Schools Drive the Market

Families don’t move to New Canaan for shorter commutes or bigger yards. They come for the schools. Year after year, Niche ranks our district among the very best in Connecticut and the nation for academics, athletics, and teacher quality. That reputation powers our housing market. It attracts families, sustains home values, and ties real estate trends directly to decisions made by the Board of Education.

The Enrollment Surge and Its Implications

According to NESDEC, New Canaan’s student population is projected to climb from about 4,200 today to nearly 6,000 within 15 years, a 40% increase. The pattern is familiar: five years after births rise, kindergarten fills; five years later, the middle schools swell; four years after that, the high school follows. If these numbers hold, by 2035 our classrooms will be stretched to capacity.

The question is whether this surge is real enough to plan, or even build, for now Limits of Forecasting

But projections fail. A 2015 forecast expected 4,345 students by 2024; actual enrollment came in closer to 3,990. COVID scrambled migration patterns. Remote work reshuffled family choices. Even the National Center for Education Statistics concedes that 10-year forecasts carry 2–3% error rates.

Short-term projections are more reliable: NESDEC’s 2023 estimate for 2024–25 missed by just 59 students — a 1.5% margin, close enough to staff classrooms accurately.

Still, how confident should we be? Confident enough to bet $100 million on permanent growth?

The High-Stakes Question

That’s the question now before the Board of Education. This month, the board began studying the possibility of building a new North School, a major investment meant to handle projected growth. The proposal envisions a new elementary school to relieve overcrowding across the district.

But if projections miss, we could build a school we don’t need. If they’re right, we risk running out of space. Either way, the decision will define New Canaan’s schools, and housing market, for a generation.

What Really Moves Enrollment

Enrollment isn’t driven by statistics, it’s driven by housing. Every time a home changes hands, a new family enters the district. Each year, the largest share of buyers still come from New York City and Westchester, with smaller but steady numbers from Stamford and Norwalk.

But here’s the shift: fewer homes are turning over. Seniors are staying put longer, and their share of the population is rising fast, projected to climb from about 15 percent today to over 20 percent within a decade. At the same time, families with children continue to arrive, pushing enrollment higher. Both trends are true. Yet housing supply is finite. Zoning limits new construction, and high land costs deter large-scale development. Between 2010 and 2020, the town’s housing stock grew just 4.5 percent.

You can’t have both more children and more seniors without more housing, and New Canaan isn’t building much. That’s the real constraint beneath every forecast.

Demographic Crosscurrents

Here’s the paradox: New Canaan has one of the highest shares of children in Connecticut, 28.5 percent of residents under 18, far above the national average. Yet the actual number of children fell slightly between 2010 and 2020, from 6,329 to 6,048.

At the same time, the share of residents over 65 climbed to 15 percent and continues to grow. More kids. More seniors. Almost no new housing. Zoning reforms, ADUs, and transit-oriented districts add only a trickle of supply. So, the competition intensifies: seniors with cash compete against families with kids for the same limited number of homes. That pressure drives prices up, and shapes who can afford to live here next.

Structural Constraints

This isn’t just a demographic story, it’s a structural one. Even if New Canaan wanted to add more housing, the math doesn’t work easily. Most of the town is zoned for one- or two-acre lots, and development costs are among the highest in the region. The few zoning changes we’ve adopted, accessory dwelling units, multi-family overlays near transit, modest density bonuses, add dozens of homes, not hundreds.

With so little new supply, the housing market becomes a closed system: every new family depends on another family leaving. When seniors stay longer, turnover slows, and school enrollment projections start to diverge from reality.

Wild Cards and Black Swans

Every forecast assumes stability, steady growth, predictable turnover, normal migration. But it rarely works that way. COVID and the rise of remote work shattered past models overnight. A sudden boom in housing construction, a financial crisis, or a policy change in New York could do it again.

In 2009, during the financial collapse, New Canaan recorded a month with no home sales at all. That’s how fast the equation can change.

And sometimes the wild card isn’t a crisis at all, it’s innovation. The very things that make our schools and town exceptional can also disrupt the models.

The Innovation Factor

New Canaan has long been a leader in curriculum, athletics, and the arts. Our teams win, our programs shine, and yes, we have The Dome. But excellence doesn’t stop there. This year, the district is installing a new, smart sound system in every classroom.

It’s not just an upgrade from tinny speakers. Each room is sound-mapped. Every teacher wears a wireless microphone so students hear clearly from any seat. The system links instantly to the nurse, the main office, or emergency services. It can even translate in real time between English and other languages, making classrooms safer, smarter, and more inclusive for international families.

What does this have to do with enrollment? Everything. Education rankings now reward inclusivity and innovation as much as test scores. A district known for welcoming multilingual learners and embracing technology earns a different kind of reputation, one that resonates globally.

Realtors already hear it: families often move for one thing that’s excellent, not for a dozen things that are merely good. The number of international families seeking exceptional schools is growing. A small innovation like this could have an outsized impact on who chooses New Canaan next.

Why It Matters

This is the real engine of New Canaan. Great schools bring families from New York and Westchester. Seniors stay put, supply stays tight, and demand stays wide. That’s why prices remain strong, and why every innovation, every accolade, every program in our schools eventually echoes through our housing market.

The Board of Education may soon decide whether to build a new North School. Whether we’ll need it depends on more than projections. It depends on who can afford to live here, who chooses to stay, and how our town continues to define excellence, in the classroom and beyond.

John Engel is a broker on the Engel Team at Douglas Elliman, and he had to come all the way to Las Vegas this week to run into fellow New Canaan agents Michelle Sloan and Taylor Tait in the lobby of the Bellagio. Small world. New Canaan agents occasionally do leave town. 

Check out John Engel’s Podcast, Boroughs & Burbs, the National Real Estate Conversation here.

Read this article on the New Canaan Sentinel website here.