Greener Pastures? Not So Fast!
Category: Retirement Planning
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 Coastal Florida. Once there they found they just couldn’t fit in. Kate is white, and husband Terry is black. To their dismay, they realized their new area was not a good fit: “Our neighborhood, it turned out, was very Republican — and we weren’t.” She noted in the article that the couple experienced racism and prejudice there. So they pulled up stakes and headed back north again, exploring western Massachusetts and ending up in rural Connecticut. 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.
Comments on "Greener Pastures? Not So Fast!"
AL says:
The article doesn’t state if the couple bought or rented. Rent before you even think about buying in a new location. Buying a home makes sense when raising a family but why buy as a retiree? There are rarely any so called affordable homes to buy in desirable areas these days. Resting isn’t cheap either. But at least with renting you have flexibility and you’re not tied down to an illiquid investment.
Patricia Mc says:
I moved from SoCal to South Florida in 2018. After 3 summers there I had still not acclimated to the humidity. I moved to the Phoenix area and could not believe how much more comfortable heat can be when it is dry heat. Have now been here 5 years and I'm never leaving.
Bill DiBlasi says:
Very interesting, but you allowed Kate F to offend Republicans, by associating racism with Republicans, which I am yet to experience. Based on the 3 extremely liberal-leaning locations she favors (Hudson Valley, NY, Colorado, Western Massachusetts) I think Kate should have said, Central Florida "featured too many conservatives trying to live a life guided by the Bible, out of gratitude to our loving/forgiving God."
Rufus says:
Careful Bill, I've been enjoying this site for many years and have discovered beyond a shadow of a doubt that the powers that be, lean solid left and for some reason find it very difficult to let them dang conservatives make very logical points and get away with it. In fact what I just wrote will no doubt be deleted.
Admin says:
Bill and Rufus. We were merely reporting what Kate said her experience was. No attempt to brand every Republican that way - plenty of racism in the other party too. Let's hope that everyone abides by the God I know, the one who loves everybody. Thanks for your comments.
George says:
Bill, you are spot on. Admin’s statement that they did not intend to brand “every Republican” as a racist is less than satisfying. Additionally, if they actually read The NY Times story (possibly rather than relying on AI?), they would see that the couple lived in coastal, not central, Florida. They moved from there to New Mexico, didn’t like it there, then moved to Connecticut (not western Massachusetts). I will be canceling my subscription.
Jes says:
I moved from upstate NY to coastal SC. It was beautiful, easy and a much better fit climate-wise; I rented for 7 or so years. But it just wasn't "my place." I have now moved to Savannah which is a much better fit. There are things I miss about NY but I could never afford to move back and could never deal with the weather again. It is nearly impossible to know what a place is like until you have lived there a while, and perfection probably doesn't exist.
Daryl says:
What would bother me about a community is how “in your face” the politics are—in either direction. I don’t want to run the gauntlet through opposing billboards every time I leave my house. There’s a big difference between not being invited to a picnic and someone putting dog poop in your golf cart because they disagree with your political affiliation. As far as racism, sexism, classism, I would do my homework first before moving.
Admin says:
Over the years I have known people personally as well as heard from many subscribers about why they moved a second, or even third or fourth time in retirement. They did so for a lot of reasons. Some include moving because they wanted to be near their children, who then moved. Or because they moved to be near the children but never liked the area or didn't find friends. Frequently the new area became too expensive, or their homes appreciated so much they moved to capture that equity and a better lifestyle. There are others who just got tired of the new area, and went back home or tried out another spot. You can't research too much, but even sometimes that doesnt overtake events. The good think about retirement is you can (usually) move anywhere and anytime you want.
(PS) George was correct. We erred in referring to some of the couple's moves: It was Coastal Florida and rural Connecticut. Now corrected.
Steve T says:
Moving in retirement should not be an automatic assumption. It's the second most critical event in retirement behind the inevitable. If you truly want to relocate and have identified the new area, I strongly recommend you spend at least three months renting and getting used to daily life in the new area. I did that and was amazed how different a place can be if you actually spend time there vs how it appears on paper. Even though it appeared to be my ideal place, after being there for three months it became a firm "no way", and I researched the heck out of the place. Many of the things I thought were agreeable turned out to be unacceptable and there were other things I had not even thought of which turned out to be major negatives. I feel that any move at all, even within the same town, will be a major adjustment. In my case even involved a culture shock. If you do move just accept that it will be different and an adjustment and you need to be willing to embrace the change.
Patricia Reynolds says:
So glad I have no family to effect my decision. I chose Tucson for the perfect weather except a bit chilly in January and february but I cruise then or drive to Mexico as I'm only 30 miles from the border. I'm in an area where 80 percent of the people are from other states so it's very diverse and easy to find friends. Lots to do and see. I've been here 8 years and will only move if I decide to move internationally
Rick says:
We tried a 55+ community in VA and had friends there but the HOA’s management company was terrible and so were a series of elected members of the Board. You can’t know that till you move in. We left for another community in VA and they are run properly so the whole atmosphere and offerings are better.
Admin says:
Frequent contributor Larry Gavrich thought this article, inspired by one in the NY Times, and the subsequent comments were pretty interesting. So he wrote a great article for his newsletter about it: "Heh NY Times: It's Not Nice Scaring Old People". Check it out!
Daryl says:
I enjoyed Larry’s article, and his noting that “If they hadn’t paid all those moving expenses previously, they probably could have afforded life back in the Hudson Valley, where they were originally settled and, apparently, happy,” made me think of other willing and unwilling journeys like Ulysses, Rasselas, even Dorothy (really.) They all returned not the same people who left, but wiser, more experienced, stronger, full of new stories and tips for the rest of us still sitting in our little mouse holes worried about making the “wrong” choice. Life’s an adventure, right? And they had one, and can have more. Home prices might just slide enough that they can then again live where they wanted, but it might not seem so shiny the second time around, because they’ve grown.
Admin says:
I love your comment Daryl. Such a positive take on the situation. Life is an adventure!
Jan Cullinane, author says:
We relocated several times during our working careers for corporate transfers, so it was easy for us to decide to relocate when we retired. We moved to Florida and have been here about 18 years. A few things that are worth considering (beyond the weather and ocean, which we knew we'd love): consider a new/developing community - much easier to meet people when most are new/more recent to the community; if you can afford it, buy into a community with a "club" component - including amenities such as golf, tennis, exercise classes, pickleball, and activities organized by our club itself (Trivia, special dinners, socials with dancing, guest speakers, etc.). We go to socials, plays, outings - all arranged by our club. Made the transition easy, fun, and it's easy to volunteer as well serve on committees, run a member book club, raise money for charities, etc.
Jan Cullinane, best-selling retirement author
Larry Gavrich says:
Thank you Daryl for your kind and insightful comments. And you as well, Jan, for your (as always) excellent advice. I was particularly interested in your comment about targeting “new” or developing communities. That idea relates to the next article I am working on, about the costs and challenges of building the home of your dreams. Based on some research I’ve done, the costs to build and the pricetag of a comparable existing home have narrowed. Yes, there are additional challenges to building a home, but couples with an organized plan can wind up with a home that has virtually everything they want.