View 12919 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6381746
$674,000
4

Beds

3.1

Baths

2,508

Sq.Ft.

12919 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 17422 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5112284
$671,415
4

Beds

2.1

Baths

2,235

Sq.Ft.

17422 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5040 BREEZY ACRES STREET Winter Garden, FL MLS# O6409467
$670,000
4

Beds

3.1

Baths

2,724

Sq.Ft.

5040 BREEZY ACRES STREET

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 15026 SUMMER HARVEST STREET Winter Garden, FL MLS# S5153036
  • Recently Listed with Virtual Tour
1 of 41
$669,990
5

Beds

4.1

Baths

2,930

Sq.Ft.

15026 SUMMER HARVEST STREET

Winter Garden, FL

View 9717 WATERWAY PASSAGE DRIVE Winter Garden, FL MLS# O6413773
$669,500
4

Beds

3.0

Baths

2,117

Sq.Ft.

9717 WATERWAY PASSAGE DRIVE

Winter Garden, FL

View 6315 WILD PERSIMMON WAY Winter Garden, FL MLS# G5105013
$668,990
4

Beds

3.0

Baths

2,102

Sq.Ft.

6315 WILD PERSIMMON WAY

Winter Garden, FL

View 5942 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5107158
$668,990
4

Beds

3.0

Baths

2,102

Sq.Ft.

5942 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 12513 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6397713
$668,000
4

Beds

3.1

Baths

2,807

Sq.Ft.

12513 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 16277 HONEY HARVEST STREET Winter Garden, FL MLS# O6411737
$668,000
4

Beds

4.1

Baths

2,930

Sq.Ft.

16277 HONEY HARVEST STREET

Winter Garden, FL

View 17379 CHANNEL WAY Winter Garden, FL MLS# O6412749
$668,000
4

Beds

3.0

Baths

2,782

Sq.Ft.

17379 CHANNEL WAY

Winter Garden, FL

View 14744 FIELD DAISY DRIVE Winter Garden, FL MLS# O6383550
  • New Construction with Virtual Tour
1 of 42
$664,075
4

Beds

3.1

Baths

2,441

Sq.Ft.

14744 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 13184 DENDY WAY Winter Garden, FL MLS# O6384386
  • New Construction with Virtual Tour
1 of 46
$664,000
4

Beds

2.1

Baths

2,211

Sq.Ft.

13184 DENDY WAY

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View Address not provided Winter Garden, FL MLS# G5113600
$663,645
4

Beds

2.1

Baths

2,235

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14517 BLACK LAKE PRESERVE STREET Winter Garden, FL MLS# A4674838
$660,000
4

Beds

2.1

Baths

2,569

Sq.Ft.

14517 BLACK LAKE PRESERVE STREET

Winter Garden, FL

Courtesy of DALTON WADE INC
View 16466 OLIVE HILL DRIVE Winter Garden, FL MLS# O6409922
$660,000
3

Beds

2.1

Baths

2,020

Sq.Ft.

16466 OLIVE HILL DRIVE

Winter Garden, FL

Courtesy of ON ME REALTY
View 1209 CASTLEPORT ROAD Winter Garden, FL MLS# O6390760
$659,000
5

Beds

3.0

Baths

2,812

Sq.Ft.

1209 CASTLEPORT ROAD

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
View 14006 FRASIER STREET Winter Garden, FL MLS# O6398760
$658,000
4

Beds

2.1

Baths

2,098

Sq.Ft.

14006 FRASIER STREET

Winter Garden, FL

View 8878 BISMARCK PALM DRIVE Winter Garden, FL MLS# O6418128
$656,500
4

Beds

3.1

Baths

2,581

Sq.Ft.

8878 BISMARCK PALM DRIVE

Winter Garden, FL

View 15143 KIRSTY ALLEY Winter Garden, FL MLS# O6344886
$654,900
5

Beds

3.1

Baths

2,934

Sq.Ft.

15143 KIRSTY ALLEY

Winter Garden, FL

Courtesy of ARION REALTY
View 14008 JOMATT LOOP Winter Garden, FL MLS# O6376903
$650,000
4

Beds

3.0

Baths

2,952

Sq.Ft.

14008 JOMATT LOOP

Winter Garden, FL

Courtesy of THE AGENCY 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

939

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 - 200K21
$200K - 300K89
$300K - 400K64
$400K - 500K134
$500K - 600K163
$600K - 700K105
$700K - 800K95
$800K - 900K86
$900K - 1M63
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family640
Townhouse130
Condo135
Commercial11
Rental199
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/13/2026)

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 7/13/2026.

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.

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 7/13/2026.