--- canonical: "https://caiolafinehomes.com/insights/market-update/fairfield-county-price-per-square-foot-by-town" tenant: "fairfield" brand: "Matt Caiola Luxury Properties" category: "Market Update" category_slug: "market-update" title: "What a Square Foot Costs in Fairfield County, Town by Town" author: "Matt Caiola" published_at: "2026-07-27T09:00:00Z" generated_at: "2026-07-28T03:30:49.843Z" last_modified: "2026-07-28T01:39:38Z" --- # What a Square Foot Costs in Fairfield County, Town by Town _Published 2026-07-27 — Market Update — by Matt Caiola_ The most expensive town in Fairfield County depends entirely on which number you ask for. Sort by median sale price and New Canaan wins, at $2,737,500 over the past twelve months. Sort by price per square foot and New Canaan drops to fourth, behind Greenwich, Darien, and Westport. Both rankings come from the same set of closed sales. They measure different things, and treating them as interchangeable is the most common mistake people make when comparing towns from the outside. So here is what a square foot actually cost across the nine towns I work in, using single-family homes that closed in the twelve months through July 2026. These are sale prices, not asking prices. The gap between those two turns out to matter quite a bit, and I will come back to it. ## What a Square Foot Cost, Town by Town Median price per square foot for single-family homes, twelve months ending July 27, 2026. Greenwich: $764 per square foot. Median sale price $2,405,000 across 176 sales. Darien: $756 per square foot. Median sale price $2,705,000 across 211 sales. Westport: $615 per square foot. Median sale price $2,425,000 across 303 sales. New Canaan: $595 per square foot. Median sale price $2,737,500 across 212 sales. Fairfield: $467 per square foot. Median sale price $1,160,000 across 567 sales. Wilton: $421 per square foot. Median sale price $1,410,000 across 211 sales. Norwalk: $409 per square foot. Median sale price $810,000 across 516 sales. Stamford: $397 per square foot. Median sale price $976,000 across 572 sales. Ridgefield: $396 per square foot. Median sale price $1,200,000 across 222 sales. Across all nine towns together, the median single-family sale closed at $473 per square foot on 2,990 transactions. One caveat on Greenwich: the town runs its own local MLS alongside SmartMLS, so a SmartMLS-only view can understate how much actually trades there. The figure above reflects the sales visible in the SmartMLS feed. ## Why New Canaan Leads on Price but Not on Price Per Square Foot The answer is size. The median single-family home that sold in New Canaan measured 4,642 square feet. In Greenwich, the median was 3,170. That is a difference of roughly 1,500 square feet, about the footprint of an entire starter house, and it is enough to lift New Canaan's total price above Greenwich's while its per-foot number sits nearly $170 lower. Buyers moving between the two towns often read this backwards. A $2.7 million budget in New Canaan buys noticeably more interior space than the same budget in Greenwich or Darien. What it does not buy is Greenwich's position at the state line and the shorter train ride that comes with it. Neither town is overpriced relative to the other. They are selling different things at similar totals. Darien is the interesting middle case. Its median sale of $2,705,000 sits within $32,500 of New Canaan's, but its median house is 3,506 square feet, more than a thousand feet smaller. Darien buyers are paying for land, schools, and a shoreline address, and the per-foot figure shows it. ## The Bigger the House, the Less Each Foot Costs This pattern holds in every town I checked, and it catches sellers of large homes off guard more than anything else in the data. Split a town's sales by house size and the per-foot figure falls as the houses get bigger. In Westport, homes under 2,500 square feet sold at a median of $726 per square foot. Homes between 2,500 and 3,999 came in at $667. Homes of 4,000 square feet and up sold at $573, roughly 21 percent below the smallest group. Stamford shows the same shape at a different level: $430 per square foot under 2,500 feet, $375 in the middle band, and $338 above 4,000. Greenwich runs $771, $763, and $713. Fairfield runs $489, $478, and $426. The reason is not complicated. A kitchen, a set of bathrooms, a heating system, and a piece of land cost close to what they cost whether the house around them is 2,200 square feet or 5,500. Spread those costs across more floor area and the average per foot comes down. The extra space in a large house tends to be bedrooms, playrooms, and finished lower levels, which are the least expensive square feet in any home to build and the least expensive to buy. If you own a 5,000-square-foot house, this matters. Pricing off your town's headline median per square foot will produce a number well above what large homes in