Property Attributes
- MLS#620222
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityKey West
- AreaKey West
- NeighborhoodOld Town - Unlisted
- Zip33040
- StyleConch
- Year Built1928
- Taxes$ 9955
- Price$ 3,495,000
- Bedrooms4
- Full Bathrooms4
- Half Bathrooms1
- Sqr Footage2250
- Lot Size0.04 Acres
Data Source:
Florida Keys MLS (FLKMLS)
Property Description
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.
| Price History | |
|---|---|
| 6/10/2026 | Listed $3,595,000 |
| 8/4/2026 | 3$3,495,000 |
General Features
| Living Area | 2250.00 |
|---|---|
| Construction | Frame |
| Utilities | FKAA,Cable Available,Municipal Sewer |
| Roof | Metal Roof |
| Appliances | Washer,Stainless Steel Appliance(s),Wine Cooler,Freezer,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer |
| Flood Zone | AE |
| Zoning | HMDR - Historic Medium Density Residential |
| HOA Fee | 0.00 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 4 |
| Half Baths | 1 |
| Year Built | 1928 |
| Subdivision | Old Town - Unlisted (1.0) |
| Style | Single Family |
| View | No Waterview |
| Property Type | A |
| Fee Includes | None |
| Acres | 0.04 |
| Lot Sqft | 1849.00 |
| Rental Allowed | Yes |
| Building Style: Above Flood | Yes |
| Building Style: Stories | 2 Stories |
| Dockage | None |
| KW Neighborhood | Old Town-N of Truman |
| Min Rental Days | 28.00 |
| License Info | Non Trans Rntl Lic |
Interior Features
| Interior Amenities | Drapes/Blinds Incl,Window Treatments,Quartz Countertops,Built-in Cabinets,Walk-in Closet(s),Smoke Alarms,Fire Sprinkler,Dade County Pine,Entrance Foyer,Split Bedroom |
|---|---|
| Total Units | 0.00 |
| Furnished Y/N | Furnished |
| Flooring | Tile,Marble,Other,Combo,Terrazzo |
| Specialty Rooms | Loft,Other |
| GF-Interior Features | Tankless Hot Wtr Htr,LED Lighting,Programmable Thermst |
| Pre-Wired | Cable,Cat 5 |
Exterior Features
| Exterior Amenities | Fencing,Sprinkler System,Lighting,Hot Tub,Rain Gutters |
|---|---|
| Pool | Yes |
| Waterfront | None |
| Building Style | Conch |
| Lot Size | X |
| Land Size | Less Than 1/4 Acre |
| Pool Info | In Ground,Decked,Concrete |
| Pool Info: Heated | Yes |
| Porch/Balcony | Open Porch/Balcony,Deck |
| Public Sewer Hookup | Yes |
| Side | Bay/Gulf |
| Windows/Doors | Wood Windows,Impact Rstnce Window |
| Off Shore Island | No |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33040
In The Neighborhood
Key West
$ 1,050,000
- Type
- Single Family
- Size
- 1,281 SqFt
- Rooms
- 3 Beds + 2 Baths
Key West
$ 1,890,000
- Type
- Single Family
- Size
- 1,495 SqFt
- Rooms
- 2 Beds + 2.5 Baths
Key West
$ 1,395,000
- Type
- Single Family
- Size
- 1,092 SqFt
- Rooms
- 2 Beds + 3 Baths
Key West
$ 6,750,000
- Type
- Single Family
- Size
- 3,663 SqFt
- Rooms
- 5 Beds + 4.5 Baths
Key West
$ 999,000
- Type
- Single Family
- Size
- 1,416 SqFt
- Rooms
- 3 Beds + 1.5 Baths
Key West
$ 3,500,000
- Type
- Single Family
- Size
- 2,575 SqFt
- Rooms
- 5 Beds + 4.5 Baths
Key West
$ 3,300,000
- Type
- Single Family
- Size
- 2,573 SqFt
- Rooms
- 4 Beds + 3.5 Baths
Key West
$ 2,249,000
- Type
- Single Family
- Size
- 1,724 SqFt
- Rooms
- 3 Beds + 3 Baths
Key West
$ 2,395,000
- Type
- Single Family
- Size
- 1,456 SqFt
- Rooms
- 3 Beds + 2 Baths
Key West
$ 949,000
- Type
- Single Family
- Size
- 1,520 SqFt
- Rooms
- 3 Beds + 3 Baths
Key West
$ 3,750,000
- Type
- Single Family
- Size
- 3,015 SqFt
- Rooms
- 7 Beds + 7.5 Baths
Key West
$ 2,033,000
- Type
- Single Family
- Size
- 888 SqFt
- Rooms
- 2 Beds + 1 Baths
Information is deemed to be reliable, but is not guaranteed. © 2026 MLS and FBS. Prepared by Florida Keys MLS, Inc. on September 11, 2026 7:48 AM UTC The information on this sheet has been made available by the MLS and may not be the listing of the provider. The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information