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
Rent To Own
 
Townhouse/Condo
Lexington, KY 40508
2
2
1144 ft2
2011
650 S MILL ST #115
Rent To Own
 
Townhouse/Condo
Lexington, KY 40508
2
2
1144 ft2
2011
650 S MILL ST #120
Rent To Own
 
Townhouse/Condo
Lexington, KY 40508
2
2
1144 ft2
2011
1 of 61 101 KIRK DR
Rent To Own
 
Single Family Home
Nicholasville, KY 40356
5
5
5800 ft2
1999
Hot
919 SCAFFOLD CANE RD
Rent To Own
 
Single Family Home
Berea, KY 40403
4
2
1636 ft2
1960
1007 FAIRWAY DR
Rent To Own
 
Single Family Home
Georgetown, KY 40324
4
3
2697 ft2
Hot
1 of 33 22 APACHE TRL
Rent To Own
 
Single Family Home
Winchester, KY 40391
4
2
1250 ft2
1999
Hot
1 of 38 129 HIBISCUS LN
Rent To Own
 
Single Family Home
Winchester, KY 40391
4
2
1970 ft2
1999
163 AVAWAM DR
Rent To Own
 
Single Family Home
Richmond, KY 40475
6
4
5300 ft2
2006
Hot
1 of 16 3021 LYNNWOOD DR
Rent To Own
 
Single Family Home
Paris, KY 40361
3
2
2520 ft2
1955
3201 ORCHARD GRASS RD
Rent To Own
Boone Creek
Single Family Home
Lexington, KY 40509
6
5
3345 ft2
2008
1 of 67 1308 WAKEHURST CT
Rent To Own
Boone Creek
Single Family Home
Lexington, KY 40509
5
5
4580 ft2
2001
1 of 11 4101 SnowCreek Road
Rent To Own
 
Multifamily (2 - 4 Units)
Clay City, KY 40312
2
1
0 ft2
Hot
1 of 9 1783 TIMBER CREEK DR
Rent To Own
Boone Creek
Single Family Home
Lexington, KY 40509
3
2
1297 ft2
1995
3416 CHESTNUT HILL LN
Rent To Own
Andover Hills
Single Family Home
Lexington, KY 40509
5
4
3570 ft2
1990
1 of 43 Kentucky River Parkway
Rent To Own
 
Multifamily (2 - 4 Units)
Lexington, KY 40515
3
3
4234 ft2
1995
Hot
1 of 20 308 WILSHIRE WAY
Rent To Own
 
Single Family Home
Richmond, KY 40475
3
2
1480 ft2
2013
Hot
1 of 49 3541 SQUIRES WOODS WAY
Rent To Own
Boone Creek
Townhouse/Condo
Lexington, KY 40515
2
2
1056 ft2
1996
Hot
1 of 14 2589 CASHEL CT
Rent To Own
Boone Creek
Single Family Home
Lexington, KY 40509
3
2
1050 ft2
1996
Hot
1 of 28 1837 WAYLAND DR
Rent To Own
Bryan Station
Single Family Home
Lexington, KY 40505
3
1
1359 ft2
1956
Hot
1 of 8 1796 GERALD DR
Rent To Own
 
Single Family Home
Lexington, KY 40511
4
2
1152 ft2
1994
1142 DUNBARTON LN
Rent To Own
 
Townhouse/Condo
Lexington, KY 40502
3
4
2574 ft2
1988
Hot
1 of 62 1100 PEPPERHILL CIR
Rent To Own
 
Single Family Home
Lexington, KY 40502
3
3
3030 ft2
1979
Hot
360 MCNEASE RD
Rent To Own
 
Single Family Home
Paris, KY 40361
3
3
2994 ft2
2005
4700 SUNNY PT
Rent To Own
Boone Creek
Single Family Home
Lexington, KY 40515
4
3
4480 ft2
1995
Hot
1 of 39 425 DELCAMP DR
Rent To Own
Northside
Single Family Home
Lexington, KY 40508
3
2
1230 ft2
1910
Hot
1 of 20 791 TYRUS CT
Rent To Own
 
Single Family Home
Lexington, KY 40515
3
3
2310 ft2
1990
1 of 7 505 RIDGEWATER CT
Rent To Own
Waterford
Single Family Home
Lexington, KY 40515
4
3
2494 ft2
1992
1 of 57 120 STERLING DR
Rent To Own
 
Single Family Home
Georgetown, KY 40324
3
3
4000 ft2
1999
1 of 23 342 Waller Avenue
Rent To Own
Picadome
Multifamily (2 - 4 Units)
Lexington, KY 40504
1
1
660 ft2
1969
1 of 36 5104 GREY OAK LN
Rent To Own
Brannon Crossing
Single Family Home
Nicholasville, KY 40356
5
3
2963 ft2
2013
Hot
1 of 12 145 VANDERBILT DR
Rent To Own
 
Single Family Home
Lexington, KY 40517
3
3
2200 ft2
1960
Hot
1 of 51 3512 NICHOLASVILLE RD
Rent To Own
 
Single Family Home
Lexington, KY 40503
4
3
2720 ft2
1958
1 of 18 104 GRABLE LN
Rent To Own
 
Single Family Home
Georgetown, KY 40324
3
3
2825 ft2
2010
1 of 17 1100 Horsemans Lane
Rent To Own
 
Multifamily (2 - 4 Units)
Lexington, KY 40504
3
2
1232 ft2
1997
1 of 7 402 DUBB LN
Rent To Own
 
Single Family Home
Nicholasville, KY 40356
3
3
2100 ft2
1994
Hot
1 of 12 600 VINCENT WAY #1111
Rent To Own
Wellington
Townhouse/Condo
Lexington, KY 40503
2
2
1442 ft2
2003
629 TWIN PINES WAY
Rent To Own
 
Single Family Home
Lexington, KY 40514
3
3
1710 ft2
1993
Hot
1 of 31 512 CROMWELL WAY
Rent To Own
 
Single Family Home
Lexington, KY 40503
3
2
1519 ft2
1974
1 of 40 1304 SADDLE CLUB WAY
Rent To Own
 
Single Family Home
Lexington, KY 40504
4
5
3796 ft2
2001
1 of 36 1084 CHASEWOOD WAY
Rent To Own
Beaumont Residential
Single Family Home
Lexington, KY 40513
4
4
5300 ft2
1998
Hot
1 of 35 208 PLEASANT VIEW DR
Rent To Own
 
Single Family Home
Georgetown, KY 40324
4
3
1926 ft2
2018
1 of 100 2156 CAROLINA LN
Rent To Own
Beaumont Residential
Single Family Home
Lexington, KY 40513
5
5
6372 ft2
2003
Hot
1 of 12 108 DUNLAP DR
Rent To Own
 
Single Family Home
Georgetown, KY 40324
3
2
1406 ft2
2011
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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 2024 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 2024 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.