that town have actually been closing at. ## The Spread Inside a Town Is Wider Than the Gap Between Towns A median is one point in a wide distribution, and in this county the distribution is very wide. In Greenwich, a quarter of single-family sales closed below $608 per square foot while the top tenth closed above $1,128. That range is larger than the entire distance between Greenwich's median and Stamford's. Darien runs from $631 at the 25th percentile to $1,031 at the 90th. Westport runs $505 to $946. Fairfield runs $386 to $764. Even the towns people assume are uniform are not. Ridgefield, the tightest of the nine, still spans $332 to $528. What separates a house at the bottom of its town's range from one near the top is rarely mysterious: condition, whether the kitchen and baths have been updated recently, lot quality, and how close it sits to a village center or a train station. Two houses of identical size on the same street can trade 40 percent apart per foot, and both prices can be completely rational. ## Asking Prices Tell a Different Story Everything above comes from closed sales. Current listings are saying something else. The single-family homes on the market in Westport right now are asking a median of $821 per square foot. Westport homes that closed over the past year sold at $615. That gap is not proof of overpricing across the board. It mostly reflects what is still sitting in late July, which skews toward the larger, newer, and more expensive end of the inventory, while the more ordinary houses moved in the spring. Greenwich shows a narrower version of the same thing, $858 asked against $764 paid. Two towns run the other way. Darien listings ask a median of $733 against $756 paid, and Wilton listings ask $407 against $421 paid, which tells you the standing inventory in both towns is modest relative to what has been selling. So when you see a price-per-square-foot figure quoted without a label, it is worth asking which set it came from. Asking prices describe what sellers want. Closed prices describe what a buyer and a seller agreed on. ## Where the Number Moved This Year Compared with the previous twelve months, the nine-town median rose from $433 to $473 per square foot, an increase of about 9 percent on a nearly identical number of sales: 2,990 this year against 3,002 last year. That combination is worth sitting with. Volume was flat. Price per foot was not. The gains were not evenly spread. Greenwich and Wilton both rose about 11 percent. Darien rose 10 percent, with Stamford just behind at close to 10. Fairfield and Ridgefield landed in the 8 percent range, and New Canaan at 7.5. Norwalk was the slowest by a clear margin at roughly 4.5 percent, about half the nine-town gain. These are backward-looking figures covering sales that have already closed. They describe what happened, not what comes next. ## Using the Number Without Being Misled by It Price per square foot is a useful sanity check and a poor valuation. Used well, it answers one question: is the price on this house in the same neighborhood as what comparable homes have been trading at? A Fairfield listing asking $700 per square foot in a town with a $467 median and a $764 ninetieth percentile is not automatically wrong, but it needs an explanation, and the listing should be able to give you one. Three cautions before applying any of these numbers to a specific house. First, they cover single-family homes only. Condominiums price on a separate scale, and not always a lower one. Greenwich condos closed at a median of $702 per square foot and Darien condos at $725, while Stamford condos came in at $377 and Ridgefield condos at $350. Second, town-level figures are too coarse for most real decisions. Greenwich contains both Byram and the back country. Stamford contains both Shippan and North Stamford. A neighborhood number beats a town number every time. Third, square footage itself is not measured consistently across listings. A finished lower level or a converted attic may or may not be included, and that single choice can move a per-foot calculation by 20 percent without anything about the house changing. If you want a starting point on your own home, the estimate tool on this site will give you one, though it is a starting point and not an appraisal. If you want the version that accounts for your street, your renovation history, and the three sales that actually matter, that is a conversation, and I am glad to have it. Figures reflect SmartMLS closed single-family sales for the twelve months ending July 27, 2026, in Greenwich, Darien, Westport, New Canaan, Fairfield, Wilton, Norwalk, Stamford, and Ridgefield. ## Citation - Canonical URL: https://caiolafinehomes.com/insights/market-update/fairfield-county-price-per-square-foot-by-town - Tenant: Matt Caiola Luxury Properties - Category: [Market Update](https://caiolafinehomes.com/insights/market-update)