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
Single-familyProperty Type
1869Year Built
6,610 sq ftLot Size
$1,729Est. Price/Sq.Ft.
3 spacesParking
Listed by Lisa Swanson• Berkshire Hathaway HomeServices Knight & Gardner Realty
The city of Key West Planning Department has indicated that this property qualifies for transient license receivership. Possible owner financing with 30% down. This is one of the most historic and iconic homes in Key West. Built in the 1860’s there have only been two families to reside here since the home was built. The architecture is unique for Key West with a stepped façade and four separate porches on the front of the house. Perfectly sited with ample sized front and side yards and large rear yard. Architect conceptual plans are available. The property requires a complete renovation and is uninhabitable in its current condition.
Public Records
Mar 28, 2005
Sold
$850,000
$254/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$39,289 (+111.9%)
$1,908,638 + $2,927,018
$4,835,656
2025
$18,538 (+3.2%)
2024
$17,959 (+1.5%)
2023
$17,689 (+19.5%)
2022
$14,797 (+203.5%)
2021
$4,876 (+1.7%)
2020
$4,795 (+1.5%)
2019
$4,724 (−24.5%)
2018
$6,257 (−10.5%)
$639,504 + $9,371
$648,875
2017
$6,995 (−11.2%)
$639,504 + $86,918
$726,422
2015
$7,874 (+3.6%)
$567,849 + $80,191
$648,040
2014
$7,600
Tax history for 522 Simonton St
Year
Property tax
Land + Additions
Assessment*
2026
$39,289 (+111.9%)
$1,908,638 + $2,927,018
$4,835,656
2025
$18,538 (+3.2%)
2024
$17,959 (+1.5%)
2023
$17,689 (+19.5%)
2022
$14,797 (+203.5%)
2021
$4,876 (+1.7%)
2020
$4,795 (+1.5%)
2019
$4,724 (−24.5%)
2018
$6,257 (−10.5%)
$639,504 + $9,371
$648,875
2017
$6,995 (−11.2%)
$639,504 + $86,918
$726,422
2015
$7,874 (+3.6%)
$567,849 + $80,191
$648,040
2014
$7,600
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
The historic neighborhood commercial district Truman/Simonton HNC-1 consists of Simonton, Truman Avenue, and White Street South Corridors. The HNC-1 district is located along major segments of Simonton Street, from Caroline South to United Street; Truman Avenue, from Simonton Street northeast to White Street; and White Street, from Truman Avenue south to United Street; and generally includes larger scale commercial uses oriented toward the motoring public.
Permitted uses
Include but are not limited to:
Religious facility
Commercial & retail
Hospital / medical center
Housing-Group
Housing-Single unit
Housing-Multiple units
Hotel / motel
Office
Veterinary clinic
Park & open space
May 21, 2026 • Final
Electrical
Electrical
May 21, 2026 • Final
Electrical
Electrical
Pool and hot tub
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Property details
Parking
Parking / Garage Information
Vehicle Storage: Auto Door Opener, Off Street Parking
Vehicle Storage: Car(s): 3
Interior
Virtual Tour
Interior Features
Interior Features: Drapes/Blinds Incl, Window Treatments, Quartz Countertops, Pull Down Stairs, Bar, Built-in Cabinets, Walk-in Closet, Storage, Smoke Alarms, Security System, Dade County Pine, Pantry, Cathedral Ceilings, Wet Bar
Green Features: Interior: Tankless Hot Wtr Htr, LED Lighting, Dual Flush, Programmable Thermst