Compare towns

Upton vs Dedham vs Winchester

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

What stands out worked out from the figures below

Upton has the most affordable homes ($577k median).
Dedham has the most renters (26.6% rent).
Winchester has the most expensive homes ($1215k median).

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.

MeasureUptonDedhamWinchester
People
Population
8,189Lowest
25,237Highest
23,406
Growth since 20102010 → 2020 census
+6.1%
MA: +7.4%
+2.6%Lowest
MA: +7.4%
+7.5%Highest
MA: +7.4%
Median age
46.4±4.8Highest
16% above MA
44.6±1.6
12% above MA
42.5±1.9Lowest
6% above MA
Upton and Dedham are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
23.2%±4.5
MA: 19.4%
18.6%±1.9Lowest
MA: 19.4%
27.6%±2.3Highest
MA: 19.4%
Winchester and Upton are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
20.7%±4.9
MA: 17.9%
21.9%±2Highest
MA: 17.9%
18%±2Lowest
MA: 17.9%
Dedham and Upton are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
53.5%Lowest
MA: 47.3%
55%
MA: 47.3%
79.5%Highest
MA: 47.3%
Enrolled in collegeshare of residents
2.4%±1.3Lowest
MA: 7.9%
5.6%±1Highest
MA: 7.9%
4.9%±1.3
MA: 7.9%
Dedham and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$155,508±$33k
50% above MA
$128,955±$10kLowest
24% above MA
$230,198±$21kHighest
121% above MA
Home valuemedian, owner-occupied
$576,700±$41kLowest
about the MA average
$661,800±$16k
18% above MA
$1,215,200±$39kHighest
116% above MA
Rentmedian gross, monthly
$948±$599Lowest
46% below MA
$2,042±$182
16% above MA
$2,279±$481Highest
29% above MA
Winchester and Dedham are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$8,376
40% above MA
$7,918Lowest
32% above MA
$10,000+Highest
at least 67% above MA
Renters paying 30%+of income on rent
52.8%±31
MA: 51.8%
56.4%±10Highest
MA: 51.8%
39.3%±13.3Lowest
MA: 51.8%
Dedham and Upton are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
3.2%Lowest
MA: 10%
5.6%Highest
MA: 10%
4.7%
MA: 10%
Housing
Homeownersof occupied homes
86.7%Highest
MA: 62.5%
73.4%Lowest
MA: 62.5%
81.7%
MA: 62.5%
Typical home builtmedian year
1981Highest
17 yrs newer than MA
1956
8 yrs older than MA
1954Lowest
10 yrs older than MA
Getting to work
Average commuteone way
35 minHighest
22% above MA
29 minLowest
about the MA average
31 min
8% above MA
Work from home
22.8%±5.3
MA: 18.6%
20%±2.7Lowest
MA: 18.6%
33.8%±3Highest
MA: 18.6%
Schools
Public school scoresrank in state, math + reading #46 of 282 in MA #119 of 282 in MA #11 of 282 in MA
School district Blackstone Valley Regional Vocational Technical · Mendon-Upton Dedham Winchester
High school in town Blackstone Valley Dedham High Winchester High School
Students per teacherat that high school
11.2
10.4Lowest
14.8Highest
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.