Old Town, Key West Neighborhood Guide

Old Town Key West, also known as The Key West Historic District, is the southernmost city of the continental United States.

Old Town Key West, also known as The Key West Historic District, is the southernmost city of the continental United States. 

The island is 4 miles by 1 mile in diameter. Old Town Key West encompasses over 5,000 acres of space, with it bordered by White, Angela, Windsor, Passover, Thomas, and Whitehead Streets and the Gulf of Mexico. It is the majority of the western part of the island and is home to the central business district and numerous tourist destinations. 

The Community

The community of Key West boasts a little more than 25,000 people comprising predominantly a Caucasian ethnicity, the median age is 39 years old, and the typical house size is a mix of families, couples, and singles, with 2.84 persons per household.

Household income averages $42,000 for single-income households with multiple earner homes averaging $50,000. The island is a combination of transplants and locals, known as “Conchs,” an ethnicity of European descent by way of the Bahamas.  

Residents are made up of “Conchs,” people in the hospitality industry, and active duty service members. Due to its warm weather, over 2 million people have visited the island a year, making the Keys a prime tourist destination in Southern Florida. 


Old Key West has a higher crime rate than all but 11% of cities in Florida. Due to the nature of a tourist destination, the level of crime tends to be on the property side rather than violent crime, though lately, there is an increase in local violent crime. 

The police department of Old Town Key West is part of the Florida accredited police departments. Unfortunately, there is only one station on the island that accommodates all the city’s police services. 

Three fire stations located around the northern parts of the island provide fire suppression and emergency rescue services. 

The Schools

Schools in Key West are operated and maintained by the Monroe School District, and residents can choose public schools and Charter schools options to choose from. Poinciana on the northeastern side of Key West instructs elementary-aged students. The Horace O’Bryant School highlights middle school education for the residents of Old Key West, matriculating to Key West High School. Sigsbee on the east side offers residents K-8 instructional opportunities. 

The Culture

Influenced by a mixture of European, Caribbean, and Cuban cultures, Old Key West resembles the hegemony of many large urban areas while maintaining a small island personality. 

There is a large creative community in Old Key West that is spotlighted by the Ernest Hemingway House and the Tennesee Williams house. 

As a historic district, Old Town Key West has most of the tourist destinations identified by the iconic bungalows, with destinations including Mallory Square, Duval Street, and Fort Zachary Taylor – the historic state park built around the Civil-War era fortress. 

The Lifestyle

With summer weather year-round, the lifestyle in Old Town Key West is relaxed. An area less than 4 miles makes Old Town Key West accessible on foot or bike, boasting another primary form of transportation and entertainment. As a tourist destination, there are plenty of eateries and museums, and outdoor activities for people of all ages. 

Here are a few of our favorites

Fort Zachary Taylor State Park is a pristine beach and historical landmark. For snorkelers, there is abundant marine life just off the shore in the warm waters of the Gulf of Mexico, and for the family, there is plenty of space to relax and play under the shadows of the Civil War era fortress. 

The short-90 miles from Cuba hosts the southernmost tip of the contiguous United States known as the Southernmost Point in Old Town Key West. The tourist destination gets crowded early and late, so plan to spend some time getting a picture at the obelisk that denotes the southernmost tip. 

The enigmatic Ernest Hemingway left behind more than his writings. He left behind Ernest Hemingway Home that has since become the Ernest Hemingway Home and Museum. The daily tours will take you along the grounds populated by local cats known as polydactyl – or 6 toes – before exploring the principal residence, swimming pool, and writer’s room. 

For chef-inspired versions of Southern Cuisine, look no further than Firefly Key West, located on Petronia Street in the Bahama Village neighborhood in Old Town Key West, known for unique dishes that bring together Southern hospitality and contemporary cuisine. So come hungry for the bacon-crab beignets as a starter before moving on to low-country gumbo or Tri-Tip Steak dinner before finishing it all off dessert and after-dinner drinks. 

After dinner or a day at the beach, if you’re looking for a nightcap, check out Better Than Sex. Conveniently located in Old Town Key West, Better Than Sex is a perfect destination for drinks, dates, and fun. The small intimate setting here is often at capacity, so plan to spend time waiting for your reservation on a table, but the wait is worth it! Try the chocolate and caramel rimmed wines and unique house-made cocktails. 

The one-stop sip and shop liquor bar in Old Town Key West is the Tipsy Rooster. Established in 2018, the Tipsy Rooster is known for unique house-made infused cocktails. So grab a drink and relax on the deck while basking in the sunlight or relax in the shade. Located conveniently nearby most hotels, the Tipsy Rooster is the bar in Old Town Key West to whet your whistle.  

Real Estate

Due to the historic district and limits of the island, new construction is rare. 

The median detached single-family home price in Old Town Key West is just a tick over $750,000, and home prices have appreciated on average 7% per annum. For more luxurious living, Old Town Key West homes can run upwards of $2 million for 5 bedrooms though some listings run over $5 million. 

Condos can run $800,000 for a 2-bedroom unit of just under 900 square feet. 


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