415 S Upper Street, Lexington, KY 40508

bedrooms 3
bathrooms 2
|Apartment
NZD $2,489,465
USD $1,400,000
Published on: 19 Jun 2026
Last updated on: 14 Oct 2026
415 S Upper Street, Lexington, KY 40508
415 S Upper Street, Lexington, KY 40508
415 S Upper Street, Lexington, KY 40508
+21
415 S Upper Street, Lexington, KY 40508
  • 21
Property ID: 110108871783
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Residential, Lexington, KY

415 S Upper Street, Lexington, KY 40508
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.

Property Details

Basic Info

Property Type
Apartment
Listing Status
Active
Building Size
264.40 m2
Year Built
2009
Rooms
3 bedroom(s), 2 bathroom(s)
County
Fayette
Parcel ID
38224250
Provider
ImagineMLS
Subdivision
Downtown
Brokerage Office Name
Bluegrass Sotheby's International Realty
Brokerage Office Phone
2680099
Neighbourhoods
Downtown
Address
415 S Upper Street, Lexington, KY 40508

Nearby Schools

TypeSchool nameDistrict name
HighLafayetteNot available
Not availableNot availableNot available
ElementaryHarrisonNot available
Not availableNot availableNot available
MiddleLexington TradNot available
Not availableNot availableNot available
JuniorhighLexington TradNot available
Not availableNot availableNot available
Contact Agent
Ken J Donworth
Bluegrass Sotheby's International Realty
1999 Richmond Road Ste 400 , Lexington, KY 40502
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Ken J Donworth
1999 Richmond Road Ste 400 , Lexington, KY 40502
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      Property ID: 110108871783

      Original Property ID: 3yd-LBARKY-26014172
      Data provided by ImagineMLS, MLS #: 26014172
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