Winchester vs Woburn
You are paying about $1.02M more for a 4BR in Winchester, and in exchange you get the stronger schools. That is the trade in plain terms: $1.02M for two tiers of schooling.
Winchester is about 5 minutes closer to downtown Boston at peak. Over a decade of commuting that gap is worth more than most people price it at.
On tax, look past the rate: Woburn works out roughly $13,000 a year cheaper on its own median 4BR.
Choose Winchester if you want the stronger schools of the two, or the commute matters most.
All Winchester numbers →Choose Woburn if you want the lower price.
All Woburn numbers →Side by side
The better of the two is highlighted on each row. Where a row is not highlighted, the two are close enough that calling a winner would be false precision.
| Winchester | Woburn | |
|---|---|---|
| School tier | top schoolsT1 | solid schoolsT3 |
| MCAS percentile | 97th | 31st |
| Niche district rank | 8th of 236 | — |
| 4BR house | $1.85MT4 | $825kT2 |
| 2BR condo | $925k | $480k |
| Commute to Boston | 31 minT2 | 36 minT2 |
| MBTA rail | Commuter rail · ~20 min to terminal | Commuter rail · ~30 min to terminal |
| Tax rate | $11.08T2 | $9.15T1 |
| Est. tax bill on that 4BR | ≈$20,500 | ≈$7,500 |
| 3BR rent | $3,743/mo | $3,887/mo |
Prices are estimates calibrated to the Zillow Home Value Index and Redfin; tax rates are FY2026 residential rates and the bill applies that rate to the town’s own median 4BR estimate; commutes take the rail leg from the MBTA timetable and still model the drive; rents are HUD FY2026 Small Area Fair Market Rents. School tiers are editorial and shown next to the state’s own MCAS figures. Data last reviewed — see the methodology. This comparison never uses demographics as an input.
