Ecclesiastes (and Pete Seeger) weare right: To everything there is a season.
A time to be born. A time to die. A time to plant. A time to reap.
A time to move to Westport. A time to move away.
And a time to move back again.
David Loffredo lived here as a child. He went to the Nature Center pre-school, Riverview kindergarten and 3 elementary schools.
He was a Westport YMCA Water Rat, and caught the final out in the 1976 Little League Cap League championship game. He rode the Minnybus everywhere, and saw “Star Wars” at the Fine Arts Theater.
A remnant of David Loffredo’s Westport youth.
He returned as an adult, with a wife and toddler. Over 2 stints totaling 27 years, the family grew and thrived. He works in private equity. His wife — an obstetrician/gynecologist — is at Columbia University.
A couple of years ago, the Loffredos relocated New York’s Upper West Side. But David remains connected to Westport, through “06880.”
His journey is not unique. In fact it mirrors the arcs of many lives. I’ve often thought about families’ movements in and out of town — what brings them here, and what pushes (or pulls) them away.
But the other day, David articulated it far better than I could. He describes the various seasons of Westport life this way:
A family moves here. (“It’s the rare childless couple who moves before kids,” he notes. “We came with a 3 year old, then added 2 more.”)
The family “spends 20+ years doing all the 06880 stuff. The kids grow up, go to college, hopefully don’t move home, and ideally move to New York so you can still see them.” All 3 of theirs did.
The parents “suddenly feel old, disconnected from long time friends who either retire somewhere or fade away because the kids as glue are gone.” With their children not planning to return for at least a decade — if at all — the parents sell. David says, “I exchanged my property tax bill for an entertainment budget.”
With kids gone, empty nesters often look for a smaller place. There are many in New York City. (Photo/Dave Matlow)
With everyone in New York — David’s family is scattered across 4 apartments — there is time and space for “family dinners, concerts, plays, movies, etc. This makes all that parenting worth it.”
As time passes, “kids become adults.” They exchange roommates for “partners.” That’s where David and his wife are now, with 1 child.
As the young couple matures, “they get a French bulldog. Eventually they create a human (one of the only free activities in New York). As that human grows, they realize how intimidating it is to raise a kid in the city.”
The new family moves back to Westport “to recreate their upbringing, because how do you top it?” Hopefully, David adds, “they don’t have to commute full-time like their parent(s) most likely did.”
Meanwhile, their parents — former Westporters — “realize how much fun it is to be around their new grandchild.” So they ditch Manhattan and retake Westport — either in “a fancy condo” or less expensive rental apartment.
Residences like The Mill attract former residents back to Westport.
David and his wife are partway through the process. But they’ve seen friends go all the way through it. He’s sure they’ll eventually do the same.
Of course, this is just one scenario. It’s not for everyone. Everyone’s life, lifestyle and life circumstances vary.
But to everything there is a season.
A time to kill. A time to heal.
A time to laugh. A time to weep.
A time to cash out, and a time to buy or rent again — keeping the Westport real estate market turning.
(“06880” regularly covers Westport real estate, Westport life — and the lives of people who live here. If you enjoy stories like this, please click here to support our work. Thank you!)
