525 Simonton Street, Key West, FL 33040
$7,695,000
Property Type:
Commercial Sale
Bedrooms:
11
Baths:
11
Square Footage:
3,034
Lot Size (sq. ft.):
8,269
Status:
Active
Current Price:
$7,695,000
List Date:
7/01/2025
Last Modified:
1/29/2026
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
Current Price: $7,695,000
Listing Date: 2025-07-01
Listing Board: Key West Association
List Price: $7,695,000
Limited Representation: No
Potential Short Sale: No
Bank Owned: No
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
General Property Description
Realtor.COM Type: Commercial
Style: Residential Income
Lot Size: 61x139
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
Status Change Info
Status: Active
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
Vehicle Storage
Car(s): 4+
Financial Status
Bank Owned: No
Potential Short Sale: No
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: January - 29 - 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.
