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Winchester, KY Homes for Rent

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    Call for Price

    • 1 - 3 Beds

    300 C G Stephenson Dr, Winchester, KY 40391

    This community is open by appt only. Office hours are 9am to 12pm and 1pm to 4pm. Please call to schedule your appt!Cambridge Square is a community with beautifully maintained grounds, offering one, two and three bedroom apartment homes with some one bedroom homes reserved for the elderly/dis-abled, all rent based on income. We are located in quiet Winchester, Kentucky, with easy

    Cambridge Square Apartments - Income Based

    300 C G Stephenson Dr, Winchester, KY 40391
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    Starting at $800 Per Month

    • 1 - 3 Beds

    260 Oxford Dr, Winchester, KY 40391

    The Summit located in Winchester; KY is just minutes away from major employers. We are just a short drive from Lexington, KY. Come see our pet friendly community with lots of green space. We have spacious one-, two-, and three-bedroom apartment homes with caring on-site management. Our homes feature walk-in closets, new Laminate Vinyl Plank Flooring, fully equipped kitchens, washer/dryer

    Summit Apartments

    260 Oxford Dr, Winchester, KY 40391
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    Call for Price

    • 1 - 3 Beds

    900 Westwood Dr, Winchester, KY 40391

    Pick up your application for our WAIT LIST at the office door! Westwood is a charming property in a great location in Winchester, Kentucky with rents based on income. Spacious one, two and three bedroom apartments for rent, each featuring a fully equipped kitchen, your choice of a patio or balcony, and they are wired for cable. Fun in the sun is just a outside your door at our playground, or

    Westwood Apartments - Income Based

    900 Westwood Dr, Winchester, KY 40391
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    Starting at $814 Per Month

    • Studio - 1 Bed

    27 E Washington St, Winchester, KY 40391

    *One Month Free Rent!* All Utilities Included! Nice Studio Apt Near Downtown Winchester!Marketing DescriptionStudio Apartment Available at Studio 29 Apartments, Winchester, KY! One Bath; Only 5 Minutes from Downtown! Off-Street Parking, Small Pets Ok; All Utilities Included! Kitchen includes a Stove, Refrigerator, and Microwave; Non-smoking.Conveniently located near Shopping, Grocery

    Studio 28

    27 E Washington St, Winchester, KY 40391
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    Starting at $1,049 Per Month

    • 2 - 3 Beds

    510 College St, Winchester, KY 40391

    Lovely 2 Bedroom and One Bath Apartment at the Lofts of Winchester, located at 508 College Street, Winchester, KY! Near Downtown, Shopping, Restaurants, Hwy 64 and Hwy 60. Off-street Parking; Small Pets Ok! Beautiful Updated Flooring and Stainless Steel Appliances. Kitchen includes Stove and Refrigerator. Central Heat & AC.Local Schools are: Willis H. Justice Elementary; Robert D.

    The Lofts at Winchester

    510 College St, Winchester, KY 40391
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    $1,495 Per Month

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    17 Apache Trail, Winchester, KY 40391

    AVAILABLE SEPTEMBER 1! Check out this 3 bedroom, 2 full bathroom rental located just minutes from Downtown Winchester with convenient access to Lexington. This home features a functional layout, a spacious kitchen with stainless steel appliances and updated backsplash, comfortable living space, and a large fenced-in backyard with a storage building. Tenant is responsible for electric, water,

    Austin Polley The Polley Group

    17 Apache Trail, Winchester, KY 40391
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    $1,150 Per Month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    1028 W Lexington Ave Unit 4, Winchester, KY 40391

    Welcome to 1028 W Lexington Ave, a cozy and well-maintained 1-bedroom, 1-bathroom apartment offering comfortable and affordable living in the heart of Winchester, KY. With a spacious living area, a functional kitchen, and a thoughtfully designed layout, this home is perfect for students, working professionals, or anyone looking to downsize.Property Features:1 Bedroom1 Full

    1028 W Lexington Ave Unit 4, Winchester, KY 40391
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    $1,750 Per Month

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    135 Winn Ave Unit A, Winchester, KY 40391

    Welcome to this beautifully renovated 3-bedroom, 2-bathroom home, offering the perfect combination of modern style and everyday comfort. The bright and spacious living area flows seamlessly into a stylish, updated kitchen, creating an inviting space for relaxing or entertaining. Thoughtfully designed with contemporary finishes and a functional layout, this move-in-ready home is ideal for

    135 Winn Ave Unit A, Winchester, KY 40391
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    $1,475 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    101 E Lexington Ave, Winchester, KY 40391

    Make yourself at home in this charming 2-bedroom, 1-bathroom house, offering a spacious yet practical layout designed for comfortable everyday living. With bright living spaces, a functional kitchen, and two well-sized bedrooms, this home is ideal for small families, roommates, or anyone looking for extra space.This well-maintained home provides a welcoming atmosphere and the convenience

    101 E Lexington Ave, Winchester, KY 40391
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    $1,550 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    202 S Maple St Unit C, Winchester, KY 40391

    Bright and comfortable 2-bedroom, 1-bathroom upstairs unit with all bills paid! Conveniently located at the corner of Hickman and Maple, directly across from Walgreens and Speedway gas station.Move-In Special:Free application50% off on your first month’s rent if you apply within 24 hourSecurity Deposit: $1,550.00Contact us today to schedule a showing or

    202 S Maple St Unit C, Winchester, KY 40391
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    $955 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    265 S Highland St Unit 1, Winchester, KY 40391

    Welcome to our charming apartment in Winchester, KY! This apartment boasts beautiful wood floors throughout, creating a warm and inviting atmosphere. Enjoy the convenience of a large yard and an in-unit laundry room. Located close to downtown and shopping, you'll have easy access to all the amenities Winchester has to offer. Don't miss out on the opportunity to call this unique apartment

