Pittsfield, MA vs Winter Park, FL
Side-by-side comparison of housing, income, commute, safety, and quality of life.
Score Snapshot
No universal winner
Scores summarize the published model. Use the objective metric differences below and your own priorities to choose.
Pittsfield
72.6
#864 nationally
Winter Park
72.4
#900 nationally
Winter Park leads in crime level (5.6 vs 14.0). Winter Park leads in median household income ($96,563 vs $66,859). Pittsfield leads in cost of living index (107 vs 139).
Metric-by-Metric Breakdown
| Metric | Pittsfield, MA | Winter Park, FL |
|---|---|---|
| WhereAtHome Score | 72.6 (#864) | 72.4 (#900) |
| Population | 43,076 | 29,894 |
| Typical Home Value (ZHVI) | $313,325 | $469,253 |
| Median Household Income | $66,859 | $96,563 |
| Average Commute | 17.8 min | 23.1 min |
| Walk Score | 40 | 44 |
| Crime Level | 14.0 | 5.6 |
| School Rating | N/A | N/A |
| Cost of Living Index | 107 | 139 |
| Political lean County 2024 presidential margin — context only, not scored | D+39.9 | D+13.6 |
C-
72.6 Score
Pittsfield, MA
Small Massachusetts city with local appeal
Median Home
$313,325
Population
43,076
Crime
Moderate-High
Walk Score
40
Northeast
View Pittsfield, MA →
C-
72.4 Score
Winter Park, FL
Small Florida city with local appeal
Median Home
$469,253
Population
29,894
Crime
Moderate-Low
Walk Score
44
Southeast
View Winter Park, FL →
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