255 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 8001 POND APPLE DRIVE Winter Garden, FL MLS# O6437864
  • Recently Listed with Virtual Tour
1 of 18
OPEN HOUSE: Saturday 9/5 3:00 PM - 5:00 PM
$785,000
5

Beds

3.0

Baths

3,289

Sq.Ft.

8001 POND APPLE DRIVE

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# G5117322
$871,315
4

Beds

3.0

Baths

2,740

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6135 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5117323
$765,490
4

Beds

3.1

Baths

2,688

Sq.Ft.

6135 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2108 TILLMAN AVENUE Winter Garden, FL MLS# O6437773
  • Recently Listed with Virtual Tour
1 of 50
$849,000
5

Beds

4.0

Baths

3,078

Sq.Ft.

2108 TILLMAN AVENUE

Winter Garden, FL

View 17418 HONEYBELL TANGELO COURT Winter Garden, FL MLS# O6437463
  • Recently Listed with Virtual Tour
1 of 50
OPEN HOUSE: Thursday 9/3 10:00 AM - 6:00 PM
$829,000
4

Beds

3.1

Baths

3,041

Sq.Ft.

17418 HONEYBELL TANGELO COURT

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 2716 GORST RD Winter Garden, FL MLS# O6437314
  • Recently Listed with Virtual Tour
1 of 30
OPEN HOUSE: Saturday 9/5 11:00 AM - 3:00 PM
$859,000
5

Beds

5.0

Baths

3,935

Sq.Ft.

2716 GORST RD

Winter Garden, FL

View 9982 BEACH PORT DRIVE Winter Garden, FL MLS# O6437583
  • Recently Listed with Virtual Tour
1 of 43
OPEN HOUSE: Saturday 9/5 11:00 AM - 2:00 PM
$825,000
4

Beds

3.1

Baths

2,921

Sq.Ft.

9982 BEACH PORT DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16771 OAKBORO STREET STREET Winter Garden, FL MLS# O6436008
$787,000
5

Beds

4.0

Baths

2,840

Sq.Ft.

16771 OAKBORO STREET STREET

Winter Garden, FL

Courtesy of DOUGLAS ELLIMAN
View 12728 CHARMED DRIVE Winter Garden, FL MLS# O6437239
  • Recently Listed with Virtual Tour
1 of 51
OPEN HOUSE: Saturday 9/5 11:00 AM - 1:00 PM
$835,000
5

Beds

4.1

Baths

3,231

Sq.Ft.

12728 CHARMED DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13112 DENDY WAY Winter Garden, FL MLS# O6437516
  • Recently Listed with Virtual Tour
1 of 58
$825,000
5

Beds

4.0

Baths

3,285

Sq.Ft.

13112 DENDY WAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 12349 SILK MIMOSA ALLEY Winter Garden, FL MLS# O6436494
$652,990
4

Beds

4.0

Baths

2,622

Sq.Ft.

12349 SILK MIMOSA ALLEY

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 17428 HONEYBELL TANGELO COURT Winter Garden, FL MLS# O6436505
  • Recently Listed with Virtual Tour
1 of 57
OPEN HOUSE: Thursday 9/3 10:00 AM - 6:00 PM
$834,000
5

Beds

4.1

Baths

3,501

Sq.Ft.

17428 HONEYBELL TANGELO COURT

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17307 BAL HARBOUR DRIVE Winter Garden, FL MLS# O6436527
  • Recently Listed with Virtual Tour
1 of 47
$660,000
3

Beds

2.0

Baths

2,123

Sq.Ft.

17307 BAL HARBOUR DRIVE

Winter Garden, FL

Courtesy of LOVELAND PROPERTIES
View 301 VALENCIA COURT Winter Garden, FL MLS# NS1089084
  • Recently Listed with Virtual Tour
1 of 29
$750,000
4

Beds

2.1

Baths

2,029

Sq.Ft.

301 VALENCIA COURT

Winter Garden, FL

View 301 VALENCIA COURT Winter Garden, FL MLS# NS1089084
  • Recently Listed with Virtual Tour
1 of 29
$750,000
4

Beds

2.1

Baths

2,029

Sq.Ft.

301 VALENCIA COURT

Winter Garden, FL

Courtesy of WHITE WHALE REAL ESTATE
View 5024 PALMETTO PARK DRIVE Winter Garden, FL MLS# O6436423
  • Recently Listed with Virtual Tour
1 of 32
$779,000
4

Beds

3.1

Baths

3,064

Sq.Ft.

5024 PALMETTO PARK DRIVE

Winter Garden, FL

View 14776 MAGNOLIA RIDGE LOOP Winter Garden, FL MLS# O6434178
  • Recently Listed with Virtual Tour
1 of 54
$849,900
4

Beds

3.1

Baths

2,876

Sq.Ft.

14776 MAGNOLIA RIDGE LOOP

Winter Garden, FL

View 2202 REDMARK LANE Winter Garden, FL MLS# O6435919
  • Recently Listed with Virtual Tour
1 of 61
$824,900
5

Beds

3.1

Baths

3,344

Sq.Ft.

2202 REDMARK LANE

Winter Garden, FL

View 2157 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# TB8532509
  • Recently Listed with Virtual Tour
1 of 31
$795,000
5

Beds

3.1

Baths

3,197

Sq.Ft.

2157 WINTERMERE POINTE DRIVE

Winter Garden, FL

View 427 TIERRA VERDE LANE Winter Garden, FL MLS# O6435267
  • Recently Listed with Virtual Tour
1 of 38
$849,988
4

Beds

3.0

Baths

2,368

Sq.Ft.

427 TIERRA VERDE LANE

Winter Garden, 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

1,003

Estimated median home price

$605,000
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 - 100K1
$100K - 200K21
$200K - 300K91
$300K - 400K75
$400K - 500K148
$500K - 600K165
$600K - 700K108
$700K - 800K108
$800K - 900K110
$900K - 1M61
$1M - Max115

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family695
Townhouse137
Condo134
Commercial9
Rental182
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 9/2/2026)

Information deemed reliable but not guaranteed.

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 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.

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 9/3/2026.