10 Cities Where Retirees Would Find Life Way Too Difficult

If you've begun planning for retirement, it's easy to dream about the lifestyle you're looking for. Beach life? Cabin in the mountains? Apartment in the city?

Before you commit to a location, check out these 10 cities where the cost of housing might price you out. 

Editor's note: All home price data for each state comes from Zillow as of October 2025.

Miami is often thought of as a retirement destination thanks to its abundant sunshine and Florida's lack of income tax. However, the city is no longer a cost-effective move for many people.

The median price for a home is just under $600,000, according to Zillow. And the cost of both homeowners and car insurance has shot up in recent years.

Add in the risk from hurricanes, and Miami might not be as appealing as it looks at first glance. Fortunately, many other cities in Florida, such as Citrus Park and Mount Dora, are more affordable.

A trip to Hawaii is on the bucket list for many retirees, but what about living there?

Unfortunately, retirement in Hawaii is a pipe dream for many people, mainly due to the state's notoriously high cost of living.

Because most items have to be imported, everyday purchases are more expensive. This is in addition to high housing costs, with Zillow pegging the median home price at over $755,000, as well as high taxes and utilities.

If you're set on retiring on the West Coast, San Diego might be on your radar, but this city isn't where you should look to retire if affordability is a priority.

Zillow reports that the median home price is more than $980,000, while PayScale says the cost of living is 46% higher than the national average. 

Zillow says the median housing price in Los Angeles is closing in on about $1 million, which puts it out of reach of many retirees who don't have a few movie credits to their name.

Add in the traffic, which could make daily tasks a pain, especially if you have to drive often, and it's probably best to steer clear of the City of Angels.

Those looking for a laid-back lifestyle within the continental U.S. find Key West to be an appealing place to visit. It feels like you've escaped to a tropical island, with a side of Jimmy Buffett fun.

So, why wouldn't you want to retire there? Well, it starts with the high cost of living, with the median home price topping $1 million, according to Zillow.

Key West is also relatively isolated from the rest of the country. It's at the southernmost point of the U.S., and there is just one highway in and out. Evacuation during a hurricane can become a challenging endeavor, which may not be ideal as you age.

The cost of living in San Francisco is 65% higher than the national average, according to PayScale. That makes it hard to get ahead financially if you are a retiree or a resident of any age.

For the record, Zillow says the median home price is more than $1.25 million. So, even if you are determined to retire to San Francisco, owning a home may be out of the cards for most people.

On the one hand, there are advantages to retiring in New York. You don't need a car and are surrounded by other people. You'll find culture and restaurants at every turn.

However, the city is expensive. Housing, taxes, and health care are all significantly more costly than the national average, with the median house price at over $800,000.

People often say life is hard in the Big Apple. If you can make it there, you can make it anywhere. But do you want to struggle when you're supposed to enjoy retirement?

Seattle is a city full of culture and food, with walkable neighborhoods. For retirees looking to make their home in a beloved vacation destination in the Pacific Northwest, this might seem like an obvious next stop.

But Seattle is expensive. The median housing price is around $847,000, while the average cost of living is 45% higher than the national average, according to PayScale. 

Arizona's sunshine makes it a popular destination for retirees, but not every city in the Grand Canyon State is a good fit for your golden years.

Flagstaff, located near Sedona, is a particularly expensive place to retire, with a median home price of approximately $653,000, according to Zillow. PayScale estimates the overall cost of living to be 21% higher than the national average.

Instead, consider Arizona cities such as Mesa or Sierra Vista for a more affordable retirement, particularly if you have a fixed income.

Retiring to the nation's capital could be great if you're looking for culture, great restaurants, and walkability. But there are downsides for retirees considering a new life in Washington, D.C.

The cost of living is 39% above the national average, according to PayScale. Zillow says the median home price is more than $583,000, and traffic in the surrounding suburbs can make it a challenging place to put down roots.

One of the best ways to create a stress-free retirement is to bring down your biggest monthly costs. The cost of living in your area will determine whether you can live there comfortably.

For some people, the tradeoff of a more expensive city could be worth it for the amenities. But others want a place where they can kick back, relax, and live on Social Security and savings.

If you are in the latter camp, look beyond the cities on this list when thinking about where to spend your golden years.