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3 Beds
2 Baths
2,846 sqft

$1,400,000

415 S Upper Street, Lexington KY, 40508

Price per sqft$491.92
Built in2009
Property size2,846 sqft
Property typeCondominium
Listed by Ken J Donworth with Bluegrass Sotheby's International Realty

Overview

Active

Listed Oct 3, 2026

Updated 9 days ago

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.

$9,314/mo

Est. mortgage payment based on a $1,400,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
26014172

Interior Features

Bedrooms
3
Bathrooms
2
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
No

Other Property Details

Association Fee Frequency
Yearly
MLS provider logo

Listing Contact:  

The IDX display contains information sourced from the Bluegrass REALTORS® as of 10/4/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 10/4/2026 at 4:14 AM UTC

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