For sale Residential

Listed Nov 2, 2026

$5,365,000 Est. $35,485/mo

806 Truman Avenue

  • 5

    Beds

  • 6

    Baths

  • 3,223

    Sq ft

The story

Experience the best of Old Town Key West at 806 Truman Avenue, a beautifully appointed transiently-licensed residence offering the rare combination of luxury island living and proven rental performance. This distinctive five-bedroom home features approximately 3,223 square feet of living space, thoughtfully designed for both private enjoyment and gracious entertaining. Tropical landscaping, covered porches, a private pool and spa, and separate guest accommodations create a relaxed resort atmosphere with the privacy and character buyers seek in a premier Key West property.Offered furnished, the residence is well suited as a primary home, second home, or high-end vacation rental. The property generated more than $400,000 in rental revenue in 2025, adding meaningful investment appeal to its lifestyle advantages.Ideally located in the heart of Old Town in the 'X' zone, 806 Truman Avenue places owners and guests close to Key West's renowned dining, galleries, entertainment, beaches, and historic attractions.For the buyer seeking a refined island residence with transient-rental capability, established revenue, and exceptional Old Town appeal, 806 Truman Avenue presents a truly compelling opportunity.

Facts & features

Home type

Residential

Year built

1918

Price per sq ft

$1,665

Mortgage calculator

Estimated monthly payment

$35,485 /mo

7% rate · 30-yr fixed · 20% down

  • Principal & interest $28,555
  • Property tax $5,365
  • Insurance $1,565

Includes principal, interest, taxes & insurance.

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Listing Broker

Island Life Realty Experts

Broker Name

Island Life Realty Experts

Agent

Jimmy R Lane