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40 W Smith Street

Winter Garden, FL 34787

3 beds
2 baths
2,225 sqft
9,464 sqft lot
$337 per sqft
1923 build
– on site

Under contract-accepting backup offers. Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled in the heart of downtown Winter Garden, enjoy easy access to the widely popular Plant Street farmer's market, West Orange Trail, and the famed Crooked Can Brewery. This prime location home is nestles in the heart of downtown Winter Garden with easy access to local shops, restaurants, parks, and the vibrant community events that define this sought-after area. Original architectural details reflects the home's 1920's heritage, offering a unique blend of past and present. Some of modern highlights include Brazilian Cherry hardwood floors, Roof 2018, AC 2019, and replumbed in 2020. Your spacious living amenities include 3 bedrooms with large walk-in closets, 2 full bathrooms, and an ample upstairs retreat generous enough for families or those seeking to room to grow. Don't miss the opportunity to own a piece of Winter Garden's history. Schedule your private showing today and envision the endless possibilities this home has.

Listing courtesy of STELLAR_MLS / NATIONAL REAL ESTATE LLC

Last checked: Checking… • Last updated May 21, 2025 •

MLS# O6306766 —

The Building

Year Built:

1923
New Construction:

false
Construction Materials:

Wood Frame
Levels:

Two
Stories Total:

2
Roof:

Shingle
Foundation Details:

Crawlspace
Building Area Total:

2225
Building Area Units:

Square Feet
Building Area Source:

Owner

Interior

Interior Features:

Ceiling Fan(s)
Flooring:

Engineered Hardwood
Fireplace:

true
Fireplace Features:

Family Room

Room Dimensions

Living Area:

2225
Living Area Units:

Square Feet
Living Area Source:

Owner

Location

Directions:

Plant St to Park Ave. Lt on W Smith St. Home is on the RT
Latitude:

28.563125
Longitude:

-81.587295
Coordinates:

-81.587295, 28.563125

The Property

Parcel Number:

232227809600011
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size Acres:

0.22
Lot Size Area:

9464
Lot Size SqFt:

9464
Lot Size Units:

Square Feet
Total Acres:

0 to less than 1/4
Zoning:

R-2
Direction Faces:

North
View:

false
Exterior Features:

Garden
Fencing:

Chain Link
Water Source:

Public
Road Surface Type:

Brick
Flood Zone Code:

x
Additional Parcels:

false
Homestead:

true
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

1
Tax Block:

1
Tax Legal Description:

G T SMITH SUB G/131 E1/2 OF LOTS 1 & 4
Tax Book Number:

G-131
Tax Annual Amount:

$1,679.39

Beds

Bedrooms Total:

3

Baths

Total Baths:

2
Total Baths:

2
Full Baths:

2

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/O6306766
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Public
Sewer:

Public Sewer

Appliances

Appliances:

Cooktop
Laundry Features:

Inside

Schools

Elementary School:

Dillard Street Elem
Middle Or Junior School:

Lakeview Middle
High School:

West Orange High

The Community

Subdivision Name:

G T SMITH SUB
Senior Community:

false
Waterview:

false
Water Access:

false
Waterfront:

false
Pool Private:

false
Association:

false
Ownership:

Fee Simple

Parking

Garage:

true
Attached Garage:

false
Garage Spaces:

1
Garage Dimensions:

19x22
Carport:

false
Covered Spaces:

1
Parking Features:

Garage Door Opener

Monthly cost estimate

Asking price

$750,000

Expense	Monthly cost
Mortgage	$4,016
Taxes	$139
Insurance	$206
Utilities	$213 See report
Total	$4,574/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
5/21/25 May 21, 2025	Pending	STELLAR_MLS	$750,000
5/13/25 May 13, 2025	Listed / Active	STELLAR_MLS	$750,000

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This house located in Winter Garden Downtown Historic District, Winter Garden, FL 34787 is currently pending sale for $750,000. 40 W Smith Street is a 2,225 square foot house with 3 beds and 2 baths that has been on Estately for 8 days. 40 W Smith Street is in the Winter Garden Downtown Historic District neighborhood of Winter Garden and has a WalkScore® of 92, making it a walker’s paradise. This house is in the attendance area of Dillard Street Elementary School, Lakeview Middle School, West Orange High School, Cornerstone Charter Academy High School, and Cornerstone Charter Academy K-8.

Listing Courtesy of: STELLAR_MLS and NATIONAL REAL ESTATE LLC.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing is provided exclusively 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 information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.