854 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 16175 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5104189
$920,308
4

Beds

3.0

Baths

3,108

Sq.Ft.

16175 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 9218 HOLLISTON CREEK PLACE Winter Garden, FL MLS# O6386394
  • Virtual Tour
1 of 64
OPEN HOUSE: Sunday 5/24 11:00 AM - 2:30 AM
$920,000
4

Beds

3.1

Baths

3,087

Sq.Ft.

9218 HOLLISTON CREEK PLACE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 10551 PETRILLO WAY Winter Garden, FL MLS# O6368778
  • Virtual Tour
1 of 90
$919,999
5

Beds

4.1

Baths

3,642

Sq.Ft.

10551 PETRILLO WAY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 11264 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6397733
  • New Construction with Virtual Tour
1 of 7
$919,990
5

Beds

4.1

Baths

3,225

Sq.Ft.

11264 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 12940 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6381140
$919,000
5

Beds

4.1

Baths

3,894

Sq.Ft.

12940 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 12928 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6400451
$916,000
5

Beds

4.1

Baths

3,626

Sq.Ft.

12928 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 15327 HERON HIDEAWAY CIRCLE Winter Garden, FL MLS# G5107891
$915,000
7

Beds

4.0

Baths

4,267

Sq.Ft.

15327 HERON HIDEAWAY CIRCLE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17368 WILD DAISY DRIVE Winter Garden, FL MLS# G5110440
  • New Construction
1 of 3
$909,778
6

Beds

4.0

Baths

4,236

Sq.Ft.

17368 WILD DAISY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11283 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405091
  • Recently Listed with Virtual Tour
1 of 7
$909,466
5

Beds

4.1

Baths

3,225

Sq.Ft.

11283 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 15976 CITRUS KNOLL DRIVE Winter Garden, FL MLS# O6399342
$909,000
5

Beds

3.1

Baths

2,953

Sq.Ft.

15976 CITRUS KNOLL DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 461 GERANIUM PARK WAY Winter Garden, FL MLS# O6403758
$900,000
3

Beds

3.1

Baths

2,432

Sq.Ft.

461 GERANIUM PARK WAY

Winter Garden, FL

Courtesy of THE ROSENBLOOM TEAM
View 10264 LOVE STORY STREET Winter Garden, FL MLS# O6409005
  • Recently Listed
1 of 35
$900,000
5

Beds

3.0

Baths

3,295

Sq.Ft.

10264 LOVE STORY STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 17952 LOOKOUT HILL ROAD Winter Garden, FL MLS# O6373477
$899,999
Studio

Beds

0.0

Baths

17952 LOOKOUT HILL ROAD

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 14327 WABASSO LOOP Winter Garden, FL MLS# O6347454
  • Virtual Tour
1 of 48
$899,990
5

Beds

4.0

Baths

3,710

Sq.Ft.

14327 WABASSO LOOP

Winter Garden, FL

Courtesy of KARDOSH REALTY
View 14282 CREEKBED CIRCLE Winter Garden, FL MLS# O6365928
$899,900
4

Beds

4.0

Baths

3,479

Sq.Ft.

14282 CREEKBED CIRCLE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 897 LANDRUM DRIVE Winter Garden, FL MLS# O6404632
  • Recently Listed with Virtual Tour
1 of 33
$899,900
4

Beds

3.1

Baths

3,012

Sq.Ft.

897 LANDRUM DRIVE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 615 SIGLER DRIVE Winter Garden, FL MLS# O6387120
  • New Construction 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 15506 HONEY MANDARIN WAY Winter Garden, FL MLS# O6343579
$899,000
5

Beds

4.1

Baths

3,408

Sq.Ft.

15506 HONEY MANDARIN WAY

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
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

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.

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 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.

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.

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 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

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.