Winchester may be small, but its community is very tight-knit.
The median home price in Winchester is $265,000.
The Main Street in Winchester has plenty of shops and restaurants for locals to enjoy.
Depot Road in Winchester is famous for its red bricks and being the historic train depot site.
George Rogers Clark High School is known for it's state championship athletics.

Winchester, KY

Area Guide

Avg Rent

$783

Population

19,961

Renter Mix

48% Rent

A pastoral escape in the Bluegrass Region

Rural Wooded Hiking

Located in Kentucky’s Bluegrass Region known for breeding racehorses, Winchester is a pastoral escape for nature lovers. Lush, rounded hills and abundant natural parks allow for excellent biking, hiking, and other outdoor activities. Visit the Blackfish Bison Ranch for a chance to feed buffalo, throw a tomahawk, and toss a lasso at a hay bale. You can even sample buffalo meat! Bison meat isn’t the only unique eat in town. Visit the Ale-8-One factory to sample the famous soft drink bottled in town since 1926.

Winchester invented beer cheese 75 years ago and celebrates the tasty treat through the Beer Cheese Trail tour, where you can taste five restaurants’ recipes and earn a T-shirt. The town is proud of its innovation and hosts the Beer Cheese Festival every year, the only annual beer cheese festival in the world. The cost of housing in Winchester is a bit higher than Kentucky but the scenic landscapes make it worthwhile.

Explore the City

George Rogers Clark High School is known for it's state championship athletics.

Parents can catch some shade under the huge leaf sculpture at Legacy Grove playground.

Test your skills at the skatepark in Lykins Park.

Depot Road in Winchester is famous for its red bricks and being the historic train depot site.

Homebuyers will find many bungalow and four square style homes in Winchester.

The Main Street in Winchester has plenty of shops and restaurants for locals to enjoy.

Demographics

Median Household Income

$51,344

Average: $67,584

Education

3,118

Residents Have a Degree

Job Market

9,103

Workers Employed

Age Distribution
Get a sense of this area's population profile.

Median Age

40 Years

Largest Age Group

30-39 Years

Approximately 13% of Residents

Under 20

25%

Over 65

18%

Housing Distribution

Winchester has more homeowners than renters.

Renters
48%
Non-Renters
52%

Education Distribution

Review this city's overall education levels.

Bachelor's or Higher
12%
Other Education
88%

Rent Trends

As of June 2026, the average apartment rent in Winchester, KY is $783 for one bedroom, $940 for two bedrooms, and $843 for three bedrooms. Apartment rent in Winchester has increased by 1.0% in the past year.

Property Type
Average Rent
Average Sq Ft
Apartment
$783/month
715 Sq Ft
See Rental Market Trends in Winchester, KY

Getting Around

Fairly Walkable

Walkability

40 / 100

Exceptionally Drivable

Drivability

90 / 100

Somewhat Bikeable

Bikeability

30 / 100

Schools

Rev. Henry E. Baker Sr. Interm. School

Public

Grades K-5

755 Students

Willis H Justice Elementary

Public

Grades K-5

468 Students

Shearer Elementary School

Public

Grades K-5

416 Students

Strode Station Elementary School

Public

Grades K-5

534 Students

Conkwright Elementary School

Public

Grades K-5

494 Students

Robert D Campbell Junior High School

Public

Grades 6-8

754 Students

George Rogers Clark High School

Public

Grades 9-12

1,493 Students

Points of Interest

Parks and Recreation

  • Fort Boonesborough State Park
  • Boone Station State Historic Site

Military Bases

Airports

  • Blue Grass

Top Apartments in Winchester

Houses for Rent in Winchester

Search Nearby Rentals

Methodology

† Our analysis of utilities, groceries, transportation, healthcare, home prices, and other goods and services is sourced from the Cost of Living Index, a respected benchmark published by the Council for Community and Economic Research (C2ER) that provides a thorough overview of living expenses across different regions.

Rent data is provided by CoStar Group’s Market Trend reports. As the industry leader in commercial real estate information, analytics, and news, CoStar conducts extensive research to produce and maintain a comprehensive database of commercial real estate information. We combine this data with public record to provide the most up-to-date rental information available.

Consumer goods, services, and home prices are sourced from the Cost of Living Index published by the Council for Community and Economic Research (C2ER). The data on this page is updated quarterly. It was last published in June 2026.

Demographic information comes from Neustar and combines detailed address data with U.S. Census and American Community Survey statistics to produce reliable local estimates.