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A Comprehensive Guide to Florida Keys Real Estate

The Florida Keys extend approximately 100 miles southwest off the tip of southern Florida. They curve below Everglades National Park between the Atlantic Ocean and the Gulf of Mexico. Key West, at the southern tip of the keys, is only about 90 miles from Cuba.

The Keys, surrounded by water, rich with sandy beaches, the third-largest coral reef in the world, tropical vegetation and sea life, enjoy a pleasant climate nearly year-round.

In 1916, Henry Flagler extended his railroad's route south from Miami all the way to Key West. It took more than a decade, and Flagler spent about $30 million of his own money to develop the technology and build the bridges for the planned "Overseas Highway." For Flagler, bringing the train to Key West was the culmination of a long-held dream. 

The railroad magnate's achievement opened the previously secluded Florida Keys to tourism and development, changing the character of the islands forever. It didn't take long for people to discover the mesmerizing beauty and appeal of the Keys lifestyle. They have been a “backyard playground” for Floridians for the past century, a vacation destination for visitors from around the world for decades. More recently, the various islands have become prime targets for second-home buyers and part-time residents. Florida Keys real estate for sale varies from one location to another, but, in general, potential buyers will find attractive and affordable homes in communities all along the chain of islands.

The Florida Keys Today

Much of Flagler's original track was destroyed by a massive hurricane in 1935. Today, US Route 1, part of which was built over the remaining trackbed, remains the only way to drive to the Keys. The fabled Seven Mile Bridge, made famous by a James Bond movie scene, is the longest of 42 bridges that connect the various islands along the highway. It spans the water from Knight's Key, at Marathon in the Middle Keys, to Little Duck Key, and was opened in 1982.

Although US 1 is the only, many other options exist for getting to the Keys today. Key West has a first-class international airport, cruise ships call at the port adjacent to the naval dock, and recreational boaters, as well as commercial fishing boats and excursion vessels, are active along the entire archipelago. Although the train no longer runs to the Keys, most communities have private aviation fields. Boat ownership among residents is high, and visitors arrive by bus, bike, boat and rental car, as well as by helicopter or limousine.

There are campgrounds and RV parks, rustic cabins to rent, exclusive resort hotels, budget extended-stay options, rental apartments, and single-family homes that run the gamut from simple beach cottages to luxury family compounds. Numerous recreational boaters spend part of the year in the Keys, notably in Marathon, Key West or Islamorada. Maritime excursions and fishing charters are widely available.


Real Estate in the Florida Keys

Condos are increasingly popular housing options in the Keys, but you won't find the view-blocking high rises that punctuate the Atlantic coast from Miami north to St. Augustine. Monroe County has wisely placed limits on population growth with an ordinance that limits Florida Keys real estate growth. That legislation has contributed to what is a strong and stable real estate market. Although prices still have not surpassed values reached in 2006, before the recession, Florida Keys homes for sale represent good value and continue to appreciate at a steady rate. Demand is high throughout the chain.

The full-time population in the Florida Keys remains fairly low, but the number of seasonal residents, second-home owners, and occasional long-term visitors has increased enormously in recent years. Demographics vary substantially from one community to another, as do real estate prices. The islands boast retirees, families, "snowbirds" from the north, young professionals, artists and craftspeople, restaurateurs, boat captains, tour operators, travel agents, hospitality industry workers, and a growing service force to support the expanding population. With such diversity, it is entirely possible to find homes for sale at prices that meet individual needs.

Unique Communities

Many of the communities along the more than 100-mile stretch of islands are equally attractive to thrill-seekers and those who want total escape and relaxation. There is enough activity, both on land and sea, to satisfy the most active visitors as well as those who want only sun, sea and tranquility. Vacationers come from all over the world to snorkel, scuba dive, fish, swim, play, eat and relax. Some come to stay. A growing number of regular visitors choose to find the perfect part-time residence; others purchase a vacation home with the intention of retiring to "paradise."

If you're interested in Florida Keys property for sale, this guide will serve as an introduction to some of the more popular locations. This overview, however, only briefly touches on the distinctive features of the best-known keys. A large part of the appeal of the Florida Keys is their diversity. Settling into the daily lifestyle of a Key Largo neighborhood, or in Marathon, will be different from life in Key West. The charm, however, is that living in any community puts you in relatively close proximity to all that’s available. 

Key Largo

The city of Key Largo is at the southern end of the island of the same name. The name in Spanish means "long." It is the northernmost island of the Keys Archipelago and the largest. Biscayne National Park exists on a separate island just to the north of Key Largo.

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This narrow piece of land boasts waterfront property on both the Atlantic shore and along Biscayne Bay, extending south from Miami. Numerous residential neighborhoods have been developed along canals dug through the interior of the island.

More than 90 separate communities are situated on Key Largo, with homes and condos that range in price from the mid-200s to upwards of $2.5 million. The population, at the time of the 2010 census, was 10,433. 

Close to the mainland with all the associated conveniences of metropolitan South Florida, Key Largo real estate is ideal for anyone who wants easy access to major business and transportation hubs. It's only about an hour's drive south of Miami. Naples, on the Gulf Coast, can be reached by car in only about three hours.

