By John Engel When my wife and I bought our first house on South Avenue, we paid $230,000 for a small antique on a quarter-acre lot. Behind the detached one-car garage was a patch of overgrown scrub: weeds, brush, vines, volunteer trees, the kind of neglected little corner every first-time
Low inventory is only the starting point. The Hotness Index asks which markets are hot, and why. By John Engel When a house “just like yours” sells for a million dollars over asking on the first weekend, the instinct is to take that result to the bank. But one big
18 takeaways from this week’s ‘Boroughs and Burbs’ show, with Jonathan Miller and Scott Hobbs joining Roberto Cabrera and John Engel. By John Engel Low interest rates do not automatically make housing more affordable. This is probably the strongest idea in the whole conversation. Jonathan’s point is contrarian and memorable:
Why Emotion, Not Logic, Determines What Sells and What Doesn’t By John Engel We would like to believe real estate is a numbers business. But people don’t make rational decisions under pressure. The outcome of almost every deal is determined by how the people involved understand and manage emotion. Emotional
Public and Private, Planned and Accidental—What Grows Here, and What It Takes to Keep It By John Engel Driving down Ponus Ridge in late March, I’ll see small patches of purple pushing up through the snow. Not in beds, right in the lawn. Crocus. One week and they’re gone. But
By John Engel This may sound like a story about a classroom. Or artificial intelligence. Or people gaming a system. It’s all of those things. And it’s about the difference between the rules people think matter and the ones that actually do. In the spring of 1985, we were juniors
By John Engel Manhattan reacts like a stock market. Deals are made or pulled in real time, so when uncertainty hits, you see it immediately in contract data. Fairfield County behaves more like private equity. Transactions depend first on what is available to buy, and supply has been consistently tight.
By John Engel “Land is the only thing in the world that amounts to anything, for ’tis the only thing in this world that lasts.” That observation comes from Gerald O’Hara in Gone with the Wind. If he had been looking for a town in Fairfield County, he might have
By John Engel Darien is, in many ways, the very best of Fairfield County. That’s a begrudging admission from this third-generation New Canaanite because the towns are so similar. From a distance, they look almost identical. Up close, the personalities feel very different. Both towns look nearly identical on paper:
By John Engel I just met a man from Nebraska in the lobby who said, “What is the Glass House?” After my brief explanation he asked, “So, why is this important?” I’ve written about some of New Canaan’s midcentury modern houses in this column, the Leuthold and Round Houses, and
By John Engel Fourteen years ago, I wrote “Top 10 Reasons New Canaan is Unique” in the New Canaan Advertiser. The article was reprinted in the Patch, where you can still find it. It’s time to update that list and note what has changed. 1. Schools In 2012, we had
By John Engel Super Bowl Sunday ads were dominated by AI companies, the single largest category of advertiser. That felt like a signal. We are fascinated and afraid at the same time, curious about a future we don’t fully understand, eager to lean in, and quietly anxious about where usefulness
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
By John Engel Dear Abby’s advice column is more than 70 years old and still read by 110 million people in 1,400 newspapers. This week, I’m using that format to answer the most common Google questions about moving to Connecticut. Dear John E: I’m paying $7,000 a month in rent
By John Engel In this two-part series, John Engel examines national residential real estate trends from 2025 and compares them to the New Canaan market. Last week, John revealed what buyers and sellers are thinking. In this week’s second part, he delves into what’s changing in the way houses are
By John Engel In this two-part series, John Engel examines national residential real estate trends from 2025 and compares them to the New Canaan market. This week’s column zooms in on what buyers and sellers are thinking. 2025 was a year where everyone seemed to be looking for a sign.
