For sale Residential

Listed Jun 28, 2026

$3,500,000 Est. $23,149/mo

416 Fleming Street

  • 5

    Beds

  • 5

    Baths

  • 2,575

    Sq ft

The story

Unbeatable Old Town Location only 3 properties to Duval Street! Live extraordinary in this Historic Victorian estate right in the middle of everything! 416 Fleming is a rare opportunity to own one of Key West's iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches, timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

Facts & features

Home type

Residential

Year built

1938

Price per sq ft

$1,359

Parking

4-car garage

Included features

  • Cooling

    Central Air, Wall/Window Unit(s)

  • Heating

    Electric

  • Appliances

    Dryer, Microwave, Oven, Refrigerator, Dishwasher

  • Flooring

    Tile, Wood

  • Roof

    Metal

  • Exterior

    Storage, Rain Barrel/Cistern(s)

  • Water Source

    Well

  • Sewer

    Public Sewer

Mortgage calculator

Estimated monthly payment

$23,149 /mo

7% rate · 30-yr fixed · 20% down

  • Principal & interest $18,628
  • Property tax $3,500
  • Insurance $1,021

Includes principal, interest, taxes & insurance.

Your Property Journey

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Listing Broker

Keller Williams Key West Compass Realty

Broker Name

Keller Williams Key West Compass Realty

Agent

Robin G Nilsson