REAL ESTATE MARKET The median sale price in Westport hit $2,100,000 in February 2026, up 22.9% over the prior twelve months. That number is not a fluke.
Westport is the most expensive town in Fairfield County by median sale price. Buyers who arrive knowing that tend to stay anyway.
| Median Home Value | $2,009,999 |
|---|---|
| Median Sold Price | $2,100,000 |
| 12-Month Change | +22.9% |
| Avg Days on Market | 53 |
| Months of Inventory | 1.24 |
| Sale-to-List Ratio | 100.3% |
The median sale price in Westport hit $2,100,000 in February 2026, according to SmartMLS data. That is a 22.9% increase over the prior twelve months, one of the sharpest single-year price moves in Fairfield County. Homes are selling at 100.3% of list price, which means correctly priced properties are routinely closing at or above ask. With only 1.24 months of supply on the market and an average of 53 days to contract, this is not a buyer’s market. It is not even close. For context, Darien and New Canaan both carry more inventory relative to demand. Westport’s constraint is structural: the town is largely built out, the zoning is protective, and the buyers who want to be here are not price-sensitive in ways that create negotiating leverage.
If you want to understand how this market moves month to month, the Westport market report breaks down current inventory, price trends, and absorption. The listing report shows what is actively on the market right now. I covered Westport alongside New Canaan, Darien, and Wilton in the January 2026 edition of my New Canaan Sentinel column – the pricing dynamics I described there are playing out exactly as anticipated. For a deeper look at what drives these numbers and the buyers behind them, the Boroughs and Burbs episode on super-luxury condo sales in Westport is worth an hour of your time.
The Westport mill rate is currently 16.86, which translates to an annual tax bill of roughly $35,400 on a $2.1M purchase assessed at current ratios. That is not a low number, but it is competitive with Greenwich for a town offering comparable school quality and waterfront access. Buyers comparing Westport to Norwalk should know the entry price is roughly double, but the resale liquidity and price appreciation history in Westport have consistently outperformed.
Westport has two Metro-North stations on the New Haven Line: Westport station on Saugatuck Avenue and Green’s Farms station further east. Peak express trains from Westport to Grand Central run approximately 67 to 75 minutes. Local trains add 10 to 15 minutes. Off-peak service runs hourly. Green’s Farms is the quieter of the two stations, preferred by buyers in the eastern half of town who want to avoid the Post Road traffic near Westport station entirely. Monthly passes run roughly $375 to $395 depending on zone. Parking at both stations fills by 7:30 a.m. on weekdays, and permit waitlists exist. Buyers coming from Manhattan should assume the commute runs 80 to 85 minutes door to door on a realistic basis, not the station-to-station number. By car, I-95 between Westport and Midtown Manhattan is 55 miles. At 7 a.m. on a Tuesday, plan on 90 minutes minimum. The Merritt Parkway is the smarter option for anyone heading into northern Westchester or Connecticut business corridors rather than the city.
Westport operates under the Westport Public Schools district, which serves approximately 5,400 students across six elementary schools, two middle schools, and Staples High School. Staples High School consistently ranks among the top public high schools in Connecticut. Niche ranks it in the top 5% of Connecticut high schools as of 2025. The district’s college acceptance profile leans heavily toward selective institutions. Elementary schools feeding the district include Coleytown Elementary and Long Lots Elementary, two schools that come up constantly in buyer conversations around the Coleytown Road and Long Lots Road neighborhoods. The district spends well above state average per pupil, and the results are visible in test scores and extracurricular depth. Buyers with children in middle school should look hard at Bedford Middle School and Coleytown Middle School – both carry strong academic reputations and active parent communities.
Westport is a town that has been discovered and rediscovered so many times that it has developed a mild immunity to hype. The arts community has been here since the 1920s, when writers and painters found the light on the Saugatuck River irresistible. The commercial corridor on the Post Road is not a strip mall ecosystem. It is a walkable mix of independent restaurants, gallery spaces, and boutique retail that genuinely competes with anything south of Boston. The Westport Cinema on the Post Road and the Westport Country Playhouse on Powers Court are institutions, not tourist attractions. The Playhouse in particular draws Broadway-caliber productions and has been a working professional theater since 1931.
