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.
For sale
$1,400,000
415 S Upper St, Lexington, KY 40508
3beds
2,846sqft
Condominium
Built in 2009
-- sqft lot
$1,324,200 Zestimate®
$492/sqft
$300/mo HOA
What's special
Wolf gas rangeBeverage refrigeratorLoft-style residenceFreezer drawersWaterworks fixturesSoaring open floor planOriginal brickwork
- 17 days |
- 3,140 |
- 228 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Ken J Donworth 859-983-9933,
Bluegrass Sotheby's International Realty
Source: Imagine MLS,MLS#: 26014172
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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
$1,324,200
$1.26M - $1.39M
$3,553/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/18/2026 | Listed for sale | $1,400,000+27.3%$492/sqft |
Source:  Imagine MLS #26014172 Report a problem | ||
| 5/17/2022 | Sold | $1,100,000$387/sqft |
Source: Imagine MLS #22008211 Report a problem | ||
| 4/29/2022 | Pending sale | $1,100,000$387/sqft |
Source: Imagine MLS #22008211 Report a problem | ||
| 4/27/2022 | Listed for sale | $1,100,000+83.3%$387/sqft |
Source: Imagine MLS #22008211 Report a problem | ||
| 7/8/2015 | Sold | $600,000$211/sqft |
Source: Public Record Report a problem | ||
| 8/4/2014 | Sold | $600,000-24.5%$211/sqft |
Source: Public Record Report a problem | ||
| 6/26/2012 | Listing removed | $795,000$279/sqft |
Source: Bluegrass Sotheby's International Realty #1117181 Report a problem | ||
| 4/2/2012 | Price change | $795,000-9.6%$279/sqft |
Source: Bluegrass Sotheby's International Realty #1117181 Report a problem | ||
| 9/9/2011 | Listed for sale | $879,000$309/sqft |
Source: Bluegrass Sotheby's International Realty #1117181 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 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 | $246,400 |
| 2011 | -- | -- |
| 2010 | -- | -- |
| 2009 | -- | -- |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
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.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 40508
Nearby schools
GreatSchools rating
- 5/10Harrison Elementary SchoolGrades: K-5Distance: 0.6 mi
- 5/10Lexington Middle SchoolGrades: 6-8Distance: 0.8 mi
- 10/10Lafayette High SchoolGrades: 9-12Distance: 1.8 mi
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.
- Kentucky
- Fayette County
- Lexington
- 40508
- 415 S Upper St
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