500 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 15006 PIGEON PLUM LANE Winter Garden, FL MLS# S5147405
$499,900
3

Beds

2.0

Baths

2,046

Sq.Ft.

15006 PIGEON PLUM LANE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 15316 OAK APPLE COURT B Winter Garden, FL MLS# O6397688
  • Recently Listed with Virtual Tour
1 of 28
$349,999
3

Beds

2.1

Baths

1,544

Sq.Ft.

15316 OAK APPLE COURT B

Winter Garden, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 4863 LACEWING DRIVE Winter Garden, FL MLS# O6397857
  • Recently Listed with Virtual Tour
1 of 52
$540,000
3

Beds

2.1

Baths

1,788

Sq.Ft.

4863 LACEWING DRIVE

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1325 FETTLER WAY Winter Garden, FL MLS# O6393936
  • Recently Listed with Virtual Tour
1 of 38
$289,900
3

Beds

2.0

Baths

1,440

Sq.Ft.

1325 FETTLER WAY

Winter Garden, FL

Courtesy of LOTUS DOOR REALTY
View 7343 TWILIGHT BAY DRIVE Winter Garden, FL MLS# S5147747
$599,999
3

Beds

2.0

Baths

1,975

Sq.Ft.

7343 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 227 W CYPRESS STREET Winter Garden, FL MLS# O6397063
$165,000
Studio

Beds

0.0

Baths

227 W CYPRESS STREET

Winter Garden, FL

Courtesy of HOGAN REALTY GROUP INC
View 238 N MAIN STREET Winter Garden, FL MLS# O6397340
  • Recently Listed
1 of 21
$600,000
3

Beds

2.0

Baths

1,005

Sq.Ft.

238 N MAIN STREET

Winter Garden, FL

Courtesy of FOLIO REALTY LLC
View 8275 BAYVIEW CROSSING DR DRIVE Winter Garden, FL MLS# TB8496196
  • Recently Listed with Virtual Tour
1 of 35
$565,000
3

Beds

3.0

Baths

2,019

Sq.Ft.

8275 BAYVIEW CROSSING DR DRIVE

Winter Garden, FL

Courtesy of DALTON WADE INC
View 15350 OAK APPLE COURT 17B Winter Garden, FL MLS# O6396724
$329,900
3

Beds

2.1

Baths

1,544

Sq.Ft.

15350 OAK APPLE COURT 17B

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 15285 HAMLIN PARK DRIVE Winter Garden, FL MLS# TB8494889
  • New Construction with Virtual Tour
1 of 36
$489,990
3

Beds

3.1

Baths

2,072

Sq.Ft.

15285 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 14501 GROVE RESORT AVENUE 1310 Winter Garden, FL MLS# O6397317
  • Recently Listed with Virtual Tour
1 of 50
$230,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1310

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16396 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6396532
  • Recently Listed with Virtual Tour
1 of 35
$484,990
3

Beds

2.1

Baths

2,070

Sq.Ft.

16396 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 16413 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6397513
  • Recently Listed with Virtual Tour
1 of 36
$479,900
3

Beds

2.1

Baths

1,626

Sq.Ft.

16413 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14501 GROVE RESORT AVENUE 1721 Winter Garden, FL MLS# O6397131
  • Recently Listed with Virtual Tour
1 of 50
$249,500
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 1721

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14501 GROVE RESORT AVENUE 1703 Winter Garden, FL MLS# O6394100
  • Recently Listed with Virtual Tour
1 of 22
$299,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 1703

Winter Garden, FL

Courtesy of REALTY ONE GROUP INSPIRATION
View 723 SUNBURST COVE LANE Winter Garden, FL MLS# S5145002
  • Recently Listed with Virtual Tour
1 of 77
$555,000
4

Beds

2.1

Baths

2,189

Sq.Ft.

723 SUNBURST COVE LANE

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View 312 SILVERDALE AVENUE Winter Garden, FL MLS# O6396680
  • Recently Listed with Virtual Tour
1 of 29
$559,900
3

Beds

2.0

Baths

1,950

Sq.Ft.

312 SILVERDALE AVENUE

Winter Garden, FL

Courtesy of WINTER GARDEN REAL ESTATE
View 14718 MICAH STREET Winter Garden, FL MLS# O6396793
$165,000
Studio

Beds

0.0

Baths

14718 MICAH STREET

Winter Garden, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 16197 WIND VIEW LANE Winter Garden, FL MLS# O6397229
  • Recently Listed with Virtual Tour
1 of 50
$540,000
3

Beds

2.1

Baths

2,027

Sq.Ft.

16197 WIND VIEW LANE

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
View 0 9TH STREET Winter Garden, FL MLS# O6398357
  • Recently Listed with Virtual Tour
1 of 5
$299,000
Studio

Beds

0.0

Baths

0 9TH STREET

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND

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

981

Estimated median home price

$599,999
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 - 200K18
$200K - 300K97
$300K - 400K80
$400K - 500K145
$500K - 600K154
$600K - 700K121
$700K - 800K105
$800K - 900K87
$900K - 1M66
$1M - Max107

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family676
Townhouse135
Condo132
Commercial12
Rental217
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 4/22/2026)

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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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 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 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 4/23/2026.

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.

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 4/23/2026.