456 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 5374 LAKE VIRGINIA STREET Winter Garden, FL MLS# O6385721
$571,900
4

Beds

3.0

Baths

2,038

Sq.Ft.

5374 LAKE VIRGINIA STREET

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 33 TIMBERCREEK PINES CIRCLE Winter Garden, FL MLS# O6408941
  • Recently Listed with Virtual Tour
1 of 29
$570,000
3

Beds

2.0

Baths

1,584

Sq.Ft.

33 TIMBERCREEK PINES CIRCLE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 46 W VINING STREET Winter Garden, FL MLS# O6408720
  • Recently Listed with Virtual Tour
1 of 40
$569,900
3

Beds

2.0

Baths

1,273

Sq.Ft.

46 W VINING STREET

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 17061 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5110436
$565,990
4

Beds

3.1

Baths

2,515

Sq.Ft.

17061 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 16137 WIND VIEW LANE Winter Garden, FL MLS# O6335769
$565,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

16137 WIND VIEW LANE

Winter Garden, FL

Courtesy of IVRE ORLANDO
View 13151 CALMING BREEZE WAY Winter Garden, FL MLS# O6363957
  • Virtual Tour
1 of 40
OPEN HOUSE: Saturday 5/23 12:00 PM - 2:00 PM
$565,000
3

Beds

2.1

Baths

2,096

Sq.Ft.

13151 CALMING BREEZE WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 2230 ROMANUM DRIVE Winter Garden, FL MLS# O6389947
  • Virtual Tour
1 of 29
$565,000
4

Beds

4.0

Baths

2,562

Sq.Ft.

2230 ROMANUM DRIVE

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 8275 BAYVIEW CROSSING DR DRIVE Winter Garden, FL MLS# TB8496196
$565,000
3

Beds

3.0

Baths

2,019

Sq.Ft.

8275 BAYVIEW CROSSING DR DRIVE

Winter Garden, FL

Courtesy of DALTON WADE INC
View 17126 ARROWHEAD BOULEVARD Winter Garden, FL MLS# O6409499
  • Recently Listed with Virtual Tour
1 of 6
$565,000
3

Beds

2.0

Baths

2,114

Sq.Ft.

17126 ARROWHEAD BOULEVARD

Winter Garden, FL

Courtesy of Orlando - WEICHERT, REALTORS® - Hallmark Properties
View 14019 SNOWY OWL LANE Winter Garden, FL MLS# S5148173
$564,900
4

Beds

3.0

Baths

2,133

Sq.Ft.

14019 SNOWY OWL LANE

Winter Garden, FL

Courtesy of NAIM REAL ESTATE LLC
View 16736 OAKBORO STREET Winter Garden, FL MLS# O6388784
$563,900
4

Beds

3.1

Baths

2,477

Sq.Ft.

16736 OAKBORO STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 17098 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6357599
$560,000
4

Beds

3.1

Baths

2,484

Sq.Ft.

17098 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of ORLANDO BROTHERS REAL ESTATE LLC
View 16140 HARBOR MIST ALLEY Winter Garden, FL MLS# O6365057
1 of 34
OPEN HOUSE: Saturday 5/23 1:00 PM - 3:00 PM
$560,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

16140 HARBOR MIST ALLEY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 10043 SEQUEL ALLEY Winter Garden, FL MLS# O6384246
  • Virtual Tour
1 of 37
$560,000
4

Beds

3.1

Baths

2,502

Sq.Ft.

10043 SEQUEL ALLEY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 16933 OAKBORO STREET Winter Garden, FL MLS# R4910916
$560,000
3

Beds

2.1

Baths

2,027

Sq.Ft.

16933 OAKBORO STREET

Winter Garden, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 15524 AVIATION ALLEY Winter Garden, FL MLS# O6398331
$560,000
3

Beds

3.1

Baths

2,414

Sq.Ft.

15524 AVIATION ALLEY

Winter Garden, FL

Courtesy of LOKATION
View 16031 PEBBLE BLUFF LOOP Winter Garden, FL MLS# O6404448
  • Recently Listed with Virtual Tour
1 of 51
$560,000
4

Beds

3.1

Baths

2,487

Sq.Ft.

16031 PEBBLE BLUFF LOOP

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 17335 BEACHGRASS ALLEY Winter Garden, FL MLS# O6335800
  • New Construction
1 of 26
$559,990
3

Beds

2.1

Baths

2,341

Sq.Ft.

17335 BEACHGRASS ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 16845 HOBE SOUND COURT Winter Garden, FL MLS# O6362478
  • New Construction with Virtual Tour
1 of 35
$559,990
3

Beds

2.1

Baths

2,027

Sq.Ft.

16845 HOBE SOUND COURT

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA 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

Price Count
$0 - 100K 2
$100K - 200K 21
$200K - 300K 98
$300K - 400K 83
$400K - 500K 138
$500K - 600K 170
$600K - 700K 126
$700K - 800K 118
$800K - 900K 87
$900K - 1M 74
$1M - Max 125

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 716
Townhouse 139
Condo 145
Commercial 10
Rental 212
Lots and Land 29
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 2
Farms 0

(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.

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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 5/23/2026.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

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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 5/23/2026.

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 5/23/2026.