View 8750 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# O6416046
$1,849,000
5

Beds

5.1

Baths

4,641

Sq.Ft.

8750 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1211 E MAPLE STREET Winter Garden, FL MLS# O6153590
$1,800,000
Studio

Beds

0.0

Baths

1211 E MAPLE STREET

Winter Garden, FL

Courtesy of SOUTHERN HERITAGE REALTY, INC
View 68 N PARK AVENUE Winter Garden, FL MLS# O6400066
$1,799,000
4

Beds

3.2

Baths

3,555

Sq.Ft.

68 N PARK AVENUE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 902 JOHNS POINT DRIVE Winter Garden, FL MLS# O6412933
$1,799,000
4

Beds

4.0

Baths

4,085

Sq.Ft.

902 JOHNS POINT DRIVE

Winter Garden, FL

View 15717 E OAKLAND AVENUE Winter Garden, FL MLS# O6419032
  • Recently Listed with Virtual Tour
1 of 82
$1,795,000
4

Beds

3.1

Baths

3,515

Sq.Ft.

15717 E OAKLAND AVENUE

Winter Garden, FL

View 17224 OLD COUNTRY LANE Winter Garden, FL MLS# O6384075
$1,775,000
6

Beds

3.1

Baths

3,629

Sq.Ft.

17224 OLD COUNTRY LANE

Winter Garden, FL

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

View 17372 GLOSSY POMELO WAY Winter Garden, FL MLS# O6406639
  • New Construction with Virtual Tour
1 of 81
$1,740,000
5

Beds

5.1

Baths

4,977

Sq.Ft.

17372 GLOSSY POMELO WAY

Winter Garden, FL

View 2450 DAHLGREN WAY Winter Garden, FL MLS# TB8481106
$1,700,000
5

Beds

5.0

Baths

4,365

Sq.Ft.

2450 DAHLGREN WAY

Winter Garden, FL

View 720 LAKE BRIM DRIVE Winter Garden, FL MLS# O6387519
$1,699,000
4

Beds

4.0

Baths

3,781

Sq.Ft.

720 LAKE BRIM DRIVE

Winter Garden, FL

View 1144 HULL ISLAND DRIVE Winter Garden, FL MLS# O6418306
$1,699,000
5

Beds

4.1

Baths

4,102

Sq.Ft.

1144 HULL ISLAND DRIVE

Winter Garden, FL

View 16161 BARKLY RIDGE COURT Winter Garden, FL MLS# O6402785
$1,690,000
6

Beds

5.2

Baths

5,284

Sq.Ft.

16161 BARKLY RIDGE COURT

Winter Garden, FL

View 14802 SPEER LAKE DRIVE Winter Garden, FL MLS# O6425462
$1,690,000
5

Beds

4.1

Baths

3,742

Sq.Ft.

14802 SPEER LAKE DRIVE

Winter Garden, FL

View 279 ZACHARY WADE STREET Winter Garden, FL MLS# O6408014
$1,675,000
5

Beds

3.1

Baths

4,473

Sq.Ft.

279 ZACHARY WADE STREET

Winter Garden, FL

View 1101 EAGLES PASS WAY Winter Garden, FL MLS# O6408835
$1,649,999
6

Beds

5.0

Baths

4,104

Sq.Ft.

1101 EAGLES PASS WAY

Winter Garden, FL

View 325 CRYSTAL WOOD DRIVE Winter Garden, FL MLS# O6408089
$1,600,000
5

Beds

5.0

Baths

4,442

Sq.Ft.

325 CRYSTAL WOOD DRIVE

Winter Garden, FL

View 9103 MORGANA COURT Winter Garden, FL MLS# O6409652
$1,599,999
5

Beds

4.1

Baths

4,376

Sq.Ft.

9103 MORGANA COURT

Winter Garden, FL

Courtesy of HAMMOND REALTY GROUP LLC
View 261 ZACHARY WADE STREET Winter Garden, FL MLS# O6357233
$1,599,000
4

Beds

3.1

Baths

3,728

Sq.Ft.

261 ZACHARY WADE STREET

Winter Garden, FL

View 16788 MUSKGRASS DRIVE Winter Garden, FL MLS# O6388174
$1,550,000
4

Beds

4.1

Baths

4,733

Sq.Ft.

16788 MUSKGRASS DRIVE

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 2010 BOSS HEWETT STREET Winter Garden, FL MLS# O6423216
  • Recently Listed with Virtual Tour
1 of 94
$1,500,000
5

Beds

4.0

Baths

3,781

Sq.Ft.

2010 BOSS HEWETT STREET

Winter Garden, FL

Courtesy of RE/MAX ASSURED

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

1,082

Estimated median home price

$618,500
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 - 200K23
$200K - 300K95
$300K - 400K67
$400K - 500K156
$500K - 600K184
$600K - 700K115
$700K - 800K133
$800K - 900K104
$900K - 1M68
$1M - Max136

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family766
Townhouse142
Condo139
Commercial11
Rental226
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/24/2026)

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 7/24/2026.