208 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 14481 BREAKWATER WAY Winter Garden, FL MLS# S5130541
$655,000
5

Beds

3.0

Baths

3,690

Sq.Ft.

14481 BREAKWATER WAY

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
View 6321 WILD PERSIMMON WAY Winter Garden, FL MLS# G5105005
$654,990
3

Beds

2.0

Baths

1,772

Sq.Ft.

6321 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14494 BREAKWATER WAY Winter Garden, FL MLS# S5139023
$654,000
5

Beds

3.0

Baths

3,638

Sq.Ft.

14494 BREAKWATER WAY

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 14902 ARRENA ROAD Winter Garden, FL MLS# O6248982
$650,000
4

Beds

2.1

Baths

3,392

Sq.Ft.

14902 ARRENA ROAD

Winter Garden, FL

Courtesy of STAR SOLUTION PROPERTIES LLC
View 15456 GILLIGAN COURT Winter Garden, FL MLS# A4660262
$650,000
3

Beds

3.0

Baths

2,571

Sq.Ft.

15456 GILLIGAN COURT

Winter Garden, FL

Courtesy of NEXTHOME CASA BELLA ELITE
View 5439 ORANGE ORCHARD DRIVE Winter Garden, FL MLS# L4957156
$650,000
4

Beds

3.0

Baths

2,240

Sq.Ft.

5439 ORANGE ORCHARD DRIVE

Winter Garden, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 12626 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6365821
$650,000
4

Beds

3.0

Baths

2,500

Sq.Ft.

12626 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 634 BURCH AVENUE Winter Garden, FL MLS# O6371342
$650,000
4

Beds

3.1

Baths

2,351

Sq.Ft.

634 BURCH AVENUE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14525 SABAL CREST WAY Winter Garden, FL MLS# O6371508
$650,000
4

Beds

3.0

Baths

2,527

Sq.Ft.

14525 SABAL CREST WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 14008 JOMATT LOOP Winter Garden, FL MLS# O6376903
  • Recently Listed with Virtual Tour
1 of 47
$650,000
4

Beds

3.0

Baths

2,952

Sq.Ft.

14008 JOMATT LOOP

Winter Garden, FL

Courtesy of THE AGENCY FL
View 8955 LAKESHORE POINTE DRIVE Winter Garden, FL MLS# O6337042
$649,990
4

Beds

3.1

Baths

2,539

Sq.Ft.

8955 LAKESHORE POINTE DRIVE

Winter Garden, FL

Courtesy of ANA TEIXEIRA REALTY
View 15388 ARCADIA BLUFF LOOP Winter Garden, FL MLS# O6361770
$649,990
3

Beds

4.1

Baths

2,640

Sq.Ft.

15388 ARCADIA BLUFF LOOP

Winter Garden, FL

Courtesy of DOUBLE M GROUP COMPANY
View 2510 BLACK LAKE BOULEVARD Winter Garden, FL MLS# O6330638
$649,900
4

Beds

3.0

Baths

3,022

Sq.Ft.

2510 BLACK LAKE BOULEVARD

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 10318 LOVE STORY STREET Winter Garden, FL MLS# O6339686
$649,900
3

Beds

2.0

Baths

2,089

Sq.Ft.

10318 LOVE STORY STREET

Winter Garden, FL

Courtesy of ZIRO REALTY
View 15543 PEBBLE RIDGE STREET Winter Garden, FL MLS# O6250356
$649,800
4

Beds

3.0

Baths

3,359

Sq.Ft.

15543 PEBBLE RIDGE STREET

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 11045 BOSTWICK ALLEY Winter Garden, FL MLS# O6337436
$649,000
4

Beds

3.1

Baths

2,292

Sq.Ft.

11045 BOSTWICK ALLEY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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 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 15007 BLACK SCOTER DRIVE Winter Garden, FL MLS# O6349179
$645,000
4

Beds

3.0

Baths

2,715

Sq.Ft.

15007 BLACK SCOTER DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 8613 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# O6372749
$645,000
4

Beds

3.1

Baths

2,718

Sq.Ft.

8613 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES

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

817

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 - 300K78
$300K - 400K82
$400K - 500K137
$500K - 600K116
$600K - 700K101
$700K - 800K74
$800K - 900K67
$900K - 1M55
$1M - Max89

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family539
Townhouse120
Condo118
Commercial7
Rental237
Lots and Land31
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 2/2/2026)

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 2/2/2026.

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.

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 2/2/2026.

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.

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 2/2/2026.