525 Simonton Street, Key West, FL 33040

$6,500,000

Property Type: Residential Bedrooms: 11 Baths: 11 Square Footage: 3,034 Lot Size (sq. ft.): 8,269 Status: Closed

Current Price: $6,500,000 List Date: 7/01/2025 Last Modified: 6/17/2026

Overview

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 priva ... (Read more)

Listing Details MLS# 615623

Location, Tax & Legal

Street #: 525
Street Name: Simonton
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unrecord (1.0)
Area: 01 - Key West
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 - Historic Residential Commercial Core
Deed Restrictions: Unknown
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
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: No
Pool: Yes
Year Built: 1889
Lot SqFt: 8269
Living Apx SqFt: 3034
SqFt Source: Property Data Card
Total Bedrooms: 11
Full Baths: 11
Total Baths: 11
Rentals Allowed: Yes
Min Rental Days: Yes
Control Depth: 0

Status Change Info

Under Contract Date: 2026-04-15
Sold Date: 2026-06-17

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

License Info

# of City License: 2
# of County License: 2
Transient Rntl Licns: Yes

More Information

Building Style

Above Flood: Yes
Stories: 3 Stories

Vehicle Storage

Car(s): 4+
Open Parking: Yes
Off Street Parking: Yes

Pool Info

Heated: Yes
In Ground: Yes
Concrete: Yes
Decked: Yes

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.

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Freezer: Yes
Microwave: Yes
Refrigerator: Yes
Stainless Steel Appliance(s): Yes

Pets

Pets Allowed: Yes

Cooling

Central Air: Yes
Ductless: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Interior Features

Built-in Cabinets: Yes
Drapes/Blinds Incl: Yes
Sky Light(s): Yes
Smoke Alarms: Yes
Storage: Yes
Window Treatments: Yes

Construction

Frame: Yes
Hardi Board Siding: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Furnished: Yes

Utilities

Buyer to Verify: Yes

Title

Negotiable: Yes

Exterior Features

Fencing: Yes
Storage: Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Vehicle Storage: Off Street Parking; Open Parking Furnished: Furnished Cooling: Central Air; Ductless Utilities: Buyer to Verify Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Sky Light(s); Smoke Alarms; Storage; Window Treatments Appliances: Dishwasher; Dryer; Freezer; Microwave; Refrigerator; Stainless Steel Appliance(s) Exterior Features: Fencing; Storage Pool Info: In Ground; Concrete; Decked Construction: Frame; Hardi Board Siding Pets: Pets Allowed Land Size: Less Than 1/4 Acre Title: Negotiable

Listing Office: Island Home Realty Inc.

Last Updated: June - 17 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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