415 South Upper Street

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Living Room
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Buttlers Pantry
Dining Room
Kitchen
TV room
Lounge room
Office Space
Primary Bedroom
Bedroom
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Bathroom Rennovation
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Active
$1,400,000
3 beds2,846 sqft
415 South Upper Street, Lexington, KY 40508
Est: $8,908/moGet pre-approved
CondoProperty Type
2009Year Built
$492/sq ftPrice per sq ft
$3,600/yrHOA Fees

Description

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,...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.
75 days on Market
  • Listed by: Ken J Donworth 859.983.9933 kdonworth@gmail.com Brokerage DRE #674 • Bluegrass Sotheby's International Realty
Last updated: 10/03/2026 08:58 AM • Source: Imagine MLS, MLS#: 26014172

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$8,908 per month

30 year fixed, 7.03% Interest

Principal and Interest

$7,474

Property Taxes

$1,134

HOA Dues

$300

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Property Information for 415 South Upper Street

Property Details
  • MLS Type: Residential / Condominium
  • County: Fayette County
  • Subdivision Name: Downtown
  • Waterfront: No
Building Information
  • Building/Complex: 415 S Upper St
  • Floor: 1
  • Year Built: 2009
Summary
Location and General Information
  • Directions: Next to pedal Power bike shop on upper Street parking outside
  • Latitude: 38.044029
  • Longitude: -84.502707
  • MLS Area Major: 004 - Fayette County SW
  • MLS Area Minor: 004 - Fayette County SW
Taxes and HOA
  • Association: Yes
  • Association Fee: $3,600.00
  • Association Fee Frequency: Annually
  • Parcel Number: 38224250
School Information
  • Elementary School: Harrison
  • High School: Lafayette
  • High School District: Fayette County - 1
  • Middle Or Junior School: Lexington Trad
Parking
  • Attached Garage: No
  • Carport: No
  • Garage: No
  • Parking Features: Off Street
Property
Lot Information
  • Lot Size Source: Public Records
Property and Assessments
  • Above Grade Finished Area: 2846.0
  • Building Area Total: 2846.0
  • Living Area: 2846.0
  • Living Area Source: Appraiser
  • Year Built: 2009
Building Features
  • Construction Materials: Brick Veneer
  • Entry Level: 1
Farm Information
  • Horse: No
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Available, Electricity Connected, Sewer Connected, Water Connected
  • Water Source: Public
Room Information
Room 1
  • Room Type: Primary Bedroom
  • Room Level: First
Room 2
  • Room Type: Kitchen
  • Room Level: First
Interior and Exterior Features
Exterior Features
  • Pool Private: No
  • Roof: Membrane
Interior Features
  • Appliances: Dishwasher, Gas Range, Microwave, Refrigerator, Washer, Range, Vented Exhaust Fan
  • Basement: No
  • Bathrooms Full: 2
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 3
  • Cooling: Electric
  • Cooling: Yes
  • Fireplace: Yes
  • Fireplace Features: Living Room
  • Fireplaces Total: 1
  • Flooring: Ceramic Tile, Hardwood
  • Heating: Forced Air
  • Heating: Yes
  • Interior Features: Breakfast Bar, Eat-in Kitchen, Primary First Floor, Wet Bar, Walk-In Closet(s), Ceiling Fan(s)
  • Laundry Features: Electric Dryer Hookup, Gas Dryer Hookup
  • Rooms Total: 2
  • Window Features: Skylight(s), Blinds

Property History for 415 South Upper Street

DateEvent & SourcePriceAppreciation
Oct 3, 2026

Listed (Active)

Imagine MLS #26014172

$1,400,000—
Aug 31, 2026

Contract Signed

Imagine MLS #26014172

—
Jun 18, 2026

Listed (Active)

Imagine MLS #26014172

$1,400,000—
DateEvent & SourcePrice
10/03/2026

Listed (Active)

Imagine MLS #26014172

$1,400,000
08/31/2026

Contract Signed

Imagine MLS #26014172

—
06/18/2026

Listed (Active)

Imagine MLS #26014172

$1,400,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 415 South Upper Street

Taxable ValueLand-Additions-Total-
Tax Record2025$13,603 ($1,134 / month)
Home Facts
Beds3Baths2Total Finished SqFt3,154 SqFtAbove Grade Finished SqFt3,154 SqFtStories1StyleCondominiumYear Built2009Year Renovated2009ZoningR-2CountyFAYETTEAPN38224250

Schools near 415 South Upper Street

This home is within Fayette County.
Rating
School
Type
Grades
Distance
Harrison Elementary School
Public - K to 5
Lexington Middle School
Public - 6 to 8
Lafayette High School
Public - 9 to 12
Maxwell Spanish Immersion Elementary School
Public - K to 5
Rating
School
Distance
Harrison Elementary School
PublicK to 5

Lexington Middle School
Public6 to 8

Lafayette High School
Public9 to 12

Maxwell Spanish Immersion Elementary School
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 415 South Upper Street, Lexington, KY 40508

415 South Upper Street is a condo for sale in Lexington, KY 40508. This property was listed for sale on June 18, 2026 by Bluegrass Sotheby's International Realty, it's currently listed at $1,400,000. It has been on the market for a total of 75 days and was last sold on May 17, 2022. This listing's school district is Fayette County. Nearby schools include Harrison Elementary School, Lexington Middle School and Lafayette High School. 415 South Upper Street is a 3-bed, 2-bath, 2,846 sqft condo built in 2009.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Bluegrass Sotheby's International Realty

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