Welcome to 103 Front Street, an extraordinary residence tucked inside Old Town’s Truman Annex and appropriately located within a community known as The Foundry.
Built in 1918, this home dates to the era when this part of Key West was an active U.S. military installation. The Truman Annex waterfront served the military for generations, eventually becoming an important naval and submarine support facility. Historic records document foundry, machine-shop and other industrial buildings throughout the former base—places where work supporting naval ships and submarines was carried out for decades.
And the story didn’t end when the Navy left. After the base was largely decommissioned in the 1970s, some of its old industrial spaces became inexpensive studios for Key West artists. The Key West Art & Historical Society describes this period as a creative “Golden Age,” with artists working in the former foundry, warehouses and machine shops before Truman Annex was redeveloped.
Today, 103 Front Street preserves that remarkable industrial character while living as an exceptional private residence. Thick brick walls, soaring wood ceilings, massive exposed beams, dramatic ironwork and towering windows tell the story of another era—while a meticulous restoration introduced the comfort and sophistication expected of a modern Key West estate. The residence offers 3 bedrooms, 3 baths and approximately 3,000 square feet, all situated across two lots.
Outside, a large pool and spa are surrounded by mature tropical landscaping, creating a completely private retreat just steps from the waterfront, Fort Zachary Taylor, restaurants, galleries and everything we love about Old Town.
Offered at $6,850,000.
This isn’t simply a beautiful Key West home.
It’s a piece of the island’s story—reimagined for the next chapter.
103 Front Street | Old Town Key West
3 BD | 3 BA | 3,000 SF | Pool + Spa | Double Lot
Listed by Key West Sisters | Preferred Properties Key West
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