Exploring Key West neighborhoods: A comprehensive guide
Buying your very own slice of paradise generally comes with a price beyond that of the home. Lackluster amenities or a tepid or nonexistent nightlife could make that picture-perfect beachfront bungalow less than an ideal purchase.
Owning a permanent or vacation home in one of the many wonderful Key West neighborhoods is the general exception.
Looking for things to do, day or night? Check. Craving tasty food, exciting outdoor adventures, or mind-broadening cultural activities? Key West has everything you need alongside a diverse, friendly community. Plus, there’s a variety of housing options, so what ends up as your dream home may be a happy surprise for you. And the beaches…well, if you’re here, you already know how stunning they are.
In this article, you’ll get a full breakdown on all the Key West neighborhoods that matter. This should give you a little insight into the lifestyles that thrive in each neighborhood so you can start imagining your perfect future here.
And, if every one of them sounds equally amazing and you can’t choose, don’t worry – the final section covers how to narrow down your options to find the perfect fit!
Table of Contents
THE MAKING OF KEY WEST NEIGHBORHOODS
Dangling at the southern tip of Florida is Key West, a tiny island by most standards. Despite being just four miles from north to south, and a mile from east to west – with a total land area of just 4.2 square miles – Key West has been punching well above its weight since the 1820s.
Because of its location, the island has always been important to the US Navy. It was also known for its salt and cigar production in the mid-to-late 1800s. Once the Overseas Railway extension connected the island to the mainland in 1912, Key West became a premier tourist destination.
Key West is currently home to around 26,000 residents. As the island’s main industries changed, so did its population, which is reflected in some of its neighborhoods today. How many are there? It depends on who you ask, ranging from five for traditionalists to 17 for those seeking a finer level of granularity.
Wherever you fall on that spectrum, it’s hard to deny that what separates Key West neighborhoods is more than just a couple of streets. Two neighborhoods can be a few yards apart but have distinctly different vibes. So even though it’s impossible to put each neighborhood into a neat little box, having a general sense of what to expect from each area can only help you make the best Key West real estate decision.
THE 5 TRADITIONAL NEIGHBORHOODS
In the neighborhood of Old Town in Key West, FL, an investment opportunity awaits in this multifamily home consisting of four rental units and a main house
The neighborhoods listed below hark back to the early 1800s. They capture the city’s laid-back vibe, rich history, and creative energy. With diverse architecture and deep cultural roots, these areas are all about community and embracing the island’s relaxed lifestyle. They mix old-world charm with a lively artistic spirit, making Key West a unique and welcoming place that’s stayed true to its past while continuing to evolve.
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Old Town
Shipping docks and warehouses sprung up along the harbor in the late 1800s, soon to be followed by grand estates, lively bars, and restaurants that cater to the island’s well-to-do. Splashes of color from these historic Bahamian- and Victorian-style homes continue to liven up the neighborhood’s quaint, narrow streets today.
In Old Town, you’ll find Duval Street, the main drag for tourists; Mallory Square, a plaza where tourists converge every day to view the sunset and partake of a lively street festival called Sunset Celebration; and the Key West Historic Seaport, which some residents view as a separate neighborhood altogether. Alongside the waterfront bars and restaurants are museums and retail stores, as well as the hub for Key West’s thriving fishing and sailing charter industry.
Inquire about available homes for sale in this Key West neighborhood
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Truman Annex
West of Old Town is the gated community of Truman Annex, named after President Harry S. Truman, who spent most of his winters in his Front Street home.
Truman Annex has always been a great place to live and raise a family, but the extensive renovations during the 1990s have turned it into a picture-perfect neighborhood. White picket fences, manicured lawns that roll down to the waterfront, and the Truman House – now known as the Harry S. Truman Little White House Museum – all combine to make a neighborhood a source of pride.
Many of the neighborhood’s mansions used to be homes for military officers. These homes come in Greek Revival and Italianate architectural styles, especially in the north side of the area. Newer homes in the south side are partial to the Southern Cottage style, complete with classic sitting porches.
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The Meadows
The Meadows was developed in the late 1800s to the early 1900s as Key West expanded. As a fully residential neighborhood, it had wider streets with homes boasting larger yards. It’s populated by classic Key West-style homes called Conch houses, Victorian homes, bungalows, cottages, a smattering of Mid-Century-style houses, and renovated historic homes.
The neighborhood offers a more relaxed atmosphere, making it a desirable place for those seeking a tranquil living environment within close proximity to the action of Old Town.