There is also a military presence near Key Largo, with Homestead Air Force Base close by on the mainland, served by a bridge that connects directly with North Key Largo. A U.S. Coast Guard Station is situated just to the south of the city of Key Largo in Islamorada. Key Largo boasts 33 miles of prime real estate, including condos with associated yacht clubs, gated residential compounds and private estates.

Key Largo has earned a reputation as one of the key eco-tourism destinations in the county. John Pennekamp Coral Reef State Park, the first underwater park established in the United States, occupies about 70 nautical square miles and extends approximately three miles offshore on the Atlantic side of Key Largo. It is a prime destination for snorkelers and divers.

The Dagny Johnson Key Largo Hammock Botanical State Park, popular with campers, kayakers and canoers. Six miles offshore, divers can witness the formation of an artificial reef at the site of the Spiegel Grove, a former U.S. Navy ship sunk deliberately in 2002.     

The Florida Keys National Marine Sanctuary, a protected ocean reserve established in 1990, encompasses 2,900 nautical square miles stretching from South Florida along the 1,700 islands of the archipelago all the way to the Dry Tortugas. The sanctuary protects the marine environment of the Atlantic Ocean, Florida Bay and the Gulf of Mexico, including sea life, reef formations, mangrove forests, and seagrass fields. Strict regulations govern boating, fishing, diving, and land-based development in the area.


An unincorporated community just south of the city of Key Largo, Tavernier has special appeal for anyone who loves nature, small towns and a laid-back lifestyle. With a population of just over 2,100 and a median home value of nearly $400,000, it is a relatively well-to-do community with almost no unemployment.

Watersports rule here, with residents and visitors alike "hooked" on fishing, snorkeling, diving, water sports, and recreational boating. During the various seasons, serious sport fishers can charter boats and captains to catch the big ones, and bareboat charters are available for day trips. Rental kayaks and canoes abound, and exploring on a bicycle is popular. Tavernier is also the jumping-off point for visitors who want to learn the basics or become certified divers, with local companies that supply both equipment and instruction. 

Perhaps the majority of residents in this small community are associated with tourism, but if you want to live a quiet life enjoying spectacular sunrises and sunsets and fresh-caught fish from both the Atlantic and the Gulf, this might just be the perfect place to call home.

Atlantic Bay Resort, on the east side of the key, is a popular destination for both destination weddings and family vacations, with accommodations ranging from economical efficiencies to family cottages and luxury suites, a private beach and tiki bar, heated and chilled freshwater pools and dockage from private boats.

You can also bicycle to nearby beaches,  sail, swim with dolphins at Theater of the Sea just a few minutes south, meet rescued birds at the Florida Keys Wild Bird Rehabilitation Center, try your hand at spearfishing or lobster diving, and enjoy popular Cuban food at Sunrise Cuban Market and Cafe. No matter what you enjoy, you will find ample things to tempt you in Tavernier.  


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One of the more upscale and better-known villages of the Florida Keys, Islamorada is distinguished because the village extends over six separate keys. Each boasts a separate reason to enjoy the experience of being there. History buffs can immerse themselves in treasure-hunting lore at the History of Diving Museum that displays a 16th-Century treasure chest or explore ruins at Indian Key Historic State Park. Sealife and dolphin encounters at Theater of the Sea are legendary and suitable for all ages, and stunning protected coral reefs are only a short boat ride away. A former quarry has been transformed into Windley Key Fossil Reef Geological State Park, and Lignumvitae Key Botanical State Park invites visitors to take a hike through the splendor of its tropical forest.

Famous as a world-renowned sportfishing destination as well as a premier diving center, Islamorada has a number of resort hotels, lodges, spas and marinas. Islamorada real estate options include condos and apartments, attractive single-family homes and lavish estates in approximately 50 individualized neighborhoods.  As on all the islands, waterfront property commands premium prices, whether it's on the ocean or the bay. Recent prices for Islamorada homes ranged from a low of $229,900 to a high of $18 million.

Duck Key

Duck Key represents what is arguably some of the best real estate in the entire chain of islands. The 60-acre island has great ocean views, palm trees, a secluded aura and is viewed as the epitome of the tropical lifestyle, as well as a haven from the rest of the world. Duck Key feels somewhat European with landscaped canals and a multitude of architecturally-interesting bridges. However, only one road leads onto Duck Key, making it ideal for those who seek unmatched security and privacy in an upscale residential enclave. 

Home to the highly-acclaimed Hawk’s Cay Resort, Duck Key development began in the 1950s, under the direction of Canadian owner Brian Newkirk, who dredged numerous canals and built the bridges across them. Residents of Duck Key enjoy superb fishing grounds just offshore, along with fine retail shops and distinctive boutiques on land. Marina facilities are first-class, as are residential amenities for those who buy property to enjoy either year-round or only occasionally. 

