800 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 2131 TALL OAK DRIVE Winter Garden, FL MLS# O6385247
$890,000
5

Beds

3.0

Baths

3,282

Sq.Ft.

2131 TALL OAK DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1689 CRANLEIGH DR Winter Garden, FL MLS# O6387674
  • Virtual Tour
1 of 48
OPEN HOUSE: Saturday 4/4 12:00 PM - 2:00 PM
$888,800
4

Beds

4.0

Baths

2,937

Sq.Ft.

1689 CRANLEIGH DR

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 15231 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102315
  • New Construction with Virtual Tour
1 of 1
$885,385
5

Beds

4.0

Baths

3,675

Sq.Ft.

15231 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15162 CANOPY COVER DRIVE Winter Garden, FL MLS# S5139203
  • Adult Community with Virtual Tour
1 of 70
$885,000
2

Beds

2.0

Baths

2,049

Sq.Ft.

15162 CANOPY COVER DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 276 SUMMER PINE STREET Winter Garden, FL MLS# O6384565
  • New Construction with Virtual Tour
1 of 25
$885,000
5

Beds

3.0

Baths

3,147

Sq.Ft.

276 SUMMER PINE STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 12965 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6392975
  • Recently Listed with Virtual Tour
1 of 31
$882,932
5

Beds

4.1

Baths

3,101

Sq.Ft.

12965 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 3089 IRISH PEACH DRIVE Winter Garden, FL MLS# S5145627
$880,500
5

Beds

4.1

Baths

3,792

Sq.Ft.

3089 IRISH PEACH DRIVE

Winter Garden, FL

Courtesy of Kissimmee - WEICHERT, REALTORS® - Hallmark Properties
View 6340 WILD PERSIMMON WAY Winter Garden, FL MLS# G5108490
$879,760
6

Beds

4.0

Baths

4,236

Sq.Ft.

6340 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13214 DENDY WAY Winter Garden, FL MLS# O6366658
  • New Construction with Virtual Tour
1 of 71
$879,000
5

Beds

4.1

Baths

3,719

Sq.Ft.

13214 DENDY WAY

Winter Garden, FL

Courtesy of KICANTO REALTY
View 16143 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5107301
$875,595
4

Beds

3.0

Baths

2,740

Sq.Ft.

16143 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15784 SWEET LIMETTA DRIVE Winter Garden, FL MLS# O6375259
$875,000
5

Beds

4.1

Baths

3,635

Sq.Ft.

15784 SWEET LIMETTA DRIVE

Winter Garden, FL

Courtesy of REALTY HUB
View 9409 EMERALD BERRY DRIVE Winter Garden, FL MLS# S5144953
$875,000
4

Beds

3.1

Baths

2,923

Sq.Ft.

9409 EMERALD BERRY DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 931 KYLEE ALLEY Winter Garden, FL MLS# O6387922
  • Virtual Tour
1 of 53
$875,000
4

Beds

4.0

Baths

2,831

Sq.Ft.

931 KYLEE ALLEY

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 16554 RAVEN ROCK PLACE Winter Garden, FL MLS# O6390742
$875,000
4

Beds

3.0

Baths

3,032

Sq.Ft.

16554 RAVEN ROCK PLACE

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
View 15372 GILLIGAN COURT Winter Garden, FL MLS# O6367059
$870,000
4

Beds

3.1

Baths

2,781

Sq.Ft.

15372 GILLIGAN COURT

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1001 VINSETTA CIRCLE Winter Garden, FL MLS# O6392172
  • Recently Listed
1 of 57
$870,000
6

Beds

4.0

Baths

3,988

Sq.Ft.

1001 VINSETTA CIRCLE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 15672 SHOREBIRD LANE Winter Garden, FL MLS# O6375411
$869,900
4

Beds

3.1

Baths

2,800

Sq.Ft.

15672 SHOREBIRD LANE

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 4937 WILDWOOD POINTE ROAD Winter Garden, FL MLS# S5142834
$869,000
5

Beds

4.0

Baths

3,289

Sq.Ft.

4937 WILDWOOD POINTE ROAD

Winter Garden, FL

Courtesy of OLIVO REALTY GROUP, LLC
View 6019 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5102292
$867,899
4

Beds

3.1

Baths

2,688

Sq.Ft.

6019 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11181 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6382203
  • New Construction with Virtual Tour
1 of 32
$860,776
4

Beds

3.1

Baths

3,327

Sq.Ft.

11181 HOLLOW BAY DRIVE

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

950

Estimated median home price

$590,595
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 4
$100K - 200K 15
$200K - 300K 95
$300K - 400K 79
$400K - 500K 150
$500K - 600K 153
$600K - 700K 112
$700K - 800K 93
$800K - 900K 83
$900K - 1M 64
$1M - Max 102

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 647
Townhouse 140
Condo 128
Commercial 11
Rental 224
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 3/31/2026)

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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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 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 4/1/2026.

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

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 4/1/2026.

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 4/1/2026.