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Listing provided courtesy of Diamond Real Estate Group, Inc- MLS# 26008570MLS Provider

344 Madison PlaceLexington, KY 40508

Single Family · 5 Beds · 3 Full Baths · 2,942 Sq. ft. | 0.18 Acres
$799,000 Active

344 Madison Place Overview

Time on Site:
69 days
Visits:
1

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!

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344 Madison Place Facts & Features

  • Type Single Family
  • Sq. ft. 2,942
  • Price/Sq.ft. $272
  • Lot 0.18 Acres

Details

General

Association/HOA

  • Association: false

School Information

  • Elementary School: Booker T Washington
  • Middle Or Junior School: Morton
  • High School: Lafayette

Building Information

  • Year Built: 1890

Location/Region

  • County Or Parish: Fayette
  • MLS Area Major: 004 - Fayette County SW
  • MLS Area Minor: 004 - Fayette County SW
  • Subdivision Name: Downtown

Community/Development

  • Community Features: Park

General Information

  • Parcel Number: 12780100
  • Property Sub Type: Single Family Residence
  • Property Type: Residential

Interior

Parking Information

  • Garage: false

Beds/Baths

  • Bathrooms Full: 3
  • Bathrooms Half: 0
  • Bathrooms Total: 3
  • Bedrooms Total: 5

Building Interior

  • Above Grade Finished Area: 2942.0
  • Building Area Total: 2942.0

General Information

  • Appliances: Dishwasher,Gas Range,Refrigerator
  • Fireplace Features: Dining Room,Gas Log,Masonry,Primary Bedroom
  • Fireplace: true
  • Fireplaces Total: 9
  • Flooring: Hardwood,Slate,Tile,Parquet
  • Foundation Details: Stone
  • Interior Features: Entrance Foyer,Walk-In Closet(s)
  • Laundry Features: Washer Hookup
  • Levels: Three Or More
  • Living Area: 2942.0
  • Living Area Source: Listing Agent Measured
  • Rooms Total: 9
  • Window Features: Skylight(s),Window Treatments

Exterior

Parking Information

  • Parking Features: Off Street

Lot Information

  • Lot Size Acres: 0.18
  • Lot Size Area: 0.18
  • Lot Size Source: Public Records
  • Lot Size Square Feet: 7841.0
  • Lot Size Units: Acres
  • Water Source: Public

Waterfront/View

  • Waterfront: false

Building Exterior/Construction

  • Architectural Style: Craftsman,Contemporary
  • Attached Garage: false
  • Construction Materials: Wood Siding
  • Roof: Shingle
  • Structure Type: House

General Information

  • Carport: false
  • Exterior Features: Other
  • Fencing: Privacy
  • Horse: false
  • Other Structures: Shed(s)
  • Pool Private: false
  • Sewer: Public Sewer

344 Madison Place Neighborhood

Community

40508 (Lexington) Demographics

23
Median Age
6,152
Population Density (per sq. mile)
41%
College Educated
$28,850
Estimated Median Income
2,697
Estimated Total Home Owners
6,918
Estimated Total Renters
28% / 72%
Estimated Owner / Renter Divide
2
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

344 Madison Place Monthly Cost

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$ %
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$
$
* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

344 Madison Place Market Data

Based on the last 30 days in this zip code

$374,690
Average List Price
$246
Average Price per Square Foot
13
Properties Sold
65
Average Days on Market
72
Properties for Sale
Calculations provided by Reliance Network

344 Madison Place History

Date Event Value Agent
4/21/2026Source: Imagine MLS/Bluegrass Added to Database
April 21, 2026
8/12/2025Source: Imagine MLS/Bluegrass Added to Database
August 12, 2025