984 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 5526 TINY ROAD Winter Garden, FL MLS# O6334009
  • Virtual Tour
1 of 39
$1,675,000
3

Beds

2.2

Baths

2,474

Sq.Ft.

5526 TINY ROAD

Winter Garden, FL

Courtesy of BUYER REBATES REALTY
View 16788 MUSKGRASS DRIVE Winter Garden, FL MLS# O6388174
$1,600,000
4

Beds

4.1

Baths

4,733

Sq.Ft.

16788 MUSKGRASS DRIVE

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 16768 SANCTUARY DRIVE Winter Garden, FL MLS# O6374904
$1,575,000
5

Beds

4.1

Baths

4,258

Sq.Ft.

16768 SANCTUARY DRIVE

Winter Garden, FL

Courtesy of GALLOWAY REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 16826 BROADWATER AVENUE Winter Garden, FL MLS# O6387379
$1,540,000
6

Beds

5.1

Baths

4,451

Sq.Ft.

16826 BROADWATER AVENUE

Winter Garden, FL

Courtesy of ONE STOP SERVICE REALTY INC
View 241 N DILLARD STREET Winter Garden, FL MLS# O6353975
$1,499,999
3

Beds

3.0

Baths

3,507

Sq.Ft.

241 N DILLARD STREET

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 743 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6392705
$1,499,999
5

Beds

5.2

Baths

4,283

Sq.Ft.

743 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 16548 RAVEN ROCK PLACE Winter Garden, FL MLS# S5144064
  • Virtual Tour
1 of 36
OPEN HOUSE: Saturday 4/25 1:00 PM - 3:00 PM
$1,459,900
5

Beds

4.1

Baths

4,263

Sq.Ft.

16548 RAVEN ROCK PLACE

Winter Garden, FL

Courtesy of NAIM REAL ESTATE LLC
View 1698 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# V4948569
  • Recently Listed with Virtual Tour
1 of 78
OPEN HOUSE: Saturday 4/25 11:00 AM - 2:00 PM
$1,450,000
7

Beds

4.0

Baths

4,700

Sq.Ft.

1698 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of Longwood - WEICHERT, REALTORS® - Hallmark Properties
View 16115 JOHNS LAKE OVERLOOK DRIVE Winter Garden, FL MLS# O6376626
$1,420,000
5

Beds

4.1

Baths

4,965

Sq.Ft.

16115 JOHNS LAKE OVERLOOK DRIVE

Winter Garden, FL

Courtesy of POWERHOUSE REAL ESTATE NETWORK
View 16669 VARONE COVE COURT Winter Garden, FL MLS# O6375749
$1,399,900
7

Beds

5.0

Baths

5,613

Sq.Ft.

16669 VARONE COVE COURT

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 14501 WABASSO LOOP Winter Garden, FL MLS# O6386968
  • Virtual Tour
1 of 99
$1,399,000
5

Beds

4.1

Baths

4,030

Sq.Ft.

14501 WABASSO LOOP

Winter Garden, FL

Courtesy of NEXTHOME LOTT PREMIER REALTY
View 243 ZACHARY WADE STREET Winter Garden, FL MLS# O6391909
$1,398,500
5

Beds

3.1

Baths

3,097

Sq.Ft.

243 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of REGENCY REAL ESTATE LLC
View 14241 COLONIAL POINTE DRIVE Winter Garden, FL MLS# O6379808
$1,390,000
7

Beds

5.1

Baths

5,001

Sq.Ft.

14241 COLONIAL POINTE DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 13217 TOLLCROSS WAY Winter Garden, FL MLS# O6285385
  • New Construction
1 of 78
$1,350,000
6

Beds

5.0

Baths

4,152

Sq.Ft.

13217 TOLLCROSS WAY

Winter Garden, FL

Courtesy of JR CERQUEIRA REALTY CORP
View 12934 CANOPY WOODS WAY WAY Winter Garden, FL MLS# O6390704
$1,350,000
4

Beds

4.1

Baths

3,665

Sq.Ft.

12934 CANOPY WOODS WAY WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 557 W PLANT STREET Winter Garden, FL MLS# O6356390
  • Virtual Tour
1 of 38
$1,349,000
2,564

Sq.Ft.

557 W PLANT STREET

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 706 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6394059
  • Recently Listed with Virtual Tour
1 of 48
OPEN HOUSE: Sunday 4/26 12:00 PM - 2:00 PM
$1,337,000
5

Beds

5.2

Baths

4,019

Sq.Ft.

706 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 671 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6383438
$1,325,000
5

Beds

4.1

Baths

4,490

Sq.Ft.

671 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 12025 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6395850
  • Recently Listed with Virtual Tour
1 of 98
$1,325,000
5

Beds

4.0

Baths

4,321

Sq.Ft.

12025 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of NONA LEGACY POWERED BY LA ROSA
View 15200 LAKE CLAIRE OVERLOOK DRIVE Winter Garden, FL MLS# O6401205
  • Recently Listed with Virtual Tour
1 of 70
$1,325,000
5

Beds

4.0

Baths

3,844

Sq.Ft.

15200 LAKE CLAIRE OVERLOOK DRIVE

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY

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

986

Estimated median home price

$599,945
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 1
$100K - 200K 18
$200K - 300K 97
$300K - 400K 80
$400K - 500K 145
$500K - 600K 158
$600K - 700K 123
$700K - 800K 105
$800K - 900K 86
$900K - 1M 66
$1M - Max 107

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 680
Townhouse 136
Condo 132
Commercial 12
Rental 217
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 4/23/2026)

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.

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Data is updated as of 4/23/2026.

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 4/23/2026.

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 4/23/2026.