Compare towns

Middleton vs Pinehurst vs Winchester

Cost, people, housing, commute and schools, side by side, each benchmarked against Massachusetts.

What stands out worked out from the figures below

Middleton has grown the fastest since 2010 (+8.8%).
Pinehurst has the most affordable homes ($624k median).
Winchester has the most people working from home (33.8%).

What matters to you?

Pick a few. We’ll pull those rows to the top and mark which town comes out ahead on each. There’s no overall score: what matters is up to you.

MeasureMiddletonPinehurstWinchester
People
Population
9,816
6,845Lowest
23,406Highest
Growth since 20102010 → 2020 census
+8.8%Highest
MA: +7.4%
+3%Lowest
MA: +7.4%
+7.5%
MA: +7.4%
Median age
43.1±2Highest
8% above MA
42.6±2
7% above MA
42.5±1.9Lowest
6% above MA
Middleton and Pinehurst are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
17.2%±3Lowest
MA: 19.4%
19.8%±4.1
MA: 19.4%
27.6%±2.3Highest
MA: 19.4%
Age 65+
18.1%±2.9
MA: 17.9%
21.1%±3.2Highest
MA: 17.9%
18%±2Lowest
MA: 17.9%
Pinehurst and Middleton are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
41.7%
MA: 47.3%
34.2%Lowest
MA: 47.3%
79.5%Highest
MA: 47.3%
Enrolled in collegeshare of residents
3.9%±1.4Lowest
MA: 7.9%
5.5%±1.8Highest
MA: 7.9%
4.9%±1.3
MA: 7.9%
Pinehurst and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$167,402±$29k
61% above MA
$146,250±$27kLowest
41% above MA
$230,198±$21kHighest
121% above MA
Home valuemedian, owner-occupied
$742,700±$48k
32% above MA
$623,800±$22kLowest
11% above MA
$1,215,200±$39kHighest
116% above MA
Rentmedian gross, monthly
$1,407±$284Lowest
20% below MA
$1,946±$1k
10% above MA
$2,279±$481Highest
29% above MA
Winchester and Pinehurst are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$8,785
47% above MA
$6,316Lowest
5% above MA
$10,000+Highest
at least 67% above MA
Renters paying 30%+of income on rent
25.7%±25.3Lowest
MA: 51.8%
32%±58.1
MA: 51.8%
39.3%±13.3Highest
MA: 51.8%
Winchester and Pinehurst are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
3.4%
MA: 10%
2.9%Lowest
MA: 10%
4.7%Highest
MA: 10%
Housing
Homeownersof occupied homes
92.7%
MA: 62.5%
97.4%Highest
MA: 62.5%
81.7%Lowest
MA: 62.5%
Typical home builtmedian year
1986Highest
22 yrs newer than MA
1972
8 yrs newer than MA
1954Lowest
10 yrs older than MA
Getting to work
Average commuteone way
30 min
3% above MA
27 minLowest
7% below MA
31 minHighest
8% above MA
Work from home
12.5%±3.4Lowest
MA: 18.6%
13.1%±3.2
MA: 18.6%
33.8%±3Highest
MA: 18.6%
Schools
Public school scoresrank in state, math + reading #71 of 282 in MA — #11 of 282 in MA
School district Middleton — Winchester
High school in town None in town — Winchester High School
Students per teacherat that high school — —
14.8
On TownTapestry
Old photos in History None yet None yet None yet

MA average · Sources: U.S. Census Bureau, American Community Survey 5-year estimates 2020–2024; 2010 & 2020 decennial census; NCES Common Core of Data. “±” is the Census margin of error. Property tax is top-coded by the Census at $10,000+. School rank compares math and reading proficiency against the state average.