Greener Pastures? No So Fast!

November 3, 2025 — Retire and find your paradise – maybe. One study found that 40% of retirees who move in retirement don’t end up staying. Another one from Hirehelper.com reported that 28% of folks who moved in the past year regret it. In this article we will explore some of the reasons why so many people experience relocation troubles in their retirement.

Multiple Reasons for Multiple Retirement Moves

A recent NY Times article, “Retirement Moves Don’t Always Bring Greener Pastures,” profiled the sagas that tripped up some typical retirees. Many of them thought that they had carefully researched their new lives, only to discover problems.

Expense and Political Misfits

Kate Ferriter and her husband first relocated from the Hudson River Valley in New York to Colorado. Rising housing costs there drove them to a community in Central Florida. Once there they found they just couldn’t fit in. Kate is white, and husband Terry is black. To their dismay, their new area featured too many Republicans and blatant racism. So they pulled up stakes and headed back north again, this time to western Massachusetts. There they encountered a problem many retirees experience when they move – housing prices had appreciated – and the proceeds from their Florida home just weren’t big enough in their new competitive market.

Fantasy vs. Reality

Many other people entering retirement choose a new place to live from a shaky foundation. They visit in the high season (or the reverse), then find it is a completely different place at other times of the year. Traffic is too intense, or maybe the town is deserted. Moral: you can’t test the waters too long, or at enough different times of the year, to get an accurate picture of what life is really like in a place. Whether because of the weather, the cost, or the neighbors, many folks more after a year or two.

The Unexpected

Florida coastal areas look like paradise to plenty of people moving from Ohio or Minnesota. Unfortunately the experience can be ruined by unexpected factors. As a result of the tragic building collapse in Surfside, Florida legislators enacted strict building inspection and reserve requirements for many multistory condo buildings. Meanwhile, catastrophic storms have brought unprecedented increases in insurance premiums. That one-two punch has meant a doubling of condo fees and assessments for thousands of FL HOAs. Bottom line: a huge number of Florida retirees are now forced to move because current expenses are so much higher than what they were just 5 years ago.

Medical and Traffic

Diana Landau, who with her husband write a newsletter for people over 50, recently highlighted one of the prime, but unexpected reasons why so many retirees flee their retirement dream. Moving to a new area, people discover that finding a compatible general practitioner is nigh near impossible. Or, they experience a new illness or medical condition that requires a specialist. To their dismay, that medical support is either not available, or is hours away.

No Going Back

More than one person move to be near (or far away from) their children and friends. Many times it works out great – rewarding relationships with grandchildren while helping out the parents during difficult times. But in other cases it doesn’t work out as planned – they might not have signed up for so much childcare duties, or not enough. Or, the children move again, the grandkids grow up, leaving the retiring couple with the difficult choice of either moving again, staying in an area where they have few connections, or headed back to a housing market they can no longer afford.

Bottom Line

The sad fact is, for variety of reasons, there is a good chance that your retirement move won’t end up in paradise. Usually it is a function of not doing enough research, but sometimes it’s a combination of unexpected developments. If that happens, there is good news. As many Topretirements Members have outlined on this Blog, recovery is possible. Having moved once, it is a lot easier the next time. And, since retirees don’t have the added burden of having to find a job in the new location, that makes it a little easier too.

Comments? Have you either moved more once in retirement, or have thought about it? What are the factors that led to that decision. Please share your experiences in the Comments section below.