View 16435 HAMLIN HILLS ROAD Winter Garden, FL MLS# O6420316
$449,999
3

Beds

2.1

Baths

1,736

Sq.Ft.

16435 HAMLIN HILLS ROAD

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 16558 BARBOURS CREEK WAY Winter Garden, FL MLS# O6420061
  • New Construction with Virtual Tour
1 of 67
$454,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

16558 BARBOURS CREEK WAY

Winter Garden, FL

View 16503 BARBOURS CREEK WAY Winter Garden, FL MLS# O6420071
  • New Construction with Virtual Tour
1 of 67
$459,000
3

Beds

2.1

Baths

1,817

Sq.Ft.

16503 BARBOURS CREEK WAY

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 16509 BARBOURS CREEK WAY Winter Garden, FL MLS# O6420095
  • New Construction with Virtual Tour
1 of 63
$414,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16509 BARBOURS CREEK WAY

Winter Garden, FL

View 8019 JEREMY JOSEPH ALLEY Winter Garden, FL MLS# O6415530
$400,000
3

Beds

2.1

Baths

1,696

Sq.Ft.

8019 JEREMY JOSEPH ALLEY

Winter Garden, FL

Courtesy of SAUNDERS PLAKON
View 5863 CYPRESS HILL ROAD Winter Garden, FL MLS# TB8522840
$375,000
2

Beds

2.1

Baths

1,594

Sq.Ft.

5863 CYPRESS HILL ROAD

Winter Garden, FL

View 14942 WINDFLOWER ALLEY Winter Garden, FL MLS# O6420210
$405,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

14942 WINDFLOWER ALLEY

Winter Garden, FL

View 14470 PORTER ROAD Winter Garden, FL MLS# G5114165
  • New Construction
1 of 4
$461,420
3

Beds

2.1

Baths

1,764

Sq.Ft.

14470 PORTER ROAD

Winter Garden, FL

View 721 S WOODLAND STREET Winter Garden, FL MLS# O6419636
$440,000
2

Beds

1.0

Baths

1,034

Sq.Ft.

721 S WOODLAND STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 9362 WOODCRANE DRIVE Winter Garden, FL MLS# O6417277
$449,300
3

Beds

2.1

Baths

2,058

Sq.Ft.

9362 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 5754 SURPRISE LILY DRIVE Winter Garden, FL MLS# S5151845
$475,000
4

Beds

2.1

Baths

2,128

Sq.Ft.

5754 SURPRISE LILY DRIVE

Winter Garden, FL

View 12830 SUNSET WALK DRIVE Winter Garden, FL MLS# O6415339
  • New Construction with Virtual Tour
1 of 7
$471,000
3

Beds

2.1

Baths

1,857

Sq.Ft.

12830 SUNSET WALK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 14501 GROVE RESORT AVENUE 3425 Winter Garden, FL MLS# O6414956
  • Adult Community with Virtual Tour
1 of 21
$480,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3425

Winter Garden, FL

View 411 MILLWOOD PLACE Winter Garden, FL MLS# TB8518055
$459,000
3

Beds

2.0

Baths

1,696

Sq.Ft.

411 MILLWOOD PLACE

Winter Garden, FL

View 14903 DRIFTWATER DRIVE Winter Garden, FL MLS# S5151359
$370,000
3

Beds

2.1

Baths

1,745

Sq.Ft.

14903 DRIFTWATER DRIVE

Winter Garden, FL

View 6131 ELFIN HERB WAY Winter Garden, FL MLS# O6414015
$435,000
3

Beds

2.1

Baths

1,714

Sq.Ft.

6131 ELFIN HERB WAY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 15806 Gem View St Winter Garden, FL MLS# 226021734
  • Adult Community with Virtual Tour
1 of 37
$465,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

15806 Gem View St

Winter Garden, FL

Naples_Area_Board_of_Realtors
View 15511 CAMPDEN STREET Winter Garden, FL MLS# O6413461
$369,900
3

Beds

2.1

Baths

1,916

Sq.Ft.

15511 CAMPDEN STREET

Winter Garden, FL

View 1906 SHERBOURNE STREET Winter Garden, FL MLS# S5151079
$477,000
4

Beds

2.1

Baths

2,029

Sq.Ft.

1906 SHERBOURNE STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 17035 HARBOR OAK PARKWAY Winter Garden, FL MLS# O6411409
$485,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

17035 HARBOR OAK PARKWAY

Winter Garden, FL

Courtesy of DALTON WADE INC

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

998

Estimated median home price

$608,500
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 - 400K70
$400K - 500K147
$500K - 600K167
$600K - 700K105
$700K - 800K110
$800K - 900K112
$900K - 1M62
$1M - Max114

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family699
Townhouse136
Condo128
Commercial7
Rental184
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 9/6/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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 9/6/2026.