Coldwell Banker Home Page
Skip to main contentColdwell Banker Home Page

Local Realty Service Provided By: Coldwell Banker V.I.P. Realty, Inc.

Property view
Listing view 2
Listing view 3

221 S Highland Street, 
Winchester, KY 40391

$239,000

6

Beds

3

Baths

3,007

Sq Ft

Multi-Family

Pending

Listed by

Libby Vanmeter

Marshall Lane Real Estate - Lexington

502-682-1226

Last updated:

July 24, 2026, 10:16 AM

MLS#

26015897

Source:

KY LBAR

About This Home

221 S Highland Street

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.

Home Facts

Multi-Family

3 Baths

6 Bedrooms

Built in 1930

Subdivision & Development:

Downtown

Price Summary

239,000

$79 per Sq. Ft.

MLS #:

26015897

Last Updated:

July 24, 2026, 10:16 AM

Added:

2 month(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

6

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:

$239,000

Price per Sq. Ft:

$79 per Sq. Ft.

MLS Logo
The information being provided by Bluegrass REALTORS® is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bluegrass REALTORS® All rights reserved.

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.

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.