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2 Beds
2 Baths
1,472 sqft

$2,895,000

726 Simonton Street, Key West FL, 33040

Price per sqft$1,966.71
Built in1918
Property size1,472 sqft
Property typeMulti-family

Overview

Active

Listed Nov 12, 2026

Updated 4h ago

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.

$19,261/mo

Est. mortgage payment based on a $2,895,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
622051

Interior Features

Bedrooms
2
Bathrooms
2
Cooling
Yes
Basement
No

Exterior Features

Lot Size
0.05 Acres

Other Property Details

Taxes
$4,221
Tax Frequency
Annually
View
Yes
Pets Allowed
Yes
Pool
Yes
MLS provider logo

Listed by The Behmke Group with Keller Williams Key West Compass Realty
Listing Contact: 305-304-0999 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 11/12/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Florida Keys Board of REALTORS® all rights reserved.

Data last updated on 11/12/2026 at 7:20 PM UTC

 

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