The neighborhoods matter here more than in most Fairfield County towns. Compo Beach is its own real estate category – waterfront and near-waterfront homes in that zone carry a premium that compounds every year. Saugatuck is walkable to the train, younger in demographic feel, and has been appreciating fast as remote-work buyers discovered they wanted a downtown within walking distance. Green’s Farms is the quieter eastern end of town, larger lots, older money, and a distinctly different pace from the Post Road energy. Each of these sub-markets behaves independently. A Green’s Farms colonial at $3.2M and a Saugatuck townhouse at $1.4M are technically in the same town, but they are attracting completely different buyer profiles. For a thorough breakdown of what Westport’s different neighborhoods feel like on the ground, the Boroughs and Burbs episode with Jennifer Tooker and Dan Woog is one of the best overviews I have heard.
Compo Beach is the anchor. 32 acres on Long Island Sound with a swimming beach, boat launch, concessions, and a playground. Town residents pay roughly $60 per season for beach access. Non-residents do not have access at all, which is exactly how Westport residents prefer it. The Longshore Club Park adds a golf course, tennis courts, an indoor pool, a sailing school, and a marina – all operated by the town, which means the cost structure is municipal rather than private club. This combination of public waterfront access and public recreational infrastructure at the quality level Westport maintains is not common in Fairfield County. The Aspetuck Land Trust manages over 1,500 acres of preserved open space in and around Westport, including trail networks that connect to neighboring Weston. For buyers who want both water and woods without driving to either, Westport is genuinely difficult to beat.
Two videos worth watching before you visit. First, a Westport market update from earlier this year that walks through the current pricing environment, what a cooldown period means in a market this tight, and how buyers should position offers. Second, a quick take on why working with local Westport realtors matters more in this market than in most – the inventory moves too fast and the neighborhood nuance is too specific for someone who doesn’t know the difference between a Compo Beach address and a Long Lots Road address.
The Westport buyer has made a specific set of decisions. They have accepted a price point that is 15 to 20% higher than comparable square footage in New Canaan. They have accepted a commute that is longer than Darien’s. They have accepted a mill rate that is not the lowest in the county. What they have gotten in return: a school district that rivals any in the state, waterfront access that is genuinely public rather than private-club gated, a walkable downtown that does not require a car to use, and a resale market that has been one of the most consistently liquid in Fairfield County for thirty years.
The buyer profile skews toward finance, media, and technology professionals who moved from Manhattan or Brooklyn and wanted the aesthetic of a sophisticated small city rather than a quiet suburb. Westport has that. It also has a significant second-home and seasonal buyer segment, which is one reason the inventory compression is so extreme – a meaningful percentage of the housing stock is not available at any price because the owners simply are not selling. If you are serious about buying here, check this weekend’s Westport open houses and expect to move quickly on anything that is priced correctly. At 53 days on market on average and a 100.3% sold-to-list ratio, the days of extended negotiation are not a realistic strategy in this market.
Buyers who find Westport’s price point beyond reach often look at Norwalk first, specifically the Rowayton section, which offers waterfront character at a significantly lower entry price. Wilton sits directly to the north and draws buyers who want the Westport school district quality at 20 to 30% lower prices, though Wilton has its own strong school system and its own distinct character. Greenwich to the south is the only town in Fairfield County that consistently competes with Westport on median price, and its buyer profile overlaps significantly. For buyers choosing between Westport and New Canaan, the question almost always comes down to water access versus wooded acreage, and downtown walkability versus privacy. They are not interchangeable. They serve different buyers, and knowing which one fits your life is worth at least one honest conversation before you make an offer on either.
Download the Westport Market Report — Full neighborhood data including recent sales, price trends, and market conditions. Download PDF →
© 2025 DOUGLAS ELLIMAN REAL ESTATE. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY. 
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