344 Madison Pl, Lexington, KY, 40508
About This Home
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!
Getting Around
Very Walkable
Very Limited Transit
Very BikeableSchools
Construction
Condition
- Year built: 1890
Materials
- Foundation: Stone
- Roof: Shingle
- Construction materials: Wood Siding
Type & Style
- Home type: SingleFamily
- Architectural style: Craftsman,Contemporary
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Dishwasher,Gas Range,Refrigerator
- Laundry features: Washer Hookup
Basement
- Has basement: Yes
- Basement: Sump Pump,Unfinished
Bathroom1
- Level: First
Bathroom2
- Level: Second
Bathroom3
- Level: Third
Bedroom1
- Level: Second
Bedroom2
- Level: Second
Bedroom3
- Level: Second
Bedroom4
- Level: Third
Bedrooms & Bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
Features
- Entrance Foyer,Walk-In Closet(s)
- Window features: Skylight(s),Window Treatments
- Flooring: Hardwood,Slate,Tile,Parquet
- Number of fireplaces: 9
- Fireplace features: Dining Room,Gas Log,Masonry,Master Bedroom
- Fireplace: Yes
- Finished area below ground: 0
- Finished area above ground: 2,942
Heating & Cooling
- Heating features: Forced Air,Natural Gas,Zoned
- Cooling features: Electric,Heat Pump,Zoned
Interior Area
- Total structure area: 2,942
- Total interior livable area: 2,942 sqft
Kitchen
- Level: First
Master Bedroom
- Level: First
Property
Details
- Parcel number: 12780100
Features
- Levels: Three Or More
- Exterior features: Other
- Fencing: Privacy
- Has view: Yes
- View description: Neighborhood
Lot
- Lot size: 7,840 sqft
Parking
- Parking features: Off Street
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Cold Wave
- Hail
- Inland Flooding
- Ice Storm
- Lightning
- Strong Wind
- Tornado
- Winter Weather
How This Home’s Risks Compare
FEMA Declared Disasters Across Kentucky Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $4,040 | $48,480 |
| Home Insurance * | $789 | $9,468 |
| Property Taxes | $837 | $10,044 |
| Electricity | $232 | $2,788 |
| Total | $5,898 | $70,776 |
Income You'd Need if You Spent...
Kentucky FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-04-21 | Listed for sale | $799,000 |
| 2026-04-07 | Listing removed | $799,000 |
| 2025-11-06 | Listed for sale | $799,000 |
| 2025-10-31 | Listing removed | $799,000 |
| 2025-08-27 | Price change | $799,000 |
| 2025-06-29 | Price change | $814,900 |
| 2025-04-30 | Listed for sale | $850,000 |
| 2022-09-01 | Sold | $550,000 |
| 2022-08-25 | Pending sale | $579,500 |
| 2022-08-18 | Contingent | $579,500 |
| 2022-08-18 | Listed for sale | $579,500 |
| 2020-09-29 | Listing removed | $2,175 |
| 2020-09-21 | Price change | $2,175 |
| 2020-08-21 | Listed for rent | $2,350 |
| 2020-08-21 | Listing removed | $448,640 |
| 2020-06-24 | Price change | $448,640 |
| 2020-06-03 | Price change | $467,333 |
| 2020-05-02 | Listed for sale | $485,000 |
| 2009-10-17 | Listing removed | $425,000 |
| 2009-05-16 | Price change | $425,000 |
| 2009-02-22 | Listed for sale | $432,900 |
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