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!
For sale
Price cut: $35.1K (6/29)
$814,900
344 Madison Pl, Lexington, KY 40508
5beds
2,942sqft
Est.:
Single Family Residence
Built in 1890
7,840.8 Square Feet Lot
$782,300 Zestimate®
$277/sqft
$-- HOA
What's special
Multiple fireplacesHot tubSpacious deckBreakfast barThird-floor retreatChef-friendly kitchenGas range
- 117 days
- on Zillow |
- 1,112 |
- 45 |
Zillow last checked: 7 hours ago
Listing updated: June 29, 2025 at 10:30am
Listed by:
Cynthia Trgo 859-559-2534,
Diamond Real Estate Group, Inc
Source: Imagine MLS,MLS#: 25008856

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Forced Air, Natural Gas, Zoned
Cooling
- Electric, Heat Pump, Zoned
Appliances
- Included: Gas Water Heater, Electric Water Heater, Gas Range, Dishwasher, Refrigerator
- Laundry: Washer Hookup
Features
- Walk-In Closet(s), Entrance Foyer
- Flooring: Hardwood, Parquet, Tile, Slate
- Windows: Window Treatments, Skylight(s)
- Basement: Unfinished,Sump Pump
- Has fireplace: Yes
- Fireplace features: Gas Log, Masonry, Dining Room, Master Bedroom
Interior area
- Total structure area: 2,942
- Total interior livable area: 2,942 sqft
- Finished area above ground: 2,942
- Finished area below ground: 0
Property
Parking
- Parking features: Off Street
Features
- Levels: Three Or More
- Patio & porch: Porch, Deck, Patio
- Exterior features: Other
- Has spa: Yes
- Spa features: Heated
- Fencing: Privacy
- Has view: Yes
- View description: Neighborhood
Lot
- Size: 7,840.8 Square Feet
- Features: Inside New Circle Road
Details
- Additional structures: Storage
- Parcel number: 12780100
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Craftsman,Contemporary
- Property subtype: Single Family Residence
Materials
- Wood Siding
- Foundation: Stone
- Roof: Shingle
Condition
- Year built: 1890
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Park
- Subdivision: Downtown
HOA
- Has HOA: No
Location
- Region: Lexington
Financial & listing details
- Price per square foot: $277/sqft
- Tax assessed value: $328,100
- Annual tax amount: $4,191
- Date on market: 4/30/2025
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