View 14601 OLD THICKET TRACE Winter Garden, FL MLS# S5159015
$3,195
4

Beds

3.0

Baths

2,717

Sq.Ft.

14601 OLD THICKET TRACE

Winter Garden, FL

Courtesy of A+ HOME RENTALS LLC
View 15105 GROVESIDE ROAD Winter Garden, FL MLS# O6447517
  • New Construction
1 of 34
$3,100
4

Beds

3.1

Baths

1,846

Sq.Ft.

15105 GROVESIDE ROAD

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 13897 TITLE WAY Winter Garden, FL MLS# S5159043
  • New Construction with Virtual Tour
1 of 20
$2,800
4

Beds

3.0

Baths

2,042

Sq.Ft.

13897 TITLE WAY

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 9508 BAUER ALLEY Winter Garden, FL MLS# O6447482
$2,600
3

Beds

2.1

Baths

1,814

Sq.Ft.

9508 BAUER ALLEY

Winter Garden, FL

Courtesy of LUMINA PROPERTY MANAGEMENT LLC
View 13673 FRESH IVY STREET Winter Garden, FL MLS# O6447419
  • Adult Community with Virtual Tour
1 of 24
$3,995
3

Beds

2.0

Baths

1,960

Sq.Ft.

13673 FRESH IVY STREET

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 170 WINDTREE LANE U Winter Garden, FL MLS# S5158953
$1,750
2

Beds

2.0

Baths

918

Sq.Ft.

170 WINDTREE LANE U

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 1057 PRIORY CIRCLE Winter Garden, FL MLS# O6448048
  • Recently Listed with Virtual Tour
1 of 30
$2,800
3

Beds

2.1

Baths

1,790

Sq.Ft.

1057 PRIORY CIRCLE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 12934 CANOPY WOODS WAY Winter Garden, FL MLS# O6447215
$6,800
4

Beds

4.1

Baths

3,636

Sq.Ft.

12934 CANOPY WOODS WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12103 EASTMOOR DRIVE Winter Garden, FL MLS# S5158683
$2,700
3

Beds

2.0

Baths

1,604

Sq.Ft.

12103 EASTMOOR DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 4731 ABBEYWOOD ALLEY Winter Garden, FL MLS# O6443989
  • New Construction with Virtual Tour
1 of 33
$2,900
3

Beds

2.1

Baths

1,668

Sq.Ft.

4731 ABBEYWOOD ALLEY

Winter Garden, FL

Courtesy of ON ME REALTY
View 17380 SWEET MORO DRIVE Winter Garden, FL MLS# O6446098
  • New Construction with Virtual Tour
1 of 11
$2,800
3

Beds

2.1

Baths

1,675

Sq.Ft.

17380 SWEET MORO DRIVE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 16515 BARBOURS CREEK WAY Winter Garden, FL MLS# O6447169
  • New Construction with Virtual Tour
1 of 26
$2,650
3

Beds

2.1

Baths

1,567

Sq.Ft.

16515 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of PMI ORLANDO PARKS
View 16509 BARBOURS CREEK WAY Winter Garden, FL MLS# O6447170
  • New Construction with Virtual Tour
1 of 26
$2,650
3

Beds

2.1

Baths

1,567

Sq.Ft.

16509 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of PMI ORLANDO PARKS
View 11055 FOLKLORE STREET Winter Garden, FL MLS# O6446491
$3,050
4

Beds

3.1

Baths

2,475

Sq.Ft.

11055 FOLKLORE STREET

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 15199 CHAPTER WAY Winter Garden, FL MLS# O6446643
$2,900
4

Beds

3.1

Baths

2,486

Sq.Ft.

15199 CHAPTER WAY

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 727 MAGNOLIA AVENUE Winter Garden, FL MLS# O6446689
  • New Construction with Virtual Tour
1 of 31
$2,200
2

Beds

2.0

Baths

1,186

Sq.Ft.

727 MAGNOLIA AVENUE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 15821 WATER SPRING BOULEVARD Winter Garden, FL MLS# S5158632
$2,800
3

Beds

2.1

Baths

1,636

Sq.Ft.

15821 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14741 SNOWY EGRET STREET Winter Garden, FL MLS# O6446733
$3,600
5

Beds

3.1

Baths

3,448

Sq.Ft.

14741 SNOWY EGRET STREET

Winter Garden, FL

Courtesy of MAY HO REALTY
View 14200 AVALON ROAD 232 Winter Garden, FL MLS# O6445270
$2,295
2

Beds

2.0

Baths

1,203

Sq.Ft.

14200 AVALON ROAD 232

Winter Garden, FL

Courtesy of LA ROSA REALTY PREMIER LLC
View 15009 LEBEAU LOOP Winter Garden, FL MLS# O6438557
$4,395
3

Beds

2.1

Baths

2,116

Sq.Ft.

15009 LEBEAU LOOP

Winter Garden, FL

Courtesy of TOP HOUSING LLC

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

972

Estimated median home price

$599,000
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 - 200K35
$200K - 300K73
$300K - 400K73
$400K - 500K150
$500K - 600K164
$600K - 700K112
$700K - 800K107
$800K - 900K108
$900K - 1M50
$1M - Max99

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family665
Townhouse149
Condo120
Commercial6
Rental241
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 10/28/2026)

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 10/29/2026.