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Newest Homes for Rent in Winchester, KY

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  • /35

    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

    (859) 577-9164

    260 Oxford Dr, Winchester, KY 40391
  • /3

    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

    (859) 249-8752

    27 E Washington St, Winchester, KY 40391
  • /3

    Starting at $1,049 Per Month

    • 2 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

    (859) 249-8853

    510 College St, Winchester, KY 40391
  • /9

    $1,295 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • 278/276 AW

    278-276 April Way Unit 278 April way, Winchester, KY 40391

    278-276 April Way Unit 278 April way, Winchester, KY 40391
  • /4

    $1,225 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • 341/343 CPI

    341-343 Colby Ridge Blvd Unit 341 Colby Ridge, Winchester, KY 40391

    341-343 Colby Ridge Blvd Unit 341 Colby Ridge, Winchester, KY 40391
  • /2

    $1,125 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,150 Sq Ft
    • 292/294 April way

    292-294 April Way Unit 292 april way, Winchester, KY 40391

    292-294 April Way Unit 292 april way, Winchester, KY 40391
  • /6

    $1,125 Per Month

    • 3 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • 192/194 WPI

    192-194 Westside Dr Unit 192 Westside Drive, Winchester, KY 40391

    192-194 Westside Dr Unit 192 Westside Drive, Winchester, KY 40391
  • /9

    $1,295 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • 248/250 AW

    248-250 April Way Unit 250 april way, Winchester, KY 40391

    248-250 April Way Unit 250 april way, Winchester, KY 40391
  • /18

    $1,475 Per Month

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • Townhouse for Rent

    405 Paisley Ct, Winchester, KY 40391

    Available for lease. This half duplex is located in the quiet residential neighborhood of Scottish Highlands. The great room features a fireplace. Walk out from the great room to a deck that overlooks beautiful Kentucky Bluegrass. The back yard is fenced. All the appliances are available in the kitchen. Look at this duplex, it may be your home for a season.

    Craig Bridgewater Bridgewater Real Estate

    405 Paisley Ct, Winchester, KY 40391
  • /20

    $879 Per Month

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    18 Calloway St Unit 4, Winchester, KY 40391

    Available May 26,2026! – Recently Renovated Winchester Apartment!Welcome to your next home in the heart of Winchester! This beautifully updated 1-bedroom, 1-bath apartment is nestled just off Lexington Avenue and Bypass Road close to shopping, dining, and just minutes from downtown Winchester.At Bluegrass Rental Management, we strive to provide an experience that is cost-effective

    18 Calloway St Unit 4, 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
  • /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
  • /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
  • /6

    $1,095 Per Month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    1028 W Lexington Ave Unit 4, Winchester, KY 40391

    Welcome to 1028 W Lexington Ave — a cozy and well-maintained 1-bedroom, 1-bathroom apartment located in the heart of Winchester, KY.This home features a spacious living area, a functional kitchen, and all the essentials needed for comfortable everyday living. Ideal for students, professionals, or anyone looking to downsize, this apartment offers the perfect balance of comfort and

    1028 W Lexington Ave Unit 4, Winchester, KY 40391
  • /8

    $1,015 Per Month

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • 151/153 WPI

    151-153 Westside Dr Unit 151 Westside Drive, Winchester, KY 40391

    151-153 Westside Dr Unit 151 Westside Drive, 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
  • /14

    $995 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    265 S Highland St Unit 4, Winchester, KY 40391

    Welcome to our charming apartment in Winchester, KY! This apartment boasts beautiful wood floors throughout, creating a warm and inviting atmosphere. Enjoy the convenience of a large yard and an in-unit laundry room. Located close to downtown and shopping, you'll have easy access to all the amenities Winchester has to offer. Don't miss out on the opportunity to call this unique apartment

    265 S Highland St Unit 4, Winchester, KY 40391
  • /2

    $1,375 Per Month

    • 2 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Condo for Rent

    204 S Maple St Unit 204 S Maple, Winchester, KY 40391

    This charming 2-bedroom, 1-bathroom apartment features a comfortable living room and a functional kitchen. Rent includes the municipal water bill, while tenants are responsible for gas and electricity. Perfect for anyone seeking an affordable, move-in ready home with essential amenities.

    204 S Maple St Unit 204 S Maple, Winchester, KY 40391
  • /2

    $1,700 Per Month

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

    135 Winn Ave Unit A, Winchester, KY 40391

    Step into this beautifully renovated 3-bedroom, 2-bathroom home featuring a bright and open living area and a modern kitchen on the ground floor. Designed for comfort and style, this residence offers contemporary finishes, spacious layouts, and all the amenities you need for modern living. Perfect for families or anyone seeking a move-in ready home with a fresh, modern feel.

    135 Winn Ave Unit A, 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 $1,110 per month, though prices vary by neighborhood, size, and property type. As of May 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 $44,400 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 $1,110 per month in Winchester, KY, renters typically need to show $3,330 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 19.5, 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, Andover Forest, Boone Creek East, Woodhill and Hamburg, each with its own character and price range.

Rental Home Trends in Winchester, KY

Rental Home Trends

Number of Homes for Rent
19
Median Rent
$1,110
Median Single Family Home Rent
$1,800
Median Townhouse Rent
$1,475
Median Condo Rent
$1,015
How to Rent a Home