Add your chapter to the story of this iconic c. 1805 log cabin, 220 years after its construction. Thought to be the oldest surviving log residence in Lexington still on its original site, this two-story, two-bay clapboard-wrapped home offers a blend of early Kentucky heritage and downtown convenience. In 1994, the Blue Grass Trust for Historic Preservation saved the structure from demolition, undertaking a careful restoration that preserved its integrity. Today, its rich character endures through hand-hewn logs, exposed beams, very old hardwoods, two brick fireplaces, and historic cabinetry including linen ''presses.'' An updated adjoining kitchen and bath retain traditional charm. Upstairs, a sunlit bedroom provides ample space for a sitting area beside the fireplace. French doors and limestone slab steps lead to the spacious rear greenspace - a coveted & rare feature for a downtown property. A stone pathway leads to a generous, private off-street parking area accessible from Mack's Alley. Recent enhancements include a remodeled bath, exterior painting, new heat pump, a new Bosch dishwasher, and a handcrafted storm door by Bourbon Millworks. The property's R-2 zoning adds further appeal and possibilities. Design review district.
Single-familyProperty Type
1805Year Built
6,582 sq ftLot Size
$420Price/Sq.Ft.
Listed by James Turek• Bluegrass Sotheby's International Realty
The Stilfield house is arguably the most unique home in downtown Lexington and ownership comes with bragging rights. Built by John Stilfield in 1799, this house is but one of only 2 pioneer log houses in all of downtown Lexington. The foundation was restored by the Blue Grass Trust in 1994 and is part of the South Hill Historic district. The artistry and craftsmanship of the interior honor the home's history and authenticity. It has operated as a successful Airbnb for several years and has been meticulously cared for. All but 3 pieces of furniture will convey if the buyer desires to purchase it fully furnished. The property is zoned for a duplex however the Board of Architectural Review must approve any additions or changes. The location is ideal for someone employed downtown and values the one-of-a-kind living experience. All offers to be received by 9pm Wednesday 3/9
As the MLS and public records start to fill up, we'll list the details here.
Public record
Public record
Zoning
Permits
Beds
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Baths
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Stories
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Lot width
35 ft.
Lot depth
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Lot size
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Year renovated
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Finished Sq. Ft.
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Unfinished Sq. Ft.
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Total Sq. Ft.
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Year built
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Style
Single Family Residential
County
Fayette County
APN
16605600
Parking Spaces
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Basement
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Accessible
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HOA Dues
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Garage
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Features
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Last updated by owner on Aug 12, 2026.
R-2
H1
Mixed Low Density Residential Zone
The intent of this zone is to provide for a mix of low density residential development and supporting uses. This zone should be located in areas of the community where services and facilities are/will be adequate to serve the anticipated population. This zone should be established in accordance with the Goals, Objectives, Policies, and Development Criteria of the Comprehensive Plan. This zone may be used for zero-lot-line houses, patio houses, and other compact housing types.
Zone overlays
Historic District
Permitted uses
Include but are not limited to:
Housing-Single unit
Housing-Multiple units
Housing-Other
Office
Park & open space
Aug 3, 2004 • Final
Residential additions
Addition
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
4/10 Heat Factor
7 days above 101° expected this year, 19 days in 30 years
2/10 Wind Factor
1% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Lexington, KY • 40508
Average low and high temperatures (°F)
37
21
47
29
64
41
72
50
74
55
85
65
89
70
86
65
82
61
71
49
58
41
46
32
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
67/ 100
Moderate sunlight
Sunscore
There appears to be some shading by surrounding buildings, terrain, and vegetation.
7.7 hrs
4.1 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 361 S Upper St
$453,517
$26K under list price of $480K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $156K to $513K.