5

Winchester, KY Condos for Rent

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    $1,705 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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    $1,550 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
  • /13

    $875 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    1137 Dale Dr Unit 1, Winchester, KY 40391

    Winchester! We have another highly desirable Dale Drive townhome ready to move in now! 2 bedroom, 1.5 bath with washer/dryer hookup and private off street parking. Back deck over looks a yard and treeline! Vaulted ceilings in the main floor with skylight! These always go within a few days! Apply now before it's too late. Pets welcome with additional fees, some breed restrictions apply.

    1137 Dale Dr Unit 1, 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

    Bright One Bedroom Apartment with character and all utilities included. This is a basement apartment but is very bright and light with new cabinets, counters, bathtub, vanity and more! All utilities included Weekly or Monthly payment options available. Apply online at www.360mgt.group today. Approved lease applications are required before a showing is scheduled.

    7 Calloway St Unit 7 Calloway St #1, Winchester, KY 40391
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    $1,155 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • 324/326 Colby Ridge Blvd.

    324-326 Colby Ridge Blvd Unit 326 Colby Ridge, Winchester, KY 40391

    Welcome home to a spacious 2BD/1.5BA townhome with the added bonus of your own garage! Located just behind Walmart, you’re moments from the interstate, Boonesboro Road, downtown Winchester, shopping, dining, and more. With plenty of room to settle in and a location that keeps you close to it all, this one is easy to call home.**photos may vary by unit, move-in dates subject to change**

    324-326 Colby Ridge Blvd Unit 326 Colby Ridge, Winchester, KY 40391

Frequently Asked Questions

How much does it cost to rent a condo in Winchester, KY?
The median rent for a condo in Winchester, KY is $1,253 per month, though prices vary by neighborhood, size, and property type. As of August 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 $57,880 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 $1,447 per month in Winchester, KY, renters typically need to show $4,341 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 15.3, 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 condo?
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 condo include Historic South Hill, River Park, North Limestone, Stoneybrook-Brigadoon and Northside, each with its own character and price range.

Rental Home Trends

Number of Condos for Rent
5
Median Condo Rent
$1,253
Median 1 Bedroom Condo Rent
$799
Median 2 Bedroom Condo Rent
$1,253
Median 3 Bedroom Condo Rent
$1,705
How to Rent a Home