Second Homes and Vacation Destinations: When Going Home Means Going on Vacation

Second Homes and Vacation Destinations: When Going Home Means Going on Vacation. WHEN Derek Saathoff visits his native Louisville, Ky., each month, he likes to make a long weekend of it. Continental Flight 2925 out of Newark on Thursday afternoon gets him to Louisville just before 4:30, in plenty of time for a run in a park before dinner at Mojito’s Tapas and drinks at the Pink Door, a noodle and tea lounge with a bar.

Nathaniel Brooks for The New York Times
FAMILIAR WATERS Joanna Roche and John Stringer vacation at Goose Pond in Lee, Mass, where they swam growing up.
Until recently, Mr. Saathoff would have bunked with his parents or one of his siblings. But since May, he’s had a place of his own, a one-bedroom condo on the third floor of a converted Victorian house, just three blocks from his old high school.

“When I was growing up, I wanted to leave and move to New York as quickly as possible,” said Mr. Saathoff, 25, an agent at Wilhelmina Models, whose primary residence is a studio apartment in the East Village. “And now I find myself torn between the city and Louisville. I’ve got the easier life in Kentucky, and the metropolitan life here.”

“Considering the prices, I didn’t find buying something in the Hamptons or upstate New York feasible or even necessarily desirable,” he continued. “They’re not the places I’d go to rejuvenate or to recharge my batteries.”

Leaving home is a classic rite of passage; for many people it’s the great, long-deferred escape. When they visit their former homes, it’s under duress and then only for holidays and familial state occasions.

Others return after college or after a few years in the big city having decided that yes, the native sod really is a great place to raise children.

Then there are those who split the difference: they live elsewhere, but own a vacation property in their hometown or environs.

“You grow up and you move away because of your job and you find it’s a nice place to come back to,” said Tricia Dieringer, a hosiery company owner who lives on the Upper West Side of Manhattan but also has a house at a Rehoboth Beach, Del., golf resort a few minutes from Lewes, her hometown. “I come across Delaware Memorial Bridge and there’s this peaceful feeling of coming home.”

For some, the pull of home is largely emotional, a chance to relive select precious pieces of their childhoods, to revisit select landmarks — Ms. Dieringer is partial to the Lewes Beach Dairy Queen where she worked as a teenager — and to give their own children a sense of continuity.

That’s the case as well for Susan Helier, a legal assistant and single mother in Salt Lake City who grew up in East Hampton, N.Y., and who, 10 years ago, built a three-bedroom vacation home there.

“There’s a lot of history here that I share with my daughter,” she said of her Long Island hometown. “I take her to Georgica Pond, where we used to go sailing and crabbing. As a little kid I used to go to the nature trail, so I take her there as well.”

The trip down memory lane also includes stops at the tip of Montauk (as a teenager, Ms. Helier dated the son of the lighthouse keeper) and the Hampton Classic (Ms. Helier was a habitué when it was a low-key horse show.)

Similarly, Joanna Roche says she loved growing up in Lenox, Mass.

“Everyone knew me,” said Ms. Roche, the vice president of sales for Cypress, a supplier of linens to hotels and spas. “It was very safe. But growing up in such a small town, I wanted to move away.”

After several years of living in California and Hawaii, she headed back to Lenox and married her long time boyfriend John Stringer. The couple subsequently bought a weekend getaway on Goose Pond, one town over in Lee, Mass.

“My husband’s family had a house there the entire time he was growing up, and this is basically a tradition we want to pass along to our children,” said Ms. Roche.

Where she swam and boated as a child so will her two boys. The same stretch of the Appalachian Trail she hiked, “they’ll be able to do,” Ms. Roche said. “I think it’s very grounding for children to have those roots.”

And, apparently, very grounding for adults as well. Such is the case with Vanessa Jones, a real estate broker who has an apartment in Harlem and owns a vacation property a mere five blocks from her childhood home in the View Park section of Los Angeles.

“My brother’s godmother lives next door,” Ms. Jones said. “It’s a very tight-knit community, a little Mayberry. I like that small-town feeling.”

Ms. Jones decided to hang on to the two-bedroom Los Angeles bungalow, originally her primary residence, as a weekend getaway when she moved to New York seven years ago.

“It was the dead of winter and I wanted to be able to get away during the cold months,” she said. “My apartment in New York isn’t that big. I enjoy going back to L.A. where I can have people over.

