Rappaports traded Connecticut for Las Catalinas and rebuilt life on a $1.6M home

Allyson and Andrew Rappaport sold their Connecticut home for $915,000 and moved permanently to Las Catalinas, a car-free beach town in Costa Rica, in 2020. They then bought a four-bedroom home in the town for $1.6 million and spent about $200,000 renovating it, turning a retirement dream into a real estate decision with real trade-offs.

The headline hook here is simple: this was not an abstract “someday” move. In the US, their annual property taxes were about $15,000. In Costa Rica, they pay around $5,000. That delta matters because it is recurring, predictable spending, and recurring costs are what quietly break budgets for families trying to slow down.

Before the move, the Rappaports ran a veterinary practice in New York, working often six days a week, then returning at night to a four-bedroom home in Ridgefield, Connecticut. Allyson, now 50, and Andrew, 65, say they were already dreaming of slowing down and spending more time together. High costs were part of it. So was a different kind of risk calculus: school safety. Allyson pointed to the “active-shooter drills” her kids participated in back in Connecticut, calling it unsettling and saying she did not want to raise her children “in this environment where you have to worry about being shot in school.”

Once the idea of leaving the US took hold, it did not immediately land on any US alternative. They kept coming back to Costa Rica, a country they had visited multiple times and loved. When they returned for another vacation, they checked out properties and found Las Catalinas on Costa Rica’s Pacific coast, described in the source as a car-free beachfront town. Their reaction was immediate. Allyson told Business Insider, “Immediately we're like, 'Oh my God, this is where we need to be.'” Their two sons, then 6 and 8, were already excited because they had visited Costa Rica before.

The move looks lifestyle-driven, but it was also an investment-and-immigration story. The article notes that the US Embassy in Costa Rica says approximately 120,000 Americans live in the country. Costa Rica offers multiple residency options, including visas geared toward retirees, digital nomads, and investors. The investor program allows foreigners to qualify for residency by making a minimum $150,000 investment in the country, including in real estate. The Rappaports took the route that matched their capital situation: investing in property. This is the kind of policy detail that executives sometimes skim past because it is not in a quarterly earnings deck, but it can determine where talent and capital can practically go.

By the time they settled, they were already thinking in multi-year terms. The source says their current residence in Las Catalinas is the second property they owned in the country. They sold their first house in Las Catalinas for around $1.5 million, then purchased a larger home nearby for $1.6 million in 2021 and spent roughly $200,000 upgrading it. That sequence matters. It signals confidence in the local market enough to upgrade, not just to “try it out.”

What they get day to day is shaped by the town’s design and by the pace of life they say they deliberately chose. Las Catalinas is car-free, which their kids experience as safety and freedom. Andrew said they appreciate that the walkability is “so great for the kids,” because they can go out without having to worry about them getting hit by a car. The sons attend an international school and have formed friendships with kids of different ages and backgrounds.

The Rappaports also describe a friction-filled learning curve that many relocating families share: even though English is widely spoken in Costa Rica, they initially struggled with the language barrier, and now they are fluent in Spanish. They miss some American conveniences, including specialty ingredients and the ease of online shopping they had back in Connecticut. Yet they frame the slower, more manual everyday life as a forcing function for consumption discipline: they now spend more mindfully and say, in Allyson’s words, “You realize, maybe I don't really even need that.”

For business leaders and operators, the second-order implication is that “migration reasons” blend personal values with structural constraints. The Rappaports’ calculus included tax recurrence (about $15,000 US property taxes versus around $5,000 in Costa Rica), safety perceptions tied to schooling, and the availability of residency channels that make cross-border living legally durable. Their story also hints at a different labor and productivity rhythm: chores that can take several hours in Costa Rica contrast with the way their days used to run on veterinary-practice schedules, but they say they are not bored and still do not feel rushed. They describe typical days that include breakfast and getting kids ready for school, then Allyson heading to tennis courts, followed by lunch, and afternoons at the beach, by the pool, or at the gym.

The strategic stakes for peers are real: families are not only comparing temperatures and beaches. They are comparing risk environments, recurring cost lines, safety cues, school routines, and the practical friction of language, errands, and bureaucracy. When your talent is evaluating where a life can be built and sustained, those details behave like a competitive advantage for regions that can combine safety, predictability, and policy pathways.

In the Rappaports’ framing, the endgame is more time together. After seven years, Allyson said it “still feels like we're living on vacation.” That sounds like sentiment, but it is also the business truth of what incentives do: when stressors drop and daily logistics stop stealing evenings, people show up for their relationships, their routines, and their future.