254 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 15058 SAWGRASS BLUFF DRIVE Winter Garden, FL MLS# O6396640
  • Recently Listed with Virtual Tour
1 of 21
OPEN HOUSE: Saturday 4/18 12:00 PM - 4:00 PM
$579,900
4

Beds

2.1

Baths

2,626

Sq.Ft.

15058 SAWGRASS BLUFF DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15033 LAKE BESSIE LOOP Winter Garden, FL MLS# A12001224
  • Recently Listed with Virtual Tour
1 of 37
$639,900
4

Beds

3.0

Baths

2,240

Sq.Ft.

15033 LAKE BESSIE LOOP

Winter Garden, FL

Courtesy of LOKATION
View 7562 SPRING VALLEY STREET Winter Garden, FL MLS# G5111052
$582,490
4

Beds

3.0

Baths

2,102

Sq.Ft.

7562 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 6159 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5111054
$699,745
4

Beds

2.1

Baths

2,235

Sq.Ft.

6159 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6441 WILD PERSIMMON WAY Winter Garden, FL MLS# G5111080
$617,990
4

Beds

3.1

Baths

2,515

Sq.Ft.

6441 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8031 NAVEL ORANGE LANE Winter Garden, FL MLS# O6399594
  • Recently Listed with Virtual Tour
1 of 32
$675,000
4

Beds

2.0

Baths

2,298

Sq.Ft.

8031 NAVEL ORANGE LANE

Winter Garden, FL

Courtesy of BUYER REBATES REALTY
View 7550 SPRING VALLEY STREET Winter Garden, FL MLS# G5110990
$701,340
4

Beds

3.1

Baths

2,515

Sq.Ft.

7550 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17162 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5110993
$699,970
5

Beds

4.1

Baths

3,122

Sq.Ft.

17162 INGRAM BLUFF DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6166 HAMLIN RESERVE BOULEVARD Winter Garden, FL MLS# O6399123
  • Recently Listed with Virtual Tour
1 of 51
OPEN HOUSE: Saturday 4/18 12:00 PM - 2:00 PM
$675,000
4

Beds

2.1

Baths

2,818

Sq.Ft.

6166 HAMLIN RESERVE BOULEVARD

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 14788 FIELD DAISY DRIVE Winter Garden, FL MLS# O6398754
$617,500
3

Beds

3.1

Baths

1,992

Sq.Ft.

14788 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14006 FRASIER STREET Winter Garden, FL MLS# O6398760
  • Recently Listed with Virtual Tour
1 of 79
$659,000
4

Beds

2.1

Baths

2,098

Sq.Ft.

14006 FRASIER STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17031 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5110934
$646,090
5

Beds

4.0

Baths

2,680

Sq.Ft.

17031 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15524 AVIATION ALLEY Winter Garden, FL MLS# O6398331
  • Recently Listed with Virtual Tour
1 of 39
$569,900
3

Beds

3.1

Baths

2,414

Sq.Ft.

15524 AVIATION ALLEY

Winter Garden, FL

Courtesy of LOKATION
View 195 SUNSET GARDEN LANE Winter Garden, FL MLS# O6398339
$641,000
4

Beds

3.1

Baths

2,460

Sq.Ft.

195 SUNSET GARDEN LANE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 196 SUNSET GARDEN LANE Winter Garden, FL MLS# O6398349
$580,000
4

Beds

3.0

Baths

2,143

Sq.Ft.

196 SUNSET GARDEN LANE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 6237 WILD PERSIMMON WAY Winter Garden, FL MLS# G5110909
$557,589
3

Beds

2.0

Baths

1,772

Sq.Ft.

6237 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 4136 WILLOW BAY DRIVE Winter Garden, FL MLS# R4911030
  • Recently Listed with Virtual Tour
1 of 14
$655,000
3

Beds

2.0

Baths

2,472

Sq.Ft.

4136 WILLOW BAY DRIVE

Winter Garden, FL

Courtesy of AVALON LAND & COMMERCIAL, LLC
View 7680 GREEN MOUNTAIN WAY Winter Garden, FL MLS# O6389013
$658,900
4

Beds

2.1

Baths

2,385

Sq.Ft.

7680 GREEN MOUNTAIN WAY

Winter Garden, FL

Courtesy of UPSIDE REAL ESTATE INC
View 12513 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6397713
  • Recently Listed with Virtual Tour
1 of 29
$668,000
4

Beds

3.1

Baths

2,807

Sq.Ft.

12513 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 1261 E FULLERS CROSS ROAD Winter Garden, FL MLS# O6397098
  • Recently Listed with Virtual Tour
1 of 52
$675,000
3

Beds

2.0

Baths

1,832

Sq.Ft.

1261 E FULLERS CROSS ROAD

Winter Garden, FL

Courtesy of LPT REALTY, 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

974

Estimated median home price

$599,900
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 - 200K19
$200K - 300K95
$300K - 400K80
$400K - 500K148
$500K - 600K152
$600K - 700K119
$700K - 800K100
$800K - 900K88
$900K - 1M65
$1M - Max107

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family673
Townhouse134
Condo129
Commercial12
Rental231
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 4/16/2026)

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 4/16/2026.

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

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 4/16/2026.