The median home in Middlebury, Connecticut is valued at $530,429, up 3.8% year over year. Middlebury is part of the New Haven-Milford, CT metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

Home Value$530,429

+3.8%

Prices rising — worse for buyers.

Affordability

Enter your income for Middlebury.

Income (annual)

Down Payment

$106,086 on $530,429

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

Out of reach60.5% of income

Need $162,086/yr to afford.

PITI$3,782

P/I60.5%

Afford$245K

Gap-$285K

P&I $2,682Tax $950Ins $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 Middlebury 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 New Haven-Milford, CT analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the New Haven-Milford, CT metro.

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Middlebury, CT