910-914 Watson Street 617923
Active More than a residence and rarer than legend, 910-914 Watson Street stands as one of the most iconic private estates in all of Key West–a once-in-a-generation offering where historic gravitas, tropical scale, and modern refinement converge behind gated walls in the heart of Old Town. Just moments from Truman Waterfront Park and beloved local favorites such as 5 Brothers Coffee and Cafe Sole, this historic estate delivers the rare combination of island ease and cultivated sophistication. Bathed in natural light, the home’s timeless architecture artfully blurs the line between indoors and out, creating spaces that feel both expansive and intimate. Anchoring the tropical grounds is a resort-style pool and spa framed by tranquil water features and a serene koi pond. The experience is elevated further by an oversized covered pool loggia, designed for effortless island living and entertaining, featuring outdoor dining, a fully equipped outdoor kitchen, and a generous living area–all sheltered and inviting year-round. The enclosed, gated grounds offer rare privacy and practicality, including two-car garages and off-street parking for at least six additional vehicles–an exceptional luxury in Old Town. A dedicated dog run with motorized gate and lush landscaping complete the sense of a hidden tropical sanctuary. Spanning 4,387 square feet, the estate includes five bedrooms and six and a half baths, thoughtfully arranged for both togetherness and autonomy. A one bedroom suite resides in a separate guest house with its own entrance, front porch, and living space, ideal for a mother-in-law suite, long-term guests, or on-site grounds personnel. An office and library open onto a private courtyard and reveal a hidden room discreetly tucked behind a bookshelf–because every great home, like every great story, deserves a secret. Set on an expansive 13,182 square-foot lot in the coveted X-500 Flood Zone, the property is equally suited for lively gatherings or quiet moments of retreat.
| Price: | $5,995,000 |
|---|---|
| Address: | 910-914 Watson Street |
| City: | Key West |
| State: | Florida |
| Zip Code: | 33040 |
| Subdivision: | Old Town - Unlisted (1.0) |
| MLS: | 617923 |
| Year Built: | 1929 |
| Square Feet: | 4,387 |
| Bedrooms: | 5 |
| Bathrooms: | 7 |
| Half Bathrooms: | 1 |
| roof2: | Metal Roof |
|---|---|
| levels: | Ground Level |
| cooling: | Central Air, Heat Pump, Ceiling Fans(s), Ductless |
| dockage: | None |
| taxYear: | 2024 |
| flooring: | Tile, Wood, Carpet, Marble |
| garageYN: | yes |
| landSize: | 1/4 - 1/2 Acre |
| coolingYN: | yes |
| mlsStatus: | Active |
| utilities: | Whole House Generatr |
| waterview: | No Waterview |
| appliances: | Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s) |
| postalCity: | KEY WEST |
| utilities2: | FKAA, Well, Municipal Sewer, Propane, Whole House Generatr |
| waterfront: | None |
| lotSizeArea: | 13182 |
| petsAllowed: | Yes |
| listingTerms: | Cash, Conventional |
| lotSizeUnits: | Square Feet |
| mlsAreaMajor: | 02 - Key West |
| mlsAreaMinor: | 02 - Key West |
| poolFeatures: | In Ground, Concrete |
| waterfrontYN: | no |
| windowsDoors: | Single Hung Windows, Glass Doors |
| associationYN: | no |
| lotSizeSource: | Property Data Card |
| poolPrivateYN: | yes |
| otherEquipment: | Home Theater |
| specialtyRooms: | Gym, Laundry Room, Theater Room, Sauna/Steam Room, Sun/Florida Room, Workshop |
| vehicleStorage: | Garage, Carport, Attached, Auto Door Opener, Guest Parking, Off Street Parking |
| laundryFeatures: | Laundry Room |
| parkingFeatures: | Attached, Garage Door Opener |
| taxAnnualAmount: | 43086 |
| attachedGarageYN: | yes |
| exteriorFeatures: | Bar, Fencing, Gazebo, Hot Tub, Lighting, Privacy Wall/Fence, Water Display |
| interiorFeatures: | Built-in Cabinets, Granite Counter Top, Storage, Walk-in Closet(s), Gym, Sauna, Sun/Florida Room |
| interiorFeatures2: | Wet Bar, Cathedral Ceilings, Split Bedroom, Pantry, Built-in Cabinets, Granite Counter Top, Storage, Walk-in Closet(s) |
| lotSizeSquareFeet: | 13182 |
| buildingAreaSource: | Property Data Card |
| bathroomsTotalDecimal: | 6.5 |
| constructionMaterials: | Frame |
| patioAndPorchFeatures: | Patio, Screened Patio |
| associationFeeIncludes: | None |
| locationTaxLegalKwNeighborhood: | Old Town-N of Truman |
| associationInfo1stRightOfRefusal: | No |
| locationTaxLegalMarathonNeighborhood: | N/A |
©2026 Florida Keys MLS, Inc. The data relating to real estate for sale on this web site comes in part from the Florida Keys Multiple Listing Service. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Information is deemed reliable but not guaranteed. Data last updated: Friday, July 24th, 2026 at 03:47:19 PM.
Data services provided by IDX Broker
Listed by: Truman & Co. (KW) (305) 393-1267
