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522 Simonton Street, Key West, FL 33040

$5,700,000
Property Type: Residential Bedrooms: 5 Baths: 6 Square Footage: 3,342 Lot Size (sq. ft.): 6,610 Status: Closed
Current Price: $5,700,000 List Date: 11/01/2024 Last Modified: 10/03/2025

Description

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

More Information MLS# 612059

Contract Information

Listing Board: Key West Association Current Price: $5,700,000 Listing Date: 2024-11-01 Sold Price: $5,700,000

Location, Tax & Legal

KW Neighborhood: Old Town-N of Truman City: KEY WEST Mile Marker: 1 Marathon Neighborhood: N/A Side: Bay/Gulf Flood Zone: X Alternate Key #: 1009571 Parcel #: 00009320-000000 Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med Deed Restrictions: Unknown Legal: KW PT LOT 1 SQR 50 G26-267 COUNTY JUDGES SERIES 3-M9 COUNTY JUDGES DOCKET 1-73-242 Taxes: 17688.95 Tax Year: 2023 Pub Sewer HkUp: Yes Street #: 522 Street Name: Simonton Street Suffix: Street Key/Island: Key West State/Province: FL Zip Code: 33040 County: Monroe Subdivision: Old Town - Unlisted (1.0) Area: 02 - Key West

General Property Description

Realtor.COM Type: Residential - Single Family Waterfront: No Control Depth: 0 Lot Size: 58.5 x 113 Lot SqFt: 6610 Pool: Yes Total Units: 0 Acres: 0.15 SqFt Source: Property Data Card Rentals Allowed: With Restrictions Min Rental Days: 28 Style: Single Family Year Built: 1869 Living Apx SqFt: 3342 Total Bedrooms: 5 Full Baths: 5 Half Baths: 1 Total Baths: 6

Remarks & Misc

Remarks – Consumer: 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

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee $: 0

Fee Includes

None: 1

Dockage

None: 1

Tax Exemptions

Homestead: 1

Appliances

Dishwasher: 1 Disposal: 1 Dryer: 1 Freezer: 1 Gas Appliances: 1 Ice Machine: 1 Microwave: 1 Oven: 1 Range: 1 Refrigerator: 1 Stainless Steel Appliance(s): 1 Washer: 1 Wine Cooler: 1

Pets

Pets Allowed: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1

Heating

Central: 1

Waterfront

None: 1

Waterview

No Waterview: 1

Floor

Combo: 1

Interior Features

Bar: 1 Built-in Cabinets: 1 Cathedral Ceilings: 1 Dade County Pine: 1 Drapes/Blinds Incl: 1 Pantry: 1 Pull Down Stairs: 1 Quartz Countertops: 1 Security System: 1 Smoke Alarms: 1 Storage: 1 Walk-in Closet(s): 1 Wet Bar: 1 Window Treatments: 1

Specialty Rooms

Guest/Servant Qtrs: Legal Laundry Room: 1

Building Style

Above Flood: Yes Stories: 2 Stories

Windows/Doors

Double Hung Windows: 1 French Doors: 1 Glass Doors: 1 Impact Rstnce Doors: 1 Impact Rstnce Window: 1 Sliding Glass Doors: 1 Wood Windows: 1

Vehicle Storage

Car(s): 3 Auto Door Opener: 1 Off Street Parking: 1

Security

Electric Gate: 1 On Premises System: 1

Construction

Frame: 1

Land Size

Less Than 1/4 Acre: 1

Furnished

Negotiable: 1

Terms

Cash: 1 Conventional: 1

Utilities

FKAA: 1 Municipal Sewer: 1 Propane: 1 Whole House Generatr: 1

Porch/Balcony

Deck: 1 Open Porch/Balcony: 1

Title

Negotiable: 1

Exterior Features

Bar: 1 Built-in Grill: 1 Detached Guest Qtrs: 1 Fencing: 1 Hot Tub: 1 Lanai: 1 Lighting: 1 Outdoor Kitchen: 1 Outdoor Shower: 1 Privacy Wall/Fence: 1 Rain Gutters: 1 Sprinkler System: 1 Storage: 1 Water Display: 1

Pool Info

In Ground: 1 Salt Water: 1 Heated: Yes Concrete: 1 Decked: 1

Pre-Wired

Cat 5: 1

Roof

Metal Roof: 1

Shutters

Bahama: 1 Panel: 1

GF-Interior Features

Dual Flush: 1 LED Lighting: 1 Programmable Thermst: 1 Tankless Hot Wtr Htr: 1

Status Change Info

Sold Date: 2025-03-17 Sold Price: $5,700,000 Status: Closed

Property Features

Fee Includes: None Tax Exemptions: Homestead Waterfront: None Waterview: No Waterview Dockage: None Vehicle Storage: Auto Door Opener; Off Street Parking Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air Heating: Central Utilities: FKAA; Municipal Sewer; Propane; Whole House Generatr Interior Features: Bar; Built-in Cabinets; Cathedral Ceilings; Dade County Pine; Drapes/Blinds Incl; Pantry; Pull Down Stairs; Quartz Countertops; Security System; Smoke Alarms; Storage; Walk-in Closet(s); Wet Bar; Window Treatments Pre-Wired: Cat 5 Specialty Rooms: Laundry Room Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Ice Machine; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler Exterior Features: Bar; Built-in Grill; Detached Guest Qtrs; Fencing; Hot Tub; Lanai; Lighting; Outdoor Kitchen; Outdoor Shower; Privacy Wall/Fence; Rain Gutters; Sprinkler System; Storage; Water Display Pool Info: In Ground; Salt Water; Concrete; Decked Construction: Frame Shutters: Bahama; Panel Floor: Combo Roof: Metal Roof Pets: Pets Allowed Security: Electric Gate; On Premises System Land Size: Less Than 1/4 Acre Terms: Cash; Conventional Title: Negotiable GF-Interior Features: Dual Flush; LED Lighting; Programmable Thermst; Tankless Hot Wtr Htr
Listing Office: Berkshire Hathaway HomeServices Knight & Gardner Realty
Last Updated: October - 03 - 2025
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