For Sale
Single family home for sale at 344 Madison Pl, Lexington, KY 40508 | MLS# 26008570 | Listing updated on 2026-04-21
Photo 1 of Single family home for sale at 344 Madison Pl, Lexington, KY 40508 | MLS# 26008570 | Listing updated on 2026-04-21
Photo 2 of Single family home for sale at 344 Madison Pl, Lexington, KY 40508 | MLS# 26008570 | Listing updated on 2026-04-21
Photo 3 of Single family home for sale at 344 Madison Pl, Lexington, KY 40508 | MLS# 26008570 | Listing updated on 2026-04-21
Photo 4 of Single family home for sale at 344 Madison Pl, Lexington, KY 40508 | MLS# 26008570 | Listing updated on 2026-04-21
72+
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Street View

$799,000

Monthly Est:$3,977

  • Beds Icon5 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,942sqft

344 Madison Pl, Lexington, KY 40508

$3,977/moEst:

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  • 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 Lexington Bluegrass AOR (Imagine) MLS-KY

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Fayette County

  • City

    Lexington

  • 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

DateEventPrice

04/30/2025

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #25008856

Listed for Sale

$799,000 +45.27%

$272/sqft

09/01/2022

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #22018265

Sold

$550,000

$187/sqft

Nearby Homes

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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