About 415 S Upper Street
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.
Residential property for sale in Lexington, KY at 415 S Upper Street. This 3 bedroom Residential property is priced at $492/sqft
Facts & Features of 415 S Upper Street
| MLS® # | 26014172 |
|---|---|
| Price | $1,400,000 |
| Bedrooms | 3 |
| Bathrooms | 2.00 |
| Full Baths | 2 |
| Square Footage | 2,846 |
| Year Built | 2009 |
| Type | Residential |
| Sub-Type | Condominium |
| Status | Pending |
Community Information of 415 S Upper Street
| Address | 415 S Upper Street |
|---|---|
| Area | 004 - Fayette County SW |
| Subdivision | Downtown |
| City | Lexington |
| County | Fayette |
| State | KY |
| Zip Code | 40508 |
Amenities of 415 S Upper Street
| Utilities | Cable Available, Electricity Connected, Sewer Connected, Water Connected |
|---|---|
| Parking | Off Street |
| Is Waterfront | No |
| Has Pool | No |
Interior of 415 S Upper Street
| Interior Features | Breakfast Bar, Eat-in Kitchen, Other, Primary First Floor, Wet Bar, Walk-In Closet(s), Ceiling Fan(s) |
|---|---|
| Appliances | Dishwasher, Gas Range, Microwave, Other, Refrigerator, Washer, Range, Vented Exhaust Fan |
| Heating | Forced Air |
| Cooling | Electric |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Fireplaces | Living Room |
| Primary Suite On Main floor | Yes |
Exterior of 415 S Upper Street
| Windows | Skylight(s), Blinds |
|---|---|
| Roof | Membrane, Other |
| Construction | Brick Veneer |
| Foundation | Other |
School Information On 415 S Upper Street
| District | Fayette County - 1 |
|---|---|
| Elementary | Harrison |
| Middle | Lexington Trad |
| High | Lafayette |
Additional Information On 415 S Upper Street
| Date Listed | June 18th, 2026 |
|---|---|
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 3600 |
| HOA Fees Freq. | Annually |
Listing Details On 415 S Upper Street
| Office | Bluegrass Sotheby's International Realty |
|---|