813 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 4122 SHEPPERDS HOLLOW ALLEY Winter Garden, FL MLS# O6370363
  • Virtual Tour
1 of 44
OPEN HOUSE: Saturday 1/24 2:00 PM - 4:00 PM
$589,900
3

Beds

3.1

Baths

2,459

Sq.Ft.

4122 SHEPPERDS HOLLOW ALLEY

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 17490 NORTHLAKE GROVE DRIVE Winter Garden, FL MLS# TB8460402
  • New Construction with Virtual Tour
1 of 38
$499,990
3

Beds

2.1

Baths

1,675

Sq.Ft.

17490 NORTHLAKE GROVE DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 612 DHARMA CIRCLE Winter Garden, FL MLS# O6370600
  • Virtual Tour
1 of 43
$350,000
3

Beds

2.0

Baths

1,422

Sq.Ft.

612 DHARMA CIRCLE

Winter Garden, FL

Courtesy of ADVANCED AGE REALTY, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 1922 SHERBOURNE STREET Winter Garden, FL MLS# G5106212
  • Recently Listed with Virtual Tour
1 of 34
$432,500
3

Beds

2.1

Baths

1,717

Sq.Ft.

1922 SHERBOURNE STREET

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 13150 MORO COURT Winter Garden, FL MLS# S5137634
  • Virtual Tour
1 of 43
$644,900
5

Beds

3.0

Baths

3,516

Sq.Ft.

13150 MORO COURT

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 1373 WILLIAMS ROAD Winter Garden, FL MLS# O6370110
  • Virtual Tour
1 of 44
$539,990
4

Beds

3.1

Baths

2,492

Sq.Ft.

1373 WILLIAMS ROAD

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 7650 TANGERINE KNOLL LOOP Winter Garden, FL MLS# O6368043
$995,000
5

Beds

4.1

Baths

3,578

Sq.Ft.

7650 TANGERINE KNOLL LOOP

Winter Garden, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 47 OAK STREET Winter Garden, FL MLS# O6370459
  • Virtual Tour
1 of 7
$639,000
Studio

Beds

0.0

Baths

47 OAK STREET

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 16330 BRISK BREEZE ALLEY Winter Garden, FL MLS# G5106012
$575,000
3

Beds

2.1

Baths

2,170

Sq.Ft.

16330 BRISK BREEZE ALLEY

Winter Garden, FL

Courtesy of NARROW ROAD REALTY
View 9014 MORGANA COURT Winter Garden, FL MLS# O6371050
  • Recently Listed with Virtual Tour
1 of 55
$2,350,000
5

Beds

4.1

Baths

4,436

Sq.Ft.

9014 MORGANA COURT

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 15401 PORTER ROAD Winter Garden, FL MLS# S5140743
  • Virtual Tour
1 of 49
$558,000
5

Beds

3.0

Baths

2,322

Sq.Ft.

15401 PORTER ROAD

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 14090 AVENUE OF THE GROVES Winter Garden, FL MLS# O6367193
$349,990
2

Beds

2.1

Baths

1,076

Sq.Ft.

14090 AVENUE OF THE GROVES

Winter Garden, FL

Courtesy of DTB FLORIDA REALTY, INC.
View 64 ZACHARY WADE STREET Winter Garden, FL MLS# O6370095
$480,000
4

Beds

2.0

Baths

1,888

Sq.Ft.

64 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of REALTY AND COMPANY INT., LLC
View 11195 GREEN CITRON ALLEY Winter Garden, FL MLS# TB8459795
  • New Construction with Virtual Tour
1 of 39
$624,990
3

Beds

2.0

Baths

1,791

Sq.Ft.

11195 GREEN CITRON ALLEY

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 14501 GROVE RESORT AVENUE 1746 Winter Garden, FL MLS# S5140877
$210,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1746

Winter Garden, FL

Courtesy of KATHRYN VALENTINE PA
View 81 WINDTREE LANE 81 Winter Garden, FL MLS# G5105928
$215,000
2

Beds

2.0

Baths

918

Sq.Ft.

81 WINDTREE LANE 81

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6837 Pasturelands Pl Winter Garden, FL MLS# A11936347
$465,000
3

Beds

2.0

Baths

1,650

Sq.Ft.

6837 Pasturelands Pl

Winter Garden, FL

Courtesy of SPACE REAL ESTATE AGENCY
View 16632 POINT ROCK DRIVE Winter Garden, FL MLS# OM715702
$550,000
4

Beds

3.1

Baths

2,292

Sq.Ft.

16632 POINT ROCK DRIVE

Winter Garden, FL

Courtesy of RE/MAX PREMIER REALTY
View 3136 IRISH PEACH DRIVE Winter Garden, FL MLS# O6367113
$599,900
3

Beds

2.0

Baths

2,136

Sq.Ft.

3136 IRISH PEACH DRIVE

Winter Garden, FL

Courtesy of CASTLE REALTY PROFESSIONAL GROUP LLC
View 6007 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5105905
$674,475
4

Beds

2.1

Baths

2,235

Sq.Ft.

6007 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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

814

Estimated median home price

$589,945
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 7
$100K - 200K 12
$200K - 300K 72
$300K - 400K 83
$400K - 500K 142
$500K - 600K 118
$600K - 700K 97
$700K - 800K 76
$800K - 900K 67
$900K - 1M 49
$1M - Max 91

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 526
Townhouse 129
Condo 117
Commercial 7
Rental 239
Lots and Land 33
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 1/22/2026)

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 1/24/2026.

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 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 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

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 1/24/2026.

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 1/24/2026.