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Tyler Bissmeyer for The New York Times
Derek Saathoff in front of his Louisville apartment.

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Dee Marvin for The New York Times
‘PEACEFUL FEELING’ Tricia Dieringer enjoys the emotional ties of vacationing near her Delaware hometown.
“I’ve redone the house with hardwood floors, and re-landscaped. There’s a hammock and a waterfall in the back.”

Depending on her work schedule, Ms. Jones gets back home about once a month. Her mother keeps an eye on the property, and visiting family members can bunk there.

“It works out well,” she said. “I love my mother. I talk to her every day, but I can’t stay in the same hotel room or house with her. We’re very different people. With the house, I get to have my private time.”

Ms. Jones said that she could have bought something a bit closer to New York, and that she was considering buying property in the Hamptons or on Candlewood Lake in Connecticut.

“I don’t want to always fly 3,000 miles for vacation,” she said. “But then I’d have to invite all the people I love dearly to that place when they’re all in California. It works well for me to go to them.”

For Carol Zellway, a middle-school teacher in Montclair, N.J., it wasn’t that she particularly intended to buy a weekend getaway in East Hampton, her hometown. In fact, there were many handier places for her to spread her beach towel.

“I did consider the Jersey shore for a little bit because it was closer and more convenient,” she said. “I spent some time on Long Beach Island. I tried to like it.”

But all the time she tried to cozy up to the colloquially known L.B.I., Ms. Zellway found herself returning to East Hampton, even after her mother sold the family home in 1994. Finally, in 1999 she and her husband (the two have since divorced) bought a three-bedroom saltbox with a pool and skylights in the town’s Springs hamlet.

“I wanted to be back there,” said Ms. Zellway, who retained the property when the marital assets were divided. “My best friends from elementary school live in East Hampton. I still feel like a local. And being a teacher, I have summer off and can spend all of it out there.”

For some, the decision to buy in their hometown is born as much of practicality as sentimentality.

“They’re tuned in to the market and they’re also planning on returning some day and that vacation residence will become their primary residence,” said Hunter Carson Frick, a project manager for Halstead Property Development Marketing in New York. That’s exactly the plan of Ms. Dieringer and her husband in Delaware.

“We’re also finding that people who are buying in their 20s are turning to their hometowns to buy not only vacation properties but investment properties that they can rent out to build equity,” Mr. Frick said. “That way, when they’re in their 30s and continue to live in New York, they can use the money they’ve earned as a down payment on a co-op.”
A no-brainer investment — that’s how Ms. Helier characterizes her one-acre property in the Northwest Woods section of East Hampton, a retreat she visits for two or three weeks every fall and, if it hasn’t been rented out, for a month each summer. “It’s a market I know and understand,” she said.

“But,” she added, “it also had the pull of family for me. I still call the Hamptons home, though I haven’t lived there since 1976. When my mother sold the house I grew up in and retired to Florida, I felt I needed a place to come back to. I wanted to have a base there.”

Of course, watching a house increase in value isn’t the only dividend for those who buy vacation property in their hometowns. Knowing the territory often proves as useful as knowing the market.

“I know shortcuts to avoid traffic, that’s for sure,” Ms. Zellway said. “Sometimes, I’m on those back roads and there’s no one else there.”

In the Berkshires, Ms. Roche has figured out where to go to escape the tourists who flock there every summer.

“We know which restaurants won’t be crowded,” she said, mentioning the Roadside Cafe and Store in Monterey, Mass., and the Dream Away Lodge in Beckett, Mass.

For her and the others who return home, the occasional crowds, the airfare, the time spent commuting are all small prices to pay.

“It’s just such a nice lifestyle,” Mr. Saathoff said of his old — and new — Kentucky home, for which he paid just under $100,000. “My friends find it strange that I feel so deeply connected to it. They’re from similar places like Arkansas or Ohio or Michigan and couldn’t wait to leave and don’t ever want to go back.

“But I get very emotional when it’s time to leave Louisville and return to New York. It’s hard for me to go back and put on my game face.” 

Second Homes and Vacation Destinations: When Going Home Means Going on Vacation. WHEN Derek Saathoff visits his native Louisville, Ky., each month, he likes to make a long weekend of it. Continental Flight 2925 out of Newark on Thursday afternoon gets him to Louisville just before 4:30, in plenty of time for a run in a park before dinner at Mojito’s Tapas and drinks at the Pink Door, a noodle and tea lounge with a bar. Editing by Bruce Clemens

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