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For sale
    • $799,000

    344 Madison Pl, Lexington, KY 40508

    5beds
    2,942sqft
    : 
    $5,159/mo
    Get pre-qualified
    Single Family Residence
    Built in 1890
    7,840 Square Feet Lot
    $757,400 Zestimate®
    $272/sqft
    $-- HOA

    What's special

    Hot tubSpacious deckBreakfast barThird-floor retreatTwo walk-in showersCity viewsPrivate wraparound porch
    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!
    125 days
    |
    644
    |
    35
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Cynthia Trgo 859-559-2534,

    Diamond Real Estate Group, Inc

    Source: Imagine MLS,MLS#: 26008570MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 3
      • Full bathrooms: 3
      Primary bedroom
      • Level: First
      Bedroom 1
      • Level: Second
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Bedroom 4
      • Level: Third
      Bathroom 1
      • Description: Full Bath
      • Level: First
      Bathroom 2
      • Description: Full Bath
      • Level: Second
      Bathroom 3
      • Description: Full Bath
      • Level: Third
      Kitchen
      • Level: First
      Heating
      • Forced Air, Natural Gas, Zoned
      Cooling
      • Electric, Heat Pump, Zoned
      Appliances
      • Included: Dishwasher, Gas Range, Refrigerator
      • Laundry: Washer Hookup
      Features
      • Entrance Foyer, Walk-In Closet(s)
      • Flooring: Hardwood, Slate, Tile, Parquet
      • Windows: Skylight(s), Window Treatments
      • Basement: Sump Pump,Unfinished
      • Number of fireplaces: 9
      • Fireplace features: Dining Room, Gas Log, Masonry, 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
      • Exterior features: Other
      • Fencing: Privacy
      • Has view: Yes
      • View description: Neighborhood
      Lot
      • Size: 7,840 Square Feet
      Details
      • Additional structures: Shed(s)
      • 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: $272/sqft
      • Tax assessed value: $683,400
      • Annual tax amount: $8,451
      • Date on market: 4/21/2026

        Estimated market value

        $757,400

        $720,000 - $795,000

        $3,439/mo

        Price history

        DateEventPrice
        4/21/2026Listed for sale$799,000$272/sqft
        Source: Imagine MLS #26008570 Report a problem
        4/7/2026Listing removed$799,000$272/sqft
        Source: Imagine MLS #25505519 Report a problem
        11/6/2025Listed for sale$799,000$272/sqft
        Source: Imagine MLS #25505519 Report a problem
        10/31/2025Listing removed$799,000$272/sqft
        Source: Imagine MLS #25008856 Report a problem
        8/27/2025Price change$799,000-2%$272/sqft
        Source: Imagine MLS #25008856 Report a problem
        6/29/2025Price change$814,900-4.1%$277/sqft
        Source: Imagine MLS #25008856 Report a problem
        4/30/2025Listed for sale$850,000+54.5%$289/sqft
        Source: Imagine MLS #25008856 Report a problem
        9/1/2022Sold$550,000-5.1%$187/sqft
        Source: Imagine MLS #22018265 Report a problem
        8/25/2022Pending sale$579,500$197/sqft
        Source: Imagine MLS #22018265 Report a problem
        8/18/2022Contingent$579,500$197/sqft
        Source: Imagine MLS #22018265 Report a problem
        8/18/2022Listed for sale$579,500+29.2%$197/sqft
        Source: Imagine MLS #22018265 Report a problem
        9/29/2020Listing removed$2,175$1/sqft
        Source: Keller Williams Bluegrass #20017241 Report a problem
        9/21/2020Price change$2,175-7.4%$1/sqft
        Source: Keller Williams Bluegrass #20017241 Report a problem
        8/21/2020Listed for rent$2,350$1/sqft
        Source: Keller Williams Bluegrass Realty #20017241 Report a problem
        8/21/2020Listing removed$448,640$152/sqft
        Source: Keller Williams Bluegrass Realty #20008604 Report a problem
        6/24/2020Price change$448,640-4%$152/sqft
        Source: Keller Williams Bluegrass #20008604 Report a problem
        6/3/2020Price change$467,333-3.6%$159/sqft
        Source: Keller Williams Bluegrass #20008604 Report a problem
        5/2/2020Listed for sale$485,000+14.1%$165/sqft
        Source: Keller Williams Bluegrass #20008604 Report a problem
        10/17/2009Listing removed$425,000$144/sqft
        Source: Bluegrass Sotheby's Int Realty #903104 Report a problem
        5/16/2009Price change$425,000-1.8%$144/sqft
        Source: Bluegrass Sotheby's Int Realty #903104 Report a problem
        2/22/2009Listed for sale$432,900$147/sqft
        Source: Point2 #903104 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$8,451 $683,400
        2024$8,451 +24.3%$683,400 +24.3%
        2023$6,801 +62.3%$550,000 +67.6%
        2022$4,191 $328,100
        2021$4,191 $328,100
        2020$4,191 $328,100
        2019$4,191 $328,100
        2018$4,191 +4.9%$328,100
        2017$3,994 +92.9%$328,100 +35%
        2015$2,070 $243,000
        2014$2,070 $243,000 +31.4%
        2012$2,070 $185,000
        2011-- --
        2010-- --
        2009-- --
        2008-- $185,000
        2006-- --
        2005-- --
        2004-- --
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: Central Downtown

        Getting around

        84 / 100
        Very Walkable
        72 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Booker T Washington
        • Middle: Morton
        • High: Lafayette

        Source: Imagine MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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