Eyebrow Raising Historical Shelter in Key West

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Key West

Depending on how old you are, the mention of Key West, Florida, either makes you think of Ernest Hemingway, Tennesee Williams, or Jimmy Buffet — the celebrities who have, at various points in time, made the island home. 

Discovered by Ponce de Leon, Key West was claimed by Spain in 1513 and named Las Martines. By 1815, it was granted to Juan Pablo Salas for his service to Spain, who sold it to John W. Simonton of Alabama for $2,000 in 1821. The U.S. took possession of it a year later, and by 1823, it was a port of entry to the U.S. and saw its first customs house and naval depot established. 

Just six years later, the island got its first post office and by 1832, it was a full-fledged city — and at one point, the wealthiest and largest in Florida.

But no offense to Messrs. Hemmingway, Williams, and Buffett, the island’s first “celebrities” were more likely pirates such as Blackbeard and Jean LaFitte, who called Key West home in the early 1800s.

But as Old Town (one of the islands earliest neighborhoods) sprung up, an architectural detail that would become peculiar to the island emerged — the eyebrow house.

Technically a Classical Revival style home, the eyebrow houses are named as such because they have a gable roof extension that forms a large awning of sorts across the top floor windows — an eyebrow, if you will.

The true eyebrow houses, the Gator Preservationist writes, “are side oriented gable-roofed buildings usually five bays wide and 1 1/2 or two stories tall.”

The reason for it, as far as historians can figure, was climate-related. 

“Although this awninglike feature restricts the view from the upstairs windows, it keeps out direct sunlight and has a welcome cooling effect,” writes Alex Caemmerer in his “The Houses of Key West.”

“Most of Key West’s historic residences were built with one goal: block out the sun. Eyebrow houses take this to the extreme,” explains the Gator Preservationist. “Back in the late 1800s when most of these houses were constructed, sun-shading vegetation was sparse in Key West.”

“There is no natural source of freshwater on the island, so, historically, Key Wester’s relied on cisterns and desalination plants–and they sure weren’t going to waste that precious liquid on water-chugging trees and plants.”

The eyebrow house, Caemmerer postulates, may have been a hybrid of the Louisiana five-bay center hall house, or the New England saltbox.

There are about 75 left in Key West and, as luck would have it, one happens to be for sale. 

Built in 1943, the Old Town home is an easy walk to dining and shopping (as well as other neighborhood haunts), and has been stunningly renovated. 

Blessed with a cumulative five bedrooms and four baths — thanks to an addition on the main house and a detached guest cottage — the home is ideally situated to be a splendid home-away-from-home or even a potential income property in the form of short-term rentals or a bed and breakfast.

“Virtually every detail of this property has been restored or renovated to create the perfect combination of modern luxuries and historical character,” said listing agent Wendy Zintsmaster with Truman Co.

From the inviting porch beneath that “eyebrow,” that overlooks the gorgeously tropical grounds to the well-appointed interior, this home’s open floor plan is begging for island entertaining.

A gourmet kitchen is light and airy thanks to numerous windows, and is outfitted with picture-perfect finishes and stainless steel appliances.

The ground-level master suite has a spacious, luxurious bathroom with a wet room, walk-in closet, and a door that leads to a private garden area. 

The sprawling grounds include private grotto-like areas and a refreshing pool. 

The 2,253 square foot house is priced at $2.5 million. Want to see more photos? Click here.