Westport Market Report
Westport, H1 2026: Fewer Sales, $48 Million More
This spring, Westport bought fewer homes than last year — yet total volume was forty-eight million dollars higher. So instead of running the usual stats, I traced the money: where it came in, which homes it went to, and which part of town it landed in. What came out is a map. And depending on where your home sits on it, this spring either quietly repriced your biggest asset, or passed you by completely.
Three springs, side by side: 158 closings and $355.4M in 2024, 159 closings and $372.9M in 2025, and now 152 closings and $420.9M in 2026. Fewer transactions, more money. The rest of this report is the answer to a single question — where did that money go?
Clue One
Follow the new money
Split every closing at the $4 million line, and the two halves of Westport move in opposite directions.
Dollar volume by price tier
All property types · sum of closed price · Jan–Jun
Under $4M
$4M and above
| Measure | H1 2024 | H1 2025 | H1 2026 |
|---|---|---|---|
| Under $4M — dollars | $261.0M | $279.7M | $259.1M |
| Under $4M — closings | 140 | 140 | 128 |
| $4M+ — dollars | $94.3M | $93.2M | $161.8M |
| $4M+ — closings | 18 | 19 | 24 |
| $4M+ share of all dollars | 26.5% | 25.0% | 38.4% |
Bands set by closing price. Year over year, the $4M+ tier added $68.5M while the market below it lost $20.6M.
Charlie's Take
Every new dollar that entered Westport this year — plus the twenty million or so that left the rest of the market — flowed to the top. All of it. The record wasn't the town. The record was one tier of the town.
Clue Two
The money has an address
Put the properties on a map and the volume isn't spread across Westport. It is concentrated near the water.
Shore neighborhoods' share of townwide dollar volume
Compo Beach, Compo South, Greens Farms, Saugatuck, Saugatuck Island, Saugatuck Shore
Closings above $5 million
All property types · Jan–Jun
The top sale in town was $15.5 million on Beachside Avenue — direct waterfront, listed at $19.8 million with no price cuts, 105 days on market. The six largest waterfront sales together account for $57.5 million of the town's first-half volume. Of the six biggest sales overall, four are direct waterfront and all six sit in shore neighborhoods.
Charlie's Take
Roughly two-thirds of the $4M-plus market landed along the shore. That is not a town-wide story anyone can borrow — it is a specific set of streets, and the closer your home sits to that water, the more this spring changed your number.
Clue Three
A new ceiling, in six months
The number I keep coming back to: closings above $8 million.
Closings above $8 million
All property types · Jan–Jun
In the first half of 2024, one home in Westport closed above $8 million — $11.0 million on Saugatuck Avenue. Last year, none. This spring, six.
A sale like that was rare, not a market. Six in six months changes that.
Charlie's Take
That's the kind of depth you might expect in Greenwich's premium waterfront neighborhoods, and this spring it showed up here. One trophy sale is an anecdote. Six is a tier — and tiers have comps, buyers, and staying power that anecdotes don't.
Why It Matters Below The Top
Builders are paying up for land
Money at the top doesn't stay at the top. When the ceiling of a market jumps, everything below it gets re-anchored.
Single-family homes under $1.5M that sold over asking
Closing price vs. original list price · single-family only
Case Study One
1 Dexter Road
Fifty-three percent over asking, in ten days. That is not a homeowner bidding war. That is builders competing for the land underneath the house.
Case Study Two
5 Over Rock Lane
Thirty-four percent over. Same story, one price band up.
Charlie's Take
Under a million and a half, sixty percent of single-family homes sold over asking this spring. Two years ago it was thirty-five. If you own an older, smaller home on a good piece of Westport land, the buyer for it may not be a family at all — and that changes how you price it.
Behavior At The Top
The money is big, and it's patient
Before anyone gets carried away: the buyers who arrived this spring did not chase.
The clearest example is the top sale itself: 92 Beachside Avenue listed at $19.8 million and closed at $15.5 million. And the broader market got slower — the typical single-family home took twice as long to sell this spring as last.
Charlie's Take
Volume records and seller leverage usually travel together. This spring they didn't. Buyers at the top showed up in numbers we haven't seen — and still negotiated. Read that as depth of demand, not desperation on either side.
Pace
Everything took longer
Median days on market, the number that tells you how the market actually felt.
Median days on market, single-family
Jan–Jun
| Segment | H1 2024 | H1 2025 | H1 2026 |
|---|---|---|---|
| Single-family — median DOM | 21.5 | 13 | 27 |
| Condo / townhouse — median DOM | 27 | 17.5 | 44 |
| Condo / townhouse — closings | 26 | 30 | 17 |
| Mid-market SF $2.5M–$4M — median DOM | 13 | 13 | 29.5 |
| Mid-market SF $2.5M–$4M — median % of original list | 100.0% | 100.1% | 100.0% |
Charlie's Take
The middle of the market sat at asking price and took a month to sell. That is a disciplined market, not a hot one — and it's the single most misread number in this report, because the headlines from the waterfront make sellers inland expect something the data doesn't support.
