View 950 S DILLARD STREET Winter Garden, FL MLS# O6359585
  • New Construction with Virtual Tour
1 of 6
$0
4,909

Sq.Ft.

950 S DILLARD STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 186 S MAIN STREET Winter Garden, FL MLS# O6359871
  • New Construction with Virtual Tour
1 of 7
$0
16,000

Sq.Ft.

186 S MAIN STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 981 VINELAND ROAD Winter Garden, FL MLS# O6364366
  • New Construction with Virtual Tour
1 of 6
$0
8,700

Sq.Ft.

981 VINELAND ROAD

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 16071 MICELLI DRIVE Winter Garden, FL MLS# O6352547
$1,267
1

Beds

1.0

Baths

568

Sq.Ft.

16071 MICELLI DRIVE

Winter Garden, FL

Courtesy of ORLANDO REALTY & PROPERTY MGNT
View 502 DUNBAR AVENUE Winter Garden, FL MLS# O6350724
$1,525
2

Beds

1.0

Baths

816

Sq.Ft.

502 DUNBAR AVENUE

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 64 WINDTREE LANE 203 Winter Garden, FL MLS# O6366537
$1,550
2

Beds

2.0

Baths

918

Sq.Ft.

64 WINDTREE LANE 203

Winter Garden, FL

Courtesy of INNOVATIVE REALTY, LLC
View 312 ERON WAY 4 Winter Garden, FL MLS# O6366719
  • Virtual Tour
1 of 19
$1,600
1

Beds

1.0

Baths

720

Sq.Ft.

312 ERON WAY 4

Winter Garden, FL

Courtesy of ICON REALTY ASSOCIATES INC
View 304 SOUTHERN PECAN CIRCLE 203 Winter Garden, FL MLS# O6368302
  • Recently Listed with Virtual Tour
1 of 13
$1,645
1

Beds

1.0

Baths

942

Sq.Ft.

304 SOUTHERN PECAN CIRCLE 203

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 162 WINDTREE LANE 204 Winter Garden, FL MLS# G5105117
$1,650
2

Beds

2.0

Baths

918

Sq.Ft.

162 WINDTREE LANE 204

Winter Garden, FL

Courtesy of RE/MAX TITANIUM GROUP
View 505 VARSITY STREET Winter Garden, FL MLS# O6345049
$1,749
2

Beds

1.0

Baths

780

Sq.Ft.

505 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 7121 BLUE INDIGO CRESCENT Winter Garden, FL MLS# O6357690
$1,800
Studio

Beds

1.0

Baths

750

Sq.Ft.

7121 BLUE INDIGO CRESCENT

Winter Garden, FL

Courtesy of THE FLORIDA LOUNGE REALTY LLC
View 96 WINDTREE LANE 203 Winter Garden, FL MLS# O6366344
$1,800
2

Beds

2.0

Baths

918

Sq.Ft.

96 WINDTREE LANE 203

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15000 STRATUS LOOP A2 Winter Garden, FL MLS# O6308729
$1,840
1

Beds

1.0

Baths

873

Sq.Ft.

15000 STRATUS LOOP A2

Winter Garden, FL

Courtesy of THE APARTMENT BROTHERS LLC
View 1532 BROKEN OAK DRIVE B Winter Garden, FL MLS# O6368561
  • Recently Listed with Virtual Tour
1 of 29
$2,150
3

Beds

2.1

Baths

1,544

Sq.Ft.

1532 BROKEN OAK DRIVE B

Winter Garden, FL

Courtesy of BLUE MAGNOLIA REALTY LLC
View 1500 BROKEN OAK DRIVE 25B Winter Garden, FL MLS# S5139230
$2,200
3

Beds

2.1

Baths

1,544

Sq.Ft.

1500 BROKEN OAK DRIVE 25B

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 418 WESTPOINT GARDEN CIRCLE Winter Garden, FL MLS# O6369108
  • Recently Listed with Virtual Tour
1 of 5
$2,250
3

Beds

2.1

Baths

1,588

Sq.Ft.

418 WESTPOINT GARDEN CIRCLE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 15000 STRATUS LOOP B1 Winter Garden, FL MLS# O6308743
$2,284
2

Beds

2.0

Baths

1,023

Sq.Ft.

15000 STRATUS LOOP B1

Winter Garden, FL

Courtesy of THE APARTMENT BROTHERS LLC
View 15000 STRATUS LOOP B3 Winter Garden, FL MLS# O6308749
$2,372
2

Beds

2.0

Baths

1,055

Sq.Ft.

15000 STRATUS LOOP B3

Winter Garden, FL

Courtesy of THE APARTMENT BROTHERS LLC
View 1150 CHASE DRIVE Winter Garden, FL MLS# O6367573
  • Recently Listed with Virtual Tour
1 of 23
$2,375
4

Beds

2.0

Baths

1,852

Sq.Ft.

1150 CHASE DRIVE

Winter Garden, FL

Courtesy of PREMIER MANAGEMENT GROUP INC
View 1472 SCARLET OAK LOOP Winter Garden, FL MLS# O6350510
$2,399
3

Beds

2.1

Baths

1,704

Sq.Ft.

1472 SCARLET OAK LOOP

Winter Garden, FL

Courtesy of WRA BUSINESS & 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

774

Estimated median home price

$589,000
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 - 100K6
$100K - 200K8
$200K - 300K64
$300K - 400K82
$400K - 500K132
$500K - 600K123
$600K - 700K85
$700K - 800K68
$800K - 900K63
$900K - 1M49
$1M - Max94

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family502
Townhouse117
Condo110
Commercial9
Rental224
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/3/2026)

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

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 1/4/2026.