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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$5,700,000
522 Simonton Street
Key West, FL 33040
MLS# 612059
Status: Closed
5 beds  |  6 baths  |  3342 sqft

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522 Simonton St Key West
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522 Simonton St Key West Pool Pool Spa Spa Pool Firepit Front Front Sunset Kitchen Living Front Front Drioveway electric gate Best Location Best location Pool Pool Spa Spa Outdoor entertaining Outdoor kitchen 522 Simonton St (HD) 126 Outdoor shower Front Front Staircase replica of 1902 addition 522 Simonton St (HD) 087 522 Simonton St (HD) 088 522 Simonton St (HD) 089 Open Living with wet bar, copper sink Living Living Gourmet kitchen 522 Simonton St (HD) 098 Kitchen Kitchen Viking Gas Cooktop and Double Ovens Separate Butlers Pantry Outdoor kitchen Separate Guest Suite Separate Guest Suite Separate Guest Suite bathroom ensuite Separate Guest Suite walk in closet Ground Floor Primary Suite Ground Floor Primary Suite Ground Floor Primary walk in closet Walk in closet 522 Simonton St (HD) 132 Upstairs Primary Suite Upstairs Primary Suite Upstairs Primary Suite Upstairs Primary walk through closet Upstairs Primary Bathroom ensuite 522 Simonton St (HD) 148 Upstairs porch Upstairs 5th Bedroom Suite Upstairs 5th Bedroom suite Upstairs 5th bedroom ensuite bathroom Upstairs laundry Upstairs 4th bedroom suite 522 Simonton St (HD) 159 522 Simonton St (HD) 160 522 Simonton St (HD) 011 Twilight waterfall Twilight pool Twilight spa Firepit Sunset Aerial

Property 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

Details
Maps
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

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.


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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)