Key West Golf Club: The Key West Golf Club, though actually on Stock Island, is still “Key West”. Half of Stock Island was annexed to Key West in the early 1990’s and the Key West Golf Club is part of that annexed section. It is a gated community with very cookie cutter homes. The majority of the homes there are duplexes where each half is separately owned but there are some stand alone houses. About 60% of the homes have a golf course view. Their premier homes are in what is called “The Sanctuary” where they are all stand alone houses and all have private parking. The higher end house in The Sanctuary have covered parking right in the yard. The lesser houses have deeded parking spaces but it is more parking lot style. The rest of the homes have first come first serve parking. The only real negative to the Key West Golf Club is it is located next to a large marshland and it can get very buggy in the summer months.
New Town: New Town is where a lot of the working locals live. In fact, I have lived in New Town myself for over 25 years. You will get the most house for the dollar in New Town. Generally, the lots are larger. Most of the houses offer off street parking which is a big plus in Key West. The grocery stores, pharmacies and larger retail stores are also located in New Town. A lot of the larger restaurants and fast food is here too. I find New Town to be quitter than most of Key West.
Mid Town: Mid Town is similar to New Town but the houses are more money. A general rule is the closer to downtown you get the higher the home prices get. The lots in Mid Town are not as big as New Town but are still big for Key West. There isn’t anything in the line of shopping in Mid Town although there is one restaurant. Being closer to downtown and the beach you will find some vacation rental homes in Mid Town although the majority of the homes are owned or rented by year round residents.
Casa Marina Area: The Casa Marina Area is named after the Casa Marina Resort which was the first hotel built in Key West. It was built by Henry Flagler right after he completed the Flagler Railroad. The Casa Marina Area is known as being one of the most expensive sections of Key West. It is very unlikely you will find any house under $1,000,000 in the Casa Marina Area and many of the homes will sell for $4,000,000 and up. The Casa Marina Area somewhat has the best of both worlds. You can walk to the beach and Duval Street. It is close enough to Duval Street to be an easy walk but far enough away to still be quiet.
The Meadows: The Meadows is my personal favorite neighborhood in Key West. It is a series of very small streets and is one of those areas where people don’t go unless they have reason. You won’t find tourists “Sightseeing” in your front yard. The lots are much smaller but the charm of the neighborhood makes up for that. The homes are occupied by a mixture of year round residents and snowbirds. Most of the homes are very well-kept and the landscaping is beautiful. You can also easily walk or bicycle to Duval Street from The Meadows.
Old Town: Old Town and downtown are somewhat the same thing. Most of the vacation rental homes are in Old Town although there are a lot of year round locals. Parking in Old Town is very difficult unless your home has off street parking which is rare and adds a lot of money to the price of the house. Being close to Duval Street, Old Town will be a lot louder and a lot less private. The houses tend to be a lot more expensive in Old Town but slightly less than the Casa Marina Area as a general rule. There is a lot of traffic in the neighborhood due to the tourists. People seem to either love living in Old Town or wouldn’t live there if it was free.
Truman Annex: Truman Annex has many great features but its biggest attraction is to investors because the homes can be rented by the week whereas most of Key West has a 30 day minimum rental period by law. Located just blocks off of Duval Street and a short walk to Mallory Square, this place is absolutely centrally located. Close to Duval Street yet the tree lined streets and location provide everyone a quiet retreat. Fort Zachary Taylor State Park is just a quick bike ride or walk away. Practically in the back yard of Truman Annex is this wonderful park. The beach offers a place to sunbath and watch the ocean. On a clear day you can see fish swimming in the waters while snorkeling. Homes in Truman Annex range from one bedroom, one bathroom 300ish square feet condos to 4,000 plus square feet mansions worth well over $5,000,000 and everything in between.
Bahama Village: Bahama Village: Bahama Village is the most up and coming neighborhoods in Key West. Although Bahama Village is technically still “Old Town” it is its own subdivision within Old Town. If you’re in it for the long run this is the place to invest. Ten years ago I wouldn’t go near Bahama Village after dark but that has drastically changed. It is just a few blocks from Duval Street yet still quiet. Parking is very rarely a problem, and it is a tight knit neighborhood where the locals all watch out for each other.