A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House--one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom villa--each with its own private pool.Zoned with two transient licenses and off-street parking for 4+ vehicles, this exceptional property offers unmatched flexibility for luxury rentals or private use.The grand mansion was reimagined in July 2022 by a local designer, featuring fresh paint, stylish new furnishings, and 12-foot soaring ceilings. The main level includes two guest rooms with baths, formal living and dining rooms, a parlor, and a well-appointed kitchen that opens to the pool deck and outdoor dining area.Upstairs, four en suite bedrooms include two primary suites with private balconies--one overlooking Simonton Street, the other with views of the pool. A spacious third-floor suite, accessed via an interior or exterior staircase, offers a private living room, wet bar, and yet another balcony retreat.The villa, renovated to the studs in 2014, offers a clean, contemporary design with 4 bedrooms, 4 baths, full kitchen, living area, private pool, and outdoor bar--perfect for entertaining.Whether you choose to rent the estate in its entirety or as two separate homes, The Watson House is a rare asset in Key West's luxury rental market--highly sought-after and consistently booked well in advance.
For sale
Price cut: $4K (7/1)
$7,995,000
525 Simonton St, Key West, FL 33040
11beds
3,034sqft
Est.:
Single Family Residence
Built in 1889
8,269 Square Feet Lot
$7,169,900 Zestimate®
$2,635/sqft
$-- HOA
What's special
- 48 days
- on Zillow |
- 2,882 |
- 71 |
Zillow last checked: 7 hours ago
Listing updated: June 30, 2025 at 08:01pm
Listed by:
Paige Bethel 305-395-0550,
Island Home Realty Inc.
Source: FLKMLS,MLS#: 615623
Originating MLS: Key West Association

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 11
- Bathrooms: 11
- Full bathrooms: 11
Cooling
- Central Air, Ductless
Appliances
- Included: Dryer, Stainless Steel Appliance(s), Freezer, Microwave, Refrigerator, Dishwasher
Features
- Storage, Built-in Cabinets
- Windows: Drapes/Blinds Incl, Window Treatments, Skylight(s)
- Furnished: Yes
Interior area
- Total interior livable area: 3,034 sqft
Property
Parking
- Total spaces: 4
- Parking features: Open, Off Street
- Has uncovered spaces: Yes
Features
- Levels: 3 Stories
- Stories: 3
- Exterior features: Storage
- Has private pool: Yes
- Pool features: Heated, In Ground, Decked, Concrete
- Fencing: Fenced
- Water view: None
- Waterfront features: None, Dockage: None
Lot
- Size: 8,269 Square Feet
- Features: Less Than 1/4 Acre
Details
- Parcel number: 00009240000000
- Zoning: HRCC
- Zoning description: Historic Residential Commercial Core
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Frame, Hardi Board Siding
Condition
- Year built: 1889
Utilities & green energy
- Sewer: Public Sewer
- Utilities for property: Buyer to Verify
Community & HOA
Community
- Security: Smoke Detector(s)
- Subdivision: Old Town - Unrecord (1.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Key West
Financial & listing details
- Price per square foot: $2,635/sqft
- Annual tax amount: $51,759
- Date on market: 7/1/2025
- Loading
- Loading