Inquire about available homes for sale in this Key West neighborhood
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Casa Marina
Casa Marina features a mix of Mediterranean-Revival, modern, Conch-style, and historic homes, reflecting the neighborhood’s upscale, coastal vibe. Known for its luxury estates and waterfront properties, Casa Marina offers spacious layouts, elegant details, and a blend of indoor-outdoor living. Some homes date back to the early 20th century, combining historic charm with modern amenities. The neighborhood’s proximity to the beach adds to its appeal as a premier Key West location.
With restaurants, cafes, and shops lining nearby White Street, Casa Marina residents have easy access to everything they need.
Inquire about available homes for sale in this Key West neighborhood
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Mid Town
Mid Town’s original homes tend to be more modest, having been built on landfill during the 1940s. Since then, many of these homes have been revamped to make better use of the natural surroundings, leading to a property value boom at the close of the past millennium.
The neighborhood features a mix of Mid-Century homes and newer constructions, reflecting the post-World War II expansion of the city. Mid Town offered a more suburban feel compared to the older parts of Key West, catering to families and long-term residents looking for more space.
Pools, palm trees, and tropical plants are all common sights down here, and you’re never too far from the beach or vital community areas like White Street.
Inquire about available homes for sale in this Key West neighborhood
Inquire about available homes for sale in this Key West neighborhood
THE 9 NEWER NEIGHBORHOODS
In the neighborhood of New Town in Key West, FL, this custom home has 3 bedrooms, all of which open to a lush botanical garden
The newer neighborhoods in Key West have diversified the housing market by offering a range of options, from lively cultural spots to upscale resorts. They appeal to a wide range of buyers, whether you’re into modern beachfront homes or historic charm. With options that include artistic spaces and luxury living, these newer neighborhoods boost the city’s appeal, provide more choices, and help meet changing lifestyle trends, making the Key West housing market more exciting and valuable.
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Bahama Village
Bahama Village is located in the southern part of Key West, situated within walking distance of Old Town and the bustling areas around Duval Street.
This vibrant, culturally rich neighborhood offers a mix of colorful homes and local eateries. Known for its lively atmosphere and Bahamian heritage, this area is a cultural hotspot with annual festivals and a welcoming community spirit.
Many of Bahama Village’s older buildings have been restored and repurposed into charming shops, galleries, and restaurants. Restored cottage-style houses around the edges of the neighborhood are now home to young families and retirees, with a few having been converted into vacation rentals.
Inquire about available homes for sale in this Key West neighborhood
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Beachside
Hugging the southern shoreline of Key West is Beachside. Search for your dream home here if you’re partial to coastal living.
You’ll find renovated homes in Mid-Century style, which tend to be a few minutes from the beach, or luxury condominiums and modern estates for waterside options.
These newer developments are designed to capture ocean breezes and natural light without skipping on the kind of amenities today’s homeowners demand.
Inquire about available homes for sale in this Key West neighborhood
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New Town
Another neighborhood built on landfill is New Town, which is divided into three separate zones.
- New Town North is primarily residential and features a mix of single-family homes, townhouses, and condos. It offers a quieter, suburban feel and is known for its family-friendly environment, local schools, and community parks.
- New Town Central is the neighborhood’s commercial hub, with shopping centers, office buildings, and various businesses. The mix of properties are primarily condos and townhouses. ,
- New Town South is distinguished by its proximity to waterfront properties and marinas. It combines residential options with recreational facilities and waterfront access, providing a blend of residential comfort and maritime activities.
Inquire about available homes for sale in this Key West neighborhood
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Downtown
Downtown was once part of Old Town and, true to its name, features shops, restaurants, offices, bars, and hotels. While many of these spots have been updated for modern needs, the charm remains. If you wander off the main street and explore the side streets, you’ll discover a beautiful mix of old Victorian houses and quaint cottages.
Inquire about available homes for sale in this Key West neighborhood
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Uptown
As the cigar industry flourished in Key West in the 1800s, more housing was needed for workers. This resulted in the creation of many cottages and Victorian homes in the Upper Duval Gato neighborhood. Now called Uptown, this area offers a more elegant residential experience compared to the bustling downtown area.
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Heart of Old Town
The central zone of Old Town is where a lot of Key West’s rich and famous built their homes.At the center of it all is a monument dedicated to the USS Maine, a battleship that exploded in Havana Harbor in 1898, sparking the Spanish-American War.