The Full Numbers
Westport by the data
Every headline figure behind this report, three springs deep.
| Metric | H1 2024 | H1 2025 | H1 2026 | YoY |
|---|---|---|---|---|
| Closings | 158 | 159 | 152 | −7 |
| Total dollar volume | $355.4M | $372.9M | $420.9M | +$47.9M |
| Median sale price | $1,925,000 | $2,029,422 | $2,137,500 | +5% |
| Average sale price | $2,249,275 | $2,345,535 | $2,768,751 | +18% |
| Median $/sq. ft. | $516 | $597 | $644 | +8% |
| % sold at or over asking | 58.9% | 59.1% | 61.2% | +2.1 pts |
| Median days on market | 22 | 15 | 28 | +13 days |
| Metric | Single-family | Condo / townhouse | ||
|---|---|---|---|---|
| H1 2025 | H1 2026 | H1 2025 | H1 2026 | |
| Closings | 129 | 135 | 30 | 17 |
| Median sale price | $2,200,000 | $2,310,000 | $1,530,000 | $1,395,000 |
| Median $/sq. ft. | $578 | $646 | $743 | $643 |
| % sold at or over asking | 62.0% | 60.7% | 46.7% | 64.7% |
| Median days on market | 13 | 27 | 17.5 | 44 |
| Band | Closings | Median price | Median $/sf | % at/over ask | Median DOM |
|---|---|---|---|---|---|
| Under $1.5M | 30 | $1,155,010 | $668 | 70.0% | 21 |
| $1.5M–$2.5M | 45 | $2,014,000 | $651 | 71.1% | 20 |
| $2.5M–$4M | 36 | $3,200,800 | $612 | 55.6% | 29.5 |
| $4M–$5M | 7 | $4,350,000 | $625 | 28.6% | 80 |
| $5M–$8M | 11 | $5,500,000 | $821 | 45.5% | 42 |
| $8M+ | 6 | $10,650,000 | $970 | 33.3% | 29 |
| All single-family | 135 | $2,310,000 | $646 | 60.7% | 27 |
Bands by closing price, half-open — a home closing exactly on an edge counts in the higher band only. "% at/over ask" here means closing at or above the last list price, which is why the under-$1.5M band reads 70.0% here and 60% in the builder section above — that figure counts only homes closing above their original list price.
What To Do With The Map
Where your home sits
Three positions in this market, three different plays.
Position One
You own near the water
Your comps from a year ago are probably stale. The shore went from 24.8% of townwide dollars to 45.8% in twelve months. Get a real number before you anchor to an old one.
Position Two
You own inland, in the middle of the market
Don't borrow the beach's story. Your segment sat at asking price and took a month to sell. Price with discipline, and let the buyer discover the competition — not the other way around.
Position Three
You've been circling the top of this market
You just watched closings above $5 million go from seven to seventeen while sellers still gave ground on price. That combination never lasts. One of those two lines is going to move.
Know exactly where your home sits on this map
A townwide median is the wrong number for almost every individual house in Westport this spring — the shore, the mid-market, and the entry band moved in three different directions. I'll pull your street's actual comps, tell you which of the three you're in, and give you a real number you can act on. No obligation, no listing pitch.
Book a Time With CharlieMethodology & Sources
Source: SmartMLS closed-sales exports for Westport, CT — January through June of 2024, 2025 and 2026 (158 / 159 / 152 closings). All property types unless a figure is labeled single-family or condo. Price bands are set by closing price and are half-open, so nothing is double-counted. Headline figures are medians; averages are shown where useful. Sale-to-list and over-asking figures are measured against the last list price except where noted as original list — the under-$1.5M over-asking figures use original list, and every claim in this report holds under both conventions.
"Shore neighborhoods" means the MLS Neighborhood values Compo Beach, Compo South, Greens Farms, Saugatuck, Saugatuck Island and Saugatuck Shore, plus the 2024-only "Hillspoint" label, for cross-year consistency. Listings with no neighborhood recorded (12 / 7 / 6 by year) are counted as non-shore, so the shore share is if anything understated. Figures reflect a single MLS export and are not deduplicated against a second MLS; comparable-status closings (6 / 7 / 7 by year) are included throughout. Records are three springs deep — 2026 is the strongest of the three, not a verified all-time high.
Charlie Vinci · Compass · Greenwich and Westport offices · 203-952-7752 · charlievinci@gmail.com