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221 S Highland Street, 
Winchester, KY 40391

$252,500

5

Beds

3

Baths

3,007

Sq Ft

Multi-Family

Active

Listed by

Joshua Lynch

The Brokerage

859-983-7365

Last updated:

January 2, 2026, 03:56 PM

MLS#

25504956

Source:

KY LBAR

About This Home

221 S Highland Street

INVESTOR SPECIAL, could be a great option for an end of year cost seg study and bonus depreciation. You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered together, landlord does cover utility expenses. Please call with any questions, please do not disturb the tenants!

Home Facts

Multi-Family

3 Baths

5 Bedrooms

Built in 1930

Price Summary

252,500

$83 per Sq. Ft.

MLS #:

25504956

Last Updated:

January 2, 2026, 03:56 PM

Added:

2 month(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

3

Interior

Living Area:

3,007 Sq. Ft.

Structure

Structure

Building Area:

3,007 Sq. Ft.

Year Built:

1930

Lot

Lot Size (Sq. Ft):

6,970

Finances & Disclosures

Finances

Price:

$252,500

Price per Sq. Ft:

$83 per Sq. Ft.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.