLE Winter Garden, FL MLS# O6449485
$565,000
3

Beds

2.0

Baths

1,768

Sq.Ft.

1069 GLENHARBOR CIRCLE

Winter Garden, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 14017 TITLE WAY Winter Garden, FL MLS# O6448815
$429,900
3

Beds

2.1

Baths

1,717

Sq.Ft.

14017 TITLE WAY

Winter Garden, FL

Courtesy of REALTY ONE GROUP INSPIRATION
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 1947 BAY CLOVER DRIVE Winter Garden, FL MLS# O6448444
$650,000
5

Beds

4.0

Baths

2,877

Sq.Ft.

1947 BAY CLOVER DRIVE

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 15646 SWEET LEMON WAY Winter Garden, FL MLS# O6449177
  • Virtual Tour
1 of 48
OPEN HOUSE: Saturday 10/24 11:00 AM - 2:00 PM
$2,000,000
5

Beds

3.1

Baths

3,871

Sq.Ft.

15646 SWEET LEMON WAY

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 15302 HONEYBELL DRIVE Winter Garden, FL MLS# O6447326
$575,000
3

Beds

2.0

Baths

1,979

Sq.Ft.

15302 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 15066 CANOPY COVER DRIVE Winter Garden, FL MLS# O6445249
  • Adult Community with Virtual Tour
1 of 63
$967,500
3

Beds

3.1

Baths

2,955

Sq.Ft.

15066 CANOPY COVER DRIVE

Winter Garden, FL

Courtesy of IAD REAL ESTATE
View 3413 TURNINGWIND LANE Winter Garden, FL MLS# O6445840
$829,500
4

Beds

3.0

Baths

2,917

Sq.Ft.

3413 TURNINGWIND LANE

Winter Garden, FL

Courtesy of FOLIO REALTY LLC
View 8836 LAKESHORE POINTE DRIVE Winter Garden, FL MLS# O6421088
$1,175,000
4

Beds

3.1

Baths

2,914

Sq.Ft.

8836 LAKESHORE POINTE DRIVE

Winter Garden, FL

Courtesy of THE AGENCY FL
View 1362 UNION CLUB DRIVE Winter Garden, FL MLS# O6443584
$910,000
3

Beds

2.1

Baths

1,822

Sq.Ft.

1362 UNION CLUB DRIVE

Winter Garden, FL

Courtesy of OAK AVENUE REAL ESTATE LLC
View 5995 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5118526
$850,000
4

Beds

3.0

Baths

2,740

Sq.Ft.

5995 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5983 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5118528
$850,000
5

Beds

3.0

Baths

2,879

Sq.Ft.

5983 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1323 AZALEA WAY Winter Garden, FL MLS# OM733255
$189,000
3

Beds

2.0

Baths

1,216

Sq.Ft.

1323 AZALEA WAY

Winter Garden, FL

Courtesy of BLACKHORSE REAL ESTATE LLC
View 16283 HONEY HARVEST STREET Winter Garden, FL MLS# O6446119
$635,000
4

Beds

4.1

Baths

2,927

Sq.Ft.

16283 HONEY HARVEST STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY

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

986

Estimated median home price

$598,900
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 - 100K2
$100K - 200K34
$200K - 300K75
$300K - 400K77
$400K - 500K145
$500K - 600K171
$600K - 700K114
$700K - 800K111
$800K - 900K105
$900K - 1M51
$1M - Max101

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family679
Townhouse147
Condo121
Commercial6
Rental239
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 10/22/2026)

Information deemed reliable but not guaranteed.

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.

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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 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 10/22/2026.

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 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 10/22/2026.

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

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 10/22/2026.