View 12893 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6381091
  • New Construction with Virtual Tour
1 of 57
$4,400
5

Beds

4.1

Baths

3,165

Sq.Ft.

12893 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
View 16246 MERRY ALLEY Winter Garden, FL MLS# O6381155
  • New Construction with Virtual Tour
1 of 41
$2,650
3

Beds

2.1

Baths

1,683

Sq.Ft.

16246 MERRY ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 13344 HARBOR SHORE LANE Winter Garden, FL MLS# S5143640
$2,250
2

Beds

2.1

Baths

1,234

Sq.Ft.

13344 HARBOR SHORE LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 17834 ADRIFT ROAD Winter Garden, FL MLS# O6380850
$4,500
4

Beds

3.1

Baths

2,674

Sq.Ft.

17834 ADRIFT ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 431 SOUTHERN PECAN CIRCLE 201 Winter Garden, FL MLS# S5142462
$2,550
3

Beds

2.0

Baths

1,499

Sq.Ft.

431 SOUTHERN PECAN CIRCLE 201

Winter Garden, FL

Courtesy of HOMESMART
View 15481 BAY BRIDGE STREET Winter Garden, FL MLS# O6380391
  • New Construction with Virtual Tour
1 of 30
$2,850
3

Beds

2.1

Baths

1,670

Sq.Ft.

15481 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 6340 TABEBUIA PARKWAY Winter Garden, FL MLS# O6380528
  • New Construction with Virtual Tour
1 of 32
$2,600
3

Beds

2.1

Baths

1,501

Sq.Ft.

6340 TABEBUIA PARKWAY

Winter Garden, FL

Courtesy of THE CARDENAS GROUP REALTY
View 1220 PRIORY CIRCLE Winter Garden, FL MLS# O6380944
$2,995
3

Beds

2.1

Baths

1,971

Sq.Ft.

1220 PRIORY CIRCLE

Winter Garden, FL

Courtesy of REAL ESTATE FIRM OF ORLANDO
View 5519 MYRTLE PINE LANE Winter Garden, FL MLS# O6380094
$2,700
4

Beds

2.0

Baths

1,851

Sq.Ft.

5519 MYRTLE PINE LANE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 7556 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6380128
  • New Construction with Virtual Tour
1 of 95
$18,000
5

Beds

6.1

Baths

5,108

Sq.Ft.

7556 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 15493 BAY BRIDGE STREET Winter Garden, FL MLS# O6380284
  • New Construction with Virtual Tour
1 of 27
$2,825
3

Beds

2.1

Baths

1,670

Sq.Ft.

15493 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 17609 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6380304
  • New Construction with Virtual Tour
1 of 16
$3,200
3

Beds

2.1

Baths

2,103

Sq.Ft.

17609 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
View 17727 SHARP PUMMELO ALLEY Winter Garden, FL MLS# O6380310
  • New Construction with Virtual Tour
1 of 19
$3,500
4

Beds

3.0

Baths

2,100

Sq.Ft.

17727 SHARP PUMMELO ALLEY

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
View 11187 HANLON TERRACE ALLEY Winter Garden, FL MLS# O6380895
$2,890
4

Beds

3.0

Baths

2,200

Sq.Ft.

11187 HANLON TERRACE ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16234 MERRY ALLEY Winter Garden, FL MLS# S5143274
  • New Construction with Virtual Tour
1 of 37
$2,950
4

Beds

2.1

Baths

1,770

Sq.Ft.

16234 MERRY ALLEY

Winter Garden, FL

Courtesy of ALTIS REALTY
View 15836 MARINA BAY DRIVE Winter Garden, FL MLS# O6380173
$2,800
3

Beds

2.1

Baths

1,639

Sq.Ft.

15836 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of EPIC REALTY
View 8019 JEREMY JOSEPH ALLEY 8019 Winter Garden, FL MLS# O6379718
  • New Construction with Virtual Tour
1 of 23
$2,595
3

Beds

2.1

Baths

1,691

Sq.Ft.

8019 JEREMY JOSEPH ALLEY 8019

Winter Garden, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 1419 SPRING RIDGE DRIVE Winter Garden, FL MLS# O6379895
$2,750
3

Beds

2.0

Baths

1,440

Sq.Ft.

1419 SPRING RIDGE DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 665 LAKE APOPKA BOULEVARD Winter Garden, FL MLS# O6380633
$1,700
2

Beds

1.0

Baths

572

Sq.Ft.

665 LAKE APOPKA BOULEVARD

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 10070 TAWNY MEADOW ALLEY Winter Garden, FL MLS# O6379693
$2,780
3

Beds

2.1

Baths

1,567

Sq.Ft.

10070 TAWNY MEADOW ALLEY

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

941

Estimated median home price

$588,900
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

PriceCount
$0 - 100K4
$100K - 200K12
$200K - 300K92
$300K - 400K79
$400K - 500K153
$500K - 600K160
$600K - 700K111
$700K - 800K91
$800K - 900K74
$900K - 1M60
$1M - Max105

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family644
Townhouse135
Condo126
Commercial11
Rental229
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/18/2026)

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 3/20/2026.