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221 S Highland Street, 
Winchester, KY 40391

$269,900


5

Beds


3

Baths


3,007

Sq Ft


Multi-Family

Active

Listed by

Joshua Lynch

The Brokerage

859-983-7365

Last updated:

October 29, 2025, 10:48 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

269,900

$89 per Sq. Ft.

MLS #:

25504956

Last Updated:

October 29, 2025, 10:48 PM

Added:

10 day(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:

$269,900

Price per Sq. Ft:

$89 per Sq. Ft.

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By clicking Contact I agree a Coldwell Banker Agent may contact me by phone or text message including by automated means and prerecorded messages about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.