Where Westport stands among its neighbors depends a little on which numbers you use and a lot less than you might think. Three separate measures, brokerage medians for full-year 2025, brokerage medians for the first quarter of 2026 and Zillow’s home value index, put the town in the same place, fourth of the six towns most often compared with it.
The 2025 ladder
Median single-family sale price for full-year 2025
Data from Riverside Realty Group (Westport, Weston, Fairfield), Greenwich Association of Realtors (Greenwich), Jennifer Lockwood Homes (New Canaan, Darien)
Show the numbers as a table
| Area | Value |
|---|---|
| Greenwich | $3.15M |
| New Canaan | $2.60M |
| Darien | $2.40M |
| Westport | $2.30M |
| Weston | $1.40M |
| Fairfield | $1.07M |
Full-year 2025
For single-family houses, the 2025 medians ran from $3,150,000 in Greenwich to $1,072,500 in Fairfield. Westport’s was $2,300,000, up 6.4 percent, on 299 sales. Darien rose fastest, up 21.5 percent to $2,400,000, and New Canaan rose 15 percent to $2,600,000. The figures come from different brokerage reports, listed in the chart, so treat small gaps with caution.
First quarter 2026
A single source, Brown Harris Stevens, makes the cleanest comparison for early 2026.
| Area | Median, first quarter 2026 | House sales |
|---|---|---|
| Greenwich | $4,200,000 | 59 |
| New Canaan | $3,200,000 | 30 |
| Darien | $2,520,000 | 22 |
| Westport | $2,150,000 | 48 |
| Lower Fairfield County | $1,350,000 | 543 |
| Weston | $1,200,000 | 13 |
| Fairfield | $1,175,000 | 97 |
Westport sold more houses in the quarter than any of its neighbors except Greenwich and Fairfield.
Zillow’s home value index
Zillow’s typical home value covers all home types and smooths out the mix of sales.
| Area | Typical home value | One-year change | As of |
|---|---|---|---|
| Darien | $2,477,368 | +11.5% | June 30, 2026 |
| Greenwich | $2,376,620 | +13.7% | Aug. 31, 2026 |
| New Canaan | $2,228,794 | +13.1% | Aug. 31, 2026 |
| Westport | $2,077,131 | +11.0% | Aug. 31, 2026 |
| Weston | $1,399,512 | +6.4% | Aug. 31, 2026 |
| Fairfield | $1,002,047 | +7.8% | July 31, 2026 |
| Fairfield County | $693,453 | +6.0% | Aug. 31, 2026 |
The top of the market
At the very top, Greenwich is in a different league. It recorded 38 sales at $10 million or more in 2025, up from 17 in 2024, according to Moffly Media. Westport’s record, the $54 million Beachside Avenue assemblage, was a single transaction.
For the county as a whole, the September single-family median was $806,000, down 2.1 percent from a year earlier, on 516 closings, according to William Pitt Sotheby’s. Our market report has the rest of Westport’s numbers.
Sources
- Riverside Realty Group, December market report, 2025 recap, Jan. 13, 2026
- Greenwich Association of Realtors, Fourth quarter market update 2025, 2026
- Jennifer Lockwood Homes, Fairfield County real estate is not slowing down, 2026
- Brown Harris Stevens, Connecticut market report, first quarter 2026, April 2026
- Zillow, Westport home values, accessed Oct. 2026
- Moffly Media, Greenwich real estate market 2026, 2026
- William Pitt Sotheby's, Fairfield County market report, accessed Oct. 2026
