# 415 S Upper Street, Lexington, KY 40508 > **TL;DR:** 3bd/2ba condo, $1,400,000 ($492/sqft), built 2009, 2,846 sqft. > Fireplace, Hardwood, A/C. Est. $11,087/mo. Listed 135 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,400,000 | | Price/sqft | $492 | | Bedrooms | 3 | | Bathrooms | 2 full | | Square Feet | 2,846 | | Year Built | 2009 | | Property Type | Condo (Condominium) | | Status | Active | | Days on Market | 135 | ## Why This Home Stands Out - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $7,079 | | Estimated Insurance | $408 | | HOA | $3,600 | | **Total** | **$11,087** | ## Nearby Schools - **Elementary:** Harrison - **Middle:** Lexington Trad - **High:** Lafayette ## Key Amenities - Fireplace - Hardwood - A/C ## Property Highlights - Built in 2009 - Fireplace ## Description ### Agent 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, 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. ## Location - **Address:** 415 S Upper Street, Lexington, KY 40508 - **County:** Fayette - **Neighborhood:** Downtown - **Coordinates:** 38.044029, -84.502707 - **Google Maps:** https://www.google.com/maps?q=38.044029,-84.502707 ## Virtual Tour & Media - **Video Tour:** https://drive.google.com/file/d/1zfkFPMJ1bIAI6M2-DFOX_2OaHZPq9Tu0/view?usp=sharing ## Listing Agent - **Name:** Ken J Donworth - **Brokerage:** Bluegrass Sotheby's International Realty - **Broker Phone:** 2680099 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/415-S-Upper-St_Lexington_KY_40508_M39040-21603?f=listhub&s=LBARKY&m=26014172&c=propsimple) ## Photos ![415 S Upper Street - Photo 1](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f4214245017r.jpg) ![415 S Upper Street - Photo 2](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f816792252r.jpg) ![415 S Upper Street - Photo 3](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f2784675372r.jpg) ![415 S Upper Street - Photo 4](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f1588804580r.jpg) ![415 S Upper Street - Photo 5](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f2406411090r.jpg) ![415 S Upper Street - Photo 6](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f2436107886r.jpg) ![415 S Upper Street - Photo 7](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f1300537981r.jpg) ![415 S Upper Street - Photo 8](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f363492677r.jpg) ![415 S Upper Street - Photo 9](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f420099817r.jpg) ![415 S Upper Street - Photo 10](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f3234742547r.jpg) ![415 S Upper Street - Photo 11](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f3617305162r.jpg) ![415 S Upper Street - Photo 12](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f91425029r.jpg) ![415 S Upper Street - Photo 13](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f3460780347r.jpg) ![415 S Upper Street - Photo 14](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f188795017r.jpg) ![415 S Upper Street - Photo 15](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f1195381437r.jpg) ![415 S Upper Street - Photo 16](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f2460312789r.jpg) ![415 S Upper Street - Photo 17](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f1907560962r.jpg) ![415 S Upper Street - Photo 18](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f4007363384r.jpg) ![415 S Upper Street - Photo 19](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f1084619985r.jpg) ![415 S Upper Street - Photo 20](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f1298179460r.jpg) ![415 S Upper Street - Photo 21](http://lh.rdcpix.com/e2888753cf51ff5222a499e7ab558c98l-f2704566847r.jpg) --- **MLS#:** 26014172 | **Updated:** 2026-10-20 **Source:** listhub *Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/415-s-upper-street-lexington-ky-40508-d5fb210b57ca4f58b009a08768c46ccc) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/415-s-upper-street-lexington-ky-40508-d5fb210b57ca4f58b009a08768c46ccc#listing", "url": "https://www.propertysimple.ai/listing/415-s-upper-street-lexington-ky-40508-d5fb210b57ca4f58b009a08768c46ccc", "name": "415 S Upper Street, Lexington, KY 40508", "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. 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