Rent to Own Homes near Winchester, KY

Top 4 Reasons to Live in Winchester, KY

  • Home to nearly 18,400 people, Winchester is located in Clark County and just east of Lexington. The city has a strong connection to Daniel Boone. And it's easy to see why the area was so attractive to Boone, as today that beauty can be seen in the rolling hills and horse pastures that lead to a charming downtown core. Winchester is an inviting mix of gorgeous countryside and bustling town action, and is a true gem of the Bluegrass Region.

Check out Winchester, KY Craigslist homes for sale, for rent, and rent to own

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Listing Type
Description
Price
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Details
3 Beds, 1 Bath on Estes Dr
Listing Type
Rent-To-Own
Description

3 Beds, 1 Bath

Winchester, KY 40391

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Price
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Nearest
School: Calvary 'S Kids Christian School
Grocery: Walmart Supercenter
Restaurant: Kroger Deli
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3 Beds, 3 Baths on Buckingham Ln
Listing Type
For Sale By Owner
Description

3 Beds, 3 Baths

Winchester, KY 40391

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Price
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Nearest
School: Clark County Christian School
Grocery: Full Circle Market-Health Food
Restaurant: Don Senor
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3 Beds, 1 Bath on Monroe Ave
Listing Type
REO Foreclosure
Description

3 Beds, 1 Bath

Winchester, KY 40391

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Price
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Nearest
School: Hannah Mcclure Elementary School
Grocery: Hays Street Market
Restaurant: Jade Garden
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4 Beds, 3 Baths on Hood Ave
Listing Type
For Sale By Owner
Description

4 Beds, 3 Baths

Winchester, KY 40391

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Price
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School: Hannah Mcclure Elementary School
Grocery: South Main Grocery
Restaurant: Gaunce's Deli & Cafe
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4 Beds, 2 Baths on Geronimo Ct
Listing Type
For Sale By Owner
Description

4 Beds, 2 Baths

Winchester, KY 40391

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Price
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School: Shearer Elementary School
Grocery: H & M Market Corp
Restaurant: Breakfast & Billiards
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3 Beds, 2 Baths on Alabama St
Listing Type
For Sale By Owner
Description

3 Beds, 2 Baths

Winchester, KY 40391

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Price
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School: Saint Agatha Academy
Grocery: Calloway Market
Restaurant: Winchester Opera House
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3 Beds, 1 Bath on Watts Rd
Listing Type
For Sale By Owner
Description

3 Beds, 1 Bath

Winchester, KY 40391

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Price
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Nearest
School: Central Elementary School
Grocery: Winn Avenue Market
Restaurant: Breakfast & Billiards
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4 Beds, 2 Baths on Two Mile Rd
Listing Type
For Sale By Owner
Description

4 Beds, 2 Baths

Winchester, KY 40391

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Price
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Nearest
School: Saint Agatha Academy
Grocery: South Main Grocery
Restaurant: Engine House Deli
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4 Beds, 2 Baths on S Main St
Listing Type
For Sale By Owner
Description

4 Beds, 2 Baths

Winchester, KY 40391

Accepting Offers

Price
Click for Deals
Nearest
School: Saint Agatha Academy
Grocery: South Main Grocery
Restaurant: Engine House Deli
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  • Enjoy the region's rich heritage! Sites and annual events put Winchester's history into the spotlight throughout the year. What's even better is that a variety of sites ensure different interests are satisfied. For instance, those who love classic architecture are certain to love a stroll through the historic downtown district and viewing landmarks such as Clark County Courthouse and Leeds Theater. The Bluegrass Historic Museum covers the region's remarkable past in exquisite detail. The Civil War Fort at Boonesboro is certain to captivate those interested in military history. The Daniel Boone Pioneer Festival, which is held each year during late summer, celebrates the explorer's influence on the area and features music, a mini-marathon, arts and crafts, food, and more.
  • Find a historic home! Winchester has lots of history, and with that comes a good amount of historic homes. In fact, 15.0% of housing units in Winchester were erected before 1940. Although living inside a historic landmark like the Clark Mansion or Oakwood Estate isn't really possible, newcomers can find time-honored homes for sale and rent in the rural sections of town, such as Colby Road, and around the center of town, such as near College Park.
  • Order some delicious food! Skip the chains and go order something at one of the many locally owned eateries in Winchester. For a home-style buffet, head to Cantuckee Diner. Maddie's Cafe on Main is great for a casual meal. And JK's at Forest Grove is known for soups and sandwiches. If you want to cook at home, the Beech Springs Farm Market is the place to buy fresh produce grown in the area and other foods. Foodies should also make a point of doing the Beer Cheese Trail by stopping at establishments like DJ's Bar and Grill and Hall's on the River and ordering a beer cheese dish.
  • Lease a pad easily! Finding a rental property in Winchester isn't that hard, as 50.1% of the city rents, which is much higher than Kentucky's average. There are also some rent to own deals in town. To see a range of listings, look throughout Winchester, from near Winchester Country Club in the south to near Lykins Park and Interstate-64 in the north.