What a Home's Build Year Does to Its Price Here in Fairfield County

Every listing sheet carries a build year, and it is one of the first lines a buyer reacts to. Most people arrive at that line with a rule of thumb attached: older means a discount, newer means a premium.

I have a good sense of how buyers react to the age of a house, but I wanted to see what the data showed, so I took every single-family home that closed across Greenwich, Darien, New Canaan, Westport, Wilton, Ridgefield, Fairfield, Stamford and Norwalk between September 2025 and August 2026, a total of 3,102 sales, and grouped them by build year.

As it turns out, the relationship between price and build year does not trend in a straight line. Price per square foot starts high on the oldest houses, bottoms out on the houses built between 1980 and 1999, and climbs again on new construction.

A Year of Closings, Grouped by Build Year

The median home that closed here during the 12 month period was built in 1959. Every figure below is a median, and the chart carries the square footage and acreage behind each group.

Built before 1940. 665 sales, 21.4% of total single-family transaction volume for the year, at $532 per square foot. 19 days on market, and 61.1% closed above their asking price. The oldest home sold during the period was built in 1690, a colonial in Darien.

1940 to 1959. 899 sales, the largest group at 29.0% of the year, at $483 per square foot. 15 days on market, the fastest of the six, and 68.2% closed above asking.

1960 to 1979. 750 sales, 24.2% of the year, at $437 per square foot on a median of a full acre of land. 17 days on market, and 68.3% closed above asking, the highest share of any group.

1980 to 1999. 309 sales, 10.0% of the year, at $413 per square foot, the lowest of the six. 19 days on market, and 56.0% closed above asking.

2000 to 2015. 277 sales, 8.9% of the year, at $539 per square foot. 24 days on market, and 46.6% closed above asking.

2016 and newer. 202 sales, 6.5% of the year, at $571 per square foot, the highest of the six. 33 days on market, the longest of any group, and 36.1% closed above asking, the lowest share of any group.

Why the Oldest Houses Hold Their Value the Best

Within the same town and price range, a bigger house usually carries a lower price per square foot, which I have written about before, even though across the market as a whole the number climbs with the budget. The newer houses here are also much bigger: 4,675 square feet for the median 2016-and-newer sale compared to 2,393 before 1940. So what I controlled for is size and budget, holding one of the two roughly still.

Among the 557 sales between 4,000 and 5,999 square feet, the pre-1940 houses closed at $610 per square foot, the 1940 to 1979 group at $468, the 1980 to 1999 group at $385, and 2000 and newer at $539. Same shape, with the size argument removed.

The acreage column explains a good part of the rest. The median pre-1940 sale came with 0.32 acres of land, the smallest of the six groups, and the median 1980 to 1999 sale with 1.45 acres, the largest. A small lot here is usually a location, because the oldest houses sit where the towns were first built.

What This Data Cannot See

Renovation does not appear anywhere in these records. A 1925 colonial taken down to the studs in 2022 still carries 1925 as its build year, in the same group as a 1925 colonial with a dated kitchen. That is most likely part of why the oldest group does not sell at a discount, and nothing here measures how often it happens.

The Same Budget, Different Age

Sorted by what the homes sold for, using the same price ranges as what each budget affords in these nine towns. Between $1.5 million and $3 million, 915 sales: homes built before 1940 sold at $645 per square foot with a median size of 3,239 square feet, homes built between 1940 and 1979 sold for $596 per foot with a median size of 3,512 square feet, homes built between 1980 and 1999 were a median 4,581 square feet and went for $425 per foot, and for homes built in 2000 or later the median home was 4,199 square feet and sold for $500 per foot.

Above $3 million, of which there were 457 sales, the order still holds: $843 before 1940, $781 from 1940 to 1979, $578 from 1980 to 1999, and $704 for 2000 and newer. Under $1 million, 1,074 total sales, the pre-1940 group ran $427 and the 1940 to 1979 group $406, and everything built in 1980 or later had to be merged into one line of 66 sales at $350, because the 2000-and-newer group had just 26 sales.

What changes with the build year is how much house the budget buys and how old the systems inside it are.

Which Towns Sell the Oldest Houses, and Which Sell the Newest

Sorted by the median build year of last year's sales, Darien is the oldest of the nine at 1953 and Ridgefield the newest at 1968. Darien sold the largest share of pre-1940 houses at 32.5% of its 212 sales and Ridgefield the smallest at 12.9%, while Ridgefield and Wilton carried the largest 1980 to 1999 shares, at 24.9% and 20.0%. Westport is the outlier on newer construction, with 34.3% of its 321 sales built in 2000 or later, more than five times Stamford at 6.3%.

None of that ranks one town over another. It is a record of when each one did most of its building. Greenwich figures here are from SmartMLS only and exclude Greenwich MLS listings, so Greenwich activity is likely understated.

What New Construction Costs on the Selling Side

The sharpest difference in this data shows up in the pace rather than in the price. Houses built in 2016 or later took a median of 33 days on market to get under contract, compared to 17 days on market for the 1960 to 1979 group, with just 36.1% of the newer homes closing above their asking price, compared to 68.3% for homes built between 1960 and 1979.

Two things before that gets read as soft demand. A new house is often listed before it is finished, so part of those 33 days on market can be time a buyer could not have moved in. And a builder usually prices to a number rather than pricing to start a bidding war.

What to Look At, by the Age of the House

In a house built before 1940, the frame is usually the least of the worry. The questions are the systems: the electrical panel and whether any original wiring is still in service, whether the house runs on an oil boiler and where the tank sits (underground tanks carry their own list of concerns), insulation in the walls, the windows, how dry the basement stays, and whether past additions were permitted. Federal law requires a lead paint disclosure on anything built before 1978.

A house from the 1960s or 1970s asks a different set of questions. The layout is closer to what a buyer expects today, but the roof, the siding, the windows, the boiler and the original kitchen and baths are all fifty to sixty years old, and catching that up is often a larger figure. Asbestos was commonly used into the late 1970s, and north of the Merritt a house of that vintage is usually on a well and a septic system.

With new construction the systems questions mostly go away and the questions move outside: what the lot is doing with its water, how the site was graded, what the builder's warranty covers, and what the town will assess the finished house at. That last one catches people out on a rebuilt lot, because the tax figure on a listing from before the rebuild reflects the house that got torn down, or the vacant land. If you own an older house and are weighing what to fix before you sell, I have written separately about where that money comes back.

How to Use Any of This

If you are buying, stop filtering on the build year and start filtering on the budget, then read the age of each house as a description of what you would be taking on. Sign up today and create a free account for live email alerts on new listings. Setting one up on the home search on my site takes just a minute.

If you own an older home and have spent years being told its age works against it, this data says otherwise, at least on a per-foot basis. One limit: condition is still the biggest reason two houses of the same age on the same street close at different numbers. If you're thinking about selling this Fall, the free home valuation on my site is a good place to start, and I'd be happy to have a quick conversation about where your house lands!

Figures are from SmartMLS single-family closings, September 2025 through August 2026, across Greenwich, Darien, New Canaan, Westport, Wilton, Ridgefield, Fairfield, Stamford and Norwalk. Greenwich figures exclude Greenwich MLS listings.