525 Simonton Street, KEY WEST, FL

$7,995,000

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11

Beds

11

Baths

4,295

Square feet

About 525 Simonton Street

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.

Features of 525 Simonton Street

MLS® # 615622
Price $7,995,000
Bedrooms 11
Bathrooms 11.00
Full Baths 11
Square Footage 4,295
Year Built 1889
Type Commercial Sale
Sub-Type Residential Income
Status Active

Community Information

Address 525 Simonton Street
Area 01 - Key West
Subdivision Old Town - Unrecord (1.0)
City KEY WEST
County Monroe
State FL
Zip Code 33040

Amenities

Utilities FKAA
Parking Off Street Parking
View No Waterview
Is Waterfront No
Waterfront None

Interior

Interior Features Wet Bar, Window Treatments, Furnished, Laundry Room, Cathedral Ceilings
Appliances Refrigerator, Dishwasher, Dryer, Washer, Disposal, Range
Heating Central Air
# of Stories 3

Exterior

Lot Description Less Than 1/4 Acre
Construction Frame

Additional Information

Date Listed June 29th, 2025
Days on Market 106
Zoning HRCC(1 - 4) - Hist Res Comm Core 1-4 SF Specl
Short Sale No
RE / Bank Owned No

Listing Details

AgentPaige Bethel
OfficeIsland Home Realty Inc.

Listing Map

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