$7,995,000
 $42,919 est/mo Sourced by Back At You

525 Simonton Street,KEY WEST, FL 33040

KEY WEST, FL 33040

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Description

A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson Houseone 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 villaeach 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 balconiesone 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 barperfect 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 markethighly sought-after and consistently booked well in advance.

Details

MLS #615623
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusActive
Year1889
Days On Site20
Listing Provided ByIsland Home Realty Inc. | Paige Bethel

Features

Bed(s)11
Bath(s) 11 Total
SQ Feet3,034
PoolYes
ZoningHRCC - Historic Residential Comm
Acreage0.19
Water FrontNone
Property ViewNo Waterview

Taxes

Property51759

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The data relating to real estate for sale on this web site come s in part from the Internet Data Exchange program of the Marathon and Lower Keys Association of REALTORS®, Inc. MLS. Real Estate listings held by brokerage firms other than Key Colony Beach Realty, Inc. are marked with the MLS logo and detailed information about them includes the name of the listing broker’s office.

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Learn More About This Property

StateFL
CountyMonroe
CityKEY WEST
Zip Code33040
Area01 Key West
Community NameOld Town Unrecord (1.0)
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $5.996M - $9.993M
SqFt: 2,000 - 3,500
Nearby Listings Property ImageNearby Listings Details
525 Simonton Street Property Photo 1
$7,995,000
525 Simonton Street
Key West, FL 33040
421 - 423 Simonton Street Property Photo 1
$6,500,000
421 - 423 Simonton Street
Key West, FL 33040
Listing Updated: July 7, 2025 at 11:40:20 AM PDT