
522 Simonton St Key West, FL 33040
Old Town NeighborhoodEstimated Value: $4,738,368 - $5,828,000
About This Home
As of March 2025Historic 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
Last Agent to Sell the Property
Berkshire Hathaway HomeServices Knight & Gardner Realty License #BK3226537 Listed on: 11/01/2024

Last Buyer's Agent
outside of mls
Outside Of MLS
Ownership History
Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Purchase Details
Similar Homes in Key West, FL
Home Values in the Area
Average Home Value in this Area
Purchase History
Date | Buyer | Sale Price | Title Company |
---|---|---|---|
David Tenney Living Trust | $5,700,000 | None Listed On Document | |
Anderson Glenn R | $1,300,000 | Attorney | |
Framarin Robert | -- | -- | |
Framarin Robert | $850,000 | -- |
Mortgage History
Date | Status | Borrower | Loan Amount |
---|---|---|---|
Open | David Tenney Living Trust | $3,800,000 | |
Previous Owner | Anderson Glenn R | $500,000 | |
Previous Owner | Anderson Catherine Mary | $1,250,000 | |
Previous Owner | Anderson Glenn R | $910,000 | |
Previous Owner | Framarin Robert | $1,000,000 |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
03/17/2025 03/17/25 | Sold | $5,700,000 | -7.3% | $1,706 / Sq Ft |
02/24/2025 02/24/25 | Pending | -- | -- | -- |
11/01/2024 11/01/24 | For Sale | $6,150,000 | +373.1% | $1,840 / Sq Ft |
02/06/2018 02/06/18 | Sold | $1,300,000 | -21.2% | $490 / Sq Ft |
12/19/2017 12/19/17 | Pending | -- | -- | -- |
12/30/2015 12/30/15 | For Sale | $1,649,999 | -- | $622 / Sq Ft |
Tax History Compared to Growth
Tax History
Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
---|---|---|---|---|
2024 | $17,689 | $2,164,010 | -- | -- |
2023 | $17,689 | $2,100,981 | $0 | $0 |
2022 | $14,797 | $1,779,931 | $0 | $0 |
2021 | $4,876 | $548,603 | $0 | $0 |
2020 | $4,795 | $541,135 | $0 | $0 |
2019 | $4,724 | $528,969 | $0 | $0 |
2018 | $6,257 | $648,875 | $639,504 | $9,371 |
2017 | $6,995 | $726,422 | $0 | $0 |
2016 | $6,704 | $648,040 | $0 | $0 |
2015 | $7,875 | $764,144 | $0 | $0 |
2014 | $7,600 | $728,088 | $0 | $0 |
Agents Affiliated with this Home
-
Seller's Agent in 2025
Lisa Swanson
Berkshire Hathaway HomeServices Knight & Gardner Realty
(305) 924-3777
18 in this area
132 Total Sales
-
o
Buyer's Agent in 2025
outside of mls
Outside Of MLS
-
Seller's Agent in 2018
Roger Emmons
Truman & Co. (KW)
(305) 304-7446
27 in this area
91 Total Sales
-
K
Seller Co-Listing Agent in 2018
Kenneth Edwards
Truman & Co. (KW)
-
G
Buyer's Agent in 2018
Gary Thomas
Dunaway McKenzie Realtors (KW)
Map
Source: Key West Association of REALTORS®
MLS Number: 612059

APN: 00009320-000000
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