May 2026 Market Update: What's Happening in Westport, Fairfield, Weston & Wilton
Published by The Riverside Realty Group | theriversiderealtygroup.com
If you've been watching the Fairfield County market this spring, you already know things are moving — just not always in a straight line. May's data tells a nuanced story: prices are climbing in most towns, but buyers are taking a little longer to commit, and the inventory picture varies significantly depending on where you're looking. Here's a town-by-town breakdown of what the numbers are telling us.
Fairfield: Prices Surge, Competition Remains Strong
Fairfield's single-family market had a standout May in terms of pricing. The median sales price jumped to $1,212,500 — a 31.8% increase over May 2025 — and homes are still selling above list price, averaging 105.6% of asking. New listings picked up meaningfully (99 vs. 77 last year), giving buyers a bit more to choose from, though inventory remains tight at just 2.8 months of supply.
The one note of caution: days on market rose to 36 from 26, and closed sales were down year-over-year. That suggests buyers have options but are being more deliberate before writing offers. Year-to-date, the median is up 20.2% to $1,175,000 — a strong signal that Fairfield's appreciation trend has real momentum behind it.
The condo market tells a different story. Prices pulled back sharply in May, though this is largely a reflection of the small sample sizes involved — just 7 units closed. Don't read too much into a single month's swings here.
The takeaway: Fairfield remains a seller's market with serious price appreciation. If you're a buyer here, expect to compete — and come prepared.
Westport: Luxury Demand Holds Firm
Westport continues to be one of the most coveted addresses in Fairfield County, and the May data reflects that. The single-family median hit $2,385,000, up 8.4% from a year ago, with average prices approaching $3 million. Pending sales surged 19.4% in May, and year-to-date closed sales are actually up 7.9% — a sign that transaction volume is healthy despite the premium price point.
Inventory has tightened considerably. The town had 92 homes for sale versus 119 last May, pushing months of supply down to 3.5. Buyers in this market are still clearing list price (103.3% received on average), and days on market, while up modestly, remain reasonable at 43.
The condo segment in Westport is a different animal this year — new listings are down sharply (3 vs. 10 in May 2025), and the handful of sales that are occurring are taking much longer to find buyers. With only 5 condos currently on the market, it's a very thin, unpredictable segment right now.
The takeaway: Westport's single-family market is as competitive as ever. Luxury buyers relocating from NYC continue to drive demand, and with inventory shrinking, well-priced homes are moving quickly.
Weston: A Quieter Market, But Prices Stay Elevated
Weston operates on its own rhythm — smaller volume, larger lots, and a distinctly private character — and May's numbers reflect that. New listings were down 29% from last year, and inventory has dropped to just 35 homes (from 51 a year ago), tightening months of supply to 3.3.
Despite fewer listings, 10 homes closed in May (up from 6 last year), and buyers are still paying a premium — the list price received ratio held at 106.2%. Days on market did double to 34, which isn't alarming given Weston's characteristically deliberate pace, but it's worth noting.
The median sales price slipped slightly to $1,510,000 for the month, though year-to-date the median is actually up 7.7% to $1,405,000 — a better read on the underlying trend. Weston has no condo market to speak of, so this is purely a single-family story.
The takeaway: Weston is for buyers seeking privacy, acreage, and a strong school district. Supply is shrinking, and those who find the right home here are still paying over asking.
Wilton: Strong Fundamentals, Elevated Days on Market
Wilton's numbers this May require a bit of context. Days on market spiked to 55 — up nearly 300% year-over-year — which sounds alarming until you remember that May 2025 was an unusually fast month (just 14 days). The year-to-date figure of 47 days is a more useful benchmark and reflects a market that's active but not frenetic.
What stands out positively: pending sales were up 36% in May, and year-to-date they're up 17.1% — one of the strongest demand signals in this group. The median sales price rose 16.8% to $1,461,000, and homes are receiving 109.2% of list price year-to-date, the highest ratio among the four towns we're tracking. Inventory has tightened to just 2.5 months of supply.
The condo market in Wilton is very small (just a handful of sales), so monthly price swings there should be viewed with appropriate skepticism.
The takeaway: Wilton is quietly one of the most competitive markets in Fairfield County right now. Strong schools, a walkable downtown, and relatively more accessible price points compared to Westport are drawing serious buyer attention.
The Big Picture
Across all four towns, a few themes emerge from the May data:
Prices are up. Whether it's Fairfield's 31.8% monthly jump or Wilton's steady 16.8% gain, sellers in this market are in a strong position.
Inventory is tight — but improving in some spots. Fairfield added listings year-over-year; Westport and Weston have less to choose from. Buyers need to move decisively when the right home appears.
Demand signals are healthy. Rising pending sales in Westport and Wilton suggest the pipeline stays full heading into summer.
Days on market are creeping up. This isn't a reason for alarm — it reflects buyers being more selective, not markets slowing down. Proper pricing and presentation still matter enormously.
Whether you're thinking about making a move this summer or just keeping an eye on the market, we're here to help you navigate it. Reach out to the team at The Riverside Realty Group — we know these towns deeply and we're happy to talk through what the numbers mean for your situation.
Data sourced from SmartMLS, current as of June 8, 2026.
