The median home in Chester, Connecticut is valued at $503,324, up 12.1% year over year. Chester is part of the Hartford-East Hartford-Middletown, CT metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

Home Value$503,324

+12.1%

Prices rising — worse for buyers.

Affordability

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Income (annual)

Down Payment

$100,665 on $503,324

Example: $75,000 household income. Change it above to see your own.

Out of reach57.6% of income

Need $154,157/yr to afford.

PITI$3,597

P/I57.6%

Afford$245K

Gap-$258K

P&I $2,545Tax $902Ins $150

6.50% 30yr, 20% down, county tax + CT ins. 28% per HUD.

Home Buying Kit For Dummies (2025)Financing, negotiation, closing

Other cities in Connecticut

Compare Chester with other housing markets across Connecticut.

Darien$2.24M Greenwich$2.19M New Canaan$2.03M Westport$1.9M Weston$1.3M Wilton$1.18M Washington$998K Ridgefield$945K

Full Hartford-East Hartford-Middletown, CT analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Hartford-East Hartford-Middletown, CT metro.

View Hartford-East Hartford-Middletown, CT metro

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Chester, CT