525 Simonton Street, KEY WEST, FL

$7,995,000

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11

Beds

11

Baths

3,034

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® # 615623
Price $7,995,000
Bedrooms 11
Bathrooms 11.00
Full Baths 11
Square Footage 3,034
Year Built 1889
Type Residential
Sub-Type Single Family
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 Buyer to Verify
Parking Spaces 4
Parking Open Parking, Off Street Parking
View No Waterview
Is Waterfront No
Waterfront None
Has Pool Yes
Pool In Ground, Decked, Concrete

Interior

Interior Features Drapes/Blinds Incl, Window Treatments, Storage, Smoke Alarms, Sky Light(s), Built-in Cabinets
Appliances Dryer, Stainless Steel Appliance(s), Freezer, Microwave, Refrigerator, Dishwasher
Cooling Central Air, Ductless
Fireplace No
Stories 3 Stories

Exterior

Exterior Features Fencing, Storage
Lot Description Less Than 1/4 Acre
Construction Frame, Hardi Board Siding

Additional Information

Date Listed June 29th, 2025
Days on Market 106
Zoning HRCC - Historic Residential Commercial Core
Short Sale No
RE / Bank Owned No
HOA Fees 0.00

Listing Details

AgentPaige Bethel
OfficeIsland Home Realty Inc.

Listing Map

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