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Buying a home in Winchester, Kentucky

The typical owner-occupied home in Winchester is worth about $188,300, 8% below the Kentucky median of $205,600 and 43% below the national median of $332,700. Owners pay a median $1,362 a year in property taxes, about 0.72% of their home's value, close to the Kentucky rate of 0.75%. The median household earns $54,378 a year, so the median home costs 3.5 times the median income (3.2 times for Kentucky). 60% of occupied homes here are lived in by their owners, and 68% of those owners still have a mortgage.

Winchester at a glance

Winchester Kentucky U.S.
Median home value $188,300 $205,600 $332,700
Median property tax paid per year $1,362 $1,544 $3,119
Property tax as a share of value 0.72% 0.75% 0.94%
Median household income $54,378 $63,726 $80,734
Homes lived in by their owners 60% 68% 65%
Owner homes with a mortgage 68% 56% 61%
Median monthly costs, owners with a mortgage $1,292 $1,433 $1,963
Those costs as a share of the owners' income 20.4% 18.8% 21.0%
Median rent $916 $967 $1,413
Rent as a share of renters' income 31.4% 28.1% 30.6%
Median year homes were built 1972 1982 1980
Vacant homes 10.3% 10.3% 10.1%
Population 19,213 4,534,824 334,922,499

What a typical home costs per month in Winchester

At this week's average 30-year rate of 7.11%, buying the median Winchester home of $188,300 with 20% down costs about $1,205 a month, including property taxes and insurance. With an FHA loan and 3.5% down, it's about $1,518, because the loan is bigger and FHA adds mortgage insurance.

Lenders usually want housing costs under about 28% of gross income, which means an income of roughly $51,634 for the 20%-down payment. That payment is 27% of the median Winchester household income of $54,378; at that income and 20% down, the 28% guideline points to a home of about $198,000.

The median rent here is $916 a month, so owning the median home costs about $289 a month more than renting, before you count the equity you build and any tax benefits.

20% down, 30-year conventional loan
Down payment$37,660
Loan amount$150,640
Principal and interest$1,013
Property taxes (0.72% a year)$113
Homeowners insurance (our estimate, 0.5% a year)$78
PMI$0
Total per month$1,205

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3.5% down, 30-year FHA loan
Down payment$6,590
Loan amount$184,889
Principal and interest$1,244
Property taxes (0.72% a year)$113
Homeowners insurance (our estimate, 0.5% a year)$78
FHA mortgage insurance$83
Total per month$1,518

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Questions about home buying in Winchester

What is the median home value in Winchester?

About $188,300 for owner-occupied homes, according to the Census Bureau's 2020–2024 American Community Survey.

How much are property taxes in Winchester?

Homeowners pay a median $1,362 a year, which is about 0.72% of the median home value. Your bill depends on your home's assessed value and local rates.

What income do you need to buy a home in Winchester?

For the median home with 20% down at 7.11%, the payment is about $1,205 a month. Keeping that under 28% of gross income takes about $51,634 a year.

More about Winchester

Sources: U.S. Census Bureau, American Community Survey 2020–2024 5-year estimates; Freddie Mac Primary Mortgage Market Survey, week of November 12, 2026. Estimates for small places have wide margins of error. About our data