229 S Highland Street, Winchester, KY 40391

$180,000
Property Type: Residential Bedrooms: 4 Baths: 3 Square Footage: 3,462 Lot Size (sq. ft.): 4,792 Status: Active
Current Price: $180,000 List Date: 4/22/2026 Last Modified: 4/30/2026

Overview

Description

Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

Listing Details MLS# 26008701

Listing Information

Comp Sale YN
No
Property Sub Type
Single Family Residence

Status Change Information

Status Change Timestamp
2026-04-22

Address

County
Clark
Street Number
229
Street Direction Prefix
S
Street Name
Highland
Street Suffix
Street
State
KY
Zip Code
40391
Directions
From I64, take Maple Expressway towards town. Left on Lexington Ave. Go thru light and make a right on Highland St. Go thru stop sign. House will be on left on corner of Highland and Calloway.
Parcel Number
054-3012-014-00

Contract

Original List Price
180000
Start Showing Date
2026-04-22
Listing Contract Date
2026-04-22
Listing Agreement
Exclusive Right To Sell
Occupant Type
Vacant
Office Exclusive YN
No
List Price/SqFt
51.99

Tax Legal

MLS Area Major
007 - Clark County
Subdivision Name
South Park Addition
High School District
Clark County - 7

Interior

Bedrooms Total
4
Bathrooms Total
3
Bathrooms Full
3
Above Grade Finished Area
3462
Living Area
3462
Living Area Source
Public Records
Basement YN
Yes
Fireplace YN
Yes
Fireplaces Total
3
Bathrooms Half
0
Below Grade Finished Area
0
Above Grade Unfinished Area
0
Below Grade Unfinished Area
0

More Information

Parking Information

Garage YN
Yes
Garage Spaces
Yes
Carport YN
No

Building

Year Built
1930
Accessibility Features YN
No

Lot

Lot Size Source
Public Records
Lot Size Acres
0.11
Lot Size Square Feet
4791.6
Pool Private YN
No
Waterfront YN
No
Water Body Access YN
No
Horse YN
No

Utilities

Cooling YN
Yes
Heating YN
Yes
Electricity Connected
Yes
Natural Gas Connected
Yes
Water Connected
Yes

Remarks

Public Remarks
Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

Amenity Fee Details

Amenity Fee YN
No

Showing Information

Showing Instructions
ShowingTime

Room Types

Bathroom 1 Level
First
Bathroom 2 Level
Second
Bathroom 3 Level
Second
Bedroom 1 Level
Second
Bedroom 2 Level
Second
Bedroom 3 Level
Second
Bedroom 4 Level
Second
Dining Room Level
First
Family Room Level
First
Foyer Level
First
Kitchen Level
First
Living Room Level
First
Primary Bedroom Level
First
Bathroom 1
Yes
Bathroom 2
Yes
Bathroom 3
Yes
Bedroom 1
Yes
Bedroom 2
Yes
Bedroom 3
Yes
Bedroom 4
Yes
Dining Room
Yes
Family Room
Yes
Foyer
Yes
Kitchen
Yes
Living Room
Yes
Primary Bedroom
Yes

Currently Not Used

List Price/Acre
1636363.64

Tax & Legal

Elementary School
Shearer
Middle Or Junior School
Robert Campbell
High School
GRC
Tax Rate
0.123

Association/Community

Association YN
No

Appliances

Refrigerator
Yes

Architectural Style

Colonial
Yes

Attic Features

Floored
Yes
Permanent Stairs
Yes
Walk-In Attic
Yes

Basement

Crawl Space
Yes
Interior Entry
Yes
Walk-Out Access
Yes

Construction Materials

HardiPlank Type
Yes
Wood Siding
Yes

Cooling

Electric
Yes

Fencing

None
Yes

Fireplace Features

Living Room
Yes

Flooring

Hardwood
Yes

Foundation Details

Stone
Yes

Heating

Forced Air
Yes
Natural Gas
Yes

Levels

Two
Yes

Parking Features

Basement
Yes
Garage Faces Side
Yes

Patio And Porch Details

Covered Porch
Yes
Front Porch
Yes

Patio And Porch Features

Porch
Yes

Possession

Close Of Escrow
Yes

Roof

Metal
Yes

Sewer

Public Sewer
Yes

Structure Type

House
Yes

Water Heater

Gas
Yes

Water Source

Public
Yes

Showing Requirements

Show Anytime
Yes
Showing Service
Yes

Property Features

Utilities: Electricity Connected; Natural Gas Connected; Water Connected; Electricity Connected; Natural Gas Connected; Water Connected Appliances: Refrigerator Architectural Style: Colonial Attic Features: Floored; Permanent Stairs; Walk-In Attic Basement: Crawl Space; Interior Entry; Walk-Out Access Construction Materials: HardiPlank Type; Wood Siding Cooling: Electric Fencing: None Fireplace Features: Living Room Flooring: Hardwood Foundation Details: Stone Heating: Forced Air; Natural Gas Levels: Two Parking Features: Basement; Garage Faces Side Patio And Porch Details: Covered Porch; Front Porch Patio And Porch Features: Porch Possession: Close Of Escrow Roof: Metal Sewer: Public Sewer Structure Type: House Water Heater: Gas Water Source: Public Showing Requirements: Show Anytime; Showing Service Room Types: Bathroom 1; Bathroom 2; Bathroom 3; Bedroom 1; Bedroom 2; Bedroom 3; Bedroom 4; Dining Room; Family Room; Foyer; Kitchen; Living Room; Primary Bedroom

Room Information

Room Name Level
Foyer First
Living Room First
Dining Room First
Family Room First
Kitchen First
Primary Bedroom First
Bathroom 1 First
Bedroom 1 Second
Bedroom 2 Second
Bedroom 3 Second
Bedroom 4 Second
Bathroom 2 Second
Bathroom 3 Second
Listing Office: RE/MAX Creative, Winchester
Last Updated: April - 30 - 2026
Information deemed reliable but not guaranteed.