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100 N Main Street

Winter Garden, FL 34787

7 beds
4 baths
3,589 sqft
10,908 sqft lot
$118 per sqft
1925 build
– on site

Incredible location in the HISTORIC DISTRICT of DOWNTOWN WINTER GARDEN-great opportunity to buy now and build your own custom home in the GOLF CART DISTRICT. Currently the property is home to TWO EXISTING/OCCUPIED RENTAL HOMES! The VALUE OF THIS PROPERTY IS PRIMARILY IN THE LAND! Both of the existing buildings need significant repairs and are sold as-is/where is. The buyer is responsible for determining any/all allowable future use with the City of Winter Garden. Zoned R-2 RESIDENTIAL/TWO FAMILY, this .25 acre property is located across the street from Foundation Academy/preschool, and less than 1/10 mile from Plant Street. Building 1 (a white wood frame 2 story with asbestos siding & metal roof) was built in 1925 and consists of 2, 2 bedroom, 1 bath units, labeled A and B. This building is approximately 1902 sq. ft heated per tax records. Building 2 (located behind bldg 1) is a two story concrete block structure with storage on the ground level and an attached carport/shed. Building 2 was built in 1960 and contains a second floor apartment (C) with 2 bedrooms/1 bath, and (D) a 1st floor efficiency apartment. Building 2 is occupied by two tenants and has a large storage room below the 2nd floor apartment. The tax records indicate the heated square footage of Building 2 is 1687. Both buildings are connected to city water, sewer and Lake Apopka natural gas with Duke Energy for electricity. The West Orange Trail and all of the most desirable amenities of Downtown Winter Garden are just steps from your front door, including the national award winning Farmer's Market, numerous restaurants, bars, coffee and ice cream shops, boutiques/gift shops, The Crooked Can Brewery, Plant Street Market, Railroad & Heritage Museums, Winter Garden Theatre, Splash Pad, SOBO Art Gallery, doctors/dentists, and lash/nail/beauty & barber shops. Locals and visitors enjoy the many seasonal events like Spring Fever in the Garden, Oktoberfest, Winter Garden Halloween Experience, and Light Up Winter Garden. Quick and easy access to public schools and daycares too! SOLD AS-IS/Seller will make no repairs. Tenants are on month to month leases and the new owner inherits the tenants. Leases available for review upon acceptance of an offer. Buyer/Buyer's agent are responsible for verifying all information contained herein.

Listing courtesy of STELLAR_MLS / HOMEVEST REALTY

Last checked: Checking… • Last updated Mar 14, 2025 •

MLS# O6288690 —

The Building

Year Built:

1925
New Construction:

false
Construction Materials:

Asbestos
Levels:

Multi/Split
Stories Total:

2
Roof:

Metal
Foundation Details:

Crawlspace
Window Features:

Aluminum Frames
Patio And Porch Features:

Covered
Floor Number:

2
Building Area Total:

4576
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Built-in Features
Furnished:

Unfurnished
Flooring:

Ceramic Tile
Additional Rooms:

Attic
Fireplace:

false

Room Dimensions

Living Area:

3589
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

North on Dillard St. left on Plant Street, right on N. Main St. Property is located on left side of street. Homes included are the white wood frame building in front and the concrete block 2 story in back.
Latitude:

28.567137
Longitude:

-81.585893
Coordinates:

-81.585893, 28.567137

The Property

Parcel Number:

142227565600680
Property Type:

Residential
Property Subtype:

Single Family Residence
Property Condition:

Fixer
Property Attached:

false
Lot Features:

City Lot
Lot Size Acres:

0.25
Lot Size Area:

10908
Lot Size SqFt:

10908
Lot Size Dimensions:

90 x 121.33 x 90 x 121.33
Lot Size Units:

Square Feet
Total Acres:

1/4 to less than 1/2
Zoning:

R-2
Direction Faces:

East
View:

false
Exterior Features:

Sidewalk
Fencing:

Board
Water Source:

Public
Road Responsibility:

Public Maintained Road
Road Surface Type:

Brick
Road Frontage Type:

Street Brick
Flood Zone Code:

X
Flood Zone Panel:

12095CO2O5H
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

68
Tax Legal Description:

PLAT OF WINTER GARDEN D/32 N 40 FT OF LOT 68 & ALL OF LOT 71
Tax Book Number:

D-32
Tax Annual Amount:

4827

Beds

Bedrooms Total:

7

Baths

Total Baths:

4
Total Baths:

4
Full Baths:

4

The Listing

Virtual Tour URL Unbranded:

https://realestate.febreframeworks.com/sites/benxzwb/unbranded
Virtual Tour URL Unbranded 2:

https://www.propertypanorama.com/instaview/stellar/O6288690
Special Listing Conditions:

None
Home Warranty:

false

Heating & Cooling

Heating:

Electric
Heating:

true
Cooling:

Wall/Window Unit(s)
Cooling:

true

Utilities

Utilities:

Electricity Connected
Sewer:

Public Sewer

Appliances

Appliances:

Gas Water Heater
Laundry Features:

Outside

Schools

Elementary School:

Dillard Street Elem
Middle Or Junior School:

Lakeview Middle
High School:

West Orange High

The Community

Subdivision Name:

MILLERS PT WINTER GARDEN
Senior Community:

false
Community Features:

Golf Carts OK
Waterview:

false
Water Access:

false
Waterfront:

false
Spa:

false
Pool Private:

false
Pets Allowed:

Yes
Pet Restrictions:

Buyer to confirm any/all pet restrictions with governing bodies/municipalities.
Association:

false
Ownership:

Fee Simple
Association Approval Required:

false

Parking

Garage:

false
Attached Garage:

false
Carport:

true
Carport Spaces:

1
Covered Spaces:

1
Open Parking:

true
Parking Features:

Off Street

Extra Units

Other Structures:

Additional Single Family Home

Monthly cost estimate

Asking price

$425,000

Expense	Monthly cost
Mortgage	$2,275
Taxes	$402
Insurance	$116
Utilities	$282 See report
Total	$3,075/mo.^*
	^*This is an estimate

Explore the Area

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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
3/12/25 Mar 12, 2025	Pending	STELLAR_MLS	$425,000
3/12/25 Mar 12, 2025	Listed / Active	STELLAR_MLS	$425,000

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This house located in Winter Garden Downtown Historic District, Winter Garden, FL 34787 is currently pending sale for $425,000. 100 N Main Street is a 3,589 square foot house with 7 beds and 4 baths that has been on Estately for 4 days. 100 N Main Street is in the Winter Garden Downtown Historic District neighborhood of Winter Garden and has a WalkScore® of 89, making it very walkable. This house is in the attendance area of Dillard Street Elementary School, West Orange High School, Cornerstone Charter Academy K-8, Cornerstone Charter Academy High School, and Lakeview Middle School.

Listing Courtesy of: STELLAR_MLS and HOMEVEST REALTY.

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.