522 Simonton St, Key West, FL 33040
Property image
Property image
OFF MARKET

522 Simonton St
Key West, FL 33040

Old Town
  • 5 Beds
  • 5.5 Baths
  • 3,342 sqft

$5,733,600

Trulia Estimate
as of Jul 31, 2026
Est. Refi. Payment $32,684/mo*
Refinance Your Home

$5,733,600

Trulia Estimate
as of Jul 31, 2026
Est. Refi. Payment $32,684/mo*
Refinance Your Home
5 Beds
5.5 Baths
3,342 sqft

Local Information

  • Map ViewExplore the area around 522 Simonton St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1869
Living Area
3,342 sqft
Price/Sqft
$1,716
Parking
Garage
HOA
None

About this House

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/522Si
522 Simonton St, Key West, FL 33040 is a 5 bedroom, 6 bathroom, 3,342 sqft single-family home in Old Town, built in 1869. It last sold for $5,700,000 on Mar 17, 2025 (7% below the $6,150,000 asking price). It is currently off market. The Trulia Estimate is $5,733,600, with a rent estimate of $7,830/month.

Home Details for 522 Simonton St

Interior Features

Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3342 Square Feet
Appliances & Utilities
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Ice Maker, Wine Cooler, Stainless Steel Appliance(s)DishwasherDisposalDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Has Heating Unspecified Type
Fireplace & Spa
Spa: HeatedHas a Spa
Gas & Electric
Electric: Cat 5
Windows, Doors, Floors & Walls
Flooring: Combination
Levels, Entrance, & Accessibility
Floors: Combination
View
No View
Security
Security: Security Gate, On Premises System, Security System

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, Deck, LanaiFencing: Fenced, PrivacyOther Structures: Guest HouseExterior: Bar, Built-in Barbecue, Rain Gutters, Lighting, Outdoor Kitchen, Outdoor Shower, Storage, Water DisplayHas a Private Pool
Parking & Garage
Has a GarageNo Attached GarageParking: Garage Door Opener
Pool
Pool: In Ground, Salt Water, Concrete, DeckedPool
Frontage
Not on Waterfront

Property Information

Year Built
Year Built: 1869
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Frame
Property Information
Parcel Number: 00009320000000

Price & Status

Price
List Price: $6,150,000

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Key WestCommunity: Old Town - Unlisted (1.0)

Building

Building Area
Building Area: 3342 Square Feet

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 6534 sqft

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 612059Attic: Pull Down Stairs
Last check for updates: about 18 hours ago
Listed by Lisa Swanson
Berkshire Hathaway HomeServices Knight & Gardner Realty
Bought with: outside of mls, Outside Of MLS
Source: FLKMLS, MLS#612059

Price History for 522 Simonton St

DatePriceEventSource
03/17/2025$5,700,000Sold
FLKMLS #612059
02/26/2025$6,150,000PendingFLKMLS #612059
11/01/2024$6,150,000Listed For SaleKey West AOR #612059
11/01/2024$6,105,000ListingRemovedFLKMLS #607237
09/03/2024$6,105,000Listed For SaleKey West AOR #607237
08/19/2024ListingRemovedKey West AOR #607237
06/17/2024$6,105,000PriceChange
Key West AOR #607237
11/01/2023$6,850,000Listed For SaleKey West AOR #607237
02/06/2018$1,300,000Sold
FLKMLS #122609
11/28/2017$1,495,000Listed For SaleAgent Provided
07/28/2017$1,495,000ListingRemovedAgent Provided
04/07/2016$1,495,000PriceChange
Agent Provided
01/02/2016$1,649,999Listed For SaleAgent Provided
03/28/2005$850,000Sold
N/A

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$18,538
Assessment$3,107,636
Home facts updated by county records

Comparable Sales for 522 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
400 Aronovitz Ln, Key West, FL
0.18
Single-Family Home
$3,300,000
05/21/26
5
6
3,667
1006 & 1008 Fleming St, Key West, FL
0.27
Single-Family Home
$4,425,000
05/26/26
4
4.5
3,336
525 Simonton St, Key West, FL
0.03
Single-Family Home
$6,500,000
06/17/26
11
11
3,034
517 Elizabeth St, Key West, FL
0.12
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
515 Amelia St, Key West, FL
0.46
Single-Family Home
$4,225,000
03/16/26
5
5.5
3,434
326 Caroline St, Key West, FL
0.32
Single-Family Home
$6,350,000
01/15/26
5
5.5
4,279
101 Admirals Ln, Key West, FL
0.32
Single-Family Home
$6,300,000
10/10/25
5
4
3,173
1109 Fleming St, Key West, FL
0.48
Single-Family Home
$5,745,000
03/26/26
6
6.5
3,443
407-415 Olivia St, Key West, FL
0.38
Single-Family Home
$3,500,000
08/08/25
6
5
3,171
316 Southard St, Key West, FL
0.22
Single-Family Home
$3,500,000
10/20/25
3
3.5
2,532

