Living in New Town, Key West

Where New Town sits on the island

New Town is the eastern part of Key West, developed later than the historic west end. Much of it grew in the middle of the last century, partly on land that was filled and shaped for building. North and South Roosevelt Boulevard run along its edges, Key West International Airport is on its southern side, and Smathers Beach lines the Atlantic shore along South Roosevelt.

Most of the island's shopping centers, big grocery stores and everyday services are here, which is part of why year-round residents choose it. You arrive in New Town first when you drive onto the island on US 1.

Zillow's New Town boundary may not match what every local means by the name, so treat the index as a guide to the area, not a block-by-block price.

What the housing looks like

Where Old Town is wood frame on piers, New Town is mostly concrete block houses on slab, many built from the 1950s through the 1970s, plus condo and townhouse complexes, some along the water. Lots are generally larger than in Old Town, and driveways and carports are common.

That housing has its own checklist:

• Elevation. Older slab homes sit closer to the ground, which matters for flood insurance and storm surge. Ask for the elevation certificate.
• Roof and openings. Roof age, shutters or impact windows and roof-to-wall connections show up in the wind mitigation report and the premium.
• Plumbing. Original cast iron drain lines in homes of this age deserve a camera inspection.
• Condo complexes. Ask about roofs, reserves, recent assessments and the association's insurance.

New Town prices against the rest of the city

On Zillow's numbers, New Town fell 1.7% over the past year after rising 25.7% over five years. That five-year gain is slightly better than the city's 24.8%, so the area has held its value over time even with a soft last year.

The gap to the historic core is large. Old Town's typical value is about $1,259,886, roughly $452,000 more than New Town. Bahama Village, at about $819,399, is the only Zillow neighborhood close to New Town on price. Midtown, between the two halves of the island, is about $1,114,734.

Zillow's index for a neighborhood covers all home types. Because New Town has many condos and townhouses, its typical value is pulled down by smaller units, and a detached block house with a pool often costs more than the headline figure. For context, Key West's typical condo is about $705,769 and its typical house about $1,149,359.

Living day to day in New Town

New Town is where most errands happen. Groceries, hardware, pharmacies and offices are close, and it is easier to own a car here. Old Town is a few miles west, a short bike ride on the island's flat streets or a quick drive, though parking at the other end is the hard part.

Airport proximity is useful for frequent travelers and noticeable for houses under the flight path. Visit at different times of day if you are looking near it. Smathers Beach and the Atlantic side are close for swimming, walking and sunsets that locals argue about.

In general it is quieter than the blocks near Duval Street, with more families and full-time residents.

Taxes and insurance for a New Town purchase

A full-time resident who files for homestead gets up to $51,411 off assessed value in 2026 and the 3% Save Our Homes cap. The previous owner's taxes reset when you buy, so estimate the bill on your price, not theirs.

Insurance in New Town is often more manageable than for an old frame house in the historic district, because block construction and newer roofs earn wind credits. Low elevation can work the other way on flood. The only reliable number is a quote on the address, during your inspection period, with the roof age, wind mitigation report and flood zone in hand.

For condo and townhouse buyers in New Town, the association's master policy matters as much as your own. Ask what it covers, what the deductible is and how a storm loss would be shared among owners. Complexes of three or more habitable stories fall under Florida's milestone inspection and reserve study rules once they reach the age threshold, and many New Town complexes are old enough. Ask for the latest inspection and reserve study, and read the last two years of board minutes for talk of roof, concrete or seawall work. Resale condo buyers in Florida also get 7 days, not counting weekends and legal holidays, to cancel after receiving the association documents.

Is New Town a good place to live

New Town suits buyers who want a lower entry price for Key West, parking, more square footage and easy errands, and who do not need to walk to the historic waterfront. It suits less well if your reason for moving is the porch-and-picket-fence streets of Old Town. Buyers torn between the two often compare New Town block homes with Midtown, which sits between them on location and price.

If New Town fits, a shortlist sorted by elevation and roof age saves a lot of wasted showings.