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Street View
$799,000
Monthly Est:$3,977
5 Beds
- 3 Baths
3 full baths
2,942sqft
344 Madison Pl, Lexington, KY 40508
$799,000
$3,977/moEst:
Get Pre-Approved
Single Family Residence
Built in 1890
$-- HOA
0.18 acre lot
$272/sq.ft
Description
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!
- Houzeo last checked: 12 hours ago
- Listing updated: April 21, 2026 at 5:21 pm
- Listing Provided by: Cynthia Trgo (859) 559-2534 | Diamond Real Estate Group, Inc (859) 559-2534
- Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26008570

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1890
HOA Fees
-
Finished Area
2,942 sqft
Lot Size
0.18 acre lot
Basement Area
- sqft
MLS Name
Lexington Bluegrass AOR (Imagine) MLS
MLS Number
26008570
MLS Status
Active
Days on Market
172
Cumulative Days on Market
334

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 3
Interior
Window Features
Skylight(s), Window Treatments
Sewer
Public Sewer
Cooling
Electric, Heat Pump, Zoned
Interior Features
Entrance Foyer, Walk In Closet(s)
Appliances
Dishwasher, Gas Range, Refrigerator
Heating
Forced Air, Natural Gas, Zoned
Exterior Features
Other
Flooring
Hardwood, Parquet, Slate, Tile
Construction
Year Built
Year Built: 1890
Home type
Single Family Residence
Foundation Details
Stone
Architectural Style
Contemporary, Craftsman
Roof
Shingle
Construction Materials
Wood Siding
Utilities & Energy
Water Source
Public
Laundry Features
Washer Hookup
Parking Features
Off Street
Basement
Sump Pump, Unfinished
Fireplace Features
Dining Room, Gas Log, Masonry, Primary Bedroom
Other Features
Subdivision Name
Downtown
Patio And Porch Features
Deck, Patio, Porch
Community Features
Park
Price History
| Date | Event | Price |
|---|---|---|
04/30/2025 Source: | Listed for Sale | $799,000 +45.27% $272/sqft |
09/01/2022 Source: | Sold | $550,000 $187/sqft |
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Based on information from the IMAGINE MLS® through Oct 09, 2026, 02:30PM. Copyrighted by the Imagine MLS®. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data on this website is deemed reliable but is not guaranteed accurate by the MLS. © 2026 IMAGINE MLS®. All Rights Reserved.
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