678 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
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 5972 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5108237
$747,990
3

Beds

3.1

Baths

2,515

Sq.Ft.

5972 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5996 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5107302
$747,949
4

Beds

3.0

Baths

2,102

Sq.Ft.

5996 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 120 BLUE STONE CIRCLE Winter Garden, FL MLS# O6409811
$747,900
4

Beds

3.0

Baths

2,529

Sq.Ft.

120 BLUE STONE CIRCLE

Winter Garden, FL

View 5943 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5102277
$746,650
4

Beds

3.1

Baths

2,688

Sq.Ft.

5943 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 9503 BEAUTIFUL WAY Winter Garden, FL MLS# O6416825
$745,990
4

Beds

3.0

Baths

2,650

Sq.Ft.

9503 BEAUTIFUL WAY

Winter Garden, FL

Courtesy of WYNNMORE REALTY LLC
View 6165 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5111538
$745,130
4

Beds

3.0

Baths

3,038

Sq.Ft.

6165 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 708 ORANGE BELT LOOP Winter Garden, FL MLS# G5112211
$745,000
3

Beds

2.0

Baths

1,916

Sq.Ft.

708 ORANGE BELT LOOP

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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 17428 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5110933
$740,205
6

Beds

4.1

Baths

3,412

Sq.Ft.

17428 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5973 CYPRESS HILL ROAD Winter Garden, FL MLS# O6412179
$740,000
5

Beds

3.1

Baths

3,532

Sq.Ft.

5973 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of NEARBY REALTY
View 6051 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5113741
$737,110
4

Beds

2.1

Baths

2,235

Sq.Ft.

6051 FLOWERING CHERRY BEND

Winter Garden, FL

View 14345 WABASSO LOOP Winter Garden, FL MLS# O6376609
$735,000
5

Beds

4.0

Baths

2,878

Sq.Ft.

14345 WABASSO LOOP

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 7643 SILVER MEADOW STREET Winter Garden, FL MLS# G5108692
$732,990
5

Beds

4.1

Baths

3,122

Sq.Ft.

7643 SILVER MEADOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17452 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5108833
$732,345
4

Beds

2.1

Baths

2,688

Sq.Ft.

17452 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7685 SILVER MEADOW STREET Winter Garden, FL MLS# G5108447
$732,070
5

Beds

4.1

Baths

3,122

Sq.Ft.

7685 SILVER MEADOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7579 SPRING VALLEY STREET Winter Garden, FL MLS# G5108556
$731,055
5

Beds

4.1

Baths

3,122

Sq.Ft.

7579 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7549 SPRING VALLEY STREET Winter Garden, FL MLS# G5112279
$730,791
4

Beds

3.1

Baths

2,515

Sq.Ft.

7549 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6357 WILD PERSIMMON WAY Winter Garden, FL MLS# G5105172
$730,184
3

Beds

3.1

Baths

2,515

Sq.Ft.

6357 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15591 GENTLE RAIN DRIVE Winter Garden, FL MLS# O6411803
$730,000
5

Beds

4.0

Baths

2,896

Sq.Ft.

15591 GENTLE RAIN DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK 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

957

Estimated median home price

$605,455
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 - 300K91
$300K - 400K64
$400K - 500K133
$500K - 600K167
$600K - 700K103
$700K - 800K101
$800K - 900K92
$900K - 1M63
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family657
Townhouse129
Condo136
Commercial11
Rental199
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/10/2026)

Information deemed reliable but not guaranteed.

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 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 7/11/2026.

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 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 7/11/2026.