456 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 9652 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6409704
$445,000
4

Beds

2.1

Baths

1,948

Sq.Ft.

9652 AMBER CHESTNUT WAY

Winter Garden, FL

Courtesy of PRATT REALTY INC
View 17013 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112484
  • New Construction with Virtual Tour
1 of 5
$455,752
3

Beds

2.1

Baths

1,772

Sq.Ft.

17013 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15591 HONEYBELL DRIVE Winter Garden, FL MLS# O6408635
  • Recently Listed with Virtual Tour
1 of 48
$389,900
3

Beds

2.1

Baths

1,584

Sq.Ft.

15591 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 11 WINDTREE LANE B Winter Garden, FL MLS# O6409169
  • Recently Listed with Virtual Tour
1 of 33
$195,000
2

Beds

2.0

Baths

918

Sq.Ft.

11 WINDTREE LANE B

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 2200 ROMANUM DRIVE Winter Garden, FL MLS# O6408190
  • Recently Listed with Virtual Tour
1 of 33
$560,000
4

Beds

4.0

Baths

2,561

Sq.Ft.

2200 ROMANUM DRIVE

Winter Garden, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 16564 BARBOURS CREEK WAY Winter Garden, FL MLS# O6408256
  • New Construction with Virtual Tour
1 of 18
$459,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

16564 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 1335 DANIELS COVE DRIVE Winter Garden, FL MLS# O6402285
$325,000
3

Beds

2.0

Baths

1,371

Sq.Ft.

1335 DANIELS COVE DRIVE

Winter Garden, FL

Courtesy of KGV REALTY GROUP
View 17001 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112433
$485,705
3

Beds

2.1

Baths

1,644

Sq.Ft.

17001 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17007 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112438
$491,490
3

Beds

2.1

Baths

1,764

Sq.Ft.

17007 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7280 WINDY WILLOW STREET Winter Garden, FL MLS# G5112439
  • Recently Listed with Virtual Tour
1 of 5
$493,583
3

Beds

2.1

Baths

1,772

Sq.Ft.

7280 WINDY WILLOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 9318 MCLAREN ALLEY Winter Garden, FL MLS# S5150019
  • Recently Listed with Virtual Tour
1 of 34
$489,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

9318 MCLAREN ALLEY

Winter Garden, FL

Courtesy of MD3 HOMES LLC
View 14501 GROVE RESORT AVENUE 1439 Winter Garden, FL MLS# O6407410
  • Recently Listed with Virtual Tour
1 of 39
$180,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1439

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 12103 EASTMOOR DRIVE Winter Garden, FL MLS# O6409071
  • Recently Listed with Virtual Tour
1 of 25
$450,000
3

Beds

2.0

Baths

1,604

Sq.Ft.

12103 EASTMOOR DRIVE

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 729 MEADOW GLADE DRIVE Winter Garden, FL MLS# O6407943
$530,000
3

Beds

2.0

Baths

2,070

Sq.Ft.

729 MEADOW GLADE DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 16230 Carraway Bay Alley Winter Garden, FL MLS# 1226408
$529,999
4

Beds

3.1

Baths

2,474

Sq.Ft.

16230 Carraway Bay Alley

Winter Garden, FL

View 14501 GROVE RESORT AVE 1535 1535 Winter Garden, FL MLS# S5150001
  • Recently Listed with Virtual Tour
1 of 19
$410,990
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVE 1535 1535

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6408480
  • Recently Listed with Virtual Tour
1 of 23
$335,000
3

Beds

2.1

Baths

1,365

Sq.Ft.

13527 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 170 WINDTREE LANE Winter Garden, FL MLS# S5150050
  • Recently Listed
1 of 14
$204,900
2

Beds

2.0

Baths

918

Sq.Ft.

170 WINDTREE LANE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 12597 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6407413
  • Recently Listed with Virtual Tour
1 of 31
$520,000
3

Beds

2.0

Baths

2,322

Sq.Ft.

12597 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 5545 BOWMAN DRIVE Winter Garden, FL MLS# O6407484
  • Recently Listed with Virtual Tour
1 of 29
OPEN HOUSE: Sunday 5/24 9:00 AM - 7:00 PM
$485,000
2

Beds

2.1

Baths

1,998

Sq.Ft.

5545 BOWMAN DRIVE

Winter Garden, FL

Courtesy of OPENDOOR BROKERAGE 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

1,042

Estimated median home price

$609,945
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 - 200K21
$200K - 300K98
$300K - 400K83
$400K - 500K138
$500K - 600K170
$600K - 700K126
$700K - 800K118
$800K - 900K87
$900K - 1M74
$1M - Max125

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family716
Townhouse139
Condo145
Commercial10
Rental212
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/23/2026)

Information deemed reliable but not guaranteed.

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.

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© Copyright 2026 New Smyrna Beach Board 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 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 5/24/2026.

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 5/24/2026.

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

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.

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 5/24/2026.