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Winchester, KY Homes for Rent

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    Cambridge Square Apartments - Income Based

    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

    300 C G Stephenson Dr, Winchester, KY 40391
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    $1,850 per month

    • 3 Beds
    • 2.5 Baths
    • 1,929 Sq Ft
    • House for Rent

    312 Mcdowell Dr, Winchester, KY 40391

    Well maintained 3 bedroom home with fenced back yard and conveniently located to shopping and the interstate. The home offers beautiful hardwood flooring with an open floor plan, spacious 2 car attached garage, screened in back porch, 1st floor laundry, and large 2nd floor master bedroom. Available for occupancy available 3/1/26. 48 hour notice to show.

    S Ann Wesley Assurance Realty & Property Management

    312 Mcdowell Dr, Winchester, KY 40391
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    $800 - $1,300 per month

    Summit Apartments

    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

    260 Oxford Dr, Winchester, KY 40391
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    $2,950 per month

    • 3 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • House for Rent

    104 Colby Hills Dr, Winchester, KY 40391

    This is a beautiful stone ranch home located in Colby Hills ,this home has been updated with a new kitchen ,new bathrooms, new painting, new lighting, new garage doors, new deck.take a look Owner/broker

    Garry Milton Milton and Associates Real Estate

    104 Colby Hills Dr, Winchester, KY 40391
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    Westwood Apartments - Income Based

    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

    900 Westwood Dr, Winchester, KY 40391
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    $999 - $1,249 per month

    The Lofts at Winchester! 2 BR, 1 Bath, Off-Street Parking, Small Pets Ok!

    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.

    510 College St, Winchester, KY 40391
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    $1,660 per month

    • 3 Beds
    • 1 Bath
    • 1,475 Sq Ft
    • House for Rent

    156 Cook Ave, Winchester, KY 40391

    Highlights: OCCUPIED--DON'T GO TO THE HOUSE. MAKE ARRANGEMENTS WITH MANAGEMENT FOR VIEWING. AVAILABLE December 10th--possibly earlier. The house is 3 bedroom / 1 bathroom. Approximately 1,450 square feet. Rent is $1660 per month. Security deposit is equal to one month's rent. Flooring recently updated. Paint recently updated.

    156 Cook Ave, Winchester, KY 40391

Why Live in Winchester

Winchester, KY, the largest city in Clark County, is known for its vibrant community and unique local flavors, including the birthplace of beer cheese and Ale-8-One soda. Main Street is the hub for dining, featuring popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail, which includes around 15 restaurants with signature beer cheese recipes. The city offers practical amenities with nearby grocery stores like Kroger and Walmart Supercenter, and retail options such as TJ Maxx and Lowe’s. Housing in Winchester includes Victorian-era inspired homes and newer subdivisions, with properties often featuring gravel driveways and spacious lawns suitable for gardens. Clark County Public Schools provide strong academic programs, including AP and dual enrollment courses at George Rogers Clark High School. For outdoor activities, residents enjoy Legacy Grove Park, College Park, and Lykins Park, which offer facilities for basketball, tennis, hiking, and disc golf. Winchester hosts annual events like the Beer Cheese Festival and the Daniel Boone Pioneer Festival, attracting visitors with arts, crafts, and food. The Bluegrass Heritage Museum showcases the history of Central Kentucky. Commuting is convenient with Winchester located 16 miles from Lexington and 20 miles from Richmond. The city has a cooperative community spirit, bolstered by investments from younger residents and a thriving local economy.

Frequently Asked Questions

What are the most popular neighborhoods in Winchester, KY for renters?
The most popular neighborhoods in Winchester, KY for renters are Gleneagles, Boone Creek East, Andover Forest, Liberty Area and Woodhill.
What are the most popular zip codes in Winchester, KY for renters?
The most popular zip codes in Winchester, KY for renters include 40391, 40509, 40515, 40517 and 40502.
How to Rent a Home