7

Winchester, KY Houses for Rent

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  • 721 Wayland Dr, Winchester, KY 40391
    721 Wayland Dr, Winchester, KY 40391
    721 Wayland Dr, Winchester, KY 40391
    /39

    $2,595 Per Month

    • 4 Beds
    • 3 Baths
    • 2,160 Sq Ft
    • House for Rent

    721 Wayland Dr, Winchester, KY 40391

    Welcome home to the perfect blend of peaceful country living and modern convenience. Located in Winchester, Kentucky, this beautifully remodeled 4-bedroom, 3 full-bath home offers an easy commute to Hamburg and all the shopping, dining, and entertainment Lexington has to offer. Step inside to discover a stunning kitchen designed to be the heart of the home—perfect for gathering with family and

    S Ann Wesley Assurance Realty & Property Management

    721 Wayland Dr, Winchester, KY 40391
  • 101 E Lexington Ave, Winchester, KY 40391
    101 E Lexington Ave, Winchester, KY 40391
    /2

    $1,350 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
  • 17 Apache Trail, Winchester, KY 40391
    17 Apache Trail, Winchester, KY 40391
    17 Apache Trail, Winchester, KY 40391
    /4

    $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
  • 101 Bellbrook Ln, Winchester, KY 40391
    101 Bellbrook Ln, Winchester, KY 40391
    101 Bellbrook Ln, Winchester, KY 40391
    /14

    $1,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,612 Sq Ft
    • Now Pre Leasing 3 Bedroom 2 Bath Luxury Ranch Home In Winchester Ky!

    101 Bellbrook Ln, Winchester, KY 40391

    Welcome to a place where luxury, comfort, and convenience come together. 101 Bellbrook is a stunning 3-bedroom, 2-full-bath ranch-style home thoughtfully designed for those looking for more than just a place to live it’s a place to truly feel at home. Step inside and discover an open-concept floor plan with spacious living areas, elegant finishes, stainless steel appliances, and a

    101 Bellbrook Ln, Winchester, KY 40391
  • 222 Buffalo Trace, Winchester, KY 40391
    222 Buffalo Trace, Winchester, KY 40391
    222 Buffalo Trace, 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
  • 136 Georgia St, Winchester, KY 40391
    136 Georgia St, Winchester, KY 40391
    136 Georgia St, Winchester, KY 40391
    /12

    $1,300 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
  • 356 Oxford Dr, Winchester, KY 40391
    356 Oxford Dr, Winchester, KY 40391
    356 Oxford Dr, Winchester, KY 40391
    /18

    $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
Kentucky Clark County

Houses for Rent in Winchester, KY

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 $1,495 per month, though prices vary by neighborhood, size, and property type. As of July 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 $53,880 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 $1,347 per month in Winchester, KY, renters typically need to show $4,041 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 16.3, 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 Boone Creek East, Gleneagles, Hamburg, Tates Creek and River Park, each with its own character and price range.

Rental Home Trends in Winchester, KY

There are currently 7 single-family homes available for rent in Winchester, KY. The median rent is $1,495 per month, with 3-bedroom houses renting at $1,495 and 4-bedroom houses at $2,595.

Rental Home Trends

Number of Houses for Rent
7
Median Single Family Home Rent
$1,495
Median 3 Bedroom Single Family Home Rent
$1,495
Median 4 Bedroom Single Family Home Rent
$2,595
How to Rent a Home

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