    265 S Highland St Unit 1, Winchester, KY 40391
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    $1,395 Per Month

    • 3 Beds
    • 2 Baths
    • 975 Sq Ft
    • House for Rent

    222 Buffalo Trace, Winchester, KY 40391

    ESTIMATED TOTAL MONTHLY LEASING PRICE: $1490.99Base Rent: $1395.00*Resident Benefits Package: Starts at $30.99*Resident Internet Amenity: $65.00This three-bedroom home is perfectly situated in the desirable Buffalo Trace neighborhood of downtown Winchester, offering both convenience and comfort in a prime location. The property features luxury vinyl plank flooring throughout,

    222 Buffalo Trace, Winchester, KY 40391
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    $1,375 Per Month

    • 3 Beds
    • 1 Bath
    • 1,123 Sq Ft
    • 3-Bed 1-Bath House

    136 Georgia St, Winchester, KY 40391

    136 Georgia Street in Winchester, KY is a newly renovated 3-bedroom, 1-bath home that blends updated finishes with classic porch appeal. The property offers both a front porch and back porch for outdoor space and includes washer/dryer hook-ups for laundry convenience. Thoughtfully refreshed interiors provide a comfortable living environment in a convenient location.Rental

    136 Georgia St, Winchester, KY 40391
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    $799 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    7 Calloway St Unit 7 Calloway St #1, Winchester, KY 40391

    7 Calloway St Unit 7 Calloway St #1, Winchester, KY 40391
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    $1,125 Per Month

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Lovely Townhouse in Winchester! All Electric, Off-Street Parking, W/D Hookups, Small Pets Ok!

    356 Oxford Dr, Winchester, KY 40391

    NOW AVAILABLE! Attractive Townhouse at 356 OXFORD DRIVE, WINCHESTER! Eat-In Kitchen includes Stove, Refrigerator, and Dishwasher; Washer/Dryer hookups; Off-Street Parking with 2 parking spaces; Ceiling Fans; All Electric! Beautiful Wood-Look LVT Flooring; Lots of Closet Space.Located within an HOA in the Orchard Hill Subdivision. Private Patio. Small Pets Ok! (Cats, and Dogs 35 lbs and

    356 Oxford Dr, Winchester, KY 40391
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    $955 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    265 S Highland St Unit 4, Winchester, KY 40391

    Welcome to our charming apartment in Winchester, KY! This apartment boasts beautiful wood floors throughout, creating a warm and inviting atmosphere. Enjoy the convenience of a large yard and an in-unit laundry room. Located close to downtown and shopping, you'll have easy access to all the amenities Winchester has to offer. Don't miss out on the opportunity to call this unique apartment

    265 S Highland St Unit 4, Winchester, KY 40391
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    $1,295 Per Month

    • 2 Beds
    • 1.5 Baths
    • 2-Bed, 1.5-Bath Townhome with large kitche!

    1434 Westwood Dr, Winchester, KY 40391

    Prime Winchester Location | 1,150 Sq. Ft.2 HUGE Bedrooms – Plenty of space for comfort & storage1.5 Baths – Perfect for convenienceWasher/Dryer Hookups – In-unit laundry convenienceRent: $1,295/month-1st month due at lease signingDeposit: $1,295-due by move inTenant Pays UtilitiesRental Requirements:Income: 3x rent (take-home pay, including unearned

    1434 Westwood Dr, Winchester, KY 40391

Why Live in Winchester

Winchester, KY, the largest city in Clark County, is known for its vibrant community and unique local flavors, including the birthplace of beer cheese and Ale-8-One soda. Main Street is the hub for dining, featuring popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail, which includes around 15 restaurants with signature beer cheese recipes. The city offers practical amenities with nearby grocery stores like Kroger and Walmart Supercenter, and retail options such as TJ Maxx and Lowe’s. Housing in Winchester includes Victorian-era inspired homes and newer subdivisions, with properties often featuring gravel driveways and spacious lawns suitable for gardens. Clark County Public Schools provide strong academic programs, including AP and dual enrollment courses at George Rogers Clark High School. For outdoor activities, residents enjoy Legacy Grove Park, College Park, and Lykins Park, which offer facilities for basketball, tennis, hiking, and disc golf. Winchester hosts annual events like the Beer Cheese Festival and the Daniel Boone Pioneer Festival, attracting visitors with arts, crafts, and food. The Bluegrass Heritage Museum showcases the history of Central Kentucky. Commuting is convenient with Winchester located 16 miles from Lexington and 20 miles from Richmond. The city has a cooperative community spirit, bolstered by investments from younger residents and a thriving local economy.

Frequently Asked Questions

How much does it cost to rent a home in Winchester, KY?
The median rent for a home in Winchester, KY is $1,335 per month, though prices vary by neighborhood, size, and property type. As of July 2026, condos tend to be the most affordable option while single-family homes and townhouses are currently more expensive.
How much do you need to make to afford rent in Winchester, KY?
To comfortably afford the median rent in Winchester, KY, a household needs to earn roughly $53,400 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,335 per month in Winchester, KY, renters typically need to show $4,005 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Winchester, KY?
In Winchester, KY, the price-to-rent ratio is 16.4, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Winchester, KY are best for renting a home?
The best neighborhood for renting in Winchester, KY depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include Boone Creek East, Gleneagles, Andover Forest, Woodhill and Hamburg, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
17
Median Rent
$1,335
Median Single Family Home Rent
$1,475
Median Townhouse Rent
$1,475
Median Condo Rent
$1,053
How to Rent a Home