Expensive Places to Retire That Are Worth It

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Where you ultimately choose to retire doesn’t always come down to dollars and cents. Indeed, the top reason people move in retirement is to be closer to family, according to a survey by Merrill Lynch and Age Wave, a research firm focused on the aging population.

Or, rather than move, maybe you just want to stick where you’re comfortable and familiar and retire in your home state. For whatever reason, you may wind up retiring in a place where the living costs can be relatively high.

But it can be worth it. We pinpointed one great retirement destination in each state, taking into account safety, median incomes and poverty rates for retirement-age residents, locals’ sense of well-being, and the availability of recreational and health care facilities, as well as living expenses.

While the cost of living in each of these 14 retirement spots exceeds the national average by more than 7%, each offers plenty of attractive advantages for retirees in exchange for the higher price tag. Take a look to see if any of these pricey places to retire are worth fitting into your own budget.


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Pittsfield, Mass.

  • City population: 43,289
  • Share of population 65+: 19.0%
  • Cost of living for retirees: 7.9% above the national average
  • Average income for population 65+: $58,231
  • Community score: n/a
  • State’s tax rating for retirees: Not Tax-Friendly

New England is notoriously expensive, but Pittsfield, located in the western part of Massachusetts, offers a small pocket of relative affordability—more reasonably priced than Boston and Cambridge, where living costs are, respectively, 48.1% and 38.1% above the U.S. average.

Housing is notably affordable: The median home value in the city is $173,200, compared with $407,400 for all of Massachusetts and $592,300 for Boston proper, according to Zillow.

Leaf peeping in the fall may be enough to draw you to the Berkshires. But you have plenty to enjoy all year round, including excellent sites for camping, fishing, hiking and skiing. Nearby, enjoy musical performances at the Tanglewood Music Center, the summer home of the Boston Symphony Orchestra.

There’s also world-class art at the Clark Art Institute in Williamstown and the Massachusetts Museum of Contemporary Art (MASS MoCa, for short) in North Adams.


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Denver

  • City population: 678,467
  • Share of population 65+: 11.2%
  • Cost of living for retirees: 9.4% above the national average
  • Average income for population 65+: $59,601
  • Community score: 63.4
  • State’s tax rating for retirees: Mixed

Colorado ranks fifth in the United Health Foundation’s senior health rankings, and Denver plays a healthy role in that rating. Indeed, the Milken Institute, a think tank, ranked the metro area the 12th best big city for successful aging in large part due to Denver’s healthy and active senior population.

Other strengths of the area include high employment and economic stability, as well as quality infrastructure, with well-funded transit for older adults, highly rated nursing homes and ample continuing care.

Indeed, the Denver metro area is home to more than 24 health care facilities per 1,000 seniors, compared with just about 19 per 1,000 seniors in the U.S.


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Reno, Nev.

  • City population: 239,732
  • Share of population 65+: 13.8%
  • Cost of living for retirees: 10.4% above the national average
  • Average income for population 65+: $51,061
  • Community score: 61.2
  • State’s tax rating for retirees: Most Tax-Friendly

Whether or not you like to gamble, retiring to Reno can make you feel like you’ve hit the jackpot. Boasting a small-town feel with big-city amenities, the locale proclaims itself “The Biggest Little City in the World.” And it backs up the claim, offering a downtown full of restaurants, nightclubs, art galleries and music venues, on top of its well-known casinos.

Outdoor enthusiasts also win. The nearby Sierra Nevada mountain range and Lake Tahoe provide ample opportunities for hiking, biking and boating in warm weather, and skiing in winter.

The area’s resorts and marinas are also popular among residents of Gardnerville Ranchos, a small Nevada town near Lake Tahoe that’s home to a surprising number of millionaires.


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Easton, Md.

  • City population: 16,606
  • Share of population 65+: 23.5%
  • Cost of living for retirees: n/a
  • Average income for population 65+: n/a
  • Community score: n/a
  • State’s tax rating for retirees: Least Tax-Friendly

On the eastern shore of the Chesapeake Bay, this small town is packed with history, charm and senior residents. You can find a surprising number of eclectic dining options in town, as well as an array of boutique shops, art galleries and other cultural attractions.