Duck Key properties offer great value, and available land is still a good investment. Owners of homes and condos on the grounds of Hawk’s Cay Resort enjoy all the privileges of the world-class vacation property. Real estate prices in Duck Key range between approximately $250,000 to $900,000 for waterfront condos. Home prices on the island run from about $420,000 to almost $3 million.

The total population of Duck Key, together with another small private island known as Conch Key, is under 500 residents, with a total of fewer than 400 residences.

An interesting Duck Key diversion is Dolphin Encounter, an onsite research facility at Hawk’s Cay Resort that allows visitors to interact with a pod of Atlantic bottlenose dolphins.   


The city of Marathon extends over 13 separate but interconnected islands. Located in the Middle Keys, Marathon had an estimated 2018 population of 8,645. It was only incorporated as a city in 1999, but it is said that its name stems from a time when Henry Flagler’s railroad builders worked day and night to complete the railroad. A depot there was named “Marathon” to commemorate the effort.

Today, Marathon is a favorite for live-aboard boaters who arrive to spend the winter at its well-equipped City Marina. There is much to recommend Marathon, both on land and in the water, even for boaters who do not have cars available. In addition, there is an airport, good restaurants, and stores, and it is the primary restocking and repair center for recreational boaters in the Keys.

Because of its location at approximately the midpoint of the Florida Keys, Marathon is especially boater-friendly, with more than 2,400 slips available for residents’ use. In addition, the population of recreational boaters swells substantially each winter as a convivial community of recreational boaters arrives to take advantage of weekly and monthly slip and mooring rentals at the City Marina. Marathon is a favored destination for part-time residents because of the variety of activities and amenities available for all ages.

Marathon Florida real estate is some of the most reasonably-priced in the Florida Keys, with the median sales price for a condo just under $535,000. Individual homes on the water can reach into the multi-million dollar range, but desirable property in Marathon can be found for under $500,000. It depends, of course, what size and features you seek, but Marathon offers the best of "small-town" living in a somewhat exotic atmosphere. The lifestyle advantages of location, convenience, beauty and access to diverse activities are hard to beat. 

Marathon maintains its “Old Keys” aura, with some of the most up-to-date attractions in the area. Pigeon Key and Crane Point Museum Nature Center offer ecological insights, and the barrier reef just offshore invites scuba divers and snorkelers for spectacular viewing of coral and marine life, especially at Delta Shoals and Coffin Patch. The city stretches for 10 miles, so there is no shortage of nearby activity, and residents are able to tailor daily life to suit their individual interests.

Big Pine Key

The largest island in the Lower Keys, with a land area second only to Key Largo at the northern end of the chain, Big Pine is famed for its natural beauty as well as for its supply of still available land. It is the site of Bahia State Park and is home to endangered Key Deer, which run free on the island.

The pristine beauty of Big Pine centers on the water; most of the homes are situated on secluded waterfront lots, and there are no fast-food restaurants or shopping malls and little commercialization. Big Pine Key, which sports tantalizing vistas of ocean and untamed land, is the epitome of island living, with little to distract from the pleasures of sun, sea, surf and blue sky. This is an island almost totally focused on nature and relaxation.

Homes for sale in Big Pine Key range from the mid-$300s to almost $3 million.

Key West

You can't escape the influence of "Papa Hemingway" or Jimmy Buffett in Key West. The city flaunts its reputation as a free-wheeling party town and thrives on a characteristically unconventional approach to almost everything. There is much more to this lively little city "at the end of the road" than free-flowing liquor, fresh seafood, key lime pie, and abundant sun, but it’s hard to dispute the feeling of fun and freedom that is pervasive, from sunset celebrations and street performers at Mallory Square to the annual Key West Fantasy Fest, regular fishing tourneys and quirky holidays that include the Conch Republic Independence Celebration. Six-toed cats still stroll the grounds of the Hemingway House, and cats and chickens frequent streetside bars and cafes.  Peeling back the layers of Key West takes time, and there are a lot of reasons to love the city, apart from its lighthouse and Southernmost Point, favorite photo stops.

This city reveres its reputation as a welcoming oasis for artists, musicians, and writers, but also as a haven for the down-and-out, the wanderers and some of society’s “misfits.” Life in Key West's heyday was easy and inexpensive. Sleeping on the beach was once allowed, but now is frowned upon, and real estate values have skyrocketed. Of all the keys, Key West is the primary destination for most visitors. To handle the tourists, many of its fine old homes have been converted to B&Bs, rental compounds, offices, galleries, and restaurants.  

The median price of a home in Key West is around $600,000 today. Key West real estate, especially in the historic area, is highly sought after and always in demand. While there is still some undeveloped land available, it is pricey. The development has been extended to nearly smaller islands, reachable only by private boat. Although living "near" Key West is not the same experience as living "in" Key West, many prospective buyers prefer that option.

Key West is home to an active military training center that was established in 1940. Now known as Naval Air Station Key West,  it is an active command for all branches of the military, with ships, planes and helicopters operating from the base, as well as supporting the mission of the Department of Defense, Homeland Security, National Guard, other federal agencies and allied forces. 

For more information about buying or selling real estate in the Florida Keys, don't hesitate to contact us.