229 S Highland Street, Winchester, KY 40391 | MLS #26008701 | Semonin Realtors

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Listing provided courtesy of RE/MAX Creative, Winchester- MLS# 26008701MLS Provider

229 S Highland StreetWinchester, KY 40391

Single Family · 4 Beds · 3 Full Baths · 3,462 Sq. ft. | 0.11 Acres
$180,000 Active

229 S Highland Street Overview

Time on Site:
69 days
Visits:
3

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.

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229 S Highland Street Facts & Features

  • Type Single Family
  • Sq. ft. 3,462
  • Price/Sq.ft. $52
  • Lot 0.11 Acres

Details

General

Association/HOA

  • Association: false

School Information

  • Elementary School: Shearer
  • Middle Or Junior School: Robert Campbell
  • High School: GRC

Building Information

  • Year Built: 1930

Location/Region

  • County Or Parish: Clark
  • MLS Area Major: 007 - Clark County
  • MLS Area Minor: 007 - Clark County
  • Subdivision Name: South Park Addition

General Information

  • Parcel Number: 054-3012-014-00
  • Property Sub Type: Single Family Residence
  • Property Type: Residential

Interior

Parking Information

  • Garage Spaces: 1.0
  • Garage: true

Beds/Baths

  • Bathrooms Full: 3
  • Bathrooms Half: 0
  • Bathrooms Total: 3
  • Bedrooms Total: 4

Building Interior

  • Above Grade Finished Area: 3462.0
  • Building Area Total: 3462.0

General Information

  • Appliances: Refrigerator
  • Fireplace Features: Living Room
  • Fireplace: true
  • Fireplaces Total: 3
  • Flooring: Hardwood
  • Foundation Details: Stone
  • Levels: Two
  • Living Area: 3462.0
  • Living Area Source: Public Records
  • Rooms Total: 13

Exterior

Parking Information

  • Parking Features: Basement,Garage Faces Side

Lot Information

  • Lot Size Acres: 0.11
  • Lot Size Area: 0.11
  • Lot Size Source: Public Records
  • Lot Size Square Feet: 4791.6
  • Lot Size Units: Acres
  • Water Source: Public

Waterfront/View

  • Waterfront: false

Building Exterior/Construction

  • Architectural Style: Colonial
  • Attached Garage: false
  • Construction Materials: HardiPlank Type,Wood Siding
  • Roof: Metal
  • Structure Type: House

General Information

  • Carport: false
  • Fencing: None
  • Horse: false
  • Pool Private: false
  • Sewer: Public Sewer
  • Utilities: Electricity Connected,Natural Gas Connected,Water Connected

229 S Highland Street Neighborhood

Community

40391 (Winchester) Demographics

42
Median Age
148
Population Density (per sq. mile)
29%
College Educated
$54,868
Estimated Median Income
9,955
Estimated Total Home Owners
4,479
Estimated Total Renters
69% / 31%
Estimated Owner / Renter Divide
2
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

229 S Highland Street Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

229 S Highland Street Market Data

Based on the last 30 days in this zip code

$430,589
Average List Price
$197
Average Price per Square Foot
29
Properties Sold
114
Average Days on Market
181
Properties for Sale
Calculations provided by Reliance Network

229 S Highland Street History

Date Event Value Agent
4/22/2026Source: Imagine MLS/Bluegrass Added to Database
April 22, 2026