824 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 7025 TWILIGHT BAY DRIVE Winter Garden, FL MLS# S5156936
$435,000
3

Beds

3.0

Baths

2,024

Sq.Ft.

7025 TWILIGHT BAY DRIVE

Winter Garden, FL

View 1315 EASTERN PECAN PLACE 202 Winter Garden, FL MLS# O6437857
  • Recently Listed with Virtual Tour
1 of 22
$212,000
1

Beds

1.0

Baths

942

Sq.Ft.

1315 EASTERN PECAN PLACE 202

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7608 SUMMERLAKE GROVES ST Winter Garden, FL MLS# O6438685
$590,000
5

Beds

3.0

Baths

2,461

Sq.Ft.

7608 SUMMERLAKE GROVES ST

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 402 E MAPLE STREET Winter Garden, FL MLS# G5117336
$850,000
6

Beds

4.2

Baths

2,876

Sq.Ft.

402 E MAPLE STREET

Winter Garden, FL

Courtesy of FORTUNE REALTY OF CLERMONT
View 14145 CREEKBED CIRCLE Winter Garden, FL MLS# S5156892
  • Recently Listed with Virtual Tour
1 of 79
$739,000
4

Beds

4.0

Baths

2,823

Sq.Ft.

14145 CREEKBED CIRCLE

Winter Garden, FL

View 431 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# O6439215
$284,995
3

Beds

2.0

Baths

1,340

Sq.Ft.

431 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

View 17322 BEACHGRASS ALLEY Winter Garden, FL MLS# O6438247
  • Recently Listed with Virtual Tour
1 of 8
$669,990
4

Beds

3.1

Baths

2,791

Sq.Ft.

17322 BEACHGRASS ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 17937 LAKE STAR ROAD Winter Garden, FL MLS# O6438608
  • Recently Listed with Virtual Tour
1 of 18
$889,990
4

Beds

3.1

Baths

3,066

Sq.Ft.

17937 LAKE STAR ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 17431 WATER HEMLOCK ROAD Winter Garden, FL MLS# O6439017
  • Recently Listed with Virtual Tour
1 of 10
$789,990
4

Beds

3.0

Baths

2,908

Sq.Ft.

17431 WATER HEMLOCK ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 17425 WATER HEMLOCK ROAD Winter Garden, FL MLS# O6438971
  • Recently Listed with Virtual Tour
1 of 16
$814,990
4

Beds

3.0

Baths

2,869

Sq.Ft.

17425 WATER HEMLOCK ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 8001 POND APPLE DRIVE Winter Garden, FL MLS# O6437864
  • Recently Listed with Virtual Tour
1 of 74
$785,000
5

Beds

3.0

Baths

3,289

Sq.Ft.

8001 POND APPLE DRIVE

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# G5117322
$871,315
4

Beds

3.0

Baths

2,740

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6135 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5117323
$765,490
4

Beds

3.1

Baths

2,688

Sq.Ft.

6135 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15124 LEMON PEEL ALLEY Winter Garden, FL MLS# O6438797
  • Recently Listed with Virtual Tour
1 of 25
$627,500
4

Beds

3.1

Baths

2,496

Sq.Ft.

15124 LEMON PEEL ALLEY

Winter Garden, FL

View 1372 ROXY LANE Winter Garden, FL MLS# O6437028
  • Recently Listed
1 of 50
$519,900
4

Beds

3.0

Baths

2,030

Sq.Ft.

1372 ROXY LANE

Winter Garden, FL

View 113 W DIVISION STREET Winter Garden, FL MLS# S5156876
  • Recently Listed with Virtual Tour
1 of 24
$469,900
4

Beds

2.0

Baths

1,487

Sq.Ft.

113 W DIVISION STREET

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 11156 HANLON TERRACE ALLEY Winter Garden, FL MLS# O6438910
  • Recently Listed with Virtual Tour
1 of 47
$410,000
3

Beds

2.1

Baths

1,868

Sq.Ft.

11156 HANLON TERRACE ALLEY

Winter Garden, FL

View 13360 SUNNY RETREAT LANE Winter Garden, FL MLS# S5156584
  • Recently Listed with Virtual Tour
1 of 62
$595,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

13360 SUNNY RETREAT LANE

Winter Garden, FL

View 5887 CYPRESS HILL ROAD Winter Garden, FL MLS# O6438059
  • Recently Listed with Virtual Tour
1 of 79
$475,000
3

Beds

2.1

Baths

1,810

Sq.Ft.

5887 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
View 2108 TILLMAN AVENUE Winter Garden, FL MLS# O6437773
  • Recently Listed with Virtual Tour
1 of 50
$849,000
5

Beds

4.0

Baths

3,078

Sq.Ft.

2108 TILLMAN AVENUE

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

1,001

Estimated median home price

$610,000
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 - 200K21
$200K - 300K90
$300K - 400K70
$400K - 500K147
$500K - 600K166
$600K - 700K106
$700K - 800K109
$800K - 900K112
$900K - 1M62
$1M - Max117

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family702
Townhouse135
Condo129
Commercial7
Rental184
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 9/4/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 9/4/2026.