The homes here are grand, with large verandas and manicured gardens evoking the romance of a bygone era. If you’re a fan of Victorian architecture, this is the place to be.
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White Street Gallery
This area includes Bayview Park, one of Key West’s biggest green spaces. This park features tennis courts and a large gazebo, often used for community events and gatherings. Art galleries, in particular, are plentiful here,
The neighborhood consists mainly of year-round residences in several architectural styles from the mid-1900s to the present.
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Northside Resort
Here, U.S. Highway 1 turns into North Roosevelt Blvd. This area has changed a lot over the years, with new condo hotels and timeshares replacing older chain hotels. Living in one of the new developments along North Roosevelt Blvd gives you easy access to New Town’s bustling commercial areas.
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Southside Resort
The Southside Resort area is located along the southeast shore of Key West. It features lovely condo hotel complexes inspired by European and Caribbean designs. These resorts are surrounded by beautiful gardens and offer amenities like swimming pools, restaurants, and tennis courts, all of which are just a short walk from the beach.
Since it’s closer to the airport, this area is perfect for those seeking to buy vacation homes with luxurious amenities, available at better prices compared to Old Town.
3 NEIGHBORHOODS JUST OUTSIDE KEY WEST
In the neighborhood of Sunset Key in the vicinity of Key West, FL, this home has panoramic views of Key West Harbour and the historic waterfront
The next three neighborhoods are located just outside Key West, but with easy access to all the island has to offer. Each of these three neighborhoods are notable options alongside their island counterparts.
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Key West Golf and Country Club
The Key West Golf and Country Club is a gated community just outside of Key West, on the gulf side of the U.S. Highway 1. This neighborhood features beautiful villas and tropical townhomes surrounding a Rees Jones-designed 18-hole golf course, which is 6,500 yards long. Plantation-style homes are also quite the draw here. Inquire about homes for sale in this neighborhood
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Sunset Key
Sunset Key is a private island occupying 27 acres. It’s located 500 yards off the coast of Key West, which is just a ferry ride away. Classic Victorian cottages dot the landscape alongside some of the most luxurious homes in the Florida Keys. Framed by palm trees, brick roads, and white picket fences on one side and 5-star resort amenities on the other, Sunset Key epitomizes true island living. Inquire about homes for sale in this neighborhood
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Stock Island
This neighborhood has long been a favorite among locals seeking to escape the ubiquitous tourist crowds. Beyond the beach, locals frequent the Marina Village, Key West’s largest deep water marina. Here you’ll find bars, restaurants, art galleries, and live entertainment, offering a glimpse of the Key West community’s way of life before tourism took over. Inquire about homes for sale in this neighborhood
CHOOSING YOUR IDEAL NEIGHBORHOOD IN KEY WEST
You can’t go wrong with any of the neighborhoods in Key West.
To land your dream home in this part of the Florida Keys, focus your search on neighborhoods that answer your needs and make your life easier. Key West’s combination of natural beauty, cultural richness, and relaxed atmosphere, makes many of what you want just a walk, bike ride, or bus ride away.
Depending on your needs and your lifestyle, the following are just a few options:
- Families may prefer areas with schools and parks nearby (The Meadows, Midtown)
- Those who love the nightlife might wish proximity to Key West’s bars, restaurants, and other after-hours entertainment (Old Town or New Town)
- For those seeking upscale living, gated communities and estate homes promise privacy and luxury (Truman Annex, Sunset Keys)
- The 55+ set might want to live in neighborhoods that allow them to indulge in hobbies like sailing, fishing, and enjoying a host of social activities
The best approach is to explore different neighborhoods and see which ones you like the most. Take the time to ask locals for their thoughts and advice; they love sharing what makes Key West special!
EXPLORE YOUR KEY WEST REAL ESTATE OPTIONS WITH ALINA DAVIS
It’s no secret that the Key West real estate market can be competitive. If you’re ready to jump into the fray, you want one of the best Key West Realtors on your side.
I’m Alina Davis, a Realtor for 16 years and counting, and a Keys resident since 1982. When you hire me to help you buy or sell a home in the Keys, you get a full-time, experienced, and successful Realtor, with sales of over $200 million in the last five years.
You can be sure I know the Key West neighborhoods like the back of my hand.
Explore your Key West real estate options with me, Alina Davis. Call 305.393.0541 or send me an email to tell me about the dream home you wish to own in Key West and find out the numerous services I can offer you.
With my expert guidance, all that’s standing between you and your dream home is your signature at closing!