By John Engel There is a saying — Behind every great man is a great woman — that feels especially apt in New Canaan this week, with the passing of Pamela Gores. To understand why, you have to understand not just her husband, Landis Gores, but the moment in which
By John Engel Last week’s column picked up where the first one left off. After using Men Are from Mars, Women Are from Venus and Prospect Theory to frame how people process stress, risk, and potential loss, we stepped into actual living rooms and watched those instincts play out. We
By John Engel Last week’s column began with Men Are from Mars, Women Are from Venus — a book we weren’t reading for real estate but that nonetheless gave us language for patterns that show up every weekend at open houses. The point wasn’t the gender sketch itself so much
By John Engel This three-part series explores how human psychology, stress responses, and decision-making styles shape the way people buy and sell homes. Each week examines a different dimension of the same idea: Real estate reveals people more clearly than almost any other process. We begin with the framework —
By John Engel For two years, the U.S. housing market has been defined by one stubborn fact: Nobody wants to give up a 3% mortgage. Even as interest rates climbed above 7% this fall, the “lock-in effect” kept listings low and inventory throttled. Now that rates have drifted back toward
By John Engel Walk through New Canaan’s wooded back roads and you can read the history of modern architecture written in glass, stone, and timber. The Glass House (1949, Philip Johnson), Noyes House (1955, Eliot Noyes), Boissonnas House (1956, Philip Johnson), Hodgson House (1951, Philip Johnson), and Tirranna House (1955,
By John Engel New Canaan is rewriting its zoning code for the first time in decades, one year after the town adopted its updated Plan of Conservation and Development. Those two processes — zoning and planning — determine what kind of town we will leave to the next generation. We’re
By John Engel 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
If she’s even half right, $40 trillion in new wealth could rewrite the rules of real estate, where productivity rises but not all homes rise equally. By John Engel Cathie Wood says your house is going to the moon. Not literally, but bear with me as I connect a few
By John Engel Dear Abby’s advice column is now 70 years old and still read by 110 million people in 1,400 newspapers. My column this week is inspired by the letters she might be getting lately. DEAR JOHN E: My good friend is a Realtor, but I don’t want to
By John Engel The phrase “Buyers are liars” comes from car sales, but it’s found a comfortable home in real estate. It’s the industry’s way of explaining why a buyer’s stated needs rarely match their final purchase. Usually it’s one of four things: They don’t yet understand their own needs;
By John Engel Photos are the #1 factor when selling a house. For 87% of buyers, the photos determine their initial assessment of a property, and 83% cite it as the most useful resource for evaluating. That’s why we must get this piece right. It is a common misconception that
By John Engel Compass will acquire Anywhere Real Estate in an all-stock deal valued at $1.6 billion, while assuming about $2.6 billion of Anywhere’s debt. The combined enterprise value is about $10 billion. Reported targets include $225-$255 million in annual cost savings and a combined footprint of roughly 100,000 company
By John Engel Affordable housing is NOT what I want to write about, but New Canaan is undergoing an existential crisis because of House Bill 5022. It’s like a meteor hurtling toward Earth, in that we are unaware of the implications or believe nothing can be done about it. In
By John Engel I baked bread today, and it was a failure. I followed the recipe, used all the right ingredients, and still, the loaf collapsed. Housing, too, can fail despite having all the right ingredients. Most new homes are built speculatively, based on yesterday’s tastes, with some imagined buyer
By John Engel Now that it’s September, we in Connecticut inevitably turn our eyes toward New York. It’s a season of rivalries, and while the Yankees and Red Sox may dominate the headlines, the deeper rivalry has always been with New York itself. Just as baseball loyalties run hot in
By John Engel “According to the latest S&P CoreLogic Case-Shiller Home Price Index, U.S. home prices continued to decelerate in May 2025, recording a 2.3% year-over-year gain. The 10-City Composite Index rose 3.4% y/y, while the 20-City Composite rose 2.8%. Among the 20 cities tracked, New York led with a
By John Engel As co-host of Boroughs & Burbs, a weekly real estate show with over one million YouTube views, I’ve spent five years tracking the high-end property markets that matter: Aspen, Palm Beach, Hilton Head, Marbella, Dubai. Co-host Roberto Cabrera and I also bring in experts: architects, economists, designers,
By Deke Rothfuss The passage of the “One Big Beautiful Bill” (OBBB) through the U.S. Senate on July 1 and the House on July 3 and its signing into law by President Trump on July 4 has ignited a wave of emotions across the United States. Individuals and corporations alike
By John Engel Twice this week, builders have asked me, “Why isn’t my new house selling?” It’s painful and expensive. With monthly carrying costs around $25,000, mistakes get expensive fast. I’ve written plenty about buyer psychology, staging, showing strategy, copy that sells, and the role of photography. Houses don’t sell
By John Engel To cut through month-to-month noise, I looked at rolling 3-month data on median sales prices, supply, and closed sales. Prices All four towns — New Canaan, Darien, Westport, and Wilton — saw strong price increases through the first half of 2025. New Canaan and Darien both posted
By John Engel Why do some houses sell in a weekend while others linger? It’s not interest rates or inventory. It’s about pulling the right lever, and we only have three: Price, Presentation, and Time. Sellers often justify prices with what they’ve spent or point to unsold neighbors, but the
