Historic home in Key West Florida Keys

Key West is the heart of the Florida Keys, with historic conch houses in Old Town, waterfront condos, quiet residential streets in New Town and a few private island neighborhoods just offshore. Over the past year the median sale price was about $987,000, with homes typically selling in about 86 days.

The Island Collective Realty is based in Key West and broker-led. Greg Gordon works directly with every buyer, including the many buying a second home from out of state.

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Key West Real Estate

FLORIDA KEYS AREA GUIDE

Key West is the only place in the Keys with a true walkable town: restaurants, galleries, marinas, music and the sunset at Mallory Square, all within a bike ride. It also has the Keys' main airport, which makes a second home here easy to reach from anywhere.

The market has real range. Buyers choose between historic homes with porches and gardens in Old Town, low-maintenance condos with pools and docks, and larger single-family homes in New Town and nearby canal neighborhoods.

Why buyers choose Key West

AREA OVERVIEW

Waterfront home in Key West Florida Keys

What people love about Key West

THE LIFESTYLE

Old Town's historic district is full of 19th-century conch houses, wide porches and tropical gardens.

History and character

Key West International Airport has direct flights to many U.S. cities, so a second home here works even for long weekends.

Easy to get to

Walk or bike everywhere

In Old Town you can leave the car at home: dinner on Duval, the farmers market, the beach and the harbor are all a short ride away.

Residential street view in Key West Florida Keys

Key West real estate includes historic homes, condos, Key West's median sale price was about $987,000 over the past year, roughly flat from the year before, with about 260 homes on the market in fall 2026, which gives buyers more choice than in recent years. Old Town and nearby neighborhoods such as Truman Annex and Casa Marina are among the most sought-after, for historic homes close to the water and downtown.

For lower-maintenance options, condo communities ranged widely: about $490,000 to $600,000 at Salt Pond and Key West by the Sea, about $975,000 at 1800 Atlantic, and about $2.9 million at Martello Towers. Homes in the Key West Golf Club community had a median of about $662,000, and private Sunset Key about $6.6 million.

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Key West neighborhoods and home prices

NEIGHBORHOODS AND PRICES

Old Town charm

A major draw for buyers looking for historic homes, iconic streets, and a strong sense of character in the heart of Key West.

What makes Key West unique

THE AREA

Buyers are drawn to Key West for its restaurants, galleries, walkability, energy, and the feeling of living in one of the most unique communities in the Florida Keys.

Lifestyle and location

Waterfront and island living

From canal and marina access to ocean views and private outdoor space, Key West offers a wide range of ways to enjoy the water.

Daily life in Key West mixes island ease with real-town convenience. You'll find grocery stores, a hospital, schools and services on the island, plus world-class fishing, diving and sailing from the harbors. Evenings mean sunset at Mallory Square, live music and some of the best restaurants in Florida.

Getting here is easy. Key West International Airport is minutes from most neighborhoods, and Miami is about a three-and-a-half to four-hour drive down the Overseas Highway.

Life in Key West

LIVING HERE

Waterfront home in Key West Florida Keys

Is Key West a good place to buy a second home?

Yes, if you want a walkable town with restaurants, culture and an airport close by. Key West offers historic homes, condos and canal homes, with more inventory to choose from in 2026 than in recent years.

Key West real estate FAQs

FAQS

What do homes cost in Key West?

The median sale price was about $987,000 over the past year. Condos start around $500,000, while historic Old Town homes and waterfront properties often sell for $2 million or more.

Can I rent out my Key West home as a vacation rental?

Only if the property has a City of Key West transient license, plus a state license, for rentals of 28 days or less. Most homes without one can only be rented for 29 days or more. We confirm license status before you make an offer.

How is Key West different from the rest of the Keys?

Key West is a real town, with walkable neighborhoods, nightlife, a hospital and the region's main airport. The rest of the Keys are quieter and more residential, with more canal homes and boating at your door.

Key Haven

A quieter residential area near Key West known for waterfront homes, boating access, and a more relaxed neighborhood feel.

Explore nearby Florida Keys communities

EXPLORE MORE AREAS

A highly distinctive island community known for luxury homes, privacy, and a unique relationship to Key West.

Sunset Key

Shark Key

A private gated island community known for luxury homes, exclusivity, and close proximity to Key West.

Contact Us

Whether you're buying a historic Old Town home, a condo or a waterfront second home from out of state, Greg Gordon works with you directly, from the first video walk-through to closing day.

Buying or selling in Key West?

Homes for sale in Key West Florida Keys