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Newest Homes for Rent in Winchester, KY

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    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

    260 Oxford Dr, Winchester, KY 40391
  • /3

    Starting at $1,049 Per Month

    • 2 - 3 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

    510 College St, Winchester, KY 40391
  • /2

    $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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    $1,355 Per Month

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

    150 Cook Ave, Winchester, KY 40391

    150 Cook Ave, Winchester, KY 40391
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    $910 Per Month

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

    1136 Dale Dr Unit 2, Winchester, KY 40391

    We have another of our popular Dale Drive Townhomes available and this one comes with brand new flooring in the living space! These don't last long, so get your application in today. *Completed rental application required prior to tour.

    1136 Dale Dr Unit 2, Winchester, KY 40391
  • /2

    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

    27 E Washington St, Winchester, KY 40391
  • /6

    $825 Per Month

    • Studio
    • 1 Bath
    • 400 Sq Ft
    • Condo for Rent

    401 N Maple St Unit 11, Winchester, KY 40391

    Welcome to this charming renovated studio apartment located at 401 North Maple Street. This cozy unit is perfect for those seeking a comfortable and affordable living space.Step inside and be greeted by the stylish LVP flooring that adds a touch of elegance to the interior. The open layout creates a seamless flow between the living area, kitchenette, and sleeping quarters.One of

    401 N Maple St Unit 11, Winchester, KY 40391
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    $1,500 Per Month

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

    130 Elm St, Winchester, KY 40391

    Completely renovated and move-in ready, this beautiful 3-bedroom, 2-bathroom home offers modern finishes while maintaining a warm, inviting feel. Featuring updated flooring throughout, fresh neutral paint, stylish bathrooms, and a remodeled kitchen with stainless steel appliances, this home is perfect for anyone looking for a clean, comfortable place to call home.Large windows provide

    130 Elm St, Winchester, KY 40391
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    $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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    $1,850 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
  • /3

    $1,555 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
  • /5

    $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
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    $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
  • /6

    $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
  • /25

    $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
  • /28

    Call for Price

    • 1 - 3 Beds

    300 C G Stephenson Dr, Winchester, KY 40391

    This community is open by appt only. Office hours are 9am to 12pm and 1pm to 4pm. Please call to schedule your appt!Cambridge Square is a community with beautifully maintained grounds, offering one, two and three bedroom apartment homes with some one bedroom homes reserved for the elderly/dis-abled, all rent based on income. We are located in quiet Winchester, Kentucky, with easy

    Cambridge Square Apartments - Income Based

    300 C G Stephenson Dr, Winchester, KY 40391
  • /28

    Call for Price

    • 1 - 3 Beds

    900 Westwood Dr, Winchester, KY 40391

    Pick up your application for our WAIT LIST at the office door! Westwood is a charming property in a great location in Winchester, Kentucky with rents based on income. Spacious one, two and three bedroom apartments for rent, each featuring a fully equipped kitchen, your choice of a patio or balcony, and they are wired for cable. Fun in the sun is just a outside your door at our playground, or

    Westwood Apartments - Income Based

    900 Westwood Dr, Winchester, KY 40391

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 $1,395 per month, though prices vary by neighborhood, size, and property type. As of August 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 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 Gleneagles, Boone Creek East, Hamburg, Eastland Parkway and Woodhill, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
17
Median Rent
$1,395
Median Single Family Home Rent
$1,550
Median Townhouse Rent
$1,538
Median Condo Rent
$1,033
How to Rent a Home