Coldwell Banker Home Page
Skip to main contentColdwell Banker Home Page
Local Realty Service Provided By: Coldwell Banker Bisceglia Realty and Auction Co.
Property view
Listing view 2
Listing view 3

265 S Highland Street, 
Winchester, KY 40391

$505,000

8

Beds

4

Baths

5,058

Sq Ft

Multi-Family

Active

Listed by

J Corey Griffo

RE/MAX Elite Lexington

859-245-1165

Last updated:

March 15, 2026, 02:51 PM

MLS#

26004961

Source:

KY LBAR

About This Home

265 S Highland Street

Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8 bedrooms, 4 bathrooms, and approximately 4,750 square feet, this property provides strong rental potential in a convenient location close to downtown shopping, dining, and local amenities. The units are clean, well-maintained, and ready for new tenants, making this an excellent option for investors seeking a solid income-producing property. Schedule your showing today before this opportunity is gone!

Home Facts

Multi-Family

4 Baths

8 Bedrooms

Built in 1940

Price Summary

505,000

$99 per Sq. Ft.

MLS #:

26004961

Last Updated:

March 15, 2026, 02:51 PM

Added:

3 day(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

8

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

4

Interior

Living Area:

5,058 Sq. Ft.

Structure

Structure

Building Area:

5,058 Sq. Ft.

Year Built:

1940

Lot

Lot Size (Sq. Ft):

6,098

Finances & Disclosures

Finances

Price:

$505,000

Price per Sq. Ft:

$99 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.