The 10 Most Expensive Retirement Destinations

We\'ve taken a look at some of the most expensive places to retire across the nation.
We've taken a look at some of the most expensive places to retire across the U.S.
We’ve taken a look at some of the most expensive places to retire across the nation.

Retirement gives you the opportunity to pack up and move where you’ve always wanted. But with a fixed income and potentially limited savings, expenses must be considered before moving into an active adult community. Here, we’ve broken down some of the most expensive options in the US. While many areas are no surprise, there are a few that you might not have known about.

San Francisco

It probably comes as no surprise to see San Francisco on this list. This Bay Area city is regularly named the most expensive in the country for housing prices, cost of living, and more, surpassing even New York City.  With a variety of exciting attractions and a booming job market thanks to nearby Silicon Valley, demand is high for homes in San Francisco, meaning prices keep going up. Retirees may have better luck in smaller Northern California cities like Sacramento, where historic districts and outdoor recreation are available at a lower housing price point.

New York City

While it might be slightly less expensive than San Francisco, New York City definitely isn’t budget friendly by the standards of most retirees. Its income tax rates are the highest in the nation, and Brooklyn was named the “Least Affordable Housing Market in America.” Property taxes are no picnic, either. New York’s ranked fourth highest nationwide. The big city is definitely full of exciting entertainment options, but active adults on a fixed income might need to look toward smaller cities for more affordability.


Full of American history and some great sports teams, it’s no wonder so many people want to live in Boston. But for many, the cost of living may be just too high, ranking as the fourth highest in America. Massachusetts as a whole can be unfriendly to retirees, with the median home value for 65+ coming in at almost double the US average. Additionally, the city suffers from higher than average healthcare costs for older adults.

Orange County

Living up to its television persona, “The O.C.” is really full of multi-million dollar beachfront homes. While that may make for a perfect fantasy retirement destination, the reality is that most active adults can’t afford the exorbitant cost of living found in Orange County. While Southern California as a whole is known to be expensive, Orange County has some of the highest priced homes in the area, with the average price running buyers over half-a-million dollars.


Surrounded by nature and a hip downtown area, Portland is a sought-after city to relocate to. That being said, relocating there may be easier said than done for retirees. Oregon has the seventh-highest cost of living in the nation, and necessities like healthcare aren’t cheap. A doctor visit costs almost 28 percent more here than the national average, meaning it’s not ideal for aging adults who need accessible healthcare on a set income. Additionally, the area’s local taxes also rank higher than the US average.

Westchester County

Slightly North of New York City itself, Westchester County prices itself out of most retiring adults’ budgets. Taxes are high across the board, with property taxes highest of all, which is not ideal for adults looking to buy a home after retirement. Additionally, the big selling point of Westchester County is a great school system, which doesn’t offer any benefit to the 55+ crowd, most with grown children. If proximity to the city is what you’re looking for, parts of Long Island or New Jersey may be more affordable retirement options.


Hawaii is an amazing place to visit, but an exceptionally expensive place to live. Due to being so far off from the continental United States, commodities there are highly expensive. Simple necessities like ibuprofen could run you upwards of $15, and food and fuel are similarly pricey. Many move to Hawaii expecting paradise, only to be met with the highest cost of living in the country. Additionally, with high income taxes, you would need to have a lot saved to be able to hold your own on this island.

Dukes County

This county in Massachusetts has some of the highest real estate prices in the nation. Home to the posh Martha’s Vineyard, it’s not uncommon to find multi-million dollar homes nestled on the beaches here. The median home value is almost $700,000, over double the Massachusetts state average. For those who can afford it, Dukes County is a beach town paradise. But while most retired workers are living with limited income, the steep housing prices may place this area out of reach.


While the cost of living in Montana is only slightly above average, retirees may need to do their research before flocking to its largest major city. Kiplinger named Montana one of the least tax-friendly states for retirees, due in large to the fact that they tax almost all types of retirement income, and the taxes kick in at a relatively low amount of income. Additionally, if you’re retiring to Montana to enjoy the local nature, know that the three percent tourist tax applies to all campground rentals, making recreation more costly.

Suffolk County

This county on Long Island ranks high in a few major categories – high housing costs, high taxes, and high healthcare expenses. With all of those obstacles to tackle, it may only be a manageable retirement destination for the wealthiest of retirees. Home to the Hamptons, these beach adjacent homes run well into the millions, and nearby shopping and dining is similarly costly. While living here might mean occasionally catching a glimpse of someone famous, there are definitely less expensive beach towns on the east coast to choose from.

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