525 Simonton Street, Key West, FL 33040
$7,995,000
Property Type:
Commercial Sale
Bedrooms:
11
Baths:
11
Square Footage:
3,034
Lot Size (sq. ft.):
8,269
Status:
Active
Current Price:
$7,995,000
List Date:
7/01/2025
Last Modified:
7/01/2025
Description
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.
More Information MLS# 615622
Contract Information
Listing Board: Key West Association
Limited Representation: No
Potential Short Sale: No
Bank Owned: No
Current Price: $7,995,000
Listing Date: 2025-07-01
List Price: $7,995,000
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: X
Alternate Key #: 1009491
Parcel #: 00009240-000000
Zoning: HRCC(1 - 4) - Hist Res Comm Core 1-4 SF Specl
Legal: KW PT LOT 4 SQR 49 G8-444 OR885-189 OR890-2126 OR927-1164 OR2008-62 OR2555-1269 OR3147-0073 OR3164-0865
Taxes: 51759.18
Tax Year: 2024
Street #: 525
Street Name: Simonton
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
Subdivision: Old Town - Unrecord (1.0)
County: Monroe
Area: 01 - Key West
General Property Description
Realtor.COM Type: Commercial
Waterfront: No
Control Depth: 0
Lot Size: 61x139
Lot SqFt: 8269
Total Units: 0
# Parking Spaces: 4+
Off Street Parking: Yes
# Stories: 3
Building SqFt: 4295
Style: Residential Income
Living Apx SqFt: 3034
Year Built: 1889
Total Bedrooms: 11
Full Baths: 11
Total Baths: 11
Remarks & Misc
Remarks – Consumer: 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.
Deed Restrictions
No: 1
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
License Info
# of City License: 2
# of County License: 2
# of Transient Licns: 2
Type
Hotel/Motel: 1
Fee Includes
None: 1
Dockage
None: 1
Appliances
Dishwasher: 1
Disposal: 1
Dryer: 1
Range: 1
Refrigerator: 1
Washer: 1
Cooling
Central Air: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Interior Features
Cathedral Ceilings: 1
Furnished: 1
Laundry Room: 1
Wet Bar: 1
Window Treatments: 1
Vehicle Storage
Car(s): 4+
Off Street Parking: 1
Construction
Frame: 1
Land Size
Less Than 1/4 Acre: 1
Utilities
FKAA: 1
Title
Negotiable: 1
Property Rights
Transient License: 1
Miscellaneous
Fencing: 1
Patio: 1
Pool: 1
Storage: 1
Financial Status
Bank Owned: No
Potential Short Sale: No
Status Change Info
Status: Active
Property Features
Deed Restrictions: No
Type: Hotel/Motel
Waterfront: None
Waterview: No Waterview
Dockage: None
Vehicle Storage: Off Street Parking
Cooling: Central Air
Utilities: FKAA
Interior Features: Cathedral Ceilings; Furnished; Laundry Room; Wet Bar; Window Treatments
Appliances: Dishwasher; Disposal; Dryer; Range; Refrigerator; Washer
Miscellaneous: Fencing; Patio; Pool; Storage
Construction: Frame
Land Size: Less Than 1/4 Acre
Fee Includes: None
Title: Negotiable
Property Rights: Transient License
Listing Office:
Island Home Realty Inc.
Last Updated: July - 01 - 2025
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