8

Winchester, KY Houses for Rent

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  • /6

    $1,300

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    112 Old Bottom Rd, Winchester, KY 40391

    Great location! 3 bed 1 bath updated home with a huge backyard. Tenants pays water/sewer, electric and gas. Small dog accepted with a $300 pet fee and $25/month, Dog breed restrictions, Cats are not permitted.

    112 Old Bottom Rd, Winchester, KY 40391
  • /29

    $1,995

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 1,935 Sq Ft
    • House for Rent

    203 Inverness Ln, Winchester, KY 40391

    Spacious 3 Bedroom/2.5 Bath home for rent in one of the most sought after areas of Winchester!This beautiful home includes nearly 2,000 sq/ft of living space, real hardwood floors on the main level, a large kitchen, designated laundry room, oversized bedrooms, large master closet, backyard with a firepit, and a large 2 car garage!-Available 11/01/2026-Price does not include

    203 Inverness Ln, Winchester, KY 40391
  • /47

    $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
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    $1,795 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,879 Sq Ft
    • House for Rent

    230 Prescott Ln, Winchester, KY 40391

    Located in a desirable neighborhood, this spacious house offers 3 bedrooms and 2.5 bathrooms, providing ample space for you and your loved ones. The backyard is complete with a privacy fence, ensuring a serene and secluded atmosphere for outdoor activities. Step out onto the deck and enjoy the fresh air, and enjoy gatherings with friends and family. With a 2 car oversized attached garage, you'll

    230 Prescott Ln, Winchester, KY 40391
  • /17

    $2,500 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
  • /3

    $1,275 Per Month

    • 3 Beds
    • 1 Bath
    • 1,253 Sq Ft
    • House for Rent

    206 E Hickman St, Winchester, KY 40391

    Very cute ranch home just off of Main Street! Three large bedrooms, vaulted ceilings in living room and master bedroom. Updated eat-in kitchen. *Updated photos coming soon! This is a NO SMOKING home. Smoking is not permitted inside the house, garage, or any other structure that is considered a part of the property. Type: Single Family. Security Deposit: One Month's Rent

    206 E Hickman St, Winchester, KY 40391
  • /22

    $1,395 Per Month

    • 3 Beds
    • 1 Bath
    • 805 Sq Ft
    • House for Rent

    150 Cook Ave, Winchester, KY 40391

    150 Cook Ave, Winchester, KY 40391
  • /2

    $1,400 Per Month

    • 3 Beds
    • 2 Baths
    • 1,482 Sq Ft
    • House for Rent

    110 Pepperwood Ct, Winchester, KY 40391

    Enjoy room to spread out in this beautiful two-story townhouse in Winchester, Kentucky. The spacious layout gives you plenty of flexibility to make the home your own, while the fantastic back deck creates the perfect spot to unwind, enjoy a quiet evening, or spend time outdoors. Comfortable, inviting, and full of space, this townhouse is ready to welcome you home. Email or call us today for

    110 Pepperwood Ct, 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 $1,645 per month, though prices vary by neighborhood, size, and property type. As of September 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 $55,800 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 $1,395 per month in Winchester, KY, renters typically need to show $4,185 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 15.7, 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, Eastland Parkway and Southeastern Hills, each with its own character and price range.

Rental Home Trends

Number of Houses for Rent
8
Median Single Family Home Rent
$1,645
Median 3 Bedroom Single Family Home Rent
$1,445
Median 4 Bedroom Single Family Home Rent
$2,548
How to Rent a Home