The most expensive towns in Eastern Massachusetts
The ten highest single-family medians across 129 cities and towns, from The Context Report No. 5.
Wellesley led Eastern Massachusetts in September 2026 with a $3,075,000 single-family median, followed by Brookline, Cambridge, Hingham and Winchester. Over 12 months, Brookline, Weston and Cambridge had the highest medians.
October 2026 issue This list is updated with each Context Report. Past lists stay in the archive.
The Luxury List, September 2026 sales
| # | Town | Region | Sept. median | Sales | Carrying cost / mo | 12-mo median | FY26 tax rate |
|---|---|---|---|---|---|---|---|
| 1 | Wellesley | Metro West | $3,075,000 | 15 | $20,001 | $2,367,500 | $10.17 |
| 2 | Brookline | Greater Boston | $2,575,000 | 9 | $16,764 | $2,570,000 | $10.24 |
| 3 | Cambridge | Greater Boston | $2,400,000 | 6 | $14,910 | $2,475,000 | $6.67 |
| 4 | Hingham | South Shore | $2,030,000 | 20 | $13,255 | $1,497,500 | $10.47 |
| 5 | Winchester | Greater Boston | $1,900,000 | 11 | $12,502 | $1,755,000 | $11.08 |
| 6 | Newton | Greater Boston | $1,850,000 | 29 | $11,959 | $1,825,000 | $9.69 |
| 7 | Cohasset | South Shore | $1,783,000 | 2* | $11,773 | $1,600,000 | $11.35 |
| 8 | Dover | Metro West | $1,782,500 | 6 | $11,746 | $2,050,000 | $11.19 |
| 9 | Weston | Metro West | $1,710,850 | 13 | $11,229 | $2,565,000 | $10.88 |
| 10 | Needham | Metro West | $1,570,000 | 15 | $10,298 | $1,770,000 | $10.83 |
* Fewer than five sales; read with caution. Carrying cost is estimated principal, interest and property tax on the median with 20% down on a 30-year fixed loan.
The steadier view: highest 12-month medians
| # | Town | Region | 12-mo median | 12-mo change | Sept. median | FY26 tax rate |
|---|---|---|---|---|---|---|
| 1 | Brookline | Greater Boston | $2,570,000 | +2.4% | $2,575,000 | $10.24 |
| 2 | Weston | Metro West | $2,565,000 | -1.3% | $1,710,850 | $10.88 |
| 3 | Cambridge | Greater Boston | $2,475,000 | +6.1% | $2,400,000 | $6.67 |
| 4 | Wellesley | Metro West | $2,367,500 | +7.9% | $3,075,000 | $10.17 |
| 5 | Dover | Metro West | $2,050,000 | +14.1% | $1,782,500 | $11.19 |
| 6 | Newton | Greater Boston | $1,825,000 | -6.4% | $1,850,000 | $9.69 |
| 7 | Needham | Metro West | $1,770,000 | -1.7% | $1,570,000 | $10.83 |
| 8 | Winchester | Greater Boston | $1,755,000 | -6.4% | $1,900,000 | $11.08 |
| 9 | Lexington | Greater Boston | $1,750,000 | -5.4% | $1,487,500 | $12.31 |
| 10 | Concord | Northwest Suburbs | $1,742,500 | +1.0% | $1,550,000 | $13.05 |
Selling at the top of the market
At these prices, the buyer pool is small and each sale moves the median. Pricing depends on the specific street, lot and condition more than the town average. If you are thinking about selling, we will send a value range based on the closest comparable sales within one business day.
Sources
- The Context Report No. 5 (October 2026), MLS PIN closed single-family sales, September 2026
- Massachusetts DOR, FY2026 tax rates by class
Questions this page answers
What is the most expensive town in Massachusetts near Boston?
In September 2026, Wellesley had the highest single-family median sale price in our coverage area at $3,075,000 on 15 sales. Over the last 12 months, Brookline ($2,570,000) and Weston ($2,565,000) had the highest medians.
Which towns have the most expensive homes in Eastern Massachusetts?
The September 2026 top ten by single-family median were Wellesley, Brookline, Cambridge, Hingham, Winchester, Newton, Cohasset, Dover, Weston and Needham.
Why is Cambridge or Brookline on a single-family list?
The Context Report covers single-family homes only. In Cambridge and Brookline, single-family sales are a small share of the market, and most homes sold are condos.
How often is this list updated?
Monthly, with each issue of The Context Report.