980 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 7573 GREEN MOUNTAIN WAY Winter Garden, FL MLS# O6429288
$1,690,000
4

Beds

3.1

Baths

3,388

Sq.Ft.

7573 GREEN MOUNTAIN WAY

Winter Garden, FL

Courtesy of PRISTINE INTERNATIONAL REALTY LLC
View 279 ZACHARY WADE STREET Winter Garden, FL MLS# O6408014
$1,675,000
5

Beds

3.1

Baths

4,473

Sq.Ft.

279 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
View 1032 GALSTON ALLEY Winter Garden, FL MLS# O6441542
  • Recently Listed with Virtual Tour
1 of 47
OPEN HOUSE: Sunday 10/11 12:00 PM - 2:00 PM
$1,650,000
6

Beds

4.1

Baths

3,506

Sq.Ft.

1032 GALSTON ALLEY

Winter Garden, FL

Courtesy of OAK AVENUE REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1101 EAGLES PASS WAY Winter Garden, FL MLS# O6408835
$1,644,999
6

Beds

5.0

Baths

4,104

Sq.Ft.

1101 EAGLES PASS WAY

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 325 CRYSTAL WOOD DRIVE Winter Garden, FL MLS# O6408089
$1,600,000
5

Beds

5.0

Baths

4,442

Sq.Ft.

325 CRYSTAL WOOD DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17372 GLOSSY POMELO WAY Winter Garden, FL MLS# O6406639
$1,580,000
5

Beds

5.1

Baths

4,977

Sq.Ft.

17372 GLOSSY POMELO WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16788 MUSKGRASS DRIVE Winter Garden, FL MLS# O6388174
$1,550,000
4

Beds

4.1

Baths

4,733

Sq.Ft.

16788 MUSKGRASS DRIVE

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 7031 BILLIE COURT Winter Garden, FL MLS# O6445243
  • Recently Listed with Virtual Tour
1 of 41
$1,550,000
4

Beds

4.0

Baths

3,487

Sq.Ft.

7031 BILLIE COURT

Winter Garden, FL

Courtesy of CASTRO REALTY GROUP
View 261 ZACHARY WADE STREET Winter Garden, FL MLS# O6446065
  • Recently Listed with Virtual Tour
1 of 68
$1,500,000
4

Beds

3.1

Baths

3,728

Sq.Ft.

261 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of BALDWIN PARK REALTY LLC
View 241 N DILLARD STREET Winter Garden, FL MLS# O6353975
$1,499,999
4

Beds

3.0

Baths

3,507

Sq.Ft.

241 N DILLARD STREET

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 2450 DAHLGREN WAY Winter Garden, FL MLS# TB8481106
  • Virtual Tour
1 of 61
OPEN HOUSE: Sunday 10/11 1:00 PM - 4:00 PM
$1,499,990
5

Beds

5.0

Baths

4,365

Sq.Ft.

2450 DAHLGREN WAY

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 263 DEER ISLE DRIVE Winter Garden, FL MLS# O6440044
$1,495,000
3

Beds

2.1

Baths

2,735

Sq.Ft.

263 DEER ISLE DRIVE

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY
View 16548 RAVEN ROCK PLACE Winter Garden, FL MLS# S5155094
$1,460,000
5

Beds

4.1

Baths

4,263

Sq.Ft.

16548 RAVEN ROCK PLACE

Winter Garden, FL

Courtesy of AROD PARTNERS REALTY
View 15619 GIANT FOXTAIL COURT Winter Garden, FL MLS# O6422589
$1,450,000
4

Beds

3.1

Baths

3,086

Sq.Ft.

15619 GIANT FOXTAIL COURT

Winter Garden, FL

Courtesy of STOCKWORTH REALTY GROUP
View 228 STANTON ESTATES CIRCLE Winter Garden, FL MLS# O6447271
  • Recently Listed with Virtual Tour
1 of 47
$1,425,000
4

Beds

4.0

Baths

4,189

Sq.Ft.

228 STANTON ESTATES CIRCLE

Winter Garden, FL

Courtesy of MERDIAN REALTY LLC
View 1720 LAKE ROBERTS LANDING DRIVE Winter Garden, FL MLS# O6436608
$1,399,999
5

Beds

4.1

Baths

4,919

Sq.Ft.

1720 LAKE ROBERTS LANDING DRIVE

Winter Garden, FL

Courtesy of ACCORD REAL ESTATE SERVICES
View 16614 HARBOR SAIL WAY Winter Garden, FL MLS# O6414639
$1,399,000
6

Beds

5.1

Baths

4,882

Sq.Ft.

16614 HARBOR SAIL WAY

Winter Garden, FL

Courtesy of GLOBAL FLORIDA REALTY
View 17077 WINGSPREAD LOOP Winter Garden, FL MLS# O6437444
$1,349,000
5

Beds

4.1

Baths

4,680

Sq.Ft.

17077 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 15240 SHONAN GOLD DRIVE Winter Garden, FL MLS# O6440016
$1,348,900
4

Beds

3.1

Baths

4,000

Sq.Ft.

15240 SHONAN GOLD DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 9103 MORGANA COURT Winter Garden, FL MLS# O6409652
$1,339,000
5

Beds

4.1

Baths

4,376

Sq.Ft.

9103 MORGANA COURT

Winter Garden, FL

Courtesy of HAMMOND REALTY GROUP LLC

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

979

Estimated median home price

$595,000
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 - 100K1
$100K - 200K34
$200K - 300K69
$300K - 400K77
$400K - 500K158
$500K - 600K161
$600K - 700K105
$700K - 800K109
$800K - 900K102
$900K - 1M60
$1M - Max103

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family670
Townhouse152
Condo119
Commercial6
Rental226
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 10/9/2026)

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 10/11/2026.

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 10/11/2026.

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 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.

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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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 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 10/11/2026.