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$2,895,000
726 Simonton Street
Key West, FL 33040
MLS# 622051
2 beds  |  2 baths  |  1472 sqft


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Property Description
Experience the character and charm of historic Old Town Key West at 726 Simonton Street, a distinctive two-story island residence featuring classic architecture, beautiful Dade County pine, and a thoughtfully executed nautical motif that celebrates the island's maritime heritage. Ideally situated in the heart of Old Town, this unique property places Key West's celebrated restaurants, galleries, shopping, entertainment, and waterfront attractions within easy walking or biking distance, while offering the privacy of your own tropical retreat. The first floor features inviting living spaces and a kitchen with French doors opening directly to the lush tropical backyard and private swimming pool. This seamless connection between indoor and outdoor living captures the relaxed island lifestyle that makes Key West so special. Upstairs, an additional living area and second kitchen provide a wonderful extension of the residence, complemented by a covered private deck overlooking Simonton Street. A finished loft, accessed by a traditional ship's ladder, adds another distinctive element to the home's nautical personality and provides additional flexible bonus space. Currently enjoyed as a single-family residence, the property offers interior access between both levels, along with a separate exterior entrance that allows for additional privacy and flexibility. Its Multi-Family Duplex zoning presents an added dimension of versatility for future owners. With its century-old Conch-house architecture, warm Dade County pine interiors, maritime-inspired details, and private tropical pool, 726 Simonton Street is a home that celebrates the history and individuality of Key West.

Details
Maps
Contract Information
Listing Board: Key West Association
Current Price: $2,895,000
Listing Date: 2026-11-12
List Price: $2,895,000
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: X
Alternate Key #: 1016179
Parcel #: 00015800000000
Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Deed Restrictions: Unknown
Legal: Kw Pt Lot 3 Sqr 2 Tr 4 G12-400 B Of W C-402 Or738-726 Or739-229 Or739-241 Or741-175 Or759-1033/34 Or759-1786 Or777-1035
Taxes: 4220.55
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 726
Street Name: Simonton
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unrecord (1.0)
Area: 01 - Key West
General Property Description
Realtor.COM Type: Multi-family
Waterfront: No
Control Depth: 0
Lot Size: 28 X 68
Lot SqFt: 1972
Pool: Yes
Total Units: 0
Acres: 0.04
SqFt Source: Tax Records
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Duplex
Year Built: 1918
Living Apx SqFt: 1472
Total Bedrooms: 2
Full Baths: 2
Total Baths: 2
Remarks & Misc
Remarks – Consumer: Experience the character and charm of historic Old Town Key West at 726 Simonton Street, a distinctive two-story island residence featuring classic architecture, beautiful Dade County pine, and a thoughtfully executed nautical motif that celebrates the island's maritime heritage. Ideally situated in the heart of Old Town, this unique property places Key West's celebrated restaurants, galleries, shopping, entertainment, and waterfront attractions within easy walking or biking distance, while offering the privacy of your own tropical retreat. The first floor features inviting living spaces and a kitchen with French doors opening directly to the lush tropical backyard and private swimming pool. This seamless connection between indoor and outdoor living captures the relaxed island lifestyle that makes Key West so special. Upstairs, an additional living area and second kitchen provide a wonderful extension of the residence, complemented by a covered private deck overlooking Simonton Street. A finished loft, accessed by a traditional ship's ladder, adds another distinctive element to the home's nautical personality and provides additional flexible bonus space. Currently enjoyed as a single-family residence, the property offers interior access between both levels, along with a separate exterior entrance that allows for additional privacy and flexibility. Its Multi-Family Duplex zoning presents an added dimension of versatility for future owners. With its century-old Conch-house architecture, warm Dade County pine interiors, maritime-inspired details, and private tropical pool, 726 Simonton Street is a home that celebrates the history and individuality of Key West.
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
Dryer: 1
Range: 1
Refrigerator: 1
Washer: 1
Other: Propane stove
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Ductless: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Tile: 1
Wood: 1
Building Style
Above Flood: Unknown
Stories: 2 Stories
Windows/Doors
French Doors: 1
Wood Windows: 1
Construction
Frame: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Negotiable: 1
Utilities
Elect Separate Meter: 1
FKAA: 1
Municipal Sewer: 1
Water Separate Meter: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Title
Negotiable: 1
Pool Info
In Ground: 1
Concrete: 1
Roof
Metal Roof: 1
Shutters
Panel: 1
Other: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: Homestead
Waterfront: None
Waterview: No Waterview
Dockage: None
Furnished: Negotiable
Cooling: Ceiling Fans(s); Ductless
Utilities: Elect Separate Meter; FKAA; Municipal Sewer; Water Separate Meter
Appliances: Dishwasher; Dryer; Range; Refrigerator; Washer
Pool Info: In Ground; Concrete
Construction: Frame
Shutters: Panel; Other
Floor: Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Land Size: Less Than 1/4 Acre
Title: Negotiable

Listing Office: Keller Williams Key West Compass Realty

Last Updated: November - 12 - 2026

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.