Chelsea vs Winthrop
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 $200k more for a 4BR in Winthrop, and in exchange you get the stronger schools. That is the trade in plain terms: $200k for one tier of schooling.
Chelsea is about 10 minutes closer to downtown Boston at peak, and it has MBTA rail while Winthrop does not. Over a decade of commuting that gap is worth more than most people price it at.
On tax, look past the rate: Chelsea works out roughly $2,000 a year cheaper on its own median 4BR — despite having the higher rate of the two, because the bill follows the house.
Choose Chelsea if you want the lower price, or the commute matters most, or you want a train.
All Chelsea numbers →Choose Winthrop if you want the stronger schools of the two.
All Winthrop 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.
SchoolsWinthrop ahead on 5 of 9, 1 against
| Chelsea | Winthrop | |
|---|---|---|
| School tier | mixed schoolsT4 | solid schoolsT3 |
| MCAS achievement | 5th | 51st |
| Student growth | 46th | 56th |
| Graduation rate | 70.1% | 91.2% |
| SchoolDigger rank | 340th of 361 | 229th of 361 |
| State accountability | Moderate progress toward targets | Moderate progress toward targets |
| Spending per pupil | $24,407 | $19,308 |
| Schools in the district | 8 | 3 |
| Private schools within 12 mi | 57 | 47 |
What a home costsChelsea ahead on 6 of 8, 2 against
| Chelsea | Winthrop | |
|---|---|---|
| 4BR house | $650kT2 | $850kT2 |
| 3BR townhouse | $525k | $650k |
| 2BR condo | $390k | $480k |
| 3BR home | $622k | $733k |
| 5+ BR home | $855k | $938k |
| 3BR rent | $3,720/mo | $3,327/mo |
| Income needed for the 4BR | $175k | $226k |
| 10-year price growth | 5.4% a year | 6% a year |
What you pay the townChelsea ahead on 1 of 4
| Chelsea | Winthrop | |
|---|---|---|
| Tax rate | $11.48T2 | $11.14T2 |
| Est. tax bill on that 4BR | ≈$7,500 | ≈$9,500 |
| Town spending per resident | $6,236 | $3,250 |
| Share of budget on schools | 52% | 45% |
Getting to workChelsea ahead on 3 of 3
| Chelsea | Winthrop | |
|---|---|---|
| Commute to Boston | 24 minT1 | 34 minT2 |
| MBTA rail | Commuter rail · ~18 min to terminal | No MBTA rail |
| Miles from downtown | 3 mi | 4 mi |
Before kindergartenChelsea ahead on 3 of 4
| Chelsea | Winthrop | |
|---|---|---|
| Licensed child care programs | 55 | 21 |
| Child care places | 1,141 | 569 |
| Centers vs family programs | 9 centers | 8 centers |
| Infant places in centers | 118 | 83 |
What the place is likeDescribes the two, does not rank them
| Chelsea | Winthrop | |
|---|---|---|
| Population | 40,787 | 19,316 |
| Energy | 8/10 | 7/10 |
| Compact center | 10/10 | 8/10 |
| Family amenities | 7/10 | 7/10 |
| Culture | 8/10 | 7/10 |
| Gathering places | 7/10 | 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 FY2027 Small Area FMRs · reviewed · methodology. Never uses demographics as an input.
