789 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 15724 CUTTER SAIL PLACE Winter Garden, FL MLS# O6321602
$1,080,000
5

Beds

4.1

Baths

3,811

Sq.Ft.

15724 CUTTER SAIL PLACE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16003 TANGERINE BLOSSOM WAY Winter Garden, FL MLS# O6291109
$1,063,750
5

Beds

4.1

Baths

4,475

Sq.Ft.

16003 TANGERINE BLOSSOM WAY

Winter Garden, FL

Courtesy of RE/MAX ASSURED
View 226 WOODFALL LANE Winter Garden, FL MLS# O6325915
  • New Construction with Virtual Tour
1 of 55
$1,050,000
5

Beds

5.0

Baths

4,442

Sq.Ft.

226 WOODFALL LANE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 17552 LAKE STAR ROAD Winter Garden, FL MLS# O6344668
$1,050,000
4

Beds

3.1

Baths

2,605

Sq.Ft.

17552 LAKE STAR ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 10037 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6348960
$1,050,000
5

Beds

3.1

Baths

4,305

Sq.Ft.

10037 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of CREEGAN GROUP
View 100 TEMPLE GROVE DRIVE Winter Garden, FL MLS# NS1086151
$1,050,000
4

Beds

3.0

Baths

3,182

Sq.Ft.

100 TEMPLE GROVE DRIVE

Winter Garden, FL

View 100 TEMPLE GROVE DRIVE Winter Garden, FL MLS# NS1086151
$1,050,000
4

Beds

3.0

Baths

3,182

Sq.Ft.

100 TEMPLE GROVE DRIVE

Winter Garden, FL

Courtesy of ENGEL & VOLKERS NEW SMYRNA
View 14073 JOMATT LOOP Winter Garden, FL MLS# O6359601
$1,049,000
7

Beds

4.0

Baths

4,847

Sq.Ft.

14073 JOMATT LOOP

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 16138 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5102288
$1,040,301
5

Beds

4.0

Baths

3,675

Sq.Ft.

16138 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15274 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102343
$1,035,775
6

Beds

4.0

Baths

4,222

Sq.Ft.

15274 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 149 S PARK AVENUE Winter Garden, FL MLS# O6320977
  • Virtual Tour
1 of 46
OPEN HOUSE: Saturday 1/3 10:30 AM - 1:00 PM
$1,034,000
3

Beds

3.1

Baths

2,938

Sq.Ft.

149 S PARK AVENUE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 15261 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102316
$1,029,335
6

Beds

4.0

Baths

4,222

Sq.Ft.

15261 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17144 PHIL C PETERS ROAD Winter Garden, FL MLS# O6260547
$1,025,000
Studio

Beds

0.0

Baths

17144 PHIL C PETERS ROAD

Winter Garden, FL

Courtesy of HAMLIN REALTY
View 16079 BLACK HICKORY DRIVE Winter Garden, FL MLS# O6343640
$1,012,000
5

Beds

4.0

Baths

3,505

Sq.Ft.

16079 BLACK HICKORY DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16149 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5104655
$1,005,995
5

Beds

3.1

Baths

3,764

Sq.Ft.

16149 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 851 9TH STREET Winter Garden, FL MLS# O6306969
$1,000,000
Studio

Beds

0.0

Baths

851 9TH STREET

Winter Garden, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 9493 EMERALD BERRY DRIVE Winter Garden, FL MLS# O6325653
$1,000,000
4

Beds

3.1

Baths

3,211

Sq.Ft.

9493 EMERALD BERRY DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1711 AMSEL FALLS PARK TERRACE Winter Garden, FL MLS# O6346377
$1,000,000
5

Beds

4.0

Baths

3,863

Sq.Ft.

1711 AMSEL FALLS PARK TERRACE

Winter Garden, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 16175 LEW GEM COURT Winter Garden, FL MLS# O6366128
  • Recently Listed with Virtual Tour
1 of 32
$1,000,000
4

Beds

4.0

Baths

3,957

Sq.Ft.

16175 LEW GEM COURT

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 9207 BUSACO PARK WAY Winter Garden, FL MLS# O6366636
  • Recently Listed with Virtual Tour
1 of 96
$1,000,000
5

Beds

4.0

Baths

3,291

Sq.Ft.

9207 BUSACO PARK WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER 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

789

Estimated median home price

$589,000
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 - 100K7
$100K - 200K8
$200K - 300K66
$300K - 400K80
$400K - 500K138
$500K - 600K123
$600K - 700K88
$700K - 800K69
$800K - 900K66
$900K - 1M49
$1M - Max95

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family512
Townhouse120
Condo111
Commercial10
Rental230
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 12/30/2025)

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 2025 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.

Copyright 2025 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 12/30/2025.

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 12/30/2025.