Winchester homebuyers are working with a $1,150,000 median price point, 174% above the national figure. Against the $205,000 median household income in the area, that's a 5.6x multiple.
Winchester's 1% property tax rate runs below the 1.1% national average. That's $958/month on the median home here, not a rounding error against the mortgage payment.
Massachusetts levies a state income tax on top of the $7,432/month this mortgage runs. Model your real after-tax take-home before deciding how much payment you can carry.
Winchester's cost of living index is 180, above the 100 national baseline. That's on top of the housing numbers above, not instead of them.
Winchester's median home price runs 53% higher than nearby Boston: $750,000 there versus $1,150,000 here.