415 S Upper Street, Lexington, KY 40508
Local realty services provided by:CENTURY 21 Simpson & Associates
Listed by: ken j donworth
Office: bluegrass sotheby's international realty
MLS#:26014172
Source:KY_LBAR
Price summary
- Price:$1,400,000
- Price per sq. ft.:$491.92
- Monthly HOA dues:$300
About this home

Tucked into one of Lexington's most walkable blocks, this extraordinary loft-style residence began life as the historic Bluegrass Cigar Flats and was thoughtfully converted to residential use in mid 2000's. The result is a rare blend of urban character and refined design — a soaring open floor plan, original brickwork, reclaimed wood floors throughout, clever hidden doors, and custom built-ins, bookshelves, and storage at every turn. At its heart is a showstopping kitchen: polished concrete countertops, a Wolf gas range, dual dishwashers, Sub-Zero refrigeration, wine cooler, beverage refrigerator, and freezer drawers, anchored by an enormous butler's pantry. Spa-inspired marble baths feature Waterworks fixtures, and a generous family room invites you to gather and unwind. Currently styled as a private speakeasy for the seller's personal use, the home is ready to return to full-time residential living with purely cosmetic updates — a blank canvas with serious soul. Walk to the University of Kentucky, downtown restaurants, and shops, and enjoy a location that's convenient to absolutely everything. Loft living with this much history, craftsmanship, and location simply doesn't come along often. This one's a must-see....
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Home facts
- Year built:2009
- Listing ID #:26014172
- Added:1 day(s) ago
- Updated:June 18, 2026 at 05:39 PM
Rooms and interior
- Bedrooms:3
- Total bathrooms:2
- Full bathrooms:2
- Rooms Total:2
- Flooring:Ceramic Tile, Hardwood
- Living area:2,846 sq. ft.
Heating and cooling
- Cooling:Electric
- Heating:Forced Air
Structure and exterior
- Year built:2009
- Building area:2,846 sq. ft.
- Construction Materials:Brick Veneer
Schools
- High school:Lafayette
- Middle school:Lexington Trad
- Elementary school:Harrison
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$1,400,000
- Price per sq. ft.:$491.92
Features and amenities
- Laundry features:Electric Dryer Hookup, Gas Dryer Hookup
- Amenities:Blinds, Ceiling Fan(s), Skylight(s), Wet Bar
Parking
- Parking description:Off Street
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