344 Madison Place, Lexington, KY 40508

$799,000
Property Type: Residential Bedrooms: 5 Baths: 3 Square Footage: 2,942 Lot Size (sq. ft.): 7,841 Status: Active
Current Price: $799,000 List Date: 4/21/2026 Last Modified: 4/21/2026

Overview

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, lo ...

Listing Details MLS# 26008570

Listing Information

Comp Sale YN
No
Property Sub Type
Single Family Residence

Status Change Information

Status Change Timestamp
2026-04-21

Address

County
Fayette
Street Number
344
Street Name
Madison
Street Suffix
Place
State
KY
Zip Code
40508
Directions
High Street past Rupp Arena, left on Madison Place, house on the left.
Parcel Number
12780100
Tax District
District 01

Contract

Original List Price
799000
Start Showing Date
2026-04-21
Listing Contract Date
2026-04-21
Listing Agreement
Exclusive Right To Sell
Occupant Type
Occupied
Office Exclusive YN
No
List Price/SqFt
271.58

Tax Legal

MLS Area Major
004 - Fayette County SW
Subdivision Name
Downtown
High School District
Fayette County - 1

Interior

Bedrooms Total
5
Bathrooms Total
3
Bathrooms Full
3
Above Grade Finished Area
2942
Above Grade Unfinished Area
297
Living Area
2942
Living Area Source
Listing Agent Measured
Basement YN
Yes
Fireplace YN
Yes
Fireplaces Total
9
Bathrooms Half
0
Below Grade Finished Area
0
Below Grade Unfinished Area
0

More Information

Parking Information

Garage YN
No
Carport YN
No

Building

Year Built
1890
Accessibility Features YN
No

Lot

Lot Size Source
Public Records
Lot Size Acres
0.18
Lot Size Square Feet
7841
Pool Private YN
No
View YN
Yes
Waterfront YN
No
Water Body Access YN
No
Horse YN
No

Utilities

Cooling YN
Yes
Heating YN
Yes

Remarks

Public Remarks
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!

Amenity Fee Details

Amenity Fee YN
No

Room Types

Bathroom 1 Level
First
Bathroom 2 Level
Second
Bathroom 3 Level
Third
Bedroom 1 Level
Second
Bedroom 2 Level
Second
Bedroom 3 Level
Second
Bedroom 4 Level
Third
Kitchen Level
First
Primary Bedroom Level
First
Bathroom 1
Yes
Bathroom 2
Yes
Bathroom 3
Yes
Bedroom 1
Yes
Bedroom 2
Yes
Bedroom 3
Yes
Bedroom 4
Yes
Kitchen
Yes
Primary Bedroom
Yes

Currently Not Used

List Price/Acre
4438888.89

Tax & Legal

Elementary School
Booker T Washington
Middle Or Junior School
Morton
High School
Lafayette
Tax Rate
1.2638
Inside New Circle Road YN
Yes

Association/Community

Association YN
No

Appliances

Dishwasher
Yes
Gas Range
Yes
Refrigerator
Yes

Architectural Style

Contemporary
Yes
Craftsman
Yes

Basement

Sump Pump
Yes
Unfinished
Yes

Community Features

Park
Yes

Construction Materials

Wood Siding
Yes

Cooling

Electric
Yes
Heat Pump
Yes
Zoned
Yes

Exterior Features

Hot Tub
Yes
Other
Yes

Fencing

Privacy
Yes

Fireplace Features

Dining Room
Yes
Gas Log
Yes
Masonry
Yes
Primary Bedroom
Yes

Flooring

Hardwood
Yes
Parquet
Yes
Slate
Yes
Tile
Yes

Foundation Details

Stone
Yes

Heating

Forced Air
Yes
Natural Gas
Yes
Zoned
Yes

Interior Features

Entrance Foyer
Yes
Walk-In Closet(s)
Yes

Laundry Features

Washer Hookup
Yes

Levels

Three Or More
Yes

Other Structures

Shed(s)
Yes

Parking Features

Off Street
Yes

Patio And Porch Features

Deck
Yes
Patio
Yes
Porch
Yes

Possession

Negotiable
Yes

Roof

Shingle
Yes

Sewer

Public Sewer
Yes

Structure Type

House
Yes

View

Neighborhood
Yes

Water Heater

Electric
Yes
Gas
Yes

Water Source

Public
Yes

Window Features

Skylight(s)
Yes
Window Treatments
Yes

Showing Requirements

Showing Service
Yes

Property Features

Appliances: Dishwasher; Gas Range; Refrigerator Architectural Style: Contemporary; Craftsman Basement: Sump Pump; Unfinished Community Features: Park Construction Materials: Wood Siding Cooling: Electric; Heat Pump; Zoned Exterior Features: Hot Tub; Other Fencing: Privacy Fireplace Features: Dining Room; Gas Log; Masonry; Primary Bedroom Flooring: Hardwood; Parquet; Slate; Tile Foundation Details: Stone Heating: Forced Air; Natural Gas; Zoned Interior Features: Entrance Foyer; Walk-In Closet(s) Laundry Features: Washer Hookup Levels: Three Or More Other Structures: Shed(s) Parking Features: Off Street Patio And Porch Features: Deck; Patio; Porch Possession: Negotiable Roof: Shingle Sewer: Public Sewer Structure Type: House View: Neighborhood Water Heater: Electric; Gas Water Source: Public Window Features: Skylight(s); Window Treatments Showing Requirements: Showing Service Room Types: Bathroom 1; Bathroom 2; Bathroom 3; Bedroom 1; Bedroom 2; Bedroom 3; Bedroom 4; Kitchen; Primary Bedroom

Room Information

Room Name Level Remarks
Bathroom 1 First Full Bath
Bathroom 2 Second Full Bath
Bathroom 3 Third Full Bath
Primary Bedroom First
Bedroom 1 Second
Bedroom 2 Second
Bedroom 3 Second
Bedroom 4 Third
Kitchen First

Documents

Listing Office: Diamond Real Estate Group, Inc
Last Updated: April - 21 - 2026
Information deemed reliable but not guaranteed.
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