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 330 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# S5150108
$300,000
3

Beds

2.0

Baths

1,453

Sq.Ft.

330 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3211 Winter Garden, FL MLS# O6408877
$271,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3211

Winter Garden, FL

Courtesy of UNITED REALTY GROUP INC
The time to sell is now! THE TIME TO SELL IS NOW!
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 17013 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112484
  • New Construction with Virtual Tour
1 of 5
$455,752
3

Beds

2.1

Baths

1,772

Sq.Ft.

17013 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11 WINDTREE LANE B Winter Garden, FL MLS# O6409169
$195,000
2

Beds

2.0

Baths

918

Sq.Ft.

11 WINDTREE LANE B

Winter Garden, FL

View 17001 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112433
$485,705
3

Beds

2.1

Baths

1,644

Sq.Ft.

17001 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 1439 Winter Garden, FL MLS# O6407410
$180,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1439

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 12103 EASTMOOR DRIVE Winter Garden, FL MLS# O6409071
$440,000
3

Beds

2.0

Baths

1,604

Sq.Ft.

12103 EASTMOOR DRIVE

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 170 WINDTREE LANE Winter Garden, FL MLS# S5150050
$204,900
2

Beds

2.0

Baths

918

Sq.Ft.

170 WINDTREE LANE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 12597 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6407413
$475,000
3

Beds

2.0

Baths

2,322

Sq.Ft.

12597 ENCORE AT OVATION WAY

Winter Garden, FL

View 5545 BOWMAN DRIVE Winter Garden, FL MLS# O6407484
  • Virtual Tour
1 of 29
OPEN HOUSE: Thursday 7/16 9:00 AM - 7:00 PM
$465,000
2

Beds

2.1

Baths

1,998

Sq.Ft.

5545 BOWMAN DRIVE

Winter Garden, FL

View 441 E CYPRESS STREET Winter Garden, FL MLS# O6407560
$305,000
Studio

Beds

0.0

Baths

441 E CYPRESS STREET

Winter Garden, FL

View 342 WINDFORD COURT Winter Garden, FL MLS# O6407632
$319,900
3

Beds

2.0

Baths

1,194

Sq.Ft.

342 WINDFORD COURT

Winter Garden, FL

View 1015 WESTSIDE DRIVE Winter Garden, FL MLS# O6407229
$224,000
3

Beds

2.0

Baths

938

Sq.Ft.

1015 WESTSIDE DRIVE

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 1681 E SPRING RIDGE CIRCLE Winter Garden, FL MLS# B4902258
$469,000
4

Beds

2.0

Baths

1,858

Sq.Ft.

1681 E SPRING RIDGE CIRCLE

Winter Garden, FL

Courtesy of CRAIG BURKE REAL ESTATE GROUP, 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

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

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 7/16/2026.