View 17031 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5110934
$646,090
5

Beds

4.0

Baths

2,680

Sq.Ft.

17031 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6587 OLD CARRIAGE ROAD Winter Garden, FL MLS# O6421933
$645,000
3

Beds

2.0

Baths

2,224

Sq.Ft.

6587 OLD CARRIAGE ROAD

Winter Garden, FL

View 16936 TRADEWIND POINT Winter Garden, FL MLS# O6424578
  • Recently Listed with Virtual Tour
1 of 54
$645,000
4

Beds

3.1

Baths

2,930

Sq.Ft.

16936 TRADEWIND POINT

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 13008 SUNSET GARDEN LANE Winter Garden, FL MLS# O6398339
  • New Construction with Virtual Tour
1 of 7
$644,000
4

Beds

3.1

Baths

2,460

Sq.Ft.

13008 SUNSET GARDEN LANE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 14780 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391463
  • New Construction with Virtual Tour
1 of 43
$643,000
4

Beds

4.1

Baths

2,441

Sq.Ft.

14780 FIELD DAISY DRIVE

Winter Garden, FL

View 7649 SILVER MEADOW STREET Winter Garden, FL MLS# G5112006
$642,745
5

Beds

4.0

Baths

2,705

Sq.Ft.

7649 SILVER MEADOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7519 SPRING VALLEY STREET Winter Garden, FL MLS# G5111997
$640,050
4

Beds

3.1

Baths

2,515

Sq.Ft.

7519 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14246 CREEKBED CIRCLE Winter Garden, FL MLS# O6409378
$640,000
4

Beds

3.0

Baths

2,418

Sq.Ft.

14246 CREEKBED CIRCLE

Winter Garden, FL

Courtesy of LEGACY PLUS REALTY
View 15587 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL MLS# O6415333
$640,000
4

Beds

2.1

Baths

2,751

Sq.Ft.

15587 MURCOTT BLOSSOM BOULEVARD

Winter Garden, FL

View 8955 LAKESHORE POINTE DRIVE Winter Garden, FL MLS# O6337042
$639,990
4

Beds

3.1

Baths

2,539

Sq.Ft.

8955 LAKESHORE POINTE DRIVE

Winter Garden, FL

View 12410 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6409937
$639,990
3

Beds

2.0

Baths

1,860

Sq.Ft.

12410 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14005 ALDFORD DRIVE Winter Garden, FL MLS# O6401397
$639,000
3

Beds

2.1

Baths

2,334

Sq.Ft.

14005 ALDFORD DRIVE

Winter Garden, FL

View 17138 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5107975
$637,325
4

Beds

3.0

Baths

2,102

Sq.Ft.

17138 INGRAM BLUFF DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 16271 SILVER GROVE BLVD Winter Garden, FL MLS# O6299810
  • New Construction with Virtual Tour
1 of 46
$635,000
4

Beds

3.0

Baths

2,093

Sq.Ft.

16271 SILVER GROVE BLVD

Winter Garden, FL

Courtesy of CELEBRITY GLOBAL REALTY LLC
View 11036 ROBERT FROST DRIVE Winter Garden, FL MLS# O6410350
$634,990
4

Beds

3.0

Baths

2,136

Sq.Ft.

11036 ROBERT FROST DRIVE

Winter Garden, FL

View 14902 ARRENA ROAD Winter Garden, FL MLS# O6248982
$628,000
4

Beds

2.1

Baths

3,392

Sq.Ft.

14902 ARRENA ROAD

Winter Garden, FL

Courtesy of STAR SOLUTION PROPERTIES LLC
View 15033 LAKE BESSIE LOOP Winter Garden, FL MLS# A12001224
$628,000
4

Beds

3.0

Baths

2,240

Sq.Ft.

15033 LAKE BESSIE LOOP

Winter Garden, FL

Courtesy of LOKATION
View 17458 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5110835
$625,580
4

Beds

2.1

Baths

2,235

Sq.Ft.

17458 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1075 CHASE DRIVE Winter Garden, FL MLS# O6386607
$625,000
4

Beds

2.0

Baths

2,125

Sq.Ft.

1075 CHASE DRIVE

Winter Garden, FL

Courtesy of MAINFRAME REAL ESTATE
View 14731 FIELD DAISY DRIVE Winter Garden, FL MLS# O6410869
  • New Construction with Virtual Tour
1 of 29
$620,000
4

Beds

4.1

Baths

2,800

Sq.Ft.

14731 FIELD DAISY DRIVE

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

957

Estimated median home price

$609,611
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 - 500K137
$500K - 600K160
$600K - 700K101
$700K - 800K103
$800K - 900K89
$900K - 1M63
$1M - Max126

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family653
Townhouse134
Condo135
Commercial11
Rental201
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/15/2026)

Information deemed reliable but not guaranteed.

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 7/15/2026.