The median home in Winchester, Kentucky is valued at $248,308, up 4.1% year over year. Typical monthly rent is $1,400, producing a price-to-rent ratio of 14.8x — below the national average of 18x. Winchester is part of the Lexington-Fayette, KY metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

See the full metro analysis: Lexington-Fayette, KY stress score, crash risk, and 12-month forecast →

Home Value$248,308

+4.1%

Rent$1,400/mo

AFFORDABILITY

Enter your income for Winchester.

Income (annual)

Down Payment

$49,662 on $248,308

Affordable — 25.6% of income

Under the 28% guideline.

PITI$1,600

P/I25.6%

Afford$272K

Room+$23K

P&I $1,256Tax $178Ins $167

Renting $200/mo cheaper ($1,400 rent)6.50% 30yr, 20% down, county tax + KY ins. 28% per HUD.

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

Other cities in Kentucky

Compare Winchester with other housing markets across Kentucky.

Prospect$595K Finchville$481K Goshen$474K Crestwood$467K River Bluff$446K Wilsonville$445K Union$444K Buckner$429K

Full Lexington-Fayette, KY analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Lexington-Fayette, KY metro.

View Lexington-Fayette, KY metro →

WINCHESTER, KY