$3,500,000
 $18,789 est/mo Sourced by Back At You

416 Fleming Street,KEY WEST, FL 33040

KEY WEST, FL 33040

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Description

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!

Details

MLS #620434
Listing TypeFor Sale
StyleDuplex
Sub-TypeResale
StatusActive
Year1938
Days On Site59
Listing Provided ByKeller Williams Key West Compass Realty | Robin G Nilsson

Features

Bed(s)5
Bath(s) 5 Total
SQ Feet2,575
ZoningHRO - Historic Residential/Offic
Acreage0.15
Water FrontNone
Property ViewNo Waterview

Taxes

Property19952

Area Information

StateFL
CountyMonroe
CityKEY WEST
Zip Code33040
Area02 Key West
Community NameOld Town Unlisted (1.0)
Listing VS Median (in Old Town Unlisted (1.0))
Price:
$3,500,000
low | high
Med:
$859,000
100% of Average
sqft:
2,575
low | high
Med:
762
100% of Average
$ / sqft:
$1,359
low | high
Med:
$1,127
67.06317960255% of Average
On site:
59
low | high
Med:
201
29.353233830846% of Average
Sourced by Back At You

Market Activity 33040

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Learn More About This Property

StateFL
CountyMonroe
CityKEY WEST
Zip Code33040
Area02 Key West
Community NameOld Town Unlisted (1.0)
Listing VS Median (in Old Town Unlisted (1.0))
Price:
$3,500,000
low | high
Med:
$859,000
100% of Average
sqft:
2,575
low | high
Med:
762
100% of Average
$ / sqft:
$1,359
low | high
Med:
$1,127
67.06317960255% of Average
On site:
59
low | high
Med:
201
29.353233830846% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $2.625M - $4.375M
sqft: 1,500 - 3,000
Nearby Listings Property ImageNearby Listings Details
518 Duval Street Property Photo 1
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518 Duval Street
Key West, FL 33040
423 Duval Street B Property Photo 1
$17,600
423 Duval Street B
Key West, FL 33040
400 Duval Street B Property Photo 1
$18,052
400 Duval Street B
Key West, FL 33040
Listing Updated: July 31, 2026 at 6:28:14 AM PDT