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Winchester, KY Homes for Rent

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  • /35

    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

    (859) 577-9164

    260 Oxford Dr, Winchester, KY 40391
  • /3

    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

    (859) 249-8752

    27 E Washington St, Winchester, KY 40391
  • /3

    Starting at $1,049 Per Month

    • 2 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

    (859) 249-8853

    510 College St, Winchester, KY 40391
  • /5

    $996 Per Month

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

    362 S Main St Unit A, Winchester, KY 40391

    Property Id: 2574447Large 1 bedroom, i bath newly painted apartment. Close to shopping, gym and local grocery. Resevved off street parking, in house laundry.

    (859) 577-7730

    362 S Main St Unit A, Winchester, KY 40391
  • /17

    $2,900 Per Month

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • House for Rent

    104 Colby Hills Dr, Winchester, KY 40391

    Garry Milton Milton and Associates Real Estate

    104 Colby Hills Dr, Winchester, KY 40391
  • /2

    $1,395 Per Month

    • 2 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Condo for Rent

    204 S Maple St Unit 204 S Maple, Winchester, KY 40391

    This charming 2-bedroom, 1-bathroom apartment features a comfortable living room and a functional kitchen. Rent includes the municipal water bill, while tenants are responsible for gas and electricity. Perfect for anyone seeking an affordable, move-in ready home with essential amenities.

    204 S Maple St Unit 204 S Maple, Winchester, KY 40391
  • /49

    $1,400 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,202 Sq Ft
    • House for Rent

    1494 Amster Grove Rd, Winchester, KY 40391

    Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back

    Libby VanMeter Marshall Lane Real Estate - Lexington

    1494 Amster Grove Rd, Winchester, KY 40391
  • /6

    $1,995 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 located in the heart of Winchester, KY.This home features a spacious living area, a functional kitchen, and all the essentials needed for comfortable everyday living. Ideal for students, professionals, or anyone looking to downsize, this apartment offers the perfect balance of comfort and

    1028 W Lexington Ave Unit 4, Winchester, KY 40391
  • /2

    $1,800 Per Month

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

    135 Winn Ave Unit A, Winchester, KY 40391

    Step into this beautifully renovated 3-bedroom, 2-bathroom home featuring a bright and open living area and a modern kitchen on the ground floor. Designed for comfort and style, this residence offers contemporary finishes, spacious layouts, and all the amenities you need for modern living. Perfect for families or anyone seeking a move-in ready home with a fresh, modern feel.

    135 Winn Ave Unit A, Winchester, KY 40391
  • /2

    $1,795 Per Month

    • 3 Beds
    • 1 Bath
    • 1,974 Sq Ft
    • House for Rent

    136 Alabama St, Winchester, KY 40391

    Welcome home to this spacious 3-bedroom, 1-bath residence offering the perfect combination of comfort and convenience. With generous living space, well-sized bedrooms, and a functional layout, this home is ideal for families, roommates, or anyone looking for extra room to spread out.Enjoy comfortable living in a home designed to meet your everyday needs. Contact us today for more

    136 Alabama St, Winchester, KY 40391
  • /20

    $879 Per Month

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

    18 Calloway St Unit 4, Winchester, KY 40391

    Available May 26,2026! – Recently Renovated Winchester Apartment!Welcome to your next home in the heart of Winchester! This beautifully updated 1-bedroom, 1-bath apartment is nestled just off Lexington Avenue and Bypass Road close to shopping, dining, and just minutes from downtown Winchester.At Bluegrass Rental Management, we strive to provide an experience that is cost-effective

    18 Calloway St Unit 4, Winchester, KY 40391
  • /13

    $975 Per Month

    • 3 Beds
    • 1.5 Baths
    • 3 Bedroom 1.5 Bath Mobile Home. Please read Description!

    400 Wexford Dr, Winchester, KY 40391

    Take a look at this mobile home with several options! Rent the home only for $975/month, rent the garage only for $550/month or rent the home and garage together for $1350. Perfect if extra garage space is something you need. The home features 3 bedrooms and 1.5 baths with washer & dryer included! The two car garage has an extra space in the back, already set up with woodworking tables!

    400 Wexford Dr, Winchester, KY 40391
  • /20

    $1,450 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,255 Sq Ft
    • Newly Renovated 3-Bed, 1.5-Bath Townhome with Garage!

    1419 Westwood Dr, Winchester, KY 40391

    Granite in the Kitchen | 1,255 Sq. Ft.3 Bedrooms – Plenty of space for comfort & storage2.5 Baths – Primary Bedroom Bathroom and Jack-and Jill bathroom between the other two bedrooms! So each bedroom has a personal entrance to a bathroom!1-Car Garage – Private parking & extra storageWasher/Dryer Hookups – In-unit laundry convenienceRent: $1,450/month-1st month due at lease

    1419 Westwood Dr, Winchester, KY 40391
  • /8

    $1,015 Per Month

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • 151/153 WPI

    151-153 Westside Dr Unit 151 Westside Drive, Winchester, KY 40391

    151-153 Westside Dr Unit 151 Westside Drive, Winchester, KY 40391
  • /14

    $1,549 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,670 Sq Ft
    • House for Rent

    308 Graves Dr, Winchester, KY 40391

    Available May 20, 2026 – Recently Renovated Winchester Home!Welcome to your next home in the heart of Winchester! This beautifully updated 3-bedroom, 1.5-bath single-family residence is nestled just off Colby Rd and W Lexington Ave- across the street from Wiseman Park and close to downtown!At Bluegrass Rental Management, we strive to provide an experience that is cost-effective

    308 Graves Dr, Winchester, KY 40391
  • /14

    $995 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
  • /18

    $1,995 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,830 Sq Ft
    • Elevated Living Starts Here Now Pre-Leasing in Winchester, KY

    102 Bellbrook Ln, Winchester, KY 40391

    Now Pre-Leasing in Winchester, KYDiscover luxury two-story living in this brand-new home community. These beautifully designed homes offer 3 bedrooms, 2.5 bathrooms, and an attached two-car garage, blending comfort, style, and convenience. Each residence features modern luxury finishes and spacious layouts perfect for today’s lifestyle.Enjoy resort-style community amenities,

    102 Bellbrook Ln, Winchester, KY 40391
  • /2

    $1,125 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,150 Sq Ft
    • 292/294 April way

    292-294 April Way Unit 292 april way, Winchester, KY 40391

    292-294 April Way Unit 292 april way, 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 $1,295 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while townhouses and single-family homes 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 $51,800 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 $1,295 per month in Winchester, KY, renters typically need to show $3,885 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 16.7, 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 Becknerville, Gleneagles, Andover Forest, Boone Creek East and Woodhill, each with its own character and price range.

Rental Trends in Winchester, KY

Rental Home Trends

Number of Homes for Rent
18
Median Rent
$1,295
Median Single Family Home Rent
$1,775
Median Townhouse Rent
$1,463
Median Condo Rent
$1,225
How to Rent a Home