About 1111 Watson Street B
Secret Garden Cigar Maker's Cottage in Old Town 🌴 Tucked behind a private gate on a quiet section of Old Town in Key West, this enchanting 2-bedroom historic cottage invites you into a hidden world of tropical beauty, offering a rare blend of privacy, charm, and walkable island living--set in an X flood zone for added peace of mind. Follow a palm-lined path into a lush, private garden oasis filled with orchids, vibrant blooms, and softly glowing evening light. The outdoor pavilion and private deck create an effortless indoor-outdoor lifestyle--complemented by a spa-inspired retreat space designed for open-air relaxation, cooling rinses, and tranquil moments under the palms. Perfect for relaxing, entertaining, or simply enjoying the Key West breeze. Inside, vaulted ceilings, natural light, and original Cuban tile details reflect the home's 1890 cigar-maker heritage, while the updated kitchen features quartz countertops, stainless steel appliances, and garden views. Enjoy the charm of a boutique six-cottage enclave with a shared heated pool and spa. The home offers both connection and quiet escape. Just steps to Duval Street, the Historic Seaport, beaches, and beloved local spots -- leave the car behind and explore on foot or bike. Private. Lush. Magical. Effortlessly Pure Key West
Features of 1111 Watson Street B
| MLS® # | 618516 |
|---|---|
| Price | $1,399,000 |
| Bedrooms | 2 |
| Bathrooms | 1.00 |
| Full Baths | 1 |
| Square Footage | 1,250 |
| Acres | 0.04 |
| Year Built | 1978 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Cigar Maker |
| Status | Active |
Community Information
| Address | 1111 Watson Street B |
|---|---|
| Area | 02 - Key West |
| Subdivision | Gwynn Sub (1.0) |
| City | Key West |
| County | Monroe |
| State | FL |
| Zip Code | 33040 |
Amenities
| Utilities | FKAA, Municipal Sewer |
|---|---|
| View | No Waterview |
| Is Waterfront | No |
| Waterfront | None |
| Has Pool | Yes |
| Pool | In Ground, Decked |
Interior
| Interior Features | Drapes/Blinds Incl, Cathedral Ceilings, Built-in Cabinets, Dade County Pine, Sky Light(s), Smoke Alarms, Quartz Countertops |
|---|---|
| Appliances | Washer, Dryer, Dishwasher, Refrigerator, Microwave, Stainless Steel Appliance(s) |
| Cooling | Ceiling Fans(s), Ductless |
| Fireplace | No |
| Stories | 1 Story |
| Has Basement | No |
Exterior
| Exterior Features | Hot Tub |
|---|---|
| Lot Description | Less Than 1/4 Acre |
| Windows | Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | Frame |
Additional Information
| Date Listed | February 6th, 2026 |
|---|---|
| Days on Market | 95 |
| Zoning | HMDR - Historic Medium Density Residential |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 291.67 |
| HOA Fees Freq. | Monthly |
Listing Details
| Agent | Juan Alberto Benitez |
|---|---|
| Office | Keller Williams Key West Compass Realty |