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522 Simonton Street, Key West, FL 33040

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For Sale

$6,150,000

5 beds • 5 baths • 1 half baths • 3,342 sqft

Estimated Payment

$      /mo. †

APR for 30 years

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  • Single Family Detached
    Property type

  • $1,840.22
    Price per square foot

  • Over 50 Years Old
    Age

  • Hot Tub Spa
    Amenities

Explore this Property

Historic Luxury Meets Modern Elegance in Old Town Key West!Step into a piece of Key West history with this remarkable home built in 1869 by Robert Watson, now completely reimagined as a luxury retreat while preserving its historic charm. Located on iconic lower Simonton Street, X Flood, this 6,608 sq ft sanctuary boasts 3,342 sq ft of living space with 5 en-suite bedrooms, including two primary suites, each with its own unique luxuries. The 1st-floor suite offers a jetted shower with chromotherapy lighting, while the 2nd-floor suite includes a private porch and soaking tub.This estate blends old-world craftsmanship with modern amenities, featuring a gourmet chef's kitchen with Viking, KitchenAid, and Bosch appliances, plus a separate dining room with a private porch--perfect for morning coffee. The spacious great room, with 20-foot retractable doors, opens directly to the outdoor oasis where you'll find an 18,000-gallon saltwater pool with swim-up bar, waterfall, and color LED lighting, plus a separate spa for ultimate relaxation.The detached guest house with kitchenette is ideal for visitors or extended family. Entertain outdoors with the fully equipped outdoor kitchen and al-fresco dining areas surrounded by lush tropical landscaping for complete privacy.Historic touches, including restored windows, doors, and custom woodwork, blend seamlessly with modern upgrades like a whole-house Generac generator, hurricane shutters, and advanced smart-home technology--control everything from pool settings to security from your phone.With gated parking for 3 cars, EV charging station, and just steps from the best dining and entertainment in Key West, this estate offers the rare opportunity to own a piece of history while enjoying unparalleled luxury. Don't miss out on a home that offers everything you've been searching for, and more! Step into Luxury! For the Discerning Few: Arrange Your Exclusive Private Showing Today!Video Tour https://tinyurl.com/522Simon
MLS# 612059

Courtesy Of Berkshire Hathaway Keys Real Estate | Knight & Gardner Realty

(305) 294-5155

Property Features

  • Age
    Over 50 Years Old
  • Amenities
    Sprinkler System, Wet Bar, Ceiling Fan, Hot Tub Spa, Security System, Security System
  • Appliances
    Dishwasher, Dryer, Freezer, Garbage Disposer, Microwave, Range, Refrigerator, Washer
  • Architecture Style
    Other
  • Cooling System
    Ceiling Fan(s)
  • Lot Size
    0.15 Acres
  • Roof Type
    Metal
  • View Type
    Water

Map and Directions

Directions to 522 Simonton Street, Key West, FL 33040

Home seller CENTURY 21 All Keys, Inc.

Get to know the neighborhood. A local affiliated CENTURY 21 office will help you set up tours, give advice, and negotiate with sellers.

CENTURY 21 All Keys, Inc.

(305) 294-4200
Learn More About Us

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Monthly Payment Breakdown

  • Principle and Interest
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  • Hazard Insurance
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Calculators provided for estimating purposes only. Consult with your lender to determine precise payment requirements.

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Copyright © 2025 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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