Chesterfield, MO 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.
Chesterfield
73.2
#769 nationally
Winter Park
72.4
#900 nationally
Winter Park leads in walk score (44 vs 19). Chesterfield leads in crime level (2.6 vs 5.6). Chesterfield leads in median household income ($137,052 vs $96,563).
Metric-by-Metric Breakdown
| Metric | Chesterfield, MO | Winter Park, FL |
|---|---|---|
| WhereAtHome Score | 73.2 (#769) | 72.4 (#900) |
| Population | 49,166 | 29,894 |
| Typical Home Value (ZHVI) | $581,834 | $469,253 |
| Median Household Income | $137,052 | $96,563 |
| Average Commute | 22.2 min | 23.1 min |
| Walk Score | 19 | 44 |
| Crime Level | 2.6 | 5.6 |
| School Rating | N/A | N/A |
| Cost of Living Index | 122 | 139 |
| Political lean County 2024 presidential margin — context only, not scored | D+23.4 | D+13.6 |
C
73.2 Score
Chesterfield, MO
Small Missouri city with local appeal
Median Home
$581,834
Population
49,166
Crime
Low
Walk Score
19
Midwest
View Chesterfield, MO →
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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