By John Engel
I’ve broken lower Fairfield County down by how each town actually functions — not how it photographs.
First, the “big four” are Greenwich, Darien, New Canaan, and Westport. They’re in a class by themselves — brand-name destinations like Aspen, Palm Beach, or Palm Springs. But as with those places, each has a completely different personality.
Greenwich, at 60,000 people over 60 square miles, is roughly the size of the other three combined. It’s hard to describe it as just one place. To live in backcountry Greenwich is to drive 20 minutes to get to the train or market, while Old Greenwich is a tight beach town. The Greenwich brand is simple: Be #1. Large estates, first-class shopping on the Avenue, and great schools, at a median price of $3.8 million last year.
The kind of people who pay up to live in Greenwich usually need to be there because they want the shortest possible commute. It starts with athletes, performers, designers, financiers, and billionaires who need a top address close to New York City, along with the people, businesses, and restaurants that support them. If you’re a New York Yankee, Knick, or Ranger whose workday doesn’t end until midnight, you probably live in Greenwich.
It’s easy to say Darien, Westport, and New Canaan are just for commuters priced out of Greenwich. That’s true, but it’s oversimplified. Median prices in all are around $2.5 million, yet the towns have very different personalities. It’s not about price.
The Darien vs. New Canaan rivalry goes back 100 years — and I’ve been here for nearly 50 of them — used to be known as the “beachies” versus the “woodsies.” Prices in Darien have historically run about 10% higher on average, but Darien has a greater range. The waterfront homes in Tokeneke and Pear Tree Point push the average price higher, but they’re balanced on the lower end by smaller homes in Noroton Heights, a historically blue-collar neighborhood of antiques on quarter-acre lots. The latter are no longer the entry point they used to be; Newlyweds and young professionals have been buying, renovating, and expanding those homes for 50 years. An unrenovated starter there is now $1.5 million.
The draw for Darien comes down to a few things: a sub-60-minute commute, great schools, beaches, and low taxes. There’s no true downtown, and the arts scene is thinner than in Westport (Westport Playhouse) or New Canaan (Grace Farms, Midcentury Moderns). Darien is about to change that with the Corbin District, a seven-acre mixed-use project, 20 years in the making, meant to create a real, walkable center in the style of New Canaan.
New Canaan, just up the street, is nothing like Darien. And yet, in all the obvious ways — prices, taxes, schools, and sports — it’s exactly the same. That’s where the similarities end.
New Canaan revolves around its quaint, walkable village center. You’ll find the Holiday Stroll, the Halloween Parade, Taste of New Canaan, Caffeine & Carburetors, Fall Fair, menorah lighting, Christmas carol singing, October4Design, and the Memorial Day Parade all happening downtown throughout the year. The restaurant scene also sets the town apart. With more than 30 restaurants packed into the center, spilling onto the brick sidewalks in season, New Canaan has become the popular food court of Fairfield County.
Westport shares many of Darien’s advantages: beaches, I-95, good schools, and a mainline commute. But like New Canaan, it’s about 15 minutes farther by train to NYC, which makes it tougher for the five-day-a-week commuter. That extra distance may explain its long-standing reputation for attracting the artistic crowd more than the banking crowd. Think Paul Newman and Joanne Woodward and the Westport Playhouse. Martha Stewart, too, broadcasting for decades from Turkey Hill Farms and showing everyone what life there could look like.
That leaves Wilton, Weston, and Easton, three rural towns side by side, about five miles from the crowded, commercial coastline. Connecticut weather changes north of the Merritt. So does the personality of these towns.
Weston is one of the four wealthiest towns in Connecticut, yet it does not have a traffic light or a commercial center. Most people head south to Westport for groceries, and it can be a 20-minute drive. While Weston has two-acre minimum zoning, Easton is even more rural. It has 20 working farms, and more than 35% of its land is preserved as open space. This is where you go for apple picking or to cut your own Christmas tree, and the entry point for homes is still under $1 million.
Growing up in this area, I regarded Wilton much the same way, rural but with a few businesses along the Route 7 corridor. My Wilton relatives had horses. No longer. Wilton is roughly 40% less expensive than New Canaan and Westport, with an equally good school system, attracting young professionals who have been priced out or who just prefer a slower, more rural pace. The lower prices in these towns are offset by roughly 40% higher property tax rates, resulting in similar tax bills town by town.
That leaves three small cities that are essential to the fabric of Fairfield County.
In the 1980s, Stamford had the highest concentration of Fortune 500 headquarters outside New York City, with 18. Today it’s down to four, but the population is 140,000 strong and growing fast; it’s now the fastest-growing city in Connecticut and a hub for fintech and media. The average resident is younger than homeowners in the surrounding towns, about 38 years old and more likely to be single. Stamford was recently named the number one place in America to get rich, based on incomes relative to cost of living.
Fairfield, with a population of 65,000, has a dual personality: beaches and schools. Its public schools consistently rank in the top ten statewide, alongside Fairfield Prep, Fairfield University, and Sacred Heart. Students, teachers, and administrators make up a big share of the population, and the whole local economy revolves around education. It also has five town beaches along a five-mile coastline, some of the best public beach access in Connecticut.
That leaves Norwalk. It’s bigger and more diverse than Fairfield, smaller than Stamford, without the corporate headquarters or the college-town identity.
Norwalk is really five distinct neighborhoods. Rowayton, South Norwalk, and East Norwalk are older, denser coastal villages with homes on quarter-acre lots. South Norwalk is booming, with hundreds of new waterfront condos. West Norwalk and Silvermine are leafier, with one-acre lots bordering New Canaan. Cranbury and Old Hill feel similar and border Westport. These inland neighborhoods often attract downsizers from New Canaan and Westport who want to stay close but no longer need the top-rated schools.
I’ve stopped thinking of these places as towns and started thinking of them as stages of life.
My parents grew up in Stamford. My grandparents moved to New Canaan. I have relatives in Wilton, Weston, Rowayton, and Darien. My kids attended New Canaan and Fairfield schools. My parents bought a house in Norwalk. Five generations, same few miles. Around here, you don’t move away. You just move to the town that fits.
Notes from the Monday Meeting
It’s the week before the Super Bowl, which in our business is the unofficial start of the spring market. This is when we lay all 52 cards face down on the table and start playing concentration. We know what listings are coming. We know who’s looking. The job is to start flipping cards and making matches.
John Engel is a broker on The Engel Team at Douglas Elliman, and this week, he’s tightening up his videos. Rose pointed out the “millennial pause,” that half-second of silence at the start of every clip. Charlotte, whose Historical Society videos routinely draw millions of views, starts everything with what is known in the industry as “the Gen Z shake,” rolling mid-motion and mid-sentence. Lillian edits feature films for a living and cuts dead air on sight. John’s still learning to hit “record” and talk.
