View 16461 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6414427
$400,000
4

Beds

2.1

Baths

1,768

Sq.Ft.

16461 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

View 15511 CAMPDEN STREET Winter Garden, FL MLS# O6413461
$395,000
3

Beds

2.1

Baths

1,916

Sq.Ft.

15511 CAMPDEN STREET

Winter Garden, FL

View 420 E CYPRESS STREET Winter Garden, FL MLS# O6412414
$420,000
3

Beds

2.0

Baths

1,616

Sq.Ft.

420 E CYPRESS STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 338 WINDFORD COURT Winter Garden, FL MLS# O6413058
$330,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

338 WINDFORD COURT

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 1437 SCARLET OAK LOOP Winter Garden, FL MLS# O6411620
$350,000
3

Beds

2.1

Baths

1,684

Sq.Ft.

1437 SCARLET OAK LOOP

Winter Garden, FL

View 13232 DANIELS LANDING CIRCLE Winter Garden, FL MLS# G5112999
$350,000
2

Beds

2.1

Baths

1,232

Sq.Ft.

13232 DANIELS LANDING CIRCLE

Winter Garden, FL

View 7279 DUXBURY LANE Winter Garden, FL MLS# O6405682
$424,900
3

Beds

2.1

Baths

1,895

Sq.Ft.

7279 DUXBURY LANE

Winter Garden, FL

View 15568 BLACKBEAD STREET Winter Garden, FL MLS# O6408861
$435,000
4

Beds

3.0

Baths

1,861

Sq.Ft.

15568 BLACKBEAD STREET

Winter Garden, FL

Courtesy of MARK SPAIN REAL ESTATE
View 15625 BOGGY OAK CIRCLE 108B Winter Garden, FL MLS# G5112579
$340,000
3

Beds

2.1

Baths

1,419

Sq.Ft.

15625 BOGGY OAK CIRCLE 108B

Winter Garden, FL

Courtesy of SCATES REALTY & INVESTMENT PRO
View 9652 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6409704
$430,000
4

Beds

2.1

Baths

1,948

Sq.Ft.

9652 AMBER CHESTNUT WAY

Winter Garden, FL

View 14501 GROVE RESORT AVE 1535 1535 Winter Garden, FL MLS# S5150001
$410,990
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVE 1535 1535

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6408480
$335,000
3

Beds

2.1

Baths

1,365

Sq.Ft.

13527 DANIELS LANDING CIRCLE

Winter Garden, FL

View 243 FLORIDA AVENUE Winter Garden, FL MLS# S5149991
$335,000
2

Beds

2.0

Baths

1,100

Sq.Ft.

243 FLORIDA AVENUE

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 14501 Grove Resort 1304 Winter Garden, FL MLS# A12022081
$350,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 Grove Resort 1304

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 13307 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5112135
  • New Construction with Virtual Tour
1 of 53
$437,990
3

Beds

2.1

Baths

1,644

Sq.Ft.

13307 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15140 WINDFLOWER ALLEY Winter Garden, FL MLS# S5149180
$410,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

15140 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
View 16570 BARBOURS CREEK WAY Winter Garden, FL MLS# O6403257
  • New Construction with Virtual Tour
1 of 15
$414,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16570 BARBOURS CREEK WAY

Winter Garden, FL

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 14501 GROVE RESORT AVENUE 1614 Winter Garden, FL MLS# O6398376
$325,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 1614

Winter Garden, FL

Courtesy of LIVE MVRK LLC
View 15357 OAK APPLE COURT 4C Winter Garden, FL MLS# O6401625
$344,900
3

Beds

2.1

Baths

1,699

Sq.Ft.

15357 OAK APPLE COURT 4C

Winter Garden, 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

942

Estimated median home price

$608,645
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 - 300K91
$300K - 400K65
$400K - 500K135
$500K - 600K155
$600K - 700K102
$700K - 800K101
$800K - 900K89
$900K - 1M62
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family642
Townhouse132
Condo135
Commercial11
Rental203
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/16/2026)

Information deemed reliable but not guaranteed.

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 7/16/2026.