View 17458 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5110835
$625,580
4

Beds

2.1

Baths

2,235

Sq.Ft.

17458 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8150 GRAY KINGBIRD DRIVE Winter Garden, FL MLS# O6396729
$649,999
4

Beds

3.0

Baths

2,706

Sq.Ft.

8150 GRAY KINGBIRD DRIVE

Winter Garden, FL

Courtesy of GREEN KEY REALTY LLC
View 12983 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6397592
  • New Construction with Virtual Tour
1 of 53
$750,000
3

Beds

3.1

Baths

2,858

Sq.Ft.

12983 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 10224 ATWATER BAY DRIVE Winter Garden, FL MLS# S5147252
$759,000
5

Beds

3.1

Baths

3,227

Sq.Ft.

10224 ATWATER BAY DRIVE

Winter Garden, FL

Courtesy of NAIM REAL ESTATE LLC
View 7266 DESERT MANDARIN STREET Winter Garden, FL MLS# O6395920
$595,000
4

Beds

3.0

Baths

2,365

Sq.Ft.

7266 DESERT MANDARIN STREET

Winter Garden, FL

Courtesy of SUNNY 365 REALTY GROUP
View Address not provided Winter Garden, FL MLS# G5110452
$688,789
5

Beds

4.1

Baths

3,117

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6020 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5110387
$573,990
4

Beds

3.0

Baths

2,102

Sq.Ft.

6020 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15070 SUMMER HARVEST STREET Winter Garden, FL MLS# S5146881
$696,000
5

Beds

4.1

Baths

2,931

Sq.Ft.

15070 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of 365 REALTY, INC.
View 12390 CLEAR SAPPHIRE 260 Winter Garden, FL MLS# O6394850
  • New Construction with Virtual Tour
1 of 35
$769,990
4

Beds

3.0

Baths

2,552

Sq.Ft.

12390 CLEAR SAPPHIRE 260

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 11045 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6394192
$739,900
4

Beds

3.0

Baths

2,113

Sq.Ft.

11045 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of VOSS REALTY INC
View 15527 SWEET ORANGE AVENUE Winter Garden, FL MLS# O6394429
$685,000
3

Beds

3.1

Baths

2,383

Sq.Ft.

15527 SWEET ORANGE AVENUE

Winter Garden, FL

Courtesy of BUYER REBATES REALTY
View 12438 CLEAR SAPPHIRE DRIVE 223 Winter Garden, FL MLS# O6393877
$684,990
4

Beds

4.0

Baths

3,460

Sq.Ft.

12438 CLEAR SAPPHIRE DRIVE 223

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 17326 BAL HARBOUR DRIVE Winter Garden, FL MLS# O6393857
$769,000
5

Beds

3.0

Baths

3,196

Sq.Ft.

17326 BAL HARBOUR DRIVE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 14790 TULLAMORE LOOP Winter Garden, FL MLS# O6395287
$689,999
4

Beds

2.1

Baths

3,410

Sq.Ft.

14790 TULLAMORE LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
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

Courtesy of ORLANDO HIGHLAND REALTY LLC
View 14050 FAIRWAY WILLOW LANE Winter Garden, FL MLS# O6392994
$749,000
3

Beds

2.0

Baths

2,027

Sq.Ft.

14050 FAIRWAY WILLOW LANE

Winter Garden, FL

Courtesy of LAKEFIELD REALTY GROUP LLC
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

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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 650 SETTING SUN DRIVE Winter Garden, FL MLS# O6390644
$740,000
5

Beds

3.0

Baths

3,605

Sq.Ft.

650 SETTING SUN DRIVE

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
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

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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

1,052

Estimated median home price

$615,000
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 - 200K24
$200K - 300K87
$300K - 400K80
$400K - 500K145
$500K - 600K174
$600K - 700K130
$700K - 800K117
$800K - 900K91
$900K - 1M73
$1M - Max130

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family736
Townhouse138
Condo138
Commercial11
Rental199
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 6/6/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 6/7/2026.

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 6/7/2026.