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525 Simonton Street

Key West, FL 33040
  • $6,995,000
  • STATUS: Active
  • ON SITE: 282 Days
  • MLS #: 615622
Price Reduced
UPDATED: 52 min ago
$6,995,000
  • 11
    BEDS
  • 0.19
    ACRES
  • 11
    BATHS
  • 0
    1/2 BATHS
  • 3,034
    SQFT
  • $2,306
    $/SQFT
Neighborhood:
Type:
Multi-Family
Built:
1889
County:

School Ratings & Info

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.

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The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Florida Keys MLS, Inc. Real estate listings held by brokerage firms other than Bascom Grooms Real Estate are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
www.realtorkeywestfl.com/homes/165432457
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525 Simonton Street Key West, FL 33040

  • Price: $6,995,000
  • Status: Active
  • On Site: 282 Days
  • Updated: 52 min ago
  • MLS #: 615622
11
Beds
11
Baths
0
½ Baths
0.19
Acres
3,034
SQFT
$2,306
$/SQFT
1889
Built
Neighborhood:
Old Town-N Of Truman
County:
Monroe
Area:
01 - Key West
Property 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.
Exterior Features

Attached Garage YN No Construction Materials Frame Dockage None Exterior Features [] Parking Features [] Parking Spaces 4+ Stories 3 Vehicle Storage Off Street Parking Vehicle Storage Cars 4+ View [] Waterview No Waterview Window Features []

Interior Features

Appliances RefrigeratorRangeDisposalWasherDryerDishwasher Cooling Central Air Cooling YN Yes Flooring [] Interior Wet BarCathedral CeilingsLaundry RoomFurnishedWindow Treatments Interior Features []

Property Features

Association Fee Includes None Association YN No Association1st Right Of Refusal No Bank Owned No Business Type Hotel/Motel Control Depth 0 Deed Restrictions No Electric [] Flood Zone X Frontage Type [] KWNeighborhood Old Town-N of Truman Land Size Less Than 1/4 Acre Listing Terms [] Marathon Nbhd N/A Mile Marker 1 Miscellaneous StoragePatioFencingPool Number Of Transient License 2 Off Street Parking Yes Potential Short Sale No Property Rights Transient License Property Sub Type Residential Income Special Licenses Transient License Tax Annual Amount 51759.18 Tax Legal Description KW PT LOT 4 SQR 49 G8-444 OR885-189 OR890-2126 OR927-1164 OR2008-62 OR2555-1269 OR3147-0073 OR3164-0865 Tax Year 2024 Tenant Pays [] Title Negotiable Utilities [] Utilities Info FKAA Waterfrnt No Waterfront None Waterfront Features [] Waterfront YN No Zoning HRCC(1 - 4) - Hist Res Comm Core 1-4 SF Specl

Listing courtesy of Paige Bethel of Island Home Realty Inc.: 305-395-0550.


The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Florida Keys MLS, Inc. Real estate listings held by brokerage firms other than Bascom Grooms Real Estate are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
 
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Bascom Grooms Real Estate
1110 Truman Ave
Key West FL, 33040