$375,000
 $2,129 est/mo Sourced by Back At You

382 S Main Street,Winchester, KY 40391

Winchester, KY 40391

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Description

Built in 1893, this beautifully maintained home is filled with the charm and craftsmanship that's hard to find today, along with the modern updates buyers appreciate. Situated on a corner lot just minutes from historic downtown Winchester, you'll love the walkable location with South Main Grocery & Grill, a local favorite known for its country ham sandwiches and home-cooked meals, right across the street. The Clark County Public Library, College Park, and downtown Winchester's shops, restaurants, and local events are all just a short walk away. Inside, you'll find over 3,300 square feet featuring four bedrooms, three full baths, soaring ceilings, gorgeous hardwood floors, four fireplaces, beautiful original woodwork, and an updated kitchen that complements the home's historic character. Multiple living spaces provide plenty of room for entertaining, working from home, hosting guests, or simply spreading out, plus the convenience of a basement-entry garage. Enjoy your morning coffee or unwind in the evening from the inviting front porch, the perfect spot for a porch swing and visiting with neighbors. Out back, you'll appreciate the screened-in porch overlooking the secluded-feeling backyard, an ideal space for relaxing, grilling, or enjoying a quiet evening outdoors. Homes like this don't come along often. Rich in history, full of character, and ideally located near the heart of downtown, this home offers the perfect mixture of classic architecture, modern updates, and everyday convenience. Enjoy the charm of small-town living while still being an easy commute to Lexington for work, shopping, dining, and entertainment. If you've been dreaming of owning a home with historic charm, modern comforts, and a location that truly lets you enjoy the best of Winchester, this is one you won't want to miss.

Details

MLS #26008931
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusPending
Year1893
Days On Site119
Listing Provided ByRE/MAX Creative, Winchester | Michelle R Blackburn

Features

Bed(s)4
Bath(s) 3 Total
SQ Feet3,310
Garage2
BasementY
Story(s)2
Acreage0.27

Interior

Rooms Total14
CoolingCeiling Fan(s), Central Air, Electric
HeatingForced Air, Natural Gas
Heating Yes / NoYes
Cooling Yes / NoYes
Interior FeaturesCeiling Fan(s), Eat-in Kitchen, Entrance Foyer, Walk-In Closet(s)
Window FeaturesBlinds, Insulated Windows, Screens, Skylight(s)
AppliancesDishwasher, Dryer, Range, Refrigerator, Washer

Exterior

Exterior FeaturesOther
RoofDimensional Style, Shingle
Construction MaterialsVinyl Siding
Foundation DetailsStone
Lot FeaturesLandscaped, Many Trees
FencingWood

Parking

Garage Yes / NoYes
Attached Garage Yes / NoNo
Parking FeaturesBasement, Driveway, Garage Door Opener, Garage Faces Side

Utilities

UtilitiesElectricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
SewerPublic Sewer

Area Information

StateKY
CountyClark
CityWinchester
Zip Code40391
Area007 Clark County
SubareaClark County
Community NameThomson Addition
School DistrictClark County
Elementary SchoolShearer
High SchoolGRC
Listing VS Median (in Thomson Addition)
Price:
$375,000
low | high
Med:
$375,000
50% of Average
sqft:
3,310
low | high
Med:
3,310
50% of Average
$ / sqft:
$113
low | high
Med:
$113
50% of Average
On site:
119
low | high
Med:
119
100% of Average
Sourced by Back At You

Market Activity 40391

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Learn More About This Property

StateKY
CountyClark
CityWinchester
Zip Code40391
Area007 Clark County
SubareaClark County
Community NameThomson Addition
School DistrictClark County
Elementary SchoolShearer
High SchoolGRC
Listing VS Median (in Thomson Addition)
Price:
$375,000
low | high
Med:
$375,000
50% of Average
sqft:
3,310
low | high
Med:
3,310
50% of Average
$ / sqft:
$113
low | high
Med:
$113
50% of Average
On site:
119
low | high
Med:
119
100% of Average
Sourced by Back At You
Nearby Listings (Within 1/4 mile)
Price: $281K - $468K
sqft: 2,000 - 4,000
Nearby Listings Property ImageNearby Listings Details
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443 S Maple Street Property Photo 1
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443 S Maple Street
Winchester, KY 40391
Listing Updated: August 18, 2026 at 12:49:30 PM PDT