View 955 BUTTERFLY BOULEVARD Winter Garden, FL MLS# O6443277
$1,850
3

Beds

2.0

Baths

1,216

Sq.Ft.

955 BUTTERFLY BOULEVARD

Winter Garden, FL

Courtesy of PREFERRED RE BROKERS III
View 6119 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6443615
$3,499
5

Beds

3.1

Baths

3,297

Sq.Ft.

6119 WATERSIDE ISLAND LANE

Winter Garden, FL

Courtesy of 407 PROPERTIES
View 15352 BURGTHEATER DRIVE Winter Garden, FL MLS# O6443647
  • New Construction with Virtual Tour
1 of 40
$2,750
3

Beds

2.1

Baths

1,691

Sq.Ft.

15352 BURGTHEATER DRIVE

Winter Garden, FL

Courtesy of GARCIA REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 15824 MARINA BAY DRIVE Winter Garden, FL MLS# O6443734
$3,400
4

Beds

3.0

Baths

2,052

Sq.Ft.

15824 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of LA ROSA RTY WINTER GARDEN LLC
View 15387 HAMLIN PARK DRIVE Winter Garden, FL MLS# O6443411
  • New Construction with Virtual Tour
1 of 33
$3,500
3

Beds

3.1

Baths

2,072

Sq.Ft.

15387 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of UNITED REALTY GROUP INC
View 16880 HYPATIA ALLEY Winter Garden, FL MLS# O6443439
$3,030
3

Beds

2.1

Baths

2,200

Sq.Ft.

16880 HYPATIA ALLEY

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 12154 PLUMPTON DRIVE Winter Garden, FL MLS# S5157775
$2,700
3

Beds

2.1

Baths

1,688

Sq.Ft.

12154 PLUMPTON DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 15039 GROVESIDE ROAD Winter Garden, FL MLS# O6443019
  • New Construction with Virtual Tour
1 of 41
$2,850
3

Beds

2.1

Baths

1,846

Sq.Ft.

15039 GROVESIDE ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15051 GROVESIDE ROAD Winter Garden, FL MLS# O6443050
  • New Construction with Virtual Tour
1 of 41
$2,850
3

Beds

2.1

Baths

1,846

Sq.Ft.

15051 GROVESIDE ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15027 GROVESIDE ROAD Winter Garden, FL MLS# O6443076
  • New Construction with Virtual Tour
1 of 38
$2,990
3

Beds

2.1

Baths

1,846

Sq.Ft.

15027 GROVESIDE ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17670 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6442637
$4,650
5

Beds

4.1

Baths

3,542

Sq.Ft.

17670 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 509 VARSITY STREET Winter Garden, FL MLS# O6442711
$1,750
2

Beds

1.0

Baths

780

Sq.Ft.

509 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 9915 ALLITERATION ALLEY Winter Garden, FL MLS# S5157821
$2,800
3

Beds

2.1

Baths

1,636

Sq.Ft.

9915 ALLITERATION ALLEY

Winter Garden, FL

Courtesy of LEVO REAL ESTATE LLC
View 10242 SAND CAY DRIVE Winter Garden, FL MLS# O6442253
$3,100
4

Beds

3.1

Baths

2,477

Sq.Ft.

10242 SAND CAY DRIVE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 15055 DRIFTWATER DRIVE Winter Garden, FL MLS# O6442557
$2,900
4

Beds

2.0

Baths

2,375

Sq.Ft.

15055 DRIFTWATER DRIVE

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View Address not provided Winter Garden, FL MLS# O6442104
$4,950
5

Beds

4.0

Baths

2,840

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 16308 HAMLIN HILLS ROAD Winter Garden, FL MLS# S5157072
$2,825
3

Beds

2.1

Baths

1,736

Sq.Ft.

16308 HAMLIN HILLS ROAD

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 17546 LAKE STAR ROAD Winter Garden, FL MLS# S5157675
$6,900
5

Beds

4.1

Baths

3,767

Sq.Ft.

17546 LAKE STAR ROAD

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 17018 CLEAR MIND ALLEY Winter Garden, FL MLS# O6441101
$3,000
3

Beds

2.1

Baths

1,845

Sq.Ft.

17018 CLEAR MIND ALLEY

Winter Garden, FL

Courtesy of ALLUX REAL ESTATE LLC
View 16271 PEBBLE BLUFF LOOP Winter Garden, FL MLS# O6442568
$3,200
3

Beds

2.1

Baths

2,170

Sq.Ft.

16271 PEBBLE BLUFF LOOP

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY

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

968

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 - 200K36
$200K - 300K73
$300K - 400K72
$400K - 500K148
$500K - 600K164
$600K - 700K110
$700K - 800K107
$800K - 900K107
$900K - 1M49
$1M - Max101

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family662
Townhouse148
Condo120
Commercial6
Rental241
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 10/29/2026)

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 10/30/2026.