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525 Simonton Street

Key West, FL 33040
  • $6,995,000
  • STATUS: Active Under Contract
  • ON SITE: 292 Days
  • MLS #: 615623
Under Contract
UPDATED: 148 min ago
$6,995,000
  • 11
    BEDS
  • 0.19
    ACRES
  • 11
    BATHS
  • 0
    1/2 BATHS
  • 3,034
    SQFT
  • $2,306
    $/SQFT
Neighborhood:
Type:
Single-Family Home
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 Key West Luxury Real Estate Inc are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
www.keywestluxuryrealestateinc.com/homes/165432454
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525 Simonton Street Key West, FL 33040

  • Price: $6,995,000
  • Status: Active Under Contract
  • On Site: 292 Days
  • Updated: 148 min ago
  • MLS #: 615623
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

Architectural Style [] Attached Garage YN No Building Stories 3 Stories Construction Materials FrameHardi Board Siding Dockage None Exterior Features FencingStorage Parking Features Open Patio And Porch Features [] Pool Features In GroundConcreteDecked Pool Heated Yes Pool Private YN Yes Vehicle Storage Open ParkingOff Street Parking Vehicle Storage Cars 4+ View [] Waterview No Waterview Window Features []

Interior Features

Accessibility Features [] Appliances DryerDishwasherRefrigeratorMicrowaveFreezerStainless Steel Appliance(s) Cooling Central AirDuctless Cooling YN Yes Flooring [] Furnished Furnished Interior Drapes/Blinds InclBuilt-in CabinetsSky Light(s)Smoke AlarmsStorageWindow Treatments Interior Features Built-in CabinetsSky Light(s)Storage Laundry Features [] Levels [] Rooms Total 0

Property Features

Above Flood Yes Association Fee 0 Association Fee Includes None Association YN No Association1st Right Of Refusal No Building Features [] Community Features [] Control Depth 0 Deed Restricts Unknown Electric [] Flood Zone X Frontage Type [] Green Energy Generation [] Green Water Conservation [] KWNeighborhood Old Town-N of Truman Land Size Less Than 1/4 Acre Listing Terms [] Marathon Nbhd N/A Mile Marker 1 Min Rental Days 1 Other Equipment [] Other Structures [] Pets Allowed Yes Property Condition [] Property Sub Type Single Family Residence Public Sewer Hookup Yes Rental Allowed Yes Security Features [] Special Licenses [] 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 Title Negotiable Transient Rental License Yes Utilities [] Utilities Info Buyer to Verify Water Source [] Waterfrnt No Waterfront None Waterfront Features [] Waterfront YN No Zoning HRCC - Historic Residential Commercial Core

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 Key West Luxury Real Estate Inc are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
 
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Key West Luxury Real Estate Inc
619 Eaton Street, #2
Key West FL, 33040