8 Expensive Places to Retire that Are Worth Every Penny

Everyone’s Recommending These Places for Retirement!

I know we all discuss money, but let’s admit something: where you ultimately decide to retire has nothing to do with finances. Yes, it’s true. The top reason people decide to move in retirement is to be closer to their loved ones, as a survey conducted by Merill Lynch and Age Wave confirmed.

Or maybe it has nothing to do with moving; maybe you want to stick where you feel good and familiar and spend your golden years in your home state. But for different reasons, you could end up in a place where the living costs are weighing heavily on your funds.

Even so, have you ever considered that it might be all worth it? We did, and we also managed to pinpoint at least one amazing retirement destination in each state. We took everything into account, from safety to median incomes and, of course, poverty rates.

Even if the cost of living in each of these places exceeds the national average by over 7%, every offer comes with a ton of attractive advantages in exchange for a higher price tag. Are you curious to check the results?

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Photo by Olena Yakobchuk Shutterstock

Pittsfield, Massachusets

New England is quite expensive; everybody knows that. But Pittsfield, which is located in the western part of Massachusetts, has quite a small pocket when it comes to affordability. It’s still more reasonable than Boston and Cambridge, where the living costs are very high in the sky, so to speak.

Housing is a bit more affordable, as the median home value in the city is somewhere around $173,200, compared to $407,400 for all of Massachusetts and $592,300 for Boston. Leaf peeping during the fall is enough to convince you to move to the Berkshires.

However, you have plenty to enjoy throughout the year, including amazing sites for camping, fishing, hiking, and skiing. In its vicinity, you can always enjoy all kinds of musical performances at the Tanglewood Music Center, the well-known summer home of the Boston Symphony Orchestra. Moreover, there’s world-class art at the Clark Art Institute in Williamstown, but also at the Massachusetts Museum of Contemporary Art in North Adams.


Colorado is fifth on the list when it comes to senior health rankings. Moreover, Denver plays a healthy role in this rating. For instance, the Milken Institute, a well-known think tank, ranked the metro area as the 12th best big city for successful aging at large, mostly due to Denver’s healthy and active senior population.

Other wonderful strengths of this city include high employment rates and economic stability, but also a high-quality infrastructure with well-funded transit for older adults, highly rated nursing homes, and ample continuing care. The Denver metro area is also the home of over 24 healthcare facilities per 1,000 seniors, compared to only 19 per 1,000 seniors in the United States.

Reno, Nevada

Whether or not you’re into gambling, retiring here could make you feel like you’ve really hit the jackpot. Boasting a small-town feel with big-city ambitions and amenities, the city is known as the “Biggest Little City in the World.”

Moreover, it backs up the claim with the fact that it’s full of restaurants, nightclubs, art galleries, and music venues, on top of its well-known casinos. Outdoor enthusiasts also have a lot to win. The Sierra Nevada mountain range and Lake Tahoe offer ample opportunities for hiking, biking, and boating, especially in warm weather. In the winter, you can go skiing. There are also plenty of resorts and marinas in the area, which are fairly popular among residents of Gardnerville Ranchos, a very small Nevada town close to Lake Tahoe.

Easton, Md.

On the eastern shore of Chesapeake Bay, this tiny town is full of history, charm, and lots of senior residents. You can easily find a number of eclectic dining options in the city, as well as an array of boutique shops, art galleries, and many other cultural attractions.

As a matter of fact, in July 2019, Easton was declared one of the two emerging arts and entertainment districts in Maryland, joining the other 26 in the state with great tax incentives for local artists and creative businesses.

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

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Photo by Watchara Ritjan from Shutterstock

Burlington, Vt.

This tiny city, located on the shores of Lake Champlain, is quite a picturesque setting for tree-hugging retirees. There are lots of outdoor recreation opportunities, with miles of hiking and biking paths and beaches where you can swim freely.

An eco-friendly vibe fills the town, from the businesses bolstering the city’s flourishing economy, like household-products maker Seventh Generation, all the way to the local food movement feeding the neighborhood.

However, being green isn’t always easy on your wallet. Taxes and living costs are quite high, and while the median home value goes to a low of $206,000 in the Green Mountain State, especially compared with the median of $229,000 for the United States, it still climbs to $326,500 in Burlington.

A private room in a metro area nursing home costs around $11,498 a month, compared with $8,365 a month in the United States. The positive side is that you can save a lot of money on your academic pursuits, as the University of Vermont covers tuition for state residents aged 65 and older who want to take a class, even if it’s for credit.

Portland, Maine

The biggest city in Maine, Portland boasts quite a lively downtown and tons of urban-esque amenities in the great outdoors of the Pine Tree State. You have plenty of museums and theaters to enjoy, but also a wide array of eclectic dining.

The flagship L.L. bean store in Freeport is a wonderful must-see for many visitors, but resident shoppers also flock to Portland’s unique boutiques and outlets. At the same time, you’re never really too far from the area’s main beaches.

This also means there are many opportunities to lounge on the shore or even dive into water-based activities, such as fishing, kayaking, sailing, and even surfing. Naturally, hiking and biking trails are plentiful, so you won’t get bored there.

Middletown, Connecticut

Similar to the Northeast, Connecticut is well known as a high-cost area, and Middletown is no exception. However, the Hartford metro area, of which Middletown is a part, is a bit more affordable than other major metro areas in the state, such as Stamford and New Haven.

Local residents manage to pull in high enough incomes to live here, and that’s probably one of the reasons why the average income for households revolves around $90,977 a year. It’s even better for the older population, with incomes for residents over 60 averaging no less than $92,851 a year.

Corvallis, Oregon

The small city of Corvallis, located around 85 miles south of popular Portland, offers a very similar laidback lifestyle, but with much smaller crowds and relatively lower costs. The overall cost of living here is 19.8% above the national average.

Sure, it’s still quite expensive, but much more affordable than Portland’s living costs, which are 47.8% above average. Moreover, average incomes are comparable at $68,589 a year in Corvallis and $68,125 in Portland for all residents.

Besides financial aspects, the area has many things to recommend. You can easily enjoy the great outdoors by hiking or biking along 60 miles of wonderful trails and admiring the local wildlife.

If you found this article useful, we also recommend reading: 2024’s Best Tax-Friendly States for Retirees!


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