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
Sold for $5,700,000
$5,700,000
522 Simonton St, Key West, FL 33040
5beds
3,342sqft
Single Family Residence
Built in 1869
6,534 Square Feet Lot
$5,600,400 Zestimate®
$1,706/sqft
$7,830 Estimated rent
Home value
$5,600,400
$4.98M - $6.27M
$7,830/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: October 03, 2025 at 07:33am
Listed by:
Lisa Swanson,
Berkshire Hathaway HomeServices Knight & Gardner Realty
Bought with:
outside of mls
Outside Of MLS
Source: FLKMLS,MLS#: 612059
Originating MLS: Key West Association
Originating MLS: Key West AssociationFacts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Heating
- Central
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Stainless Steel Appliance(s), Wine Cooler, Ice Machine, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer, Tankless Water Heater
- Laundry: Laundry Room
Features
- Quartz Countertops, Bar, Built-in Cabinets, Walk-In Closet(s), Storage, Dade County Pine, Pantry, Cathedral Ceiling(s), Wet Bar, Wired for Data
- Flooring: Combination
- Doors: Impact Rstnce Doors, Sliding Glass Doors, Glass Doors, French Doors
- Windows: Drapes/Blinds Incl, Window Treatments, Double Hung Windows, Impact Rstnce Window, Wood Frames, Bahama, Panel
- Attic: Pull Down Stairs
Interior area
- Total interior livable area: 3,342 sqft
Property
Parking
- Total spaces: 3
- Parking features: Garage Door Opener, Off Street
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Lanai, Open Porch/Balcony, Deck
- Exterior features: Bar, Water Display, Storage, Sprinkler System, Outdoor Shower, Outdoor Kitchen, Lighting, Rain Gutters, Built-in Barbecue
- Has private pool: Yes
- Pool features: Heated, In Ground, Decked, Concrete, Salt Water
- Has spa: Yes
- Spa features: Private
- Fencing: Privacy,Fenced
- Water view: None
- Waterfront features: None, Dockage: None
Lot
- Size: 6,534 sqft
- Dimensions: 58.5 x 113
- Features: Less Than 1/4 Acre
Details
- Additional structures: Guest House, Detached Guest Qtrs
- Parcel number: 00009320000000
- Zoning: HNC
- Zoning description: (1-3) Hist Nghborhd Comml 1 - 3 Coastal Med
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Frame
- Roof: Metal
Condition
- Year built: 1869
Utilities & green energy
- Electric: Generator
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA, Propane
Green energy
- Energy efficient items: Lighting, Thermostat
- Water conservation: Dual Flush
Community & neighborhood
Security
- Security features: Smoke Detector(s), Security System, Electric Gate, On Premises System
Location
- Region: Key West
- Subdivision: Old Town - Unlisted (1.0)
HOA & financial
HOA
- Has HOA: No
- Services included: None
Other
Other facts
- Listing terms: Cash,Conventional
Price history
| Date | Event | Price |
|---|---|---|
| 3/17/2025 | Sold | $5,700,000-7.3%$1,706/sqft |
Source:  FLKMLS #612059 Report a problem | ||
| 2/26/2025 | Pending sale | $6,150,000$1,840/sqft |
Source: FLKMLS #612059 Report a problem | ||
| 11/1/2024 | Listed for sale | $6,150,000+0.7%$1,840/sqft |
Source:  Key West AOR #612059 Report a problem | ||
| 11/1/2024 | Listing removed | $6,105,000$1,827/sqft |
Source: FLKMLS #607237 Report a problem | ||
| 9/3/2024 | Listed for sale | $6,105,000$1,827/sqft |
Source: Key West AOR #607237 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $18,538 +3.2% | $2,226,766 +2.9% |
| 2024 | $17,959 +1.5% | $2,164,010 +3% |
| 2023 | $17,689 +19.5% | $2,100,981 +18% |
Find assessor info on the county website
Neighborhood: Old Town
Nearby schools
GreatSchools rating
- 4/10Gerald Adams Elementary SchoolGrades: PK-5Distance: 3.9 mi
- NAMonroe Virtual FranchiseGrades: K,2-3,5-12Distance: 0.6 mi
- 3/10Key West High SchoolGrades: 9-12Distance: 1.5 mi
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Estimated market value
$5,600,400
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$5,600,400
- Florida
- Monroe County
- Key West
- 33040
- Old Town
- 522 Simonton St