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For sale
  • Price cut: $4K (7/1)
    $7,995,000

    525 Simonton St, Key West, FL 33040

    11beds
    3,034sqft
    : 
    Single Family Residence
    Built in 1889
    8,269 Square Feet Lot
    $7,169,900 Zestimate®
    $2,635/sqft
    $-- HOA

    What's special

    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.
    48 days
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    Zillow last checked: 7 hours ago

    Listing updated: June 30, 2025 at 08:01pm

    Listed by:

    Paige Bethel 305-395-0550,

    Island Home Realty Inc.

    Source: FLKMLS,MLS#: 615623MLS LogoOriginating MLS: Key West Association
    Travel times

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 525 Simonton St.

    Next available tour time:Tomorrow at 11am

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 11
    • Bathrooms: 11
    • Full bathrooms: 11
    Cooling
    • Central Air, Ductless
    Appliances
    • Included: Dryer, Stainless Steel Appliance(s), Freezer, Microwave, Refrigerator, Dishwasher
    Features
    • Storage, Built-in Cabinets
    • Windows: Drapes/Blinds Incl, Window Treatments, Skylight(s)
    • Furnished: Yes
    Interior area
    • Total interior livable area: 3,034 sqft

    Property

    Parking
    • Total spaces: 4
    • Parking features: Open, Off Street
    • Has uncovered spaces: Yes
    Features
    • Levels: 3 Stories
    • Stories: 3
    • Exterior features: Storage
    • Has private pool: Yes
    • Pool features: Heated, In Ground, Decked, Concrete
    • Fencing: Fenced
    • Water view: None
    • Waterfront features: None, Dockage: None
    Lot
    • Size: 8,269 Square Feet
    • Features: Less Than 1/4 Acre
    Details
    • Parcel number: 00009240000000
    • Zoning: HRCC
    • Zoning description: Historic Residential Commercial Core

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • Frame, Hardi Board Siding
    Condition
    • Year built: 1889

    Utilities & green energy

    • Sewer: Public Sewer
    • Utilities for property: Buyer to Verify

    Community & HOA

    Community
    • Security: Smoke Detector(s)
    • Subdivision: Old Town - Unrecord (1.0)
    HOA
    • Has HOA: No
    • Services included: None
    Location
    • Region: Key West

    Financial & listing details

    • Price per square foot: $2,635/sqft
    • Annual tax amount: $51,759
    • Date on market: 7/1/2025
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