Skip main navigation
For sale
    • $1,400,000

    415 S Upper St, Lexington, KY 40508

    3beds
    2,846sqft
    : 
    $9,062/mo
    Get pre-qualified
    Condominium
    Built in 2009
    -- sqft lot
    $1,328,000 Zestimate®
    $492/sqft
    $300/mo HOA

    What's special

    Wolf gas rangeBeverage refrigeratorLoft-style residenceFreezer drawersWaterworks fixturesSoaring open floor planOriginal brickwork
    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.
    67 days
    |
    1,963
    |
    68
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Ken J Donworth 859-983-9933,

    Bluegrass Sotheby's International Realty

    Source: Imagine MLS,MLS#: 26014172MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Level: First
      Kitchen
      • Level: First
      Heating
      • Forced Air
      Cooling
      • Electric
      Appliances
      • Included: Dishwasher, Gas Range, Microwave, Other, Refrigerator, Washer, Range, Vented Exhaust Fan
      • Laundry: Electric Dryer Hookup, Gas Dryer Hookup
      Features
      • Breakfast Bar, Eat-in Kitchen, Other, Wet Bar, Walk-In Closet(s), Ceiling Fan(s)
      • Flooring: Ceramic Tile, Hardwood, Other
      • Windows: Skylight(s), Blinds
      • Has basement: No
      • Number of fireplaces: 1
      • Fireplace features: Living Room
      Interior area
      • Total structure area: 2,846
      • Total interior livable area: 2,846 sqft
      • Finished area above ground: 2,846
      • Finished area below ground: 0
      Video & virtual tour

      Property

      Parking
      • Parking features: Off Street
      Details
      • Parcel number: 38224250

      Construction

      Type & style
      • Home type: Condo
      • Property subtype: Condominium
      Materials
      • Brick Veneer
      • Foundation: Other
      • Roof: Membrane,Other
      Condition
      • Year built: 2009

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available, Electricity Connected, Sewer Connected, Water Connected

      Community & HOA

      Community
      • Subdivision: Downtown
      HOA
      • Has HOA: Yes
      • Amenities included: None
      • Services included: Other
      • HOA fee: $3,600 annually
      Location
      • Region: Lexington

      Financial & listing details

      • Price per square foot: $492/sqft
      • Tax assessed value: $1,100,000
      • Annual tax amount: $13,603
      • Date on market: 6/18/2026

        Estimated market value

        $1,328,000

        $1.26M - $1.39M

        $4,080/mo

        Price history

        DateEventPrice
        6/18/2026Listed for sale$1,400,000+27.3%$492/sqft
        Source: Imagine MLS #26014172 Report a problem
        5/17/2022Sold$1,100,000$387/sqft
        Source: Imagine MLS #22008211 Report a problem
        4/29/2022Pending sale$1,100,000$387/sqft
        Source: Imagine MLS #22008211 Report a problem
        4/27/2022Listed for sale$1,100,000+83.3%$387/sqft
        Source: Imagine MLS #22008211 Report a problem
        7/8/2015Sold$600,000$211/sqft
        Source: Public Record Report a problem
        8/4/2014Sold$600,000-24.5%$211/sqft
        Source: Public Record Report a problem
        6/26/2012Listing removed$795,000$279/sqft
        Source: Bluegrass Sotheby's International Realty #1117181 Report a problem
        4/2/2012Price change$795,000-9.6%$279/sqft
        Source: Bluegrass Sotheby's International Realty #1117181 Report a problem
        9/9/2011Listed for sale$879,000$309/sqft
        Source: Bluegrass Sotheby's International Realty #1117181 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$13,603 $1,100,000
        2024$13,603 $1,100,000
        2023$13,603 +59.5%$1,100,000 +64.7%
        2022$8,529 +11.3%$667,700 +11.3%
        2021$7,664 $600,000
        2020$7,664 $600,000
        2019$7,664 $600,000
        2018$7,664 +4.9%$600,000
        2017$7,304 +164.9%$600,000
        2015$2,757 $600,000 +30.4%
        2014$2,757 $460,000 +86.7%
        2012$2,757 $246,400
        2011-- --
        2010-- --
        2009-- --
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.
        Get pre-qualified

        Climate risks

        Neighborhood: 40508

        Getting around

        95 / 100
        Walker's Paradise
        86 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Harrison
        • Middle: Lexington Trad
        • High: Lafayette

        Source: Imagine MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes

              Nearby cities

              Nearby neighborhoods

              Nearby zip codes

              Other Lexington Topics

                Search
                Updates
                Favorites
                Plan
                Inbox