View 11045 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6394192
$724,900
4

Beds

3.0

Baths

2,113

Sq.Ft.

11045 HOLLOW BAY DRIVE

Winter Garden, FL

View 14790 TULLAMORE LOOP Winter Garden, FL MLS# O6395287
$675,000
4

Beds

2.1

Baths

3,410

Sq.Ft.

14790 TULLAMORE LOOP

Winter Garden, FL

View 15558 SANDFIELD LOOP Winter Garden, FL MLS# O6393987
$765,000
4

Beds

3.1

Baths

4,307

Sq.Ft.

15558 SANDFIELD LOOP

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 14050 FAIRWAY WILLOW LANE Winter Garden, FL MLS# O6392994
$714,999
3

Beds

2.0

Baths

2,027

Sq.Ft.

14050 FAIRWAY WILLOW LANE

Winter Garden, FL

View 17308 WILD DAISY DRIVE Winter Garden, FL MLS# G5110060
$740,205
6

Beds

4.1

Baths

3,412

Sq.Ft.

17308 WILD DAISY DRIVE

Winter Garden, FL

View 15442 ENCHANTED MELODY WAY Winter Garden, FL MLS# S5146095
$609,850
4

Beds

3.0

Baths

2,420

Sq.Ft.

15442 ENCHANTED MELODY WAY

Winter Garden, FL

Courtesy of A & V FLORIDA REALTY GROUP LLC
View 17440 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109764
$688,324
4

Beds

2.1

Baths

2,235

Sq.Ft.

17440 SUNSET PRAIRIE DRIVE

Winter Garden, FL

View 17446 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109788
$723,200
4

Beds

2.1

Baths

2,688

Sq.Ft.

17446 SUNSET PRAIRIE DRIVE

Winter Garden, FL

View 7532 SPRING VALLEY STREET Winter Garden, FL MLS# G5109790
$615,990
4

Beds

3.1

Baths

2,520

Sq.Ft.

7532 SPRING VALLEY STREET

Winter Garden, FL

View 17156 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5109791
$606,440
4

Beds

3.0

Baths

2,102

Sq.Ft.

17156 INGRAM BLUFF DRIVE

Winter Garden, FL

View 14780 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391463
  • New Construction with Virtual Tour
1 of 43
$653,118
4

Beds

4.1

Baths

2,441

Sq.Ft.

14780 FIELD DAISY DRIVE

Winter Garden, FL

View 17416 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109744
$784,490
4

Beds

2.1

Baths

2,688

Sq.Ft.

17416 SUNSET PRAIRIE DRIVE

Winter Garden, FL

View 15197 BLUE PEACOCK LANE Winter Garden, FL MLS# O6390611
$704,900
3

Beds

2.1

Baths

2,440

Sq.Ft.

15197 BLUE PEACOCK LANE

Winter Garden, FL

View 17144 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5109520
$605,455
4

Beds

3.1

Baths

2,520

Sq.Ft.

17144 INGRAM BLUFF DRIVE

Winter Garden, FL

View 1209 CASTLEPORT ROAD Winter Garden, FL MLS# O6390760
$659,000
5

Beds

3.0

Baths

2,812

Sq.Ft.

1209 CASTLEPORT ROAD

Winter Garden, FL

View 5679 ORANGE ORCHARD DRIVE Winter Garden, FL MLS# O6389469
$649,900
4

Beds

2.1

Baths

2,235

Sq.Ft.

5679 ORANGE ORCHARD DRIVE

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 7679 SILVER MEADOW STREET Winter Garden, FL MLS# G5109150
$590,490
3

Beds

2.0

Baths

1,772

Sq.Ft.

7679 SILVER MEADOW STREET

Winter Garden, FL

View 17459 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109177
$774,815
4

Beds

3.0

Baths

2,740

Sq.Ft.

17459 SUNSET PRAIRIE DRIVE

Winter Garden, FL

View 721 FOSTER AVENUE Winter Garden, FL MLS# O6388329
$699,000
7

Beds

3.0

Baths

2,293

Sq.Ft.

721 FOSTER AVENUE

Winter Garden, FL

View 17464 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109172
$754,550
3

Beds

2.1

Baths

2,718

Sq.Ft.

17464 SUNSET PRAIRIE DRIVE

Winter Garden, FL

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

1,060

Estimated median home price

$615,528
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 - 100K2
$100K - 200K24
$200K - 300K90
$300K - 400K68
$400K - 500K157
$500K - 600K178
$600K - 700K112
$700K - 800K128
$800K - 900K103
$900K - 1M63
$1M - Max135

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family747
Townhouse141
Condo137
Commercial9
Rental215
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 8/1/2026)

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 8/1/2026.