Listing provided courtesy of Bluegrass Sotheby's International Realty- MLS# 26014172MLS Provider

415 S Upper StreetLexington, KY 40508

Condo/Townhouse · 3 Beds · 2 Full Baths · 2,846 Sq. ft.
$1,400,000 Active

415 S Upper Street Overview

Time on Site:
11 days
Visits:
0

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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415 S Upper Street Facts & Features

  • Type Condo/Townhouse
  • Sq. ft. 2,846
  • Price/Sq.ft. $492

Details

General

Association/HOA

  • Association Amenities: None
  • Association Fee: 3600.0
  • Association Fee Frequency: Annually
  • Association Fee Includes: Other
  • Association: true

School Information

  • Elementary School: Harrison
  • Middle Or Junior School: Lexington Trad
  • High School: Lafayette

Building Information

  • Year Built: 2009

Location/Region

  • County Or Parish: Fayette
  • MLS Area Major: 004 - Fayette County SW
  • MLS Area Minor: 004 - Fayette County SW
  • Subdivision Name: Downtown

General Information

  • Parcel Number: 38224250
  • Property Sub Type: Condominium
  • Property Type: Residential

Interior

Parking Information

  • Garage: false

Beds/Baths

  • Bathrooms Full: 2
  • Bathrooms Half: 0
  • Bathrooms Total: 2
  • Bedrooms Total: 3

Building Interior

  • Above Grade Finished Area: 2846.0
  • Building Area Total: 2846.0

General Information

  • Appliances: Dishwasher,Gas Range,Microwave,Other,Refrigerator,Washer,Range,Vented Exhaust Fan
  • Basement: false
  • Entry Level: 1
  • Fireplace Features: Living Room
  • Fireplace: true
  • Fireplaces Total: 1
  • Flooring: Ceramic Tile,Hardwood,Other
  • Foundation Details: Other
  • Interior Features: Breakfast Bar,Eat-in Kitchen,Other,Primary First Floor,Wet Bar,Walk-In Closet(s),Ceiling Fan(s)
  • Laundry Features: Electric Dryer Hookup,Gas Dryer Hookup
  • Living Area: 2846.0
  • Living Area Source: Appraiser
  • Rooms Total: 2
  • Window Features: Skylight(s),Blinds

Exterior

Parking Information

  • Parking Features: Off Street

Lot Information

  • Lot Size Source: Public Records
  • Water Source: Public

Waterfront/View

  • Waterfront: false

Building Exterior/Construction

  • Attached Garage: false
  • Construction Materials: Brick Veneer
  • Roof: Membrane,Other

General Information

  • Carport: false
  • Horse: false
  • Pool Private: false
  • Sewer: Public Sewer
  • Utilities: Cable Available,Electricity Connected,Sewer Connected,Water Connected

415 S Upper Street Neighborhood

Community

40508 (Lexington) Demographics

23
Median Age
6,152
Population Density (per sq. mile)
41%
College Educated
$28,850
Estimated Median Income
2,697
Estimated Total Home Owners
6,918
Estimated Total Renters
28% / 72%
Estimated Owner / Renter Divide
2
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

415 S Upper Street Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

415 S Upper Street Market Data

Based on the last 30 days in this zip code

$374,690
Average List Price
$246
Average Price per Square Foot
13
Properties Sold
65
Average Days on Market
72
Properties for Sale
Calculations provided by Reliance Network

415 S Upper Street History

Date Event Value Agent
6/18/2026Source: Imagine MLS/Bluegrass Added to Database
June 18, 2026
8/12/2025Source: Imagine MLS/Bluegrass Added to Database
August 12, 2025