In fact, in July 2019, Easton was named one of two new Arts and Entertainment Districts in Maryland, joining the 26 existing Districts in the state in offering tax incentives to local artists and creative businesses.

Qualifying developers and organizations will get a property tax abatement for artistic-related improvements to their buildings, and local artists can score a state income tax deduction for all art created and sold within the 110-acre district.

And you could use the extra opportunity to save. Maryland is, by and large, a wealthy area, home to a great number of millionaires, and the living costs reflect that.

The cost of living for all residents in Easton is 13.8% above the national average, according to Sperling’s BestPlaces, which makes it at least more affordable than Annapolis, on the opposite shore of the bay, where living costs are 41% above the national average.

And water-loving retirees still have access to the same torrent of activities, such as kayaking, canoeing, boating and fishing, common on the Chesapeake Bay.


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Burlington, Vt.

City population: 42,453

Share of population 65+: 10.7%

Cost of living for retirees: 16.4% above the national average

Average income for population 65+: n/a

Community score: 64.2

State’s tax rating for retirees: Least Tax Friendly

This small mountain city on the shores of Lake Champlain is a picturesque setting for tree-hugging retirees. Outdoor recreation is plentiful with miles of hiking and biking paths, nearby beaches where you can swim, kayak or paddleboard in the warmer months, and numerous skiing options in the area.

An eco-friendly vibe permeates the town, from the businesses bolstering the city’s economy, such as household-products maker Seventh Generation, to the local food movement feeding the neighborhood.

But being green isn’t easy on your wallet. Taxes and living costs are high. While the median home value is a low $206,000 in the Green Mountain State, compared with the median $229,000 for the U.S., it climbs to $326,500 in Burlington.

A private room in a metro area nursing home costs a median $11,498 a month, compared with $8,365 a month for the U.S. At least you can save money on academic pursuits. The University of Vermont will cover tuition costs for state residents age 65 and older who wish to take a class, even if it’s for credit.


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Portland, Maine

  • City population: 66,715
  • Share of population 65+: 13.7%
  • Cost of living for retirees: 17.1% above the national average
  • Average income for population 65+: $44,769
  • Community score: 65.8
  • State’s tax rating for retirees: Mixed

The largest city in Maine, Portland offers a lively downtown and plenty of urban-esque amenities amidst the great outdoors of the Pine Tree State. You can enjoy museums, theaters and an array of eclectic dining. The flagship L.L. Bean store in nearby Freeport is a must-see for many visitors, but resident shoppers also flock to Portland’s unique boutiques and outlets.

All the while, you’re never too far from the area’s many beaches. That means ample opportunity to lounge on the shore or dive into water-based activities including fishing, kayaking, sailing and even surfing. And of course, hiking and biking trails abound—perfect in the (much) colder months, too, for cross-country skiing and snowshoeing.


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Middletown, Conn.

  • City population: 46,747
  • Share of population 65+: 14.4%
  • Cost of living for retirees: 19.2% above the national average*
  • Average income for population 65+: n/a
  • Community score: 59.8*
  • State’s tax rating for retirees: Least Tax-Friendly

Like much of the Northeast, Connecticut is known to be a high-cost area, and Middletown is no exception. But the Hartford metro area, of which Middletown is a part, is at least more affordable than other major metro areas in the state, including Stamford and New Haven, according to the Council for Community and Economic Research.

And local residents tend to pull in high enough incomes to make it work. The city’s average income for all households is $90,977 a year, and it’s even better for the older population with incomes for residents age 60 and up averaging $92,851 a year.

Plus, being home to Wesleyan University, Middletown offers all the benefits of retiring to a college town, including numerous restaurants, shops and cultural attractions. You can also take advantage of the Wesleyan Institute for Lifelong Learning, which offers no-credit courses, lectures and other educational opportunities at minimal cost and is open to the entire community.

And while the nearby city of Hartford has an alarmingly high crime rate—with 1,093.8 violent crimes per 100,000 residents reported, compared with the national rate of 473.2 for cities of similar size—Middletown is far safer with a mere 49 violent crimes total reported for the year.

*Data for the Hartford metropolitan statistical area, which includes Middletown.

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