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Rent to own Homes 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.

Winchester, KY is a great place for affordable rent-to-own homes! With a median household income of over $43,415 and a median rent of $699, the Winchester, KY rent-to-own market is more affordable than the traditional housing market which has shown tremendous growth across the U.S. and with it, aggressive competition for home purchases. With the current housing shortage trend it can make it harder to become a homeowner, including in Winchester, KY. This means higher than average down payments for homes and higher qualification standards for conventional home loans. With a rent-to-own property, tenants are also buyers. You can live in the house for a set amount of time before you purchase it, meaning that you get to know the house, your neighbors, and your community before making the final purchase. This enables you and your family to make the right choice based on both information and experience. Rent-to-own is also a great alternative way to get into a home if you have bad credit or don't have enough saved for a down payment.

Check out Winchester, KY rent to own homes for sale, which may include auction properties, for sale by owner, and more.
Showing 1 - 44 of 440
650 S MILL ST #213
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Rent To Own
 
Townhouse/Condo
Lexington, KY 40508
2
2
1144 ft2
2011
650 S MILL ST #115
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Rent To Own
 
Townhouse/Condo
Lexington, KY 40508
2
2
1144 ft2
2011
650 S MILL ST #120
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Rent To Own
 
Townhouse/Condo
Lexington, KY 40508
2
2
1144 ft2
2011
Hot
919 SCAFFOLD CANE RD
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Rent To Own
 
Single Family Home
Berea, KY 40403
4
2
1636 ft2
1960
1007 FAIRWAY DR
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Rent To Own
 
Single Family Home
Georgetown, KY 40324
4
3
2697 ft2
1 of 24 3201 ORCHARD GRASS RD
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Rent To Own
Boone Creek
Single Family Home
Lexington, KY 40509
6
5
3345 ft2
2008
1 of 30 1142 DUNBARTON LN
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Rent To Own
 
Townhouse/Condo
Lexington, KY 40502
3
4
2574 ft2
1988
1 of 166 4700 SUNNY PT
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Rent To Own
Boone Creek
Single Family Home
Lexington, KY 40515
4
3
4480 ft2
1995
1 of 60 629 TWIN PINES WAY
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Rent To Own
 
Single Family Home
Lexington, KY 40514
3
3
1710 ft2
1993
1 of 23 125 MADDOX ST
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Rent To Own
 
Single Family Home
Georgetown, KY 40324
2
1
885 ft2
1978
2410 COBHILL RD
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Rent To Own
 
Single Family Home
Irvine, KY 40336
3
2
1216 ft2
2018
Hot
803 SLATE LICK RD
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Rent To Own
 
Single Family Home
Berea, KY 40403
3
1
1700 ft2
1980
219 FIELDS RD
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Rent To Own
 
Single Family Home
Sadieville, KY 40370
3
1
0 ft2
308 MARYLAND AVE
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
1
1694 ft2
1962
12 APACHE TRL
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
1
1026 ft2
1980
210 BEAUMONT PL
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
2
1674 ft2
1998
240 COOK AVE
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
2
1176 ft2
1940
38 MACKAY AVE
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
1
958 ft2
1960
33 HAMPTON AVE
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
4
2
2313 ft2
1958
11 SPRING ST
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
2
1
1103 ft2
1945
233 E WASHINGTON ST
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
2
1
1190 ft2
1940
1896 MOUNT STERLING RD
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
2
1942 ft2
1960
35 JOHNSON ST
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
1
1800 ft2
1940
611 DIXIANA DR
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
1
1073 ft2
1990
3255 JACKSON FERRY RD
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
2
1
1400 ft2
2000
3635 JACKSON FERRY RD
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
3
2
2448 ft2
1920
New
1 of 10 219 Main Street
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Auction
 
Single Family Home
North Middletown, KY 40357
5
2
3111 ft2
1900
955 RIGHT ANGLE RD
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Winchester, KY 40391
2
1
768 ft2
1996
Hot
140 BROOKS RD
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REO Foreclosure
 
Single Family Home
Richmond, KY 40475
4
2
1813 ft2
1976
760 MAIDENCANE DR
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Pre-Foreclosure (Lis Pendens)
Boone Creek
Single Family Home
Lexington, KY 40509
4
3
3016 ft2
2008
4420 NATAL PL
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REO Foreclosure
Boone Creek
Single Family Home
Lexington, KY 40509
4
3
2545 ft2
2006
44 HORSESHOE DR
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Paris, KY 40361
3
1
1728 ft2
1 of 4 1132 VINE ST
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Auction
 
Single Family Home
Paris, KY 40361
3
1
1000 ft2
445 BELL ST
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Paris, KY 40361
2
1
816 ft2
424 BELL ST
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Paris, KY 40361
4
1
1222 ft2
1945
811 WESTWOOD DR
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Paris, KY 40361
3
1
1809 ft2
1201 PLEASANT ST
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Paris, KY 40361
3
2
2202 ft2
1 of 23 588 BULRUSH TRCE
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Auction
Boone Creek
Single Family Home
Lexington, KY 40509
4
3
3350 ft2
2010
4524 PARSONS LN
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Auction
Boone Creek
Single Family Home
Lexington, KY 40509
5
3
2975 ft2
2004
1204 ASPEN ST
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Auction
Boone Creek
Single Family Home
Lexington, KY 40509
3
2
1236 ft2
1996
1224 MCCROSKEY DR
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Pre-Foreclosure (Lis Pendens)
 
Single Family Home
Mount Sterling, KY 40353
3
2
1568 ft2
2000
3633 AMICK WAY
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Pre-Foreclosure (Lis Pendens)
Boone Creek
Townhouse/Condo
Lexington, KY 40509
3
3
1656 ft2
1997
625 WILLIAMS ST
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Auction
 
Single Family Home
Paris, KY 40361
3
1
892 ft2
2004
1 of 7 1255 MCCROSKEY DR
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Auction
 
Single Family Home
Mount Sterling, KY 40353
2
1
1288 ft2
Map
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Rent to own Homes in Cities Near Winchester, KY

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Neighborhoods in Winchester, KY

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Popular Zip Codes in Winchester, KY

40392 rent to own homes

Buying a Home in Winchester, KY

Winchester, KY is seeing rapid growth and Winchester, KY's' housing market remains optimal with an average home price that is -39% below the 2025 national average. Winchester, KY is part of Clark county and taxes are an important factor to consider when purchasing a home whether through rent to own or a traditional purchase. The average tax rate as of 2025 for county Clark is 0.68% which is below the national average, which is 0.99%.

Median Home Price in Winchester, KY

Median Rent in Winchester, KY

Rent to own homes offer low monthly payments and flexible terms.

Top 4 Reasons to Live in Winchester, KY

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.