525 Simonton Street, Key West, FL 33040
$6,995,000
Property Type:
Commercial Sale
Bedrooms:
11
Baths:
11
Square Footage:
3,034
Lot Size (sq. ft.):
8,269
Status:
Contingent/Show
Current Price:
$6,995,000
List Date:
7/01/2025
Last Modified:
4/16/2026
Listing Details MLS# 615622
Location, Tax & Legal
- 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
- 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
Contract Information
- Listing Board
- Key West Association
- Limited Representation
- No
- Potential Short Sale
- No
- Bank Owned
- No
General Property Description
- Realtor.COM Type
- Commercial
- Style
- Residential Income
- Lot SqFt
- 8269
- Waterfront
- No
- # Parking Spaces
- 4+
- Off Street Parking
- Yes
- # Stories
- 3
- Building SqFt
- 4295
- Living Apx SqFt
- 3034
- Year Built
- 1889
- Total Bedrooms
- 11
- Full Baths
- 11
- Total Baths
- 11
- Control Depth
- 0
- Total Units
- 0
Status Change Info
- Contingent
- Contingent/Show
License Info
- # of City License
- 2
- # of County License
- 2
- # of Transient Licns
- 2
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
More Information
Vehicle Storage
- Car(s)
- 4+
- Off Street Parking
- Yes
Financial Status
- Bank Owned
- No
- Potential Short Sale
- No
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
- Yes
Type
- Hotel/Motel
- Yes
Fee Includes
- None
- Yes
Dockage
- None
- Yes
Appliances
- Dishwasher
- Yes
- Disposal
- Yes
- Dryer
- Yes
- Range
- Yes
- Refrigerator
- Yes
- Washer
- Yes
Cooling
- Central Air
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Interior Features
- Cathedral Ceilings
- Yes
- Furnished
- Yes
- Laundry Room
- Yes
- Wet Bar
- Yes
- Window Treatments
- Yes
Construction
- Frame
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Utilities
- FKAA
- Yes
Title
- Negotiable
- Yes
Property Rights
- Transient License
- Yes
Miscellaneous
- Fencing
- Yes
- Patio
- Yes
- Pool
- Yes
- Storage
- Yes
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: April - 16 - 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.