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TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! 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.

Highlights

  • Commercial Sale
  • Built in 1912
  • 0.36 Acre Lot
  • Waterfront
  • 116 days on Market

  • Bedrooms
    6
  • Bathrooms
    5
  • Year Built
    1912
  • Stories
    2.0
  • Construction Materials
    Frame
  • Parking Features
    Off Street, Guest, Common
  • Appliances
    Dryer, Dishwasher, Refrigerator, Range
  • Cooling
    Ceiling Fan(s), Wall/Window Unit(s)

  • Acres
    0.36
  • Water Front
    Yes
  • View
    Bay


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Frequently Asked Questions

How do I schedule a tour of 901 Eisenhower Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 901 Eisenhower Dr.

They know commercial sales in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 901 Eisenhower Dr?

Click Ask a Question to talk with our team. You already know it is a 6 bed, 5 bath, listed for $4,750,000. We can talk through recent upgrades, potential seller motivation, how this commercial sale compares to others in Key West, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 901 Eisenhower Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 901 Eisenhower Dr at around $29,254. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 901 Eisenhower Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Monroe County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 901 Eisenhower Dr?

In most cases, yes. Whether 901 Eisenhower Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Key West's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 901 Eisenhower Dr?

We can handle that for you. Our preferred local agent specializes in commercial sales in Key West and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $4,750,000 with 3,118 sqft of space—that comes out to approximately $1,523 per square foot.

How long has this property been on the market?

901 Eisenhower Dr was listed on July 16, 2026, which means it's been on the market for 116 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1912, making it approximately 114 years old.

What is the lot size of this property?

901 Eisenhower Dr sits on a 0.36-acre lot, which is 15,682 square feet.

What are the property taxes for 901 Eisenhower Dr?

The most recent public record shows annual property taxes for 901 Eisenhower Dr were approximately $26,677. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 901 Eisenhower Dr still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Copyright 2026 Florida Keys Board of REALTORS®, Inc.