Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
5 Beds
3 Baths
2,942 sqft

$799,000

344 Madison Place, Lexington KY, 40508

Price per sqft$271.58
Built in1890
Property size2,942 sqft
Property typeResidential
Listed by Cynthia Trgo with Diamond Real Estate Group, Inc

Overview

Active

Listed Apr 21, 2026

Updated Jun 19

Historic Charm Meets Modern Living in the Heart of Downtown Lexington! Welcome to the Hall Pettit Headley House—a rare opportunity to own a piece of Lexington history in one of the city's most sought-after locations. Situated directly across from the iconic Botherum property, this beautifully maintained home blends rich character with thoughtful updates throughout. From the intricate millwork in the formal dining room to the private wraparound porch and spacious deck, every detail invites relaxation and entertaining. The lush backyard offers a serene escape and hot tub, while inside, you'll find a chef-friendly kitchen with gas range and breakfast bar, two soaking tubs, two walk-in showers, and multiple fireplaces adding warmth and elegance to the living spaces. Enjoy city views and starry nights from the third-floor retreat, complete with skylights and a walk-in closet that also makes a great fifth bedroom. An unbeatable location within walking distance to the Central Bank Arena, local dining, and entertainment this home is truly a downtown gem. Charge your vehicle with the electric charger. Currently used as an airbnb!

$5,316/mo

Est. mortgage payment based on a $799,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
26008570

Interior Features

Bedrooms
5
Bathrooms
3
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.18 Acres

Other Property Details

View
Yes
MLS provider logo

Listing Contact:  

The IDX display contains information sourced from the Bluegrass REALTORS® as of 6/19/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Bluegrass REALTORS® all rights reserved.

Data last updated on 6/19/2026 at 7:27 PM UTC

Powered by Luxury Presence