For Sale
Single family home for sale at 229 S Highland St, Winchester, KY 40391 | MLS# 26008701 | Listing updated on 2026-07-07
Photo 1 of Single family home for sale at 229 S Highland St, Winchester, KY 40391 | MLS# 26008701 | Listing updated on 2026-07-07
Photo 2 of Single family home for sale at 229 S Highland St, Winchester, KY 40391 | MLS# 26008701 | Listing updated on 2026-07-07
Photo 3 of Single family home for sale at 229 S Highland St, Winchester, KY 40391 | MLS# 26008701 | Listing updated on 2026-07-07
Photo 4 of Single family home for sale at 229 S Highland St, Winchester, KY 40391 | MLS# 26008701 | Listing updated on 2026-07-07
10+
Beds Icon

Street View

$165,000

Monthly Est:$821

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon3,462sqft

229 S Highland St, Winchester, KY 40391

$821/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1930

  • $-- HOA

  • 0.11 acre lot

  • $48/sq.ft

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.

  • Houzeo last checked: 7 minutes ago
  • Listing updated: July 7, 2026 at 4:35 pm
  • Listing Provided by: Michelle R Blackburn (859) 707-5955 | RE/MAX Creative, Winchester (859) 422-2000
  • Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26008701 Lexington Bluegrass AOR (Imagine) MLS-KY

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Clark County

  • City

    Winchester

  • Neighborhood

    --

  • Year Built

    1930

  • HOA Fees

    -

  • Finished Area

    3,462 sqft

  • Lot Size

    0.11 acre lot

  • Basement Area

    - sqft

  • MLS Name

    Lexington Bluegrass AOR (Imagine) MLS

  • MLS Number

    26008701

  • MLS Status

    Active

  • Days on Market

    171

  • Cumulative Days on Market

    76

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 3

Interior

  • Cooling

    Electric

  • Heating

    Forced Air, Natural Gas

  • Flooring

    Hardwood

  • Sewer

    Public Sewer

  • Appliances

    Refrigerator

Construction

  • Year Built

    Year Built: 1930

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial

  • Construction Materials

    Wood Siding, Hardi Plank Type

  • Foundation Details

    Stone

  • Roof

    Metal

Utilities & Energy

  • Water Source

    Public

  • Basement

    Crawl Space, Interior Entry, Walk Out Access

  • Utilities

    Electricity Connected, Natural Gas Connected, Water Connected

  • Parking Features

    Basement, Garage Faces Side

  • Fireplace Features

    Living Room

Other Features

  • Patio And Porch Features

    Porch, Front Porch

  • Subdivision Name

    South Park Addition

Price History

DateEventPrice

04/22/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26008701

Price Increased

$180,000 +9.09%

$52/sqft

04/22/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26008701

Listed for Sale

$165,000

$48/sqft

Nearby Homes

Based on information from the IMAGINE MLS® through Oct 10, 2026, 10:15PM. Copyrighted by the Imagine MLS®. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data on this website is deemed reliable but is not guaranteed accurate by the MLS. © 2026 IMAGINE MLS®. All Rights Reserved.

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