RobertandJeanie Smith

229 S Highland Street

Winchester, KY
$ 165,000 Beds 4 Baths 3 Sq 3,462
Monthly Estimate* How much can I afford?

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.

Active

  • Price
  • $ 165,000
  • City
  • Winchester
  • Bedrooms
  • 4
  • Full Bathrooms
  • 3
  • County
  • CLARK
  • Half Bathrooms
  • 0
  • Area
  • 007 - Clark County
  • Lot Size
  • 0.11 Acres
  • Zip
  • 40391
  • Sqr Footage
  • 3,462
  • Year Built
  • 1930
  • Style
  • Colonial
  • MLS#
  • 26008701
Listed By: RE/MAX Creative, Winchester - 859-422-2000
Data Source: ImagineMLS

Features

General

Sewer Public Sewer
Heating Forced Air,Natural Gas
Cooling Electric
Utilities Electricity Connected,Natural Gas Connected,Water Connected
Possession Close Of Escrow
Roof Metal
Appliances Refrigerator
Garage Spaces 1.0
Patio/Porch Features Porch,Front Porch
Architectural Style Colonial
Construction Materials Wood Siding,HardiPlank Type
Year Built 1930
Levels Two
Property Subtype Single Family Residence
Parcel Number 054-3012-014-00
County Clark
New Construction No
Property Type Residential
HOA No
Attached Garage No
Subdivision Name South Park Addition
Garage Y/N Yes
Total Rooms 13
Full Baths 3
Status Active
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.
High School GRC
City Winchester
High School District Clark County - 7
MLS Area 007 - Clark County
Lot Size Units Acres
Lot Size Square Feet 4791.6
Carport Y/N No
Elementary School Shearer
Land Lease Y/N No
Home Warranty Y/N No
Middle/Junior High School Robert Campbell
MLS Area Minor 007 - Clark County
Lease Considered Y/N No
Rent Control Y/N No
Structure Type House
Standard Status Active
MobileHomeRemainsYN No
Senior Community None
Sewer_co_Public_sp_Sewer True

Interior Features

Basement Crawl Space,Interior Entry,Walk-Out Access
Flooring Hardwood
Total Fireplaces 3
Fireplace Features Living Room
Basement (Y/N) Yes
Air Conditioning Y/N Yes
Heating Y/N Yes
Fireplace Y/N Yes
Above Grade Finished Area 3462.0
Total Bedrooms 4
Below Grade Finished Area 0.0
LivingAreaSource Public Records
Total Baths 3
Heating-Forced Air True
Heating-Natural Gas True

Exterior Features

Fencing None
Parking Features Basement,Garage Faces Side
Water Source Public
Lot Size Area 0.11
Foundation Details Stone
Building Area Total 3462.0
Lot Size Acres 0.11
Lot Size Source Public Records
Waterfront Y/N No
Crops Included Y/N No
Horse Y/N No
Irrigation Water Rights Y/N No

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Taylorsville, KY office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% 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.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Shearer Elementary School
Middle School Robert Campbell Middle School
High School GRC High School

Price History

4/22/2026 Listed $180,000
7/7/2026 9% - $165,000

Property vs Zip Code Average in 40391

Price
AVG $440K
$170K
Year Built
AVG 1981
1930
Visits
AVG 77
441
Data Provided by Inside Real Estate®

In The Neighborhood

Areas That We Cover

229 S Highland Street Winchester, KY is a Single Family Home for sale at $165000 with 3462 sqft and a lot size of 0.11 Acres Acre(s). 229 S Highland Street Winchester has 4 bedrooms, 3 baths and was built in 1930. The property's zip code is 40391 which is in Winchester, KY

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% 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.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided 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.

RobertandJeanie Smith

RobertandJeanie Smith

502-680-8543

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