If you are deciding whether to list a Westport house before winter, the most useful history is the last three falls. The real estate site of Charlie Vinci publishes Westport figures for offers accepted from Sept. 1 to Dec. 31 each year, which captures the fall market as buyers experienced it rather than as closings recorded it weeks later.
| Fall season | Single-family median | Single-family sales | Median price per square foot, all types |
|---|---|---|---|
| 2023 | $1,850,000 | 79 | $514 |
| 2024 | $2,200,000 | 90 | $551 |
| 2025 | $2,140,000 | 90 | $585 |
What the table shows
Two things stand out. First, the number of fall deals held steady at 90 in both 2024 and 2025, after 79 in 2023. Second, price per square foot rose every year, by about 7 percent from 2023 to 2024 and 6 percent from 2024 to 2025, even as the median house price slipped slightly in 2025. When the median falls while the price per square foot rises, that usually points to a change in the mix of houses sold, such as more smaller houses, rather than a drop in values.
How this fall is starting
The early read on fall 2026 is mixed. The single-family median for January through August was $2,425,000, up 5.9 percent, according to the Riverside Realty Group. September’s preliminary count from William Pitt Sotheby’s showed 16 single-family sales, half the number of a year earlier, though early counts are often incomplete. The average price per square foot in September was $668, up 4.9 percent from a year earlier.
Nationally, fall is not the strongest season for sellers. ATTOM’s study of more than 52 million sales put October’s premium over automated valuations at 7.9 percent, the lowest of any month, against 10.7 percent in March. Our guide to timing a sale weighs that against Westport’s thin inventory.
Sources
- Charlie Vinci, Westport market, accessed Oct. 2026
- Riverside Realty Group, August market update, September 2026
- William Pitt Sotheby's, Westport market report, accessed Oct. 2026
- PR Newswire, ATTOM, ATTOM analysis finds spring remains the prime window for home sellers, April 30, 2026
