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416 Fleming St, Key West, FL - photo 1
Active
416 Fleming St, Key West, FL - photo 2
416 Fleming St, Key West, FL - photo 3
416 Fleming St, Key West, FL - photo 4
416 Fleming St, Key West, FL - photo 5
+38

$3,500,000

5 beds5 baths2,575 sqft|620434 MLS#

416 Fleming St, Key West, FL 33040

Est.$21,000/moGet pre-qualified

Single Family Residence

Residential

Built in

1938

Lot size

6,534 sqft

Price/sqft

$1359

HOA

None

Listed by: Robin G Nilsson 239-221-4230, Keller Williams Key West Compass Realty 305-292-0020

Source:Florida Keys MLS (FLKMLS)|MLS #620434

Get price drop alert on this property the moment it happen

Preferred Brokerage Partner

Kinsfolk Realty

Kinsfolk Signature Realty

What's special

First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most 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!

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Facts & features

Bedrooms & bathrooms

  • Bedrooms:5
  • Bathrooms:5
  • Full bathrooms:0

Heating

  • Has Heating:Yes

Interior area

  • Total structure area:2,575 sqft
  • Total interior livable area:2,575 sqft

Parking

  • Parking features:N/A
  • Garage spaces:0
  • Has attached garage:No

Lot

  • Size:6,534 sqft

Details

  • Parcel number:N/A

Type & style

  • Home type:Single Family Residence
  • Property subtype:Residential

Materials

  • • N/A

Condition

  • Year built:1938

Contact agent

Price history

DateEventPrice
9/17/2026Listed for sale$3,500,000$1359/sqft

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