$4,750,000
 $25,499 est/mo Sourced by Back At You

901 Eisenhower Drive,KEY WEST, FL 33040

KEY WEST, FL 33040

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Description

A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

Details

MLS #620661
Listing TypeFor Sale
StyleDuplex
Sub-TypeResale
StatusActive
Year1912
Days On Site37
Listing Provided ByKeller Williams Key West Compass Realty | Sarah Dolson

Features

Bed(s)7
Bath(s) 5 Total
SQ Feet3,118
Units5
ZoningCG - General Commercial
Acreage0.36
Water FrontYes
Property ViewBay

Taxes

Property26676

Area Information

StateFL
CountyMonroe
CityKEY WEST
Zip Code33040
Area01 Key West
Community NameBenj Alburys Subd (2.0)
Listing VS Median (in Benj Alburys Subd (2.0))
Price:
$4,750,000
low | high
Med:
$3,324,500
80.010526315789% of Average
sqft:
3,118
low | high
Med:
2,418
72.46632456703% of Average
$ / sqft:
$1,523
low | high
Med:
$1,315
63.69995402017% of Average
On site:
37
low | high
Med:
107
34.579439252336% 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
Area01 Key West
Community NameBenj Alburys Subd (2.0)
Listing VS Median (in Benj Alburys Subd (2.0))
Price:
$4,750,000
low | high
Med:
$3,324,500
80.010526315789% of Average
sqft:
3,118
low | high
Med:
2,418
72.46632456703% of Average
$ / sqft:
$1,523
low | high
Med:
$1,315
63.69995402017% of Average
On site:
37
low | high
Med:
107
34.579439252336% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $3.562M - $5.937M
sqft: 2,000 - 3,500
Nearby Listings Property ImageNearby Listings Details
901 Eisenhower Drive Property Photo 1
$4,750,000
901 Eisenhower Drive
Key West, FL 33040
Listing Updated: July 16, 2026 at 6:52:53 PM PDT