By John Engel A friend sold his business and set out to do everything he’d dreamed of. He did it all. Then one April morning, walking off the golf course, he checked his scorecard: 40 rounds — and it wasn’t even May. He said, “I’m going back to work.” Not
By John Engel White dominates — in cars (27.6%), kitchens (43%), and siding (34%). And in New Canaan, Darien, Westport, Rowayton and Greenwich — where the 2025 median home price is over $2 million — a 0.61% problem, like Zillow’s sale-price loss for white bathrooms, means $12,200. So why do
By John Engel As a Planning & Zoning commissioner, I sit through every application. As a Realtor, I walk clients through the results. That gives me a front-row seat to how housing policy plays out — not in theory, but on the streets of New Canaan. From mixed-use conversions to
By John Engel “Daddy, tell me a story.” “Okay, it was December 1990, and First Infantry was—” “No, Daddy, not that kind. I mean one of your real estate stories. With a little economic theory, some obscure historical reference, maybe a personal anecdote. Like the ones you write for the
By John Engel The phrase “a game of inches” has its roots in sports, particularly football, and has evolved into a metaphor for high-stakes situations where small differences determine success or failure, whether in sports, real estate, leadership, or life. The phrase was immortalized by Al Pacino’s electrifying locker room
By John Engel “How’s the market?” It’s the question I get asked most often. Sometimes I reach for data—graphs that show trends over time. I might point out that prices are above the highs of 2007. But that kind of information, while factual, often lacks meaning. It’s like saying the
By John Engel Ryan Serhant says he won’t stop until he’s #1 in the world. The real estate agent turned star of the #3 Netflix show, Selling New York, says his drive to be the best demands every minute of his day be scheduled and monetized, what he calls the
By John Engel “How can we help our children buy their first home?” It’s a question people my age are asking. Generation X and Baby Boomers are long real estate, with second and even third homes, and we have (multiple) children of child-bearing years who now need help with the
By John Engel Sun Tzu said, “Know your audience,” and I’m writing for homeowners. My readers own their homes, sometimes several, and are expert at solving life’s problems. What real estate advice can I possibly offer? This is Part One: Winning. Next week is Part Two: Giving It to Your
By John Engel A graph of the last ten years of home sales in New Canaan shows 3,262 sales, 326 in a “normal” year, 4.38% of the roughly 7,434 housing units. By the standards of the last 50 years, 4.3% is the average turnover. In the last decade, the low
By John Engel Global Shocks, Local Spin Ray Dalio doesn’t forecast downturns; he forecasts breakdowns. “We’re not just heading for a recession,” he said. “We’re witnessing the slow unraveling of the old world order.” What he means: U.S. debt is unsustainable, trust in the dollar is eroding, internal conflict is
By John Engel What is a smart home? If “smart” means convenience, efficiency, security, and comfort, let’s start with something dumb: the closets, often overlooked. The smartest, most efficient closet I ever saw was Tommy Hilfiger’s in Greenwich back in 2009. I saw only a few white shirts. I thought,
By John Engel 60% of all sales are occurring above list price. Last month, I gave examples of 20 bidding wars where houses traded for 120% of their asking price. A good buyers’ agent provides value when asked what is a house worth, and what will it take to get
By John Engel 1. How has New Canaan’s inventory changed in February 2025 compared to 2024? New Canaan’s inventory fell from 68 homes in February 2024 to 50 in 2025, a 26.5% drop. Darien declined 21.4% to 22 homes, Westport fell 10.2% to 79, Wilton stayed flat at 34, Stamford
By John Engel Last week, I wrote about the resurgence of “pocket listings” — a practice that favors secrecy over transparency. Agents, like hostage negotiators and press secretaries, believe controlling the flow of information makes us better negotiators. However, lack of transparency leads to anxiety for both buyers and sellers
By John Engel In today’s Gospel, Jesus, sounding annoyed, says, “This is an evil generation, it seeks a sign.” It made me wonder what He would have said about this generation and about the New Canaan real estate market. In the month or so since Trump took office, in the
By John Engel A Room With a View is the 1908 novel by E.M. Forster and a 1985 Merchant & Ivory film starring Helena Bonham Carter and Julian Sands. The novel opens in Florence with Lucy and her chaperone, Charlotte, complaining about their rooms at the Pensione Bertolini. They were
By John Engel Times of crisis, of disruption or constructive change, are not only predictable, but desirable. They mean growth. Taking a new step, uttering a new word, is what people fear most. — Fyodor Dostoevsky I’ve been thinking about datamining a lot these days, what it means and how
By John Engel New Canaan is going through its annual budget review. There are two parts to the budget: operating and capital. The Selectmen have recommended a School budget of $114 million, up 4.6%, and a Town budget of $43 million, up 4.3%. The town council will cut that further.
By John Engel Last week the Dallas Mavericks traded their 25-year-old star, Luka Dončić, one of the two best players in basketball, to the Los Angeles Lakers for “not much” compared to previous blockbuster NBA trades. Instead of calling multiple teams and asking for their best offer, they called one
By John Engel The power of demographics to explain our economy and the housing market is often understated. It may be the single biggest influence on current home prices. To understand real estate, take the growth of motorcycle sales between 1960 and 1974: 1960: 575,000 registered in the U.S. 1965:
By John Engel “The Brutalist” is the hottest movie in the nation, with 10 Oscar nominations. It’s currently playing in New Canaan and has deep New Canaan roots. Why should New Canaan care and what does it mean that Brutalism is part of the conversation in 2025 (named by Zillow