6

Winchester, KY Houses for Rent

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  • /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

    $1,795 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
  • /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
  • /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
  • /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
  • /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

Frequently Asked Questions

How much does it cost to rent a single-family home in Winchester, KY?
The median rent for a single-family home in Winchester, KY is $1,775 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 single-family 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 single-family home include Gleneagles, Boone Creek East, Hamburg, Woodhill and Kenwick, each with its own character and price range.

Rental Home Trends in Winchester, KY

Rental Home Trends

Number of Houses for Rent
6
Median Single Family Home Rent
$1,775
Median 3 Bedroom Single Family Home Rent
$1,775
Median 4 Bedroom Single Family Home Rent
$2,900
How to Rent a Home