999 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 642 MEDORA WAY Winter Garden, FL MLS# O6403542
  • Recently Listed with Virtual Tour
1 of 1
$1,140,150
4

Beds

3.0

Baths

3,109

Sq.Ft.

642 MEDORA WAY

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 650 MEDORA WAY Winter Garden, FL MLS# O6403543
  • Recently Listed with Virtual Tour
1 of 1
$1,152,190
4

Beds

3.0

Baths

2,902

Sq.Ft.

650 MEDORA WAY

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 2154 OAKINGTON STREET Winter Garden, FL MLS# O6402495
  • Recently Listed with Virtual Tour
1 of 39
$469,900
3

Beds

2.0

Baths

1,585

Sq.Ft.

2154 OAKINGTON STREET

Winter Garden, FL

Courtesy of REAL LIVING R E SOLUTIONS
The time to sell is now! THE TIME TO SELL IS NOW!
View 12790 BRODLOVE LANE Winter Garden, FL MLS# O6403539
$574,900
3

Beds

2.1

Baths

2,322

Sq.Ft.

12790 BRODLOVE LANE

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 407 DOUGLAS WAY 66 Winter Garden, FL MLS# G5111695
  • Recently Listed
1 of 40
$205,000
2

Beds

2.0

Baths

930

Sq.Ft.

407 DOUGLAS WAY 66

Winter Garden, FL

Courtesy of FLORIDA LIFESTYLE REALTY GROUP
View 15419 UGLIS ALLEY Winter Garden, FL MLS# O6403047
  • Recently Listed
1 of 51
$595,000
3

Beds

2.1

Baths

2,270

Sq.Ft.

15419 UGLIS ALLEY

Winter Garden, FL

Courtesy of STOCKWORTH REALTY GROUP
View 16229 PEBBLE BLUFF LOOP Winter Garden, FL MLS# O6403777
$479,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

16229 PEBBLE BLUFF LOOP

Winter Garden, FL

Courtesy of U KEY REALTY
View 14511 ISLEVIEW DRIVE Winter Garden, FL MLS# O6403188
$3,330,000
6

Beds

5.1

Baths

5,290

Sq.Ft.

14511 ISLEVIEW DRIVE

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 11271 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6403252
  • Recently Listed with Virtual Tour
1 of 7
$869,996
5

Beds

4.0

Baths

2,866

Sq.Ft.

11271 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 16570 BARBOURS CREEK WAY Winter Garden, FL MLS# O6403257
  • Recently Listed with Virtual Tour
1 of 15
$439,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16570 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 17090 HARBOR OAK PARKWAY Winter Garden, FL MLS# G5111718
  • Recently Listed with Virtual Tour
1 of 26
$539,900
3

Beds

3.0

Baths

2,148

Sq.Ft.

17090 HARBOR OAK PARKWAY

Winter Garden, FL

Courtesy of TOWERSIDE REALTY INC
View 13603 SUNSET LAKES CIRCLE Winter Garden, FL MLS# G5111474
$787,000
4

Beds

2.1

Baths

2,425

Sq.Ft.

13603 SUNSET LAKES CIRCLE

Winter Garden, FL

Courtesy of LISA REALTY PARTNERS
View 14001 COUNTRY ESTATE DRIVE Winter Garden, FL MLS# O6403044
  • Recently Listed with Virtual Tour
1 of 70
OPEN HOUSE: Saturday 5/2 1:30 PM - 4:30 PM
$1,175,000
4

Beds

4.0

Baths

3,698

Sq.Ft.

14001 COUNTRY ESTATE DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 10361 AUSTRINA OAK LOOP Winter Garden, FL MLS# S5148904
  • Recently Listed with Virtual Tour
1 of 33
$550,000
4

Beds

2.1

Baths

2,204

Sq.Ft.

10361 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of PM ELITE REALTY LLC
View 617 MARSH REED DRIVE Winter Garden, FL MLS# O6402724
  • Recently Listed with Virtual Tour
1 of 35
OPEN HOUSE: Saturday 5/2 12:00 PM - 2:00 PM
$759,000
5

Beds

4.0

Baths

2,828

Sq.Ft.

617 MARSH REED DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 15480 SANDFIELD LOOP Winter Garden, FL MLS# O6399241
  • Recently Listed with Virtual Tour
1 of 37
$749,900
4

Beds

3.0

Baths

2,574

Sq.Ft.

15480 SANDFIELD LOOP

Winter Garden, FL

Courtesy of ORLANDO PROPERTY ADVISORS
View 17085 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5111738
$939,880
5

Beds

4.1

Baths

3,409

Sq.Ft.

17085 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View Address not provided Winter Garden, FL MLS# O6403450
$320,000
2

Beds

2.0

Baths

1,434

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of WELCOME HOME REALTY GROUP LLC
View 402 EGRET PLACE DRIVE Winter Garden, FL MLS# O6402689
  • Recently Listed with Virtual Tour
1 of 59
$689,000
4

Beds

3.0

Baths

2,711

Sq.Ft.

402 EGRET PLACE DRIVE

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 15734 SWEET LEMON WAY Winter Garden, FL MLS# O6401408
  • Recently Listed with Virtual Tour
1 of 72
$950,000
5

Beds

4.1

Baths

3,635

Sq.Ft.

15734 SWEET LEMON WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC

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

1,000

Estimated median home price

$609,875
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 - 300K100
$300K - 400K80
$400K - 500K140
$500K - 600K155
$600K - 700K129
$700K - 800K111
$800K - 900K89
$900K - 1M69
$1M - Max108

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family691
Townhouse133
Condo138
Commercial11
Rental214
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 4/30/2026)

Information deemed reliable but not guaranteed.

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 4/30/2026.

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.

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.

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 4/30/2026.

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 4/30/2026.