206 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 10356 ATWATER BAY Winter Garden, FL MLS# O6377565
  • Recently Listed with Virtual Tour
1 of 40
$600,000
4

Beds

3.0

Baths

2,181

Sq.Ft.

10356 ATWATER BAY

Winter Garden, FL

Courtesy of THE SIMON SIMAAN GROUP
View 16230 CARRAWAY BAY ALLEY Winter Garden, FL MLS# NS1087076
  • Recently Listed with Virtual Tour
1 of 27
$601,000
4

Beds

3.1

Baths

2,474

Sq.Ft.

16230 CARRAWAY BAY ALLEY

Winter Garden, FL

View 16230 CARRAWAY BAY ALLEY Winter Garden, FL MLS# NS1087076
  • Recently Listed with Virtual Tour
1 of 27
$601,000
4

Beds

3.1

Baths

2,474

Sq.Ft.

16230 CARRAWAY BAY ALLEY

Winter Garden, FL

Courtesy of WATSON REALTY CORP
The time to sell is now! THE TIME TO SELL IS NOW!
View 16827 HOBE SOUND COURT Winter Garden, FL MLS# O6376919
  • Recently Listed with Virtual Tour
1 of 18
$648,075
4

Beds

3.1

Baths

2,489

Sq.Ft.

16827 HOBE SOUND COURT

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 13360 SUNNY RETREAT LANE Winter Garden, FL MLS# S5142297
  • Recently Listed with Virtual Tour
1 of 63
$585,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

13360 SUNNY RETREAT LANE

Winter Garden, FL

Courtesy of FRONTLINE FLORIDA REALTY, INC.
View 730 RIVER GRASS LANE Winter Garden, FL MLS# G5107248
  • Recently Listed with Virtual Tour
1 of 60
$664,900
5

Beds

3.0

Baths

2,647

Sq.Ft.

730 RIVER GRASS LANE

Winter Garden, FL

Courtesy of ASSIST2SELL BUYERS & SELLERS
View 16622 PARABLE WAY Winter Garden, FL MLS# O6376696
  • Recently Listed with Virtual Tour
1 of 28
$649,000
4

Beds

3.0

Baths

2,136

Sq.Ft.

16622 PARABLE WAY

Winter Garden, FL

Courtesy of AAA GLOBAL VENTURES PA
View 5942 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5107158
$668,990
4

Beds

3.0

Baths

2,102

Sq.Ft.

5942 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 707 GRASSY STONE DRIVE Winter Garden, FL MLS# O6376356
$575,000
4

Beds

2.0

Baths

2,398

Sq.Ft.

707 GRASSY STONE DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
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 16848 HAMLIN VISTA ALLEY Winter Garden, FL MLS# O6376316
$585,000
4

Beds

3.0

Baths

2,088

Sq.Ft.

16848 HAMLIN VISTA ALLEY

Winter Garden, FL

Courtesy of MCO REALTY GROUP LLC
View 14257 LAGOON COVE LANE Winter Garden, FL MLS# O6375296
  • Recently Listed with Virtual Tour
1 of 33
$560,000
3

Beds

2.0

Baths

2,365

Sq.Ft.

14257 LAGOON COVE LANE

Winter Garden, FL

Courtesy of INTERNATIONAL REAL ESTATE LLC
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 16840 HOBE SOUND COURT Winter Garden, FL MLS# O6374947
  • Recently Listed with Virtual Tour
1 of 7
$590,700
3

Beds

2.1

Baths

2,027

Sq.Ft.

16840 HOBE SOUND COURT

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 16584 POINT ROCK DRIVE Winter Garden, FL MLS# O6374889
  • Recently Listed with Virtual Tour
1 of 70
$570,000
3

Beds

2.1

Baths

2,044

Sq.Ft.

16584 POINT ROCK DRIVE

Winter Garden, FL

Courtesy of REAL LIVING R E SOLUTIONS
View 393 Lake Amberleigh Drive Winter Garden, FL MLS# 1221794
  • Recently Listed with Virtual Tour
1 of 53
$635,000
3

Beds

2.1

Baths

2,684

Sq.Ft.

393 Lake Amberleigh Drive

Winter Garden, FL

View 16839 HOBE SOUND COURT Winter Garden, FL MLS# O6374451
  • New Construction with Virtual Tour
1 of 18
$673,170
4

Beds

3.1

Baths

2,489

Sq.Ft.

16839 HOBE SOUND COURT

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 1923 JEAN MARIE DRIVE Winter Garden, FL MLS# G5106903
$610,000
4

Beds

3.0

Baths

2,916

Sq.Ft.

1923 JEAN MARIE DRIVE

Winter Garden, FL

Courtesy of EXIT REALTY TRI-COUNTY
View 15230 HONEYBELL DRIVE Winter Garden, FL MLS# O6375726
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Saturday 1/31 12:00 PM - 4:00 PM
$599,000
4

Beds

3.0

Baths

2,445

Sq.Ft.

15230 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 7189 SUMMERLAKE GROVES STREET Winter Garden, FL MLS# O6373509
  • Recently Listed with Virtual Tour
1 of 36
$619,999
3

Beds

2.1

Baths

2,138

Sq.Ft.

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

Courtesy of MAINFRAME 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

824

Estimated median home price

$590,000
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 - 100K7
$100K - 200K11
$200K - 300K75
$300K - 400K80
$400K - 500K143
$500K - 600K118
$600K - 700K102
$700K - 800K75
$800K - 900K71
$900K - 1M52
$1M - Max90

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family542
Townhouse126
Condo115
Commercial7
Rental240
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/28/2026)

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 1/28/2026.

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 1/28/2026.