--- canonical: "https://caiolafinehomes.com/insights/community/greens-farms-westport-neighborhood-guide" tenant: "fairfield" brand: "Matt Caiola Luxury Properties" category: "Community" category_slug: "community" title: "Greens Farms: Where Westport Began, and How It Sells Now" author: "Matt Caiola" published_at: "2026-08-27T09:00:00Z" generated_at: "2026-08-28T03:34:05.312Z" last_modified: "2026-08-28T02:28:27Z" --- # Greens Farms: Where Westport Began, and How It Sells Now _Published 2026-08-27 — Community — by Matt Caiola_ Drive east past the Sherwood Island connector and Westport starts to change shape. The shops and the river fall behind you, the lots widen out past an acre, and the houses sit far enough off the road that you catch them in pieces through the trees. This is Greens Farms, the corner of town that was settled first and still sells on different terms than the rest of Westport. Over the last twelve months, 39 single-family homes changed hands here at a median of $3,135,000, the third highest median of any neighborhood in Westport. Those same homes took a median of 40 days to sell, the longest duration across the town, and closed at 95.7% of the seller's original asking price. What drives these figures is important information for a buyer or seller to understand in order to transact in this neighborhood. ## Where Greens Farms Sits Greens Farms occupies the southeastern corner of Westport, running from the Southport line west toward Compo and south to Long Island Sound. It shares Westport's 06880 ZIP code and its school district, but it has its own Metro-North station on the New Haven Line, one stop east of the Westport station at Saugatuck, which puts Grand Central roughly 65 to 75 minutes away depending on whether you catch an express or a local. The name goes back to 1648, when five families from Fairfield settled the land local tribes called Machamux and farmed the fields behind the beach. They were known as the Bankside Farmers, and their settlement predates the incorporation of Westport itself by nearly two centuries. The Greens Farms Congregational Church and the historic district around it are what remains visible of that, and the street pattern has not changed much since. Most of what draws people here now sits along the water. Sherwood Island State Park, the first state park in Connecticut, takes up a broad stretch of the shoreline with beach, picnic groves, and a nature center. Burying Hill Beach is the small town beach at the eastern end. Beachside Avenue runs behind the shore past some of the largest estates in Westport, and Greens Farms Academy, a private, independent day school, sits on its own waterfront campus off it. ## A Year of Sales, and One That Stands Above The Rest Thirty-nine single-family homes sold in Greens Farms over the trailing twelve months at a median of $3,135,000, against 20 sales at a median of $2,225,000 the year before. That looks like an enormous jump. Part of it is real, and part of it is one multi-parcel trade. On November 21 of last year, a waterfront estate comprised of 122 and 128 Beachside Avenue closed together representing Fairfield County's largest deal of 2025. They were listed separately, each asking $25,000,000, and sold together to one buyer for $45,000,000 combined: just over thirteen acres of direct waterfront bought as a single estate. The same buyer also bought a third Beachside Ave. parcel, 3.3 acres of waterfront land, closing on the same day for $9,000,000. This deal represented three of the eleven sales above five million over the past 12 months, which is worth noting when reviewing the top of the market's activity. Underneath the headline deals, the neighborhood traded normally. The lowest sale of the year was $860,000. The largest sale of a single house on its own terms was $15,500,000, a 3.55 acre waterfront estate on Beachside Avenue. In between, 11 homes traded under $2,000,000, eight between $2,000,000 and $3,000,000, 11 between $3,000,000 and $5,000,000, and nine above $5,000,000, plus two land sales at $9,000,000 and $7,000,000. A neighborhood known for its estates still sold close to a third of its houses under two million dollars. That spread is partly geographic. The two-acre zoning sits in the southern half toward the Sound, while the northern section closer to the Post Road drops to one-acre and half-acre lots, making it the more accessible part of the neighborhood. ## The Premium Is in the Land, Not the Square Footage Compo Beach carried the highest median sale price in Westport over the same period, $3,500,000, coming in just above Greens Farms, however, the two neighborhoods arrive there in very different ways. Compo Beach sales over the past 12 months ran $931 per square foot on a median lot of 0.34 acres. Greens Farms sales ran $629 per square foot on a median lot of 1.03 acres. Westport as a whole ran $615 per square foot, so a Greens Farms buyer paid close to the town rate per foot and got more house and more ground with