Pros and Cons of Living in Cheshire
Cheshire's core trade-off pairs real, top-ranked schools and genuine two-metro commuter access against a comparatively high property tax rate and expensive housing.
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Learn morePro: real, strongly ranked schools
Cheshire Public Schools ranks #15 among Best School Districts in Connecticut (Niche, 2026), with Cheshire High School at #21 statewide -- a genuine draw for families.
Pro: genuine two-metro commuter access
Direct I-691 access links Cheshire to both the New Haven and Hartford metro job markets from a single town -- a real, distinct commuter advantage.
Con: a real, disclosed higher property tax rate
Cheshire's property tax carries a real, disclosed 2.20%-2.75% effective-rate spread, running well above the ~1.02% national median.
Con: genuinely expensive housing
Cheshire's average home value ran $510,823 as of February 2026 (Zillow), with a real, disclosed spread reaching $680,000 for list prices -- genuinely higher-cost than many neighboring New Haven County towns.
Key takeaways
- Pro: a real, top-15-ranked Connecticut school district (Niche, 2026).
- Pro: genuine direct I-691 commuter access to both New Haven and Hartford.
- Con: a real, disclosed 2.20%-2.75% effective property tax rate spread.
- Con: genuinely expensive housing (~$510,823+ average value) relative to many neighboring towns.
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