Lexington vs Winchester

4BR house$200k apart
Lexington$2.05M
Winchester$1.85M
Both among the dearest third of Massachusetts towns
Tax billOn each town’s own median 4BR$4,700/yr apart
Lexington$25,200
Winchester$20,500
Both among the highest third of Massachusetts towns
To Boston7 min apart
Lexington38 min
Winchester31 min
Both among the closest third of Massachusetts towns
SchoolsMCAS percentile, statewideLevel
Lexington99th pct
Winchester97th pct
Both among the top third of Massachusetts districts

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.

On schools these two are genuinely close — same tier and within five MCAS percentiles of each other — so the schools should not decide it. Price and commute should.

Winchester is about 7 minutes closer to downtown Boston at peak, and it has MBTA rail while Lexington does not. Over a decade of commuting that gap is worth more than most people price it at.

On tax, look past the rate: Winchester works out roughly $4,700 a year cheaper on its own median 4BR.

Lexington

Choose Lexington if you prefer the town itself — the numbers do not separate them.

All Lexington numbers →
Winchester

Choose Winchester if you want the lower price, or the commute matters most, or you want a train.

All Winchester 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.

SchoolsLexington ahead on 3 of 10, 1 against
LexingtonWinchester
School tiertop schoolsT1top schoolsT1
MCAS achievementState percentile, all grades99th97th
Student growthHow far the district moves children, not who enrolled60th59th
Graduation rate98.2%96%
Niche district rank3rd of 2368th of 236
SchoolDigger rank9th of 36110th of 361
State accountabilityDESE’s own summaryMeeting or exceeding targetsMeeting or exceeding targets
Spending per pupilHigher is not better — it tracks need, not results$27,831$19,932
Schools in the districtElementary and middle buildings the rating averages96
Private schools within 12 miAccredited, the fallback if the district does not fit4561
What a home costsWinchester ahead on 3 of 8
LexingtonWinchester
4BR house$2.05MT4$1.85MT4
3BR townhouse$1.35M$1.25M
2BR condo$1M$925k
3BR homeZillow’s observed median, houses and condos together — measured, not modeled like the rows above$1.28M$1.34M
5+ BR homeZillow’s top bedroom bucket — five OR MORE, so it carries the largest houses in the town. Measured, not modeled like the rows above$2.44M$2.33M
3BR rent$4,963/mo$3,843/mo
Income needed for the 4BRHousehold income at our standard assumptions$542k$482k
10-year price growthCompound, 2016–20265.3% a year4.9% a year
What you pay the townWinchester ahead on 2 of 4
LexingtonWinchester
Tax ratePer $1,000 of value — not what you pay$12.31T2$11.08T2
Est. tax bill on that 4BRRate times the town’s own median 4BR≈$25,200≈$20,500
Town spending per residentFY2025 general fund, per head$8,108$6,257
Share of budget on schools52%46%
Getting to workWinchester ahead on 3 of 3
LexingtonWinchester
Commute to BostonDoor to door at peak38 minT231 minT2
MBTA railNo MBTA railCommuter rail · ~20 min to terminal
Miles from downtown11 mi8 mi
Before kindergartenLexington ahead on 3 of 4
LexingtonWinchester
Licensed child care programsBefore kindergarten3522
Child care placesLicensed capacity, not vacancies2,0481,600
Centers vs family programsThe rest are programs in a provider’s home25 centers18 centers
Infant places in centersFamily programs report no age split413125
What the place is likeDescribes the two, does not rank them
LexingtonWinchester
Population34,45422,970
Energy6/106/10
Compact center6/107/10
Family amenities8/108/10
Culture9/107/10
Gathering places9/108/10

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.

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