it. The median Greens Farms sale measured 4,875 square feet. Twenty-seven of the 39 sat on an acre or more, and 16 sat on two or more. That is zoning as much as taste. Much of southern Greens Farms carries a two-acre minimum lot size, which is why the estate character near the water has held while denser coastal neighborhoods elsewhere in the county were subdivided. That is the practical difference between the two ends of the Westport shoreline. At Compo you are paying for the address and the walk to the beach, on a lot where the neighbors are close enough to wave to. In Greens Farms you are paying for the ground and the privacy that comes with it. ## What Sells Here Is Old. What Is Listed Is New. The median Greens Farms sale was built in 1957. Twenty-four of the 39 predate 1980, and only nine were built in 2015 or later. The housing stock is mid-century and older, standing on land subdivided out of farm fields, and a fair share of what trades is bought for what can be done to it rather than for what it is on the day of closing. The current inventory tells the opposite story. Eight single-family homes are listed in Greens Farms right now, and five of them were built this year. New construction is where the neighborhood's available supply is concentrated, and it is priced accordingly. ## It Takes Longer Here, and It Trades Below Ask Greens Farms carries the longest median time on market of any Westport neighborhood at 40 days, against 24 for the town as a whole and 17 in Compo Beach. It also closed at a median of 95.7% of original asking price while Westport overall closed at 100.0%. A year earlier, Greens Farms homes were selling in 19 days at the full original number. This is not an indictment on the neighborhood, it mostly comes down to the nature of how higher priced homes tend to trade, but it is something a potential seller should consider regardless. Thirty-nine sales a year is roughly three a month spread across a large area of very different houses, so a Greens Farms property often has no close comparable, and pricing becomes a real question rather than a lookup. Buyers at these numbers are patient, they are cross-shopping areas like Southport, Darien and Greenwich at the same time, and they negotiate. The county-wide pattern I wrote about earlier this week shows up here in concentrated form. The further a listing gets from its first month on the market, the further below its original number it tends to close, and late reductions recover very little of the difference. ## What Is Standing on the Market Now The eight active single-family listings carry a median asking price of $7,638,000. Seven of the eight are asking above $5,000,000, and the range runs from $3,795,000 for a 1929 house on two acres up to $22,825,000 for a new 12,946 square foot house on Beachside Common. Four of the eight have been listed more than four months, with the oldest of the stock on for over 300 days. Set that against a median sale of $3,135,000 and the gap looks alarming, but asking prices are not a valuation. In a small, top-heavy neighborhood they describe the handful of houses that happen to be for sale, not what any one home in the neighborhood is worth. What they do tell a seller is what the competition looks like right now: mostly new construction, mostly above five million, and mostly in no particular hurry. ## The Right Buyer for Greens Farms This neighborhood rewards a specific buyer. Someone who wants acreage and shoreline access without leaving Westport, who has a view about what to do with an older house, and who is not working against a deadline. Children here attend Greens Farms Elementary in the Westport public system, and inventory is thin enough that the right property may simply not be listed the month you start looking. Patience is worth more here than speed. For sellers, the same numbers argue for care at the front end. Homes here are taking twice as long to sell as they did a year ago and closing several points under their original ask, and that gap opens up in the first few weeks on market rather than at the end. A Greens Farms house with no obvious comparable needs a number built from the land, the condition, and the closest recent closings, not from what the neighbor down the road is asking. If you are weighing Greens Farms against Southport, Compo Beach, or a move out from the center of Westport, I am glad to walk through what these figures mean for a particular street or a particular house. Send me a note and we can look at it together. Figures are drawn from SmartMLS single-family sale listings in Westport carrying the Greens Farms neighborhood designation, covering closings from August 2025 through August 2026 and active listings as of August 27, 2026. Rentals are excluded. ## Citation - Canonical URL: https://caiolafinehomes.com/insights/community/greens-farms-westport-neighborhood-guide - Tenant: Matt Caiola Luxury Properties - Category: [Community](https://caiolafinehomes.com/insights/community)