View 4918 WILDWOOD POINTE ROAD Winter Garden, FL MLS# S5150274
$680,000
5

Beds

3.1

Baths

2,868

Sq.Ft.

4918 WILDWOOD POINTE ROAD

Winter Garden, FL

View 8721 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# G5111855
$679,000
4

Beds

3.1

Baths

2,842

Sq.Ft.

8721 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
View 2022 BOSS HEWETT STREET Winter Garden, FL MLS# O6417697
$679,000
4

Beds

3.0

Baths

2,281

Sq.Ft.

2022 BOSS HEWETT STREET

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 7526 SPRING VALLEY STREET Winter Garden, FL MLS# G5111448
$676,245
5

Beds

4.0

Baths

2,680

Sq.Ft.

7526 SPRING VALLEY STREET

Winter Garden, FL

View 14790 TULLAMORE LOOP Winter Garden, FL MLS# O6395287
$675,000
4

Beds

2.1

Baths

3,410

Sq.Ft.

14790 TULLAMORE LOOP

Winter Garden, FL

View 14540 SUNBRIDGE CIRCLE Winter Garden, FL MLS# O6416033
$675,000
4

Beds

4.0

Baths

2,800

Sq.Ft.

14540 SUNBRIDGE CIRCLE

Winter Garden, FL

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

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

View 15026 SUMMER HARVEST STREET Winter Garden, FL MLS# S5153036
$669,990
5

Beds

4.1

Baths

2,930

Sq.Ft.

15026 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of MOSAIC PARTNERS GROUP
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 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 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

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

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 18344 OLIVER TWIST WAY Winter Garden, FL MLS# S5140531
$660,000
4

Beds

3.0

Baths

2,924

Sq.Ft.

18344 OLIVER TWIST WAY

Winter Garden, FL

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

View 402 EGRET PLACE DRIVE Winter Garden, FL MLS# O6402689
$659,000
4

Beds

3.0

Baths

2,711

Sq.Ft.

402 EGRET PLACE 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

1,063

Estimated median home price

$610,000
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 - 200K24
$200K - 300K93
$300K - 400K68
$400K - 500K154
$500K - 600K184
$600K - 700K111
$700K - 800K128
$800K - 900K103
$900K - 1M66
$1M - Max131

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family751
Townhouse140
Condo139
Commercial10
Rental218
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/28/2026)

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 7/28/2026.