788 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 14144 ALDFORD DRIVE Winter Garden, FL MLS# O6371046
  • Recently Listed with Virtual Tour
1 of 78
$1,050,000
5

Beds

4.1

Baths

3,530

Sq.Ft.

14144 ALDFORD DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 7189 SUMMERLAKE GROVES STREET Winter Garden, FL MLS# O6373509
  • Recently Listed with Virtual Tour
1 of 36
OPEN HOUSE: Saturday 1/17 1:00 PM - 3:00 PM
$619,999
3

Beds

2.1

Baths

2,138

Sq.Ft.

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

Courtesy of MAINFRAME REAL ESTATE
View 16098 MANGROVE ROAD Winter Garden, FL MLS# O6373125
  • Recently Listed
1 of 40
$595,000
4

Beds

3.1

Baths

2,472

Sq.Ft.

16098 MANGROVE ROAD

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15519 HONEYBELL DRIVE Winter Garden, FL MLS# O6374051
  • Recently Listed with Virtual Tour
1 of 42
$399,900
3

Beds

2.1

Baths

1,584

Sq.Ft.

15519 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 14501 GROVE RESORT AVENUE 3619 Winter Garden, FL MLS# O6374077
$380,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3619

Winter Garden, FL

Courtesy of REALTY ONE GROUP ESTATES
View 8613 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# O6372749
  • Recently Listed with Virtual Tour
1 of 57
OPEN HOUSE: Saturday 1/17 12:00 PM - 2:00 PM
$645,000
4

Beds

3.1

Baths

2,718

Sq.Ft.

8613 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 814 WALKERS GROVE LANE Winter Garden, FL MLS# O6373494
  • Recently Listed
1 of 37
OPEN HOUSE: Saturday 1/17 12:00 PM - 2:00 PM
$525,000
3

Beds

2.1

Baths

1,866

Sq.Ft.

814 WALKERS GROVE LANE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 14814 PEEKSKILL DRIVE Winter Garden, FL MLS# O6372624
  • Recently Listed with Virtual Tour
1 of 53
$419,497
3

Beds

2.1

Baths

1,624

Sq.Ft.

14814 PEEKSKILL DRIVE

Winter Garden, FL

Courtesy of LAKEFIELD REALTY GROUP LLC
View 2394 BARONSMEDE COURT Winter Garden, FL MLS# O6373715
  • Recently Listed with Virtual Tour
1 of 42
OPEN HOUSE: Sunday 1/18 1:00 PM - 3:00 PM
$745,000
3

Beds

2.0

Baths

2,310

Sq.Ft.

2394 BARONSMEDE COURT

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 9611 LOST CREEK DRIVE Winter Garden, FL MLS# O6373845
  • Recently Listed with Virtual Tour
1 of 57
$860,000
4

Beds

3.0

Baths

2,909

Sq.Ft.

9611 LOST CREEK DRIVE

Winter Garden, FL

Courtesy of M2M REALTY
View 6375 WILD PERSIMMON WAY Winter Garden, FL MLS# G5106743
$767,985
4

Beds

3.0

Baths

2,102

Sq.Ft.

6375 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 16031 SCARPETTA STREET Winter Garden, FL MLS# O6373345
  • Recently Listed with Virtual Tour
1 of 16
$610,000
4

Beds

3.1

Baths

2,474

Sq.Ft.

16031 SCARPETTA STREET

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 17952 LOOKOUT HILL ROAD Winter Garden, FL MLS# O6373477
  • Recently Listed with Virtual Tour
1 of 41
$995,000
Studio

Beds

0.0

Baths

17952 LOOKOUT HILL ROAD

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 16132 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5106674
$1,008,427
5

Beds

3.1

Baths

3,289

Sq.Ft.

16132 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14287 AVENUE OF THE GROVES Winter Garden, FL MLS# O6373569
  • Recently Listed with Virtual Tour
1 of 26
$333,000
2

Beds

2.1

Baths

1,152

Sq.Ft.

14287 AVENUE OF THE GROVES

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 14123 LARKSPUR LAKE DRIVE Winter Garden, FL MLS# O6372991
  • Recently Listed with Virtual Tour
1 of 36
$775,000
4

Beds

3.1

Baths

3,130

Sq.Ft.

14123 LARKSPUR LAKE DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 13067 TOLLCROSS WAY Winter Garden, FL MLS# O6367311
  • Recently Listed with Virtual Tour
1 of 64
$625,000
3

Beds

2.1

Baths

1,906

Sq.Ft.

13067 TOLLCROSS WAY

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 17621 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# TB8463652
  • Recently Listed with Virtual Tour
1 of 55
$549,990
3

Beds

2.0

Baths

1,791

Sq.Ft.

17621 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 5211 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6373067
  • Recently Listed with Virtual Tour
1 of 57
$819,000
4

Beds

3.1

Baths

2,909

Sq.Ft.

5211 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MCO REALTY GROUP LLC
View 607 E OAKLAND AVENUE Winter Garden, FL MLS# O6372870
  • Recently Listed
1 of 42
$875,000
4

Beds

3.1

Baths

3,406

Sq.Ft.

607 E OAKLAND AVENUE

Winter Garden, FL

Courtesy of RE/MAX TOWN & COUNTRY 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

797

Estimated median home price

$590,000
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

Price Count
$0 - 100K 7
$100K - 200K 12
$200K - 300K 68
$300K - 400K 77
$400K - 500K 141
$500K - 600K 115
$600K - 700K 96
$700K - 800K 77
$800K - 900K 65
$900K - 1M 48
$1M - Max 91

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 518
Townhouse 124
Condo 112
Commercial 8
Rental 240
Lots and Land 33
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 1/15/2026)

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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© 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 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 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.

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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 1/15/2026.

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 1/15/2026.