Hometrino is now on iOS & Android — download the app for the best experience.





$3,495,000
Key West, FL 33040
Estimated payment $18,248/month
HOA not listed, not included · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr
Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here.Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is original, refinished rather than replaced, and irreplaceable.What 2023 changed was everything behind it -- raised to modern flood elevation, impact-rated windows and doors, and finishes chosen by a designer who wasn't in a hurry. Native coral walls, Jerusalem limestone, terrazzo, and marble under high ceilings.Out front, double balconies span the facade -- the real living room here. Coffee on the upper, cocktails on the lower, and Caroline Street putting on its show below: the walk to the Seaport, the whole slow parade of Old Town.Out back, collapsing glass doors open to the garden: a heated and chilled plunge pool with waterfall, walled and private -- the kind of courtyard that makes 4pm the best hour of the day.Four bedrooms, four en-suite baths, plus a guest half bath. The oversized upstairs primary has walk-in closets and a spa-caliber bath with double shower, artist-made cabinetry, and coral detail you won't see twice. A second primary on the main floor adds flexibility, plus a loft/office upstairs.The kitchen was built for how people actually entertain here: a six-seat island, full JennAir appliance package, open flow to the living and dining rooms.And it earns from day one. Six-figures in booked rental revenue transfers with the sale, repeat guests already on the calendar. Residence, winter escape, or income property -- it does all three. Sold furnished. No HOA. Seller financing possible.Three minutes to Duval. One minute to the shrimp boats. Homes on this block rarely trade, and almost never finished like this.
Tour with a local agent
| Date | Event | Price |
|---|---|---|
| 11/1/2026 | Listed for sale | $3,495,000$1553/sqft |
Jesse Friedman
Real Broker, LLC
Brokerage Phone: 855-450-0442
Source: Florida Keys MLS · MLS #620222
Data Powered by Home Junction, Inc.
MONROE VIRTUAL INSTRUCTION PROGRAM
Elementary · 0.4 mi
MONROE VIRTUAL FRANCHISE
High · 0.4 mi
MONROE VIRTUAL ACADEMY (COURSE OFFERINGS)
High · 0.4 mi
Beef Jerky Experience
0.2 mi
Faustos
0.2 mi
Key West Artisan Market
0.4 mi
Harpoon Harry's Restaurant and Bar
0.1 mi
A&B Lobster House
0.2 mi
Dante's
0.2 mi
Nancy Forrester's Secret Garden
0.2 mi
Memorial Sculpture Garden
0.3 mi
Bill Butler Park
0.5 mi
South Beach
0.9 mi
Dog Beach
1.0 mi
Truman Beach
1.1 mi
Nearby amenity locations include data © OpenStreetMap contributors.