1,034 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 2123 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6412643
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Sunday 6/7 2:00 PM - 4:00 PM
$389,000
4

Beds

2.1

Baths

1,606

Sq.Ft.

2123 PORTCASTLE CIRCLE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 18422 OLIVER TWIST WAY Winter Garden, FL MLS# O6412770
  • Recently Listed with Virtual Tour
1 of 66
$815,000
5

Beds

4.1

Baths

3,231

Sq.Ft.

18422 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 15149 CANOE PLACE Winter Garden, FL MLS# O6412776
  • Recently Listed with Virtual Tour
1 of 65
OPEN HOUSE: Saturday 6/6 11:00 AM - 2:00 PM
$799,000
4

Beds

3.1

Baths

3,081

Sq.Ft.

15149 CANOE PLACE

Winter Garden, FL

Courtesy of RE/MAX ASSURED
The time to sell is now! THE TIME TO SELL IS NOW!
View 1906 SHERBOURNE STREET Winter Garden, FL MLS# S5151079
  • Recently Listed with Virtual Tour
1 of 25
$477,000
4

Beds

2.1

Baths

2,029

Sq.Ft.

1906 SHERBOURNE STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 1143 HULL ISLAND DRIVE Winter Garden, FL MLS# O6413213
  • Recently Listed with Virtual Tour
1 of 50
$779,900
4

Beds

4.0

Baths

2,788

Sq.Ft.

1143 HULL ISLAND DRIVE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 11165 GREEN CITRON ALLEY Winter Garden, FL MLS# O6413226
  • Recently Listed with Virtual Tour
1 of 61
$649,000
4

Beds

3.0

Baths

2,043

Sq.Ft.

11165 GREEN CITRON ALLEY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 17035 HARBOR OAK PARKWAY Winter Garden, FL MLS# O6411409
  • Recently Listed with Virtual Tour
1 of 40
$499,999
3

Beds

2.0

Baths

1,692

Sq.Ft.

17035 HARBOR OAK PARKWAY

Winter Garden, FL

Courtesy of DALTON WADE INC
View 440 TIERRA VERDE LANE Winter Garden, FL MLS# O6412260
  • Recently Listed with Virtual Tour
1 of 50
$1,200,000
4

Beds

3.0

Baths

3,512

Sq.Ft.

440 TIERRA VERDE LANE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1544 MISTFLOWER LANE Winter Garden, FL MLS# O6407815
$469,900
4

Beds

2.0

Baths

2,348

Sq.Ft.

1544 MISTFLOWER LANE

Winter Garden, FL

Courtesy of ENTERA REALTY LLC
View 420 E CYPRESS STREET Winter Garden, FL MLS# O6412414
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Friday 6/5 5:00 PM - 7:00 PM
$425,000
3

Beds

2.0

Baths

1,616

Sq.Ft.

420 E CYPRESS STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
View 6100 CYPRESS HILL ROAD Winter Garden, FL MLS# O6412033
  • Recently Listed with Virtual Tour
1 of 51
$950,000
5

Beds

3.0

Baths

3,777

Sq.Ft.

6100 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of DALTON WADE INC
View 11025 SUSPENSE DRIVE Winter Garden, FL MLS# G5113196
$435,000
3

Beds

2.1

Baths

1,636

Sq.Ft.

11025 SUSPENSE DRIVE

Winter Garden, FL

Courtesy of SCATES REALTY & INVESTMENT PRO
View 12541 GOLD HONEYSUCKLE STREET 280 Winter Garden, FL MLS# O6412476
$829,990
3

Beds

2.1

Baths

2,636

Sq.Ft.

12541 GOLD HONEYSUCKLE STREET 280

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 15806 GEM VIEW ST Winter Garden, FL MLS# C7526682
  • Recently Listed with Virtual Tour
1 of 37
$495,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

15806 GEM VIEW ST

Winter Garden, FL

Courtesy of FAST ACTION REALTY INC
View 73822 SUNNY TIME AVENUE Winter Garden, FL MLS# O6412326
  • Recently Listed with Virtual Tour
1 of 26
$438,890
3

Beds

2.1

Baths

1,683

Sq.Ft.

73822 SUNNY TIME AVENUE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 13843 LANYARD WAY Winter Garden, FL MLS# O6412130
  • Recently Listed with Virtual Tour
1 of 34
$648,000
4

Beds

3.1

Baths

2,568

Sq.Ft.

13843 LANYARD WAY

Winter Garden, FL

Courtesy of AAA GLOBAL VENTURES PA
View 213 S DILLARD STREET 230 Winter Garden, FL MLS# O6412912
  • Recently Listed with Virtual Tour
1 of 16
$799,000
1,448

Sq.Ft.

213 S DILLARD STREET 230

Winter Garden, FL

Courtesy of 21 NEW HOMES INC
View 181 ZACHARY WADE STREET Winter Garden, FL MLS# O6412174
$600,000
5

Beds

3.0

Baths

2,940

Sq.Ft.

181 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY
View 6246 SUNNY TIME AVENUE Winter Garden, FL MLS# O6412223
  • Recently Listed with Virtual Tour
1 of 24
$424,490
3

Beds

2.1

Baths

1,553

Sq.Ft.

6246 SUNNY TIME AVENUE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 2120 GOPHER TORTOISE TERRACE Winter Garden, FL MLS# O6412229
  • Recently Listed with Virtual Tour
1 of 33
$379,900
3

Beds

2.1

Baths

1,620

Sq.Ft.

2120 GOPHER TORTOISE TERRACE

Winter Garden, FL

Courtesy of THE AGENCY FL

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

1,037

Estimated median home price

$609,850
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 - 100K1
$100K - 200K26
$200K - 300K92
$300K - 400K78
$400K - 500K145
$500K - 600K170
$600K - 700K128
$700K - 800K113
$800K - 900K85
$900K - 1M70
$1M - Max129

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family718
Townhouse135
Condo143
Commercial10
Rental210
Lots and Land27
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 6/2/2026)

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 6/3/2026.

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 6/3/2026.

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 6/3/2026.