793 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 7833 FREESTYLE LANE Winter Garden, FL MLS# O6341451
$1,295,000
4

Beds

3.0

Baths

3,364

Sq.Ft.

7833 FREESTYLE LANE

Winter Garden, FL

Courtesy of GLOBAL SAPPHIRE REALTY LLC
View 133 S PARK AVENUE Winter Garden, FL MLS# G5103956
$1,289,000
3

Beds

3.1

Baths

2,938

Sq.Ft.

133 S PARK AVENUE

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 16894 WINGSPREAD LOOP Winter Garden, FL MLS# O6362090
$1,270,000
5

Beds

3.1

Baths

3,906

Sq.Ft.

16894 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of THE BRAHMIN GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 15716 PANTHER LAKE DRIVE Winter Garden, FL MLS# O6330120
$1,249,000
5

Beds

4.1

Baths

4,693

Sq.Ft.

15716 PANTHER LAKE DRIVE

Winter Garden, FL

Courtesy of HORIZON WEST REALTY
View 13554 SUNSET LAKES CIRCLE Winter Garden, FL MLS# O6350334
$1,232,000
3

Beds

3.0

Baths

3,136

Sq.Ft.

13554 SUNSET LAKES CIRCLE

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 17556 DEER ISLE CIRCLE Winter Garden, FL MLS# O6332919
$1,225,000
4

Beds

3.1

Baths

3,214

Sq.Ft.

17556 DEER ISLE CIRCLE

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 617 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6345429
$1,200,000
4

Beds

4.1

Baths

3,624

Sq.Ft.

617 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 10067 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6361968
$1,190,000
6

Beds

5.0

Baths

4,305

Sq.Ft.

10067 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 17335 GLOSSY POMELO WAY Winter Garden, FL MLS# O6365223
  • Recently Listed with Virtual Tour
1 of 16
$1,189,990
5

Beds

4.1

Baths

4,780

Sq.Ft.

17335 GLOSSY POMELO WAY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 16611 TOCCOA ROW Winter Garden, FL MLS# O6314995
$1,180,000
5

Beds

4.2

Baths

4,685

Sq.Ft.

16611 TOCCOA ROW

Winter Garden, FL

Courtesy of A2Z GLOBAL REALTY LLC
View 17661 DAVENPORT ROAD Winter Garden, FL MLS# O6350509
$1,175,000
3

Beds

3.0

Baths

2,400

Sq.Ft.

17661 DAVENPORT ROAD

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 16144 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5104660
$1,165,271
4

Beds

3.0

Baths

3,108

Sq.Ft.

16144 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15136 CANOE PLACE Winter Garden, FL MLS# O6358335
$1,150,000
5

Beds

4.1

Baths

3,917

Sq.Ft.

15136 CANOE PLACE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 10007 LITTLE ALCOVE LOOP Winter Garden, FL MLS# S5132434
$1,149,900
4

Beds

3.1

Baths

2,921

Sq.Ft.

10007 LITTLE ALCOVE LOOP

Winter Garden, FL

Courtesy of MBT REALTY LLC
View 15267 MARITIME PINE DRIVE Winter Garden, FL MLS# G5103775
$1,149,565
6

Beds

4.0

Baths

3,907

Sq.Ft.

15267 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8759 SONOMA COAST DRIVE Winter Garden, FL MLS# S5139789
  • Recently Listed with Virtual Tour
1 of 59
$1,135,900
5

Beds

5.0

Baths

3,416

Sq.Ft.

8759 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of MBT REALTY LLC
View 15706 CUTTER SAIL PLACE Winter Garden, FL MLS# O6366512
  • Recently Listed with Virtual Tour
1 of 63
$1,125,000
5

Beds

4.1

Baths

3,894

Sq.Ft.

15706 CUTTER SAIL PLACE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 13235 TOLLCROSS WAY Winter Garden, FL MLS# O6340109
$1,100,000
5

Beds

4.1

Baths

3,470

Sq.Ft.

13235 TOLLCROSS WAY

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 17608 DEER ISLE CIRCLE Winter Garden, FL MLS# O6350825
$1,100,000
4

Beds

2.1

Baths

3,144

Sq.Ft.

17608 DEER ISLE CIRCLE

Winter Garden, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 626 OXFORD CHASE DRIVE Winter Garden, FL MLS# O6356804
$1,090,000
5

Beds

4.1

Baths

4,478

Sq.Ft.

626 OXFORD CHASE DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE

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

794

Estimated median home price

$589,990
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 - 200K7
$200K - 300K66
$300K - 400K81
$400K - 500K138
$500K - 600K125
$600K - 700K90
$700K - 800K69
$800K - 900K66
$900K - 1M49
$1M - Max96

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family515
Townhouse123
Condo110
Commercial10
Rental229
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 12/29/2025)

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.

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 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 12/29/2025.

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 12/29/2025.