382 S Main Street Winchester, KY $ 415,000
382 S Main Street
$ 415,000
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382 S Main Street

Winchester, KY, 40391
$ 415,000
Bedrooms4 Baths3.0 Sq 3,310

Monthly Estimate*

$ 2,555

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Single Family Home for sale in Winchester, KY

for $415,000 with 4 bedrooms and 3 full baths. This 3,310 square foot home was built in 1893 on a lot size of 0.27.

Spacious and full of character, this unique 4 bedroom, 3 bath home sits on a corner lot on South Main right across from the iconic South Main Grocery. Inside, you are welcomed by a two story foyer and a layout that offers flexibility with a living room, main level bedroom, full bath, and a dining room that could also function as an office with double doors. The kitchen has space for eat in dining and connects to the laundry room, with access to the screened in porch, private hot tub area, and fenced backyard. A second staircase in the rear adds to the home's charm and functionality. Upstairs features a sitting area, the primary bedroom, and additional bedrooms with access to a shared full bath complete with a clawfoot tub. The finished attic or loft offers great bonus space that could be used as a fourth bedroom, rec room, or guest area and includes another full bath with a jacuzzi tub, along with unfinished attic space for additional storage. The basement level provides a large unfinished area for storage and includes an attached garage. Outside, you will find a covered side porch, a spacious side yard, a fenced backyard, and a storage shed. There is plenty of parking with a front parking pad and an extended side driveway. The home features a mix of flooring throughout and is filled with character including original doors, knobs, mantels, and four working fireplaces.

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Single Family Active

Price

$ 415,000

Bedrooms

4

Full Bath

3

Property Type

Single Family

Taxes

$ 0

Style

Colonial

Lot Size

0.27

Year Built

1893

Town/City

Winchester

County/Region

Clark

MLS | Web ID

26008931

Features
Interior
Interior Amenities Ceiling Fan(s) Eat-in Kitchen Entrance Foyer Walk-In Closet(s)
Basement Full Sump Pump Unfinished Walk-Out Access
Flooring Carpet Hardwood Vinyl
Total Fireplaces 4
Fireplace Features Dining Room Gas Log Living Room Primary Bedroom
Basement (Y/N) Y
Air Conditioning Y/N Y
Heating Y/N Y
Window Features Blinds Insulated Windows Screens Skylight(s)
Fireplace Y/N Y
Above Grade Finished Area 3310.0
Half Baths 0
Laundry Features Electric Dryer Hookup Main Level Washer Hookup
Total Bedrooms 4
Below Grade Finished Area 0.0
Total Baths 3
Heating-Forced Air True
Heating-Natural Gas True
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General
Sewer Public Sewer
Heating Forced Air Natural Gas
Cooling Ceiling Fan(s) Central Air Electric
Utilities Electricity Connected Natural Gas Connected Sewer Connected Water Connected
Possession Close Of Escrow Close Plus 3 Days
Roof Dimensional Style Shingle
Appliances Dishwasher Dryer Range Refrigerator Washer
Garage Spaces 2.0
Patio/Porch Features Porch Other Front Porch Side Porch
Architectural Style Colonial
Construction Materials Vinyl Siding
Year Built 1893
Levels Two
Property Subtype Single Family Residence
Parcel Number 054-2021-009-00
County Clark
New Construction N
Property Type Residential
HOA N
Attached Garage N
Subdivision Name Thomson Addition
Garage Y/N Y
Other Structures Shed(s)
Total Rooms 14
Full Baths 3
Status Active
Directions From Lexington I64 East to Winchester Exit 96 right on Maple Expressway left on Lexington Ave by Speedway right on Main Street. House is on the right on corner of Main St. and Moundale. Directly acro
High School GRC
City Winchester
High School District Clark County - 7
MLS Area 007 - Clark County
Lot Size Units Acres
Lot Size Square Feet 11761.2
Carport Y/N N
Elementary School Shearer
Land Lease Y/N N
Home Warranty Y/N N
Middle/Junior High School Robert Campbell
MLS Area Minor 007 - Clark County
Lease Considered Y/N N
Rent Control Y/N N
Structure Type House
Standard Status Active
Senior Community None
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Exterior
Exterior Amenities Other
Fencing Wood
Parking Features Basement Driveway Garage Door Opener Garage Faces Side
Lot Features Landscaped Many Trees
Water Source Public
Lot Size Area 0.27
Foundation Details Stone
Building Area Total 3310.0
Lot Size Acres 0.27
Lot Size Source Public Records
Waterfront Y/N N
Door Features Storm Door(s)
Crops Included Y/N N
Horse Y/N N
Irrigation Water Rights Y/N N
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Internal Only
Street Number 1 382
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* Excluded Features
List By
Re/Max Creative, Winchester

Broker

michelle@michelleblackburn.com

Email

Affordability Calculator

$2,555
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Monthly Principal & Interest
$2,555
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3289857 Elementary School
3291684 Middle School
GRC High School High School
Pricing History
DatePricePrice ChangeDescription
4/24/2026$415,000 Listed Price

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382 S Main Street, Winchester, KY, 40391 is a Single Family Home for sale at $415,000 with 3,310 sqft and a lot size of 0.27. 382 S Main Street has 4 bedrooms, 3.0 baths, and was built in 1893. The property's zip code is 40391 which is in Winchester, KY