263 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 11031 JACKSON COVE Winter Garden, FL MLS# O6425544
$700,000
4

Beds

3.0

Baths

2,931

Sq.Ft.

11031 JACKSON COVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13624 LARSEN LANE Winter Garden, FL MLS# O6425287
$880,000
5

Beds

4.0

Baths

3,779

Sq.Ft.

13624 LARSEN LANE

Winter Garden, FL

View 2139 TILLMAN AVENUE Winter Garden, FL MLS# O6424765
  • Adult Community with Virtual Tour
1 of 48
$860,000
4

Beds

4.0

Baths

3,078

Sq.Ft.

2139 TILLMAN AVENUE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 7773 MINUTEMEN LOOP Winter Garden, FL MLS# O6425792
$835,000
5

Beds

3.1

Baths

3,393

Sq.Ft.

7773 MINUTEMEN LOOP

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 16736 GULLFLOSS TERRACE Winter Garden, FL MLS# O6423968
$775,000
4

Beds

3.1

Baths

2,806

Sq.Ft.

16736 GULLFLOSS TERRACE

Winter Garden, FL

View 2045 SANDY GARDEN LANE Winter Garden, FL MLS# O6422461
$709,000
4

Beds

3.1

Baths

2,742

Sq.Ft.

2045 SANDY GARDEN LANE

Winter Garden, FL

View 11863 SHINE VIEW LANE Winter Garden, FL MLS# O6423774
  • New Construction with Virtual Tour
1 of 7
$850,621
5

Beds

4.0

Baths

2,866

Sq.Ft.

11863 SHINE VIEW LANE

Winter Garden, FL

View 17133 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5114884
$787,773
5

Beds

3.1

Baths

3,076

Sq.Ft.

17133 INGRAM BLUFF DRIVE

Winter Garden, FL

View 16304 WIND VIEW LANE Winter Garden, FL MLS# O6418695
$899,999
4

Beds

3.1

Baths

2,956

Sq.Ft.

16304 WIND VIEW LANE

Winter Garden, FL

View 15790 SWEET LIMETTA DRIVE Winter Garden, FL MLS# O6421864
$899,000
6

Beds

4.1

Baths

3,636

Sq.Ft.

15790 SWEET LIMETTA DRIVE

Winter Garden, FL

View 10750 PETRILLO WAY Winter Garden, FL MLS# O6423067
$695,000
3

Beds

2.1

Baths

2,613

Sq.Ft.

10750 PETRILLO WAY

Winter Garden, FL

Courtesy of SUNSHINE LIFE REALTY LLC
View 346 CRYSTAL WOOD DRIVE Winter Garden, FL MLS# O6423640
  • New Construction with Virtual Tour
1 of 28
$883,390
4

Beds

3.0

Baths

3,147

Sq.Ft.

346 CRYSTAL WOOD DRIVE

Winter Garden, FL

View 443 WRANGLER ROAD Winter Garden, FL MLS# O6423892
$775,000
4

Beds

3.1

Baths

2,877

Sq.Ft.

443 WRANGLER ROAD

Winter Garden, FL

Courtesy of PREFERRED RE BROKERS III
View 12248 Encore at Ovation Way Winter Garden, FL MLS# A12046224
$695,000
4

Beds

3.0

Baths

2,346

Sq.Ft.

12248 Encore at Ovation Way

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 2025 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6422627
$715,000
5

Beds

4.0

Baths

2,655

Sq.Ft.

2025 WINTERMERE POINTE DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6422754
$799,000
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

View 16082 HAMPTON CROSSING DRIVE Winter Garden, FL MLS# O6420606
$729,900
4

Beds

3.0

Baths

2,240

Sq.Ft.

16082 HAMPTON CROSSING DRIVE

Winter Garden, FL

Courtesy of Longwood - WEICHERT, REALTORS® - Hallmark Properties
View 13361 SUNNY RETREAT LANE Winter Garden, FL MLS# O6419110
  • Adult Community with Virtual Tour
1 of 73
$859,900
4

Beds

3.0

Baths

3,172

Sq.Ft.

13361 SUNNY RETREAT LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14301 WHITE MOSS WAY Winter Garden, FL MLS# G5114391
$899,999
5

Beds

3.1

Baths

4,053

Sq.Ft.

14301 WHITE MOSS WAY

Winter Garden, FL

View 13175 SUNNY RETREAT LANE Winter Garden, FL MLS# O6420975
  • Virtual Tour
1 of 43
OPEN HOUSE: Saturday 8/29 11:00 AM - 2:00 PM
$765,000
3

Beds

2.0

Baths

2,054

Sq.Ft.

13175 SUNNY RETREAT LANE

Winter Garden, FL

Courtesy of BUYER REBATES REALTY

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

1,034

Estimated median home price

$605,948
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 - 200K22
$200K - 300K88
$300K - 400K78
$400K - 500K158
$500K - 600K168
$600K - 700K114
$700K - 800K115
$800K - 900K108
$900K - 1M64
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family716
Townhouse149
Condo133
Commercial9
Rental183
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/28/2026)

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

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.

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 8/28/2026.