740 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 626 DUFF DRIVE Winter Garden, FL MLS# O6382820
  • Recently Listed with Virtual Tour
1 of 95
$900,000
5

Beds

4.1

Baths

3,335

Sq.Ft.

626 DUFF DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 1689 CRANLEIGH DR Winter Garden, FL MLS# O6387674
  • Recently Listed with Virtual Tour
1 of 48
OPEN HOUSE: Saturday 3/7 12:00 PM - 2:00 PM
$900,000
4

Beds

4.0

Baths

2,937

Sq.Ft.

1689 CRANLEIGH DR

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 11145 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6367437
  • New Construction with Virtual Tour
1 of 31
$899,990
4

Beds

3.2

Baths

3,327

Sq.Ft.

11145 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 615 SIGLER DRIVE Winter Garden, FL MLS# O6387120
  • Recently Listed with Virtual Tour
1 of 13
$899,840
4

Beds

3.1

Baths

2,432

Sq.Ft.

615 SIGLER DRIVE

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 15213 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102285
$899,360
4

Beds

3.0

Baths

2,879

Sq.Ft.

15213 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5217 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6363382
$899,000
4

Beds

3.1

Baths

3,144

Sq.Ft.

5217 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 17606 LAKE STAR ROAD Winter Garden, FL MLS# O6382909
  • Recently Listed with Virtual Tour
1 of 73
OPEN HOUSE: Saturday 3/7 10:00 AM - 2:00 PM
$899,000
4

Beds

3.1

Baths

2,605

Sq.Ft.

17606 LAKE STAR ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 9409 EMERALD BERRY DRIVE Winter Garden, FL MLS# S5144953
$898,000
4

Beds

3.1

Baths

2,923

Sq.Ft.

9409 EMERALD BERRY DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 16137 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5102317
$895,620
4

Beds

3.0

Baths

2,726

Sq.Ft.

16137 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 131 OAK LAUREL DRIVE Winter Garden, FL MLS# O6374501
$895,000
3

Beds

3.1

Baths

1,906

Sq.Ft.

131 OAK LAUREL DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 15498 SANDFIELD LOOP Winter Garden, FL MLS# O6376314
$895,000
4

Beds

3.1

Baths

4,307

Sq.Ft.

15498 SANDFIELD LOOP

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 14645 SCOTT KEY DRIVE Winter Garden, FL MLS# G5106818
$890,000
4

Beds

3.1

Baths

3,427

Sq.Ft.

14645 SCOTT KEY DRIVE

Winter Garden, FL

Courtesy of RIVA REALTY GROUP LLC
View 2205 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6380281
  • Recently Listed with Virtual Tour
1 of 58
$890,000
5

Beds

3.0

Baths

3,747

Sq.Ft.

2205 WINTERMERE POINTE DRIVE

Winter Garden, FL

Courtesy of HP GLOBAL REALTY LLC
View 2131 TALL OAK DRIVE Winter Garden, FL MLS# O6385247
  • Recently Listed with Virtual Tour
1 of 68
$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 276 SUMMER PINE STREET Winter Garden, FL MLS# O6384565
  • Recently Listed with Virtual Tour
1 of 25
$889,900
5

Beds

3.0

Baths

3,147

Sq.Ft.

276 SUMMER PINE STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15231 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102315
$885,385
5

Beds

4.0

Baths

3,675

Sq.Ft.

15231 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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 15372 GILLIGAN COURT Winter Garden, FL MLS# O6367059
$884,500
4

Beds

3.1

Baths

2,781

Sq.Ft.

15372 GILLIGAN COURT

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 18049 MILLHOUSE WAY Winter Garden, FL MLS# O6367428
  • New Construction with Virtual Tour
1 of 31
$882,200
4

Beds

3.1

Baths

3,327

Sq.Ft.

18049 MILLHOUSE WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
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

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

896

Estimated median home price

$595,000
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 - 100K5
$100K - 200K13
$200K - 300K87
$300K - 400K78
$400K - 500K143
$500K - 600K138
$600K - 700K108
$700K - 800K89
$800K - 900K68
$900K - 1M58
$1M - Max109

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family607
Townhouse127
Condo124
Commercial10
Rental221
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 3/5/2026)

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 3/5/2026.

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 3/5/2026.

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 3/5/2026.