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 522 Simonton St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Old Town
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Old Town

At least 1 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say people would walk alone at night

  • 100 % Say there are sidewalks

  • 100 % Say streets are well-lit

  • 100 % Say neighbors are friendly

  • 100 % Say it's quiet

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say parking is easy

  • 100 % Say car is needed

  • 67 % Say there's holiday spirit

  • 60 % Say they plan to stay for at least 5 years

  • 50 % Say there are community events

  • 50 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • David Atkinson
    "I so look forward to getting to Key West. I volunteer at the Tropic and love it. It feels like home."
    0
    Flag
  • Trulia User
    "Dogs are welcomed at 90% of the restaurants. Everyone will remember your dogs name but not yours! I love living here with my dog Jack."
    0
    Flag
  • Trulia User
    "Key West is a huge dog community. They even are allowed in some restaurants . When I walk my dog on the main tourist street (Duval St) I get stopped many times from people wanting to pet my dog. A group of dog owners meet up at the park in the morning every day."
    0
    Flag
  • Sgarvin3281
    " Bikes are all you need small island. Safe and secure. No commute I do t work here it is a vacation community."
    0
    Flag
  • Trulia User
    "Everywhere dogs are welcome here in key west, Florida. Come joining us here in key west. Most food and service places, boats, and entertainment venues are good with dogs."
    0
    Flag
  • Trulia User
    "Feels very safe, super clean, super walkable in old town, and Catholic school looks very vibrant. "
    0
    Flag
  • Trulia User
    "Great people, great neighborhood, great police, family friendly events. Lots of things to do within a decent drive. Very family friendly generally "
    0
    Flag
  • Key W. B. F.
    "Gatherings on the local Mangia Mangia bench at 900 Southard street, safe & friendly town. Feel connected & welcomed in Key West. Enjoy the peaceful neighborhood & the tropical weather! You can walk or bike to everything you need & want!"
    0
    Flag
  • Kfowler
    "I am not currently aware of any neighborhood events that would bring the neighbors closer. However, both my husband and I would be open to any such event that would do so and would improve the neighborhood. The area is beautiful and well maintained, with a few exceptions. "
    2
    Flag
  • Hannah B.
    "Vintage Cottage houses, small island feel, Duval Street in a few minutes with hundreds of worldly trendy restaurants "
    6
    Flag
  • Drlynmar
    "Neighborhood newsletter. Proximity to OldTown events, festivals and parades. Walk to everything. Parks, beaches, dog park. Grocery and restaurant delivery. "
    2
    Flag
  • Venomousink1970
    "the neighborhood is great I myself do not like living in Key West anymore and looking to relocate and Asheville North Carolina or the surrounding areas people are very friendly here except for the homeless vagrants that beg for money and yell at you when you don't give them any"
    0
    Flag
  • Lorettamdt
    "Old Town is historic. Our neighbors are friendly. We walk everywhere. No need for a car. Restaurants are within walking distance. Beaches are a bicycle ride away. "
    0
    Flag
  • mangiamangia
    "Lived in this neighborhood for 25 years. Walk and anywhere. Far enough of Duval to escape the noise and drunks."
    0
    Flag
  • Sajsk
    "vacationed in that area -- charming and great location and amenities, yet quiet."
    0
    Flag
  • Rjones
    "This is a great street and great neighborhood. Qiet, yet close enough to Duval and White streets to enjoy all Key West has to offer. "
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

19 pet-friendly rentals in Key West, FL

Explore by feature - Garage

7 rentals with a garage in Key West, FL

Explore by feature - Air Conditioning

96 rentals with air conditioning in Key West, FL

Explore by feature - Pool

66 rentals with a pool in Key West, FL

Explore by feature - Washer/dryer

72 rentals with a washer/dryer in Key West, FL

Explore by feature - Outdoor Space

11 rentals with an outdoor space in Key West, FL

Homes for sale near 522 Simonton St

Skip to last item
Skip to first item

Off Market Homes Near 522 Simonton St

Skip to last item
Skip to first item
MLS Internet Data Exchange (IDX) information is provided exclusively 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, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.