525 Simonton Street, Key West, FL 33040 (MLS# 615622)

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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