Pending
Sale Pending at 221 S Highland St, Winchester, KY 40391 | MLS# 26015897 | Listing updated on 2026-07-24
Photo 1 of Sale Pending at 221 S Highland St, Winchester, KY 40391 | MLS# 26015897 | Listing updated on 2026-07-24
Photo 2 of Sale Pending at 221 S Highland St, Winchester, KY 40391 | MLS# 26015897 | Listing updated on 2026-07-24
Photo 3 of Sale Pending at 221 S Highland St, Winchester, KY 40391 | MLS# 26015897 | Listing updated on 2026-07-24
Photo 4 of Sale Pending at 221 S Highland St, Winchester, KY 40391 | MLS# 26015897 | Listing updated on 2026-07-24
35+
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Street View

$239,000

Monthly Est:$1,190

  • Beds Icon6 Beds
  • Beds Icon
    3 Baths
  • Beds Icon3,007sqft

221 S Highland St, Winchester, KY 40391

$1,190/moEst:

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  • Triplex

  • Built in 1930

  • $-- HOA

  • 0.16 acre lot

  • $79/sq.ft

Description

Excellent investment opportunity!!! A triplex near downtown Winchester. Close to everything. The main level features a unit with 3 bedrooms, 1 full bath, 2 living areas, a large eat-in kitchen and a laundry room. The upstairs unit features 2 bedrooms, 1 full bath, a living room, and an eat-in kitchen. The lower level features a 1 bedroom, 1 full bathroom, a large living room and an eat-in kitchen. The main level unit rents for $1299 per month. The upper unit rents for $895 per month. When the lower level is rented it rents for $799 per month. You will find plenty of parking in the back. There is a carport and storage building that also goes with this property.

  • Houzeo last checked: 4 hours ago
  • Listing updated: July 24, 2026 at 12:23 am
  • Listing Provided by: Libby VanMeter (859) 771-4811 | Marshall Lane Real Estate - Lexington (502) 682-1226
  • Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26015897 Lexington Bluegrass AOR (Imagine) MLS-KY

Part of

Building
221 S Highland St
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Property Details

  • Status

    Pending

  • Type

    Multi Family

  • No. of Stories

    2

  • County

    Clark County

  • City

    Winchester

  • Neighborhood

    --

  • Year Built

    1930

  • HOA Fees

    -

  • Finished Area

    3,007 sqft

  • Lot Size

    0.16 acre lot

  • Basement Area

    - sqft

  • MLS Name

    Lexington Bluegrass AOR (Imagine) MLS

  • MLS Number

    26015897

  • MLS Status

    Pending

  • Days on Market

    90

  • Cumulative Days on Market

    9

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 6

    Bathrooms: 3

Interior

  • Cooling

    Electric, Window Unit(s)

  • Heating

    Baseboard, Electric, Floor Furnace, Other

Construction

  • Year Built

    Year Built: 1930

  • Home type

    Triplex

  • Roof

    Shingle

Utilities & Energy

  • Laundry Features

    Electric Dryer Hookup, Washer Hookup

Other Features

  • Subdivision Name

    Downtown

  • Community Features

    Park, Pool, Tennis Court(s)

Price History

DateEventPrice

07/24/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26015897

Pending

$239,000

$79/sqft

07/02/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26015897

Price Decreased

$239,000 -0.38%

$79/sqft

04/01/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26006685

Price Decreased

$239,900 -3.62%

$80/sqft

01/12/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26000780

Price Increased

$248,900 +1.01%

$83/sqft

01/12/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26000780

Price Decreased

$246,400 -4.31%

$82/sqft

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Nearby Homes

Based on information from the IMAGINE MLS® through Sep 30, 2026, 11:15AM. 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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