View 15058 SUNSTAR WAY Winter Garden, FL MLS# O6411520
  • Recently Listed with Virtual Tour
1 of 50
$1,900,000
5

Beds

3.1

Baths

3,607

Sq.Ft.

15058 SUNSTAR WAY

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 9103 MORGANA COURT Winter Garden, FL MLS# O6409652
$1,630,900
5

Beds

4.1

Baths

4,376

Sq.Ft.

9103 MORGANA COURT

Winter Garden, FL

Courtesy of HAMMOND REALTY GROUP LLC
View 1101 EAGLES PASS WAY Winter Garden, FL MLS# O6408835
  • Recently Listed with Virtual Tour
1 of 62
$1,725,000
6

Beds

5.0

Baths

4,104

Sq.Ft.

1101 EAGLES PASS WAY

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15047 GAULBERRY RUN Winter Garden, FL MLS# O6408283
  • Recently Listed with Virtual Tour
1 of 78
$1,525,000
5

Beds

4.2

Baths

4,964

Sq.Ft.

15047 GAULBERRY RUN

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 325 CRYSTAL WOOD DRIVE Winter Garden, FL MLS# O6408089
  • Recently Listed with Virtual Tour
1 of 96
$1,600,000
5

Beds

5.0

Baths

4,442

Sq.Ft.

325 CRYSTAL WOOD DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17372 GLOSSY POMELO WAY Winter Garden, FL MLS# O6406639
  • Recently Listed with Virtual Tour
1 of 78
$1,849,000
5

Beds

5.1

Baths

4,977

Sq.Ft.

17372 GLOSSY POMELO WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 217 W BAY STREET Winter Garden, FL MLS# S5149527
  • Virtual Tour
1 of 79
OPEN HOUSE: Saturday 5/30 11:00 AM - 3:00 PM
$1,450,000
5

Beds

4.0

Baths

2,800

Sq.Ft.

217 W BAY STREET

Winter Garden, FL

Courtesy of WATSON REALTY CORP.
View 279 ZACHARY WADE STREET Winter Garden, FL MLS# O6408014
  • Recently Listed with Virtual Tour
1 of 78
$1,675,000
5

Beds

3.1

Baths

4,473

Sq.Ft.

279 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
View 398 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6405194
  • New Construction with Virtual Tour
1 of 52
$1,498,440
5

Beds

5.0

Baths

4,442

Sq.Ft.

398 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 16161 BARKLY RIDGE COURT Winter Garden, FL MLS# O6402785
$1,800,000
6

Beds

5.2

Baths

5,284

Sq.Ft.

16161 BARKLY RIDGE COURT

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 68 N PARK AVENUE Winter Garden, FL MLS# O6400066
$1,849,000
4

Beds

3.2

Baths

3,555

Sq.Ft.

68 N PARK AVENUE

Winter Garden, FL

Courtesy of VISTA CAY REALTY COMPANY
View 1698 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# V4948569
  • Virtual Tour
1 of 78
OPEN HOUSE: Saturday 5/30 1:00 PM - 4:00 PM
$1,450,000
7

Beds

4.0

Baths

4,700

Sq.Ft.

1698 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of Longwood - WEICHERT, REALTORS® - Hallmark Properties
View 743 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6392705
$1,499,999
5

Beds

5.2

Baths

4,283

Sq.Ft.

743 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 720 LAKE BRIM DRIVE Winter Garden, FL MLS# O6387519
$1,770,000
4

Beds

4.0

Baths

3,781

Sq.Ft.

720 LAKE BRIM DRIVE

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY
View 1021 TEMPLE GROVE PLACE Winter Garden, FL MLS# O6387876
$1,895,000
4

Beds

4.1

Baths

3,185

Sq.Ft.

1021 TEMPLE GROVE PLACE

Winter Garden, FL

Courtesy of MAINFRAME REAL ESTATE
View 16826 BROADWATER AVENUE Winter Garden, FL MLS# O6387379
$1,449,000
6

Beds

5.1

Baths

4,451

Sq.Ft.

16826 BROADWATER AVENUE

Winter Garden, FL

Courtesy of ONE STOP SERVICE REALTY INC
View 16788 MUSKGRASS DRIVE Winter Garden, FL MLS# O6388174
$1,600,000
4

Beds

4.1

Baths

4,733

Sq.Ft.

16788 MUSKGRASS DRIVE

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 2450 DAHLGREN WAY Winter Garden, FL MLS# TB8481106
  • Virtual Tour
1 of 68
OPEN HOUSE: Saturday 5/30 11:00 AM - 2:00 PM
$1,700,000
5

Beds

5.0

Baths

4,365

Sq.Ft.

2450 DAHLGREN WAY

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 906 ALLENDALE LANE Winter Garden, FL MLS# G5107489
$1,765,000
5

Beds

4.0

Baths

3,784

Sq.Ft.

906 ALLENDALE LANE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 16768 SANCTUARY DRIVE Winter Garden, FL MLS# O6374904
$1,575,000
5

Beds

4.1

Baths

4,258

Sq.Ft.

16768 SANCTUARY DRIVE

Winter Garden, FL

Courtesy of GALLOWAY REAL ESTATE

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

1,035

Estimated median home price

$609,900
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

Price Count
$0 - 100K 1
$100K - 200K 25
$200K - 300K 96
$300K - 400K 79
$400K - 500K 138
$500K - 600K 171
$600K - 700K 127
$700K - 800K 113
$800K - 900K 89
$900K - 1M 71
$1M - Max 125

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 715
Townhouse 134
Condo 143
Commercial 10
Rental 212
Lots and Land 29
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 2
Farms 0

(Data as of 5/30/2026)

Information deemed reliable but not guaranteed.

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 5/30/2026.