View 642 MEDORA WAY Winter Garden, FL MLS# O6403542
  • New Construction with Virtual Tour
1 of 1
$1,140,150
4

Beds

3.0

Baths

3,109

Sq.Ft.

642 MEDORA WAY

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 650 MEDORA WAY Winter Garden, FL MLS# O6403543
  • New Construction with Virtual Tour
1 of 1
$1,152,190
4

Beds

3.0

Baths

2,902

Sq.Ft.

650 MEDORA WAY

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 17085 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5111738
$939,880
5

Beds

4.1

Baths

3,409

Sq.Ft.

17085 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 461 GERANIUM PARK WAY Winter Garden, FL MLS# O6403758
$900,000
3

Beds

3.1

Baths

2,432

Sq.Ft.

461 GERANIUM PARK WAY

Winter Garden, FL

Courtesy of THE ROSENBLOOM TEAM
View 15734 SWEET LEMON WAY Winter Garden, FL MLS# O6401408
$950,000
5

Beds

4.1

Baths

3,635

Sq.Ft.

15734 SWEET LEMON WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15196 LAKE CLAIRE OVERLOOK DRIVE Winter Garden, FL MLS# O6397637
$1,155,000
5

Beds

4.0

Baths

3,505

Sq.Ft.

15196 LAKE CLAIRE OVERLOOK DRIVE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 10174 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6402434
$1,050,000
4

Beds

3.1

Baths

2,758

Sq.Ft.

10174 MERRYMEETING BAY DRIVE

Winter Garden, FL

Courtesy of LUXE PROPERTIES LLC
View 16827 SANCTUARY DRIVE Winter Garden, FL MLS# S5148416
$998,000
4

Beds

3.0

Baths

2,281

Sq.Ft.

16827 SANCTUARY DRIVE

Winter Garden, FL

Courtesy of EASY REALTY SERVICES INC
View 9942 SUMMERLAKE GROVES STREET Winter Garden, FL MLS# O6402319
$899,000
4

Beds

3.1

Baths

2,935

Sq.Ft.

9942 SUMMERLAKE GROVES STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 8911 SONOMA COAST DRIVE Winter Garden, FL MLS# O6402068
$949,990
5

Beds

4.1

Baths

3,227

Sq.Ft.

8911 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 12513 SCARLETT SAGE COURT Winter Garden, FL MLS# O6393138
$875,000
5

Beds

3.0

Baths

3,570

Sq.Ft.

12513 SCARLETT SAGE COURT

Winter Garden, FL

Courtesy of KARDOSH REALTY
View 15976 CITRUS KNOLL DRIVE Winter Garden, FL MLS# O6399342
$909,000
5

Beds

3.1

Baths

2,953

Sq.Ft.

15976 CITRUS KNOLL DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17876 ADRIFT ROAD Winter Garden, FL MLS# O6400461
$899,000
5

Beds

4.0

Baths

2,866

Sq.Ft.

17876 ADRIFT ROAD

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 12928 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6400451
$916,000
5

Beds

4.1

Baths

3,626

Sq.Ft.

12928 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 7692 GREEN MOUNTAIN WAY Winter Garden, FL MLS# O6401130
$875,000
5

Beds

4.0

Baths

3,855

Sq.Ft.

7692 GREEN MOUNTAIN WAY

Winter Garden, FL

Courtesy of FIRST REGION REALTY
View 13536 SUNSET LAKES CIRCLE Winter Garden, FL MLS# O6399227
$1,100,000
5

Beds

4.0

Baths

3,389

Sq.Ft.

13536 SUNSET LAKES CIRCLE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 6249 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5111078
$941,015
6

Beds

4.0

Baths

4,236

Sq.Ft.

6249 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13043 SANDCASTLE DRIVE Winter Garden, FL MLS# O6399529
  • Adult Community with Virtual Tour
1 of 41
$899,000
3

Beds

2.0

Baths

1,943

Sq.Ft.

13043 SANDCASTLE DRIVE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 14140 COUNTRY ESTATE DRIVE Winter Garden, FL MLS# O6397262
$996,975
4

Beds

3.0

Baths

2,346

Sq.Ft.

14140 COUNTRY ESTATE DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 11264 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6397733
  • New Construction with Virtual Tour
1 of 7
$919,990
5

Beds

4.1

Baths

3,225

Sq.Ft.

11264 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA 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

1,035

Estimated median home price

$609,900
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 - 100K1
$100K - 200K25
$200K - 300K96
$300K - 400K79
$400K - 500K138
$500K - 600K171
$600K - 700K127
$700K - 800K113
$800K - 900K89
$900K - 1M71
$1M - Max125

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family715
Townhouse134
Condo143
Commercial10
Rental212
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/30/2026)

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 5/30/2026.