Winchester vs Woburn
marks the Massachusetts median on each scale. The better of the two is picked out where the gap is big enough to call; where neither is, they are level.
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
Some rows have no better. Town character describes a place rather than ranking it, and per-pupil spending tracks need rather than results, so neither is picked out.
SchoolsWinchester ahead on 5 of 8
| Winchester | Woburn | |
|---|---|---|
| School tier | top schoolsT1 | solid schoolsT3 |
| MCAS achievement | 97th | 31st |
| Student growth | 59th | 45th |
| Graduation rate | 96% | 91.1% |
| State accountability | Meeting or exceeding targets | Moderate progress toward targets |
| Spending per pupil | $19,932 | $24,148 |
| Schools in the district | 6 | 9 |
| Private schools within 12 mi | 61 | 44 |
What a home costsWoburn ahead on 5 of 6
| Winchester | Woburn | |
|---|---|---|
| 4BR house | $1.85MT4 | $825kT2 |
| 3BR townhouse | $1.25M | $650k |
| 2BR condo | $925k | $480k |
| 3BR rent | $3,743/mo | $3,887/mo |
| Income needed for the 4BR | $482k | $213k |
| 10-year price growth | 4.9% a year | 5.4% a year |
What you pay the townWoburn ahead on 2 of 4
| Winchester | Woburn | |
|---|---|---|
| Tax rate | $11.08T2 | $9.15T1 |
| Est. tax bill on that 4BR | ≈$20,500 | ≈$7,500 |
| Town spending per resident | $6,257 | $4,739 |
| Share of budget on schools | 46% | 47% |
Getting to workWinchester ahead on 7 of 8
| Winchester | Woburn | |
|---|---|---|
| Commute to Boston | 31 minT2 | 36 minT2 |
| MBTA rail | Commuter rail · ~20 min to terminal | Commuter rail · ~30 min to terminal |
| Miles from downtown | 8 mi | 10 mi |
| Rail to Downtown | 20 min | 30 min |
| Rail to Back Bay | 30 min | 39 min |
| Rail to Kendall Sq | 35 min | 43 min |
| Rail to the Seaport | 31 min | 39 min |
| Rail to Longwood | 48 min | 56 min |
Before kindergartenWoburn ahead on 3 of 4
| Winchester | Woburn | |
|---|---|---|
| Licensed child care programs | 22 | 63 |
| Child care places | 1,600 | 2,343 |
| Centers vs family programs | 18 centers | 27 centers |
| Infant places in centers | 125 | 558 |
What the place is likeDescribes the two, does not rank them
| Winchester | Woburn | |
|---|---|---|
| Population | 22,970 | 40,876 |
| Energy | 6/10 | 7/10 |
| Compact center | 7/10 | 7/10 |
| Family amenities | 8/10 | 7/10 |
| Culture | 7/10 | 7/10 |
| Gathering places | 8/10 | 8/10 |
The tax bill is each town’s own rate on its own median 4BR, so a lower rate does not always mean a lower bill. School tiers are editorial, shown beside the state’s own MCAS figures rather than derived from them.
Prices calibrated to Zillow ZHVI and Redfin · FY2026 residential tax rates · rail leg from the MBTA timetable, drive modeled · rents are HUD FY2026 Small Area FMRs · reviewed · methodology. Never uses demographics as an input.
