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3760 Old Boonesboro Road, 
Winchester, KY 40391

$1,290,000


5

Beds


5

Baths


5,666

Sq Ft


Single Family

Active

Listed by

Joshua Wood

Greg E Wood

Freedom Realty & Property Management

859-771-0777

Last updated:

April 12, 2026, 02:42 PM

MLS#

26006697

Source:

KY LBAR

About This Home

3760 Old Boonesboro Road

Step through the striking red front doors and into a home where craftsmanship, character, and comfort come together. This beautifully maintained property sits on nearly 13 acres at the edge of Winchester, offering a peaceful retreat with the charm of a mid century floorplan and rich woodwork, tile, and hardwood floors throughout. The spacious kitchen and all three full baths feature high end finishes, and the home offers multiple unique spaces for relaxing or entertaining. From the second floor, enjoy your own private balcony overlooking the expansive backyard and in ground pool. On the main level, a covered porch provides easy access to the pool area, along with a convenient exterior door leading directly to a small bathroom—perfect for swimmers. The basement is also a cozy retreat including a living area with a stone fireplace and a bar, another full bed and bathroom, plus a bonus space that could be used as an exercise room or a creative space. Recent updates include new tile and hardwood flooring and fresh interior paint. Outside, the fully fenced yard is beautifully landscaped with mature trees and manicured lawn. This property also includes a separate garage ideal for hobbyists, a storage building with a screened room suitable for chickens or small animals, and a full 2,000 sq ft barn—offering endless possibilities for country living.

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 1985

Price Summary

1,290,000

$227 per Sq. Ft.

MLS #:

26006697

Last Updated:

April 12, 2026, 02:42 PM

Added:

5 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

5

Interior

Living Area:

5,666 Sq. Ft.


Structure

Structure

Architectural Style:

Contemporary

Building Area:

5,666 Sq. Ft.

Year Built:

1985


Lot

Lot Size (Sq. Ft):

565,408


Finances & Disclosures

Finances

Price:

$1,290,000

Price per Sq. Ft:

$227 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.