Rent to own Homes in Chestertown, MD

Chestertown, MD is a great place for affordable rent-to-own homes! With a median household income of over $39,682 and a median rent of $873, the Chestertown, MD 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 Chestertown, MD. 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 Chestertown, MD rent to own homes for sale, which may include auction properties, for sale by owner, and more.
Showing 1 - 44 of 440
134 HARMONY WAY
Rent To Own
 
Single Family Home
Centreville, MD 21617
3
4
3533 ft2
2005
518 RISEN STAR CT
Rent To Own
Havre De Grace
Single Family Home
Havre De Grace, MD 21078
4
4
3611 ft2
2017
7818 RENSHAW RD
Rent To Own
 
Single Family Home
Pasadena, MD 21122
4
3
1192 ft2
1986
529 MIDDLESEX DR
Rent To Own
 
Single Family Home
Middletown, DE 19709
4
6
3755 ft2
2007
1 of 26 5493 CEDONIA AVE
Rent To Own
Cedonia
Townhouse/Condo
Baltimore, MD 21206
3
2
1152 ft2
1959
32 MIDDLE WALLOP RD
Rent To Own
Glasgow
Single Family Home
Bear, DE 19701
4
1
1325 ft2
1985
1 of 34 1808 REDWOOD AVE
Rent To Own
 
Single Family Home
Parkville, MD 21234
2
1
1168 ft2
1942
1 of 25 26 MACKAY LN
Rent To Own
Brookside Park
Single Family Home
Newark, DE 19713
4
2
1340 ft2
1954
4949 BONNIEWOOD DR
Rent To Own
 
Single Family Home
Shady Side, MD 20764
3
2
942 ft2
1942
1 of 31 213 DUKE OF KENT ST
Rent to Own Eligible
 
Single Family Home
Chestertown, MD 21620
3
2
1512 ft2
1991
1 of 62 223 DEVON DR
Rent to Own Eligible
 
Single Family Home
Chestertown, MD 21620
4
3
2186 ft2
2007
1 of 16 557 FEY RD
Rent to Own Eligible
 
Single Family Home
Chestertown, MD 21620
4
3
1629 ft2
1972
1 of 4 109 FAIRVIEW DR
Rent to Own Eligible
 
Single Family Home
Chestertown, MD 21620
3
1
1232 ft2
1977
1 of 22 126 PARMA RD
Rent to Own Eligible
 
Single Family Home
Chestertown, MD 21620
2
1
840 ft2
1980
1 of 30 1001 ROLPHS WHARF RD
Rent to Own Eligible
 
Single Family Home
Chestertown, MD 21620
3
2
3582 ft2
2007
1 of 40 10634 MILLBROOK DR
Rent to Own Eligible
 
Single Family Home
Chestertown, MD 21620
3
2
1404 ft2
2002
1 of 30 26290 LAMBS MEADOW RD
Rent to Own Eligible
 
Single Family Home
Worton, MD 21678
3
3
3062 ft2
1900
New
24969 BELLEAU WOOD RD
Rent to Own Eligible
 
Single Family Home
Worton, MD 21678
4
3
3051 ft2
2022
1 of 38 11901 DAIRY ST
Rent to Own Eligible
 
Single Family Home
Kennedyville, MD 21645
4
3
2458 ft2
2007
1 of 61 114 GATHERING CT
Rent to Own Eligible
 
Single Family Home
Sudlersville, MD 21668
4
4
4700 ft2
2007
1 of 14 225 BURCHARD SAWMILL RD
Rent to Own Eligible
 
Single Family Home
Chestertown, MD 21620
4
2
2080 ft2
1972
1 of 42 114 EAGLE MANOR DR
Rent to Own Eligible
 
Single Family Home
Church Hill, MD 21623
3
3
1813 ft2
2013
1 of 30 1775 SUDLERSVILLE RD
Rent to Own Eligible
 
Single Family Home
Sudlersville, MD 21668
3
2
1324 ft2
2008
1 of 14 609 PRICE STATION RD
Rent to Own Eligible
 
Single Family Home
Church Hill, MD 21623
4
3
2568 ft2
1990
1 of 60 107 ANDREW CT
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
4
4
3604 ft2
2003
1 of 219 6006 ROCK HALL RD
Rent to Own Eligible
 
Single Family Home
Rock Hall, MD 21661
5
2
4188 ft2
1920
1 of 110 138 GRANARD AVE
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
5
3
2778 ft2
2002
1 of 88 717 CHURCH HILL RD
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
2
2
2374 ft2
1953
1 of 119 120 LENTLY FARM LN
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
3
3
1856 ft2
1995
1 of 62 109 KINGS CT
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
3
3
1968 ft2
1990
1 of 92 130 KINGS CT
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
2
2
1582 ft2
1994
New
1 of 33 227 N COMMERCE ST
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
4
4
2317 ft2
1790
114 HAPPY LADY LN
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
3
1
1128 ft2
1974
1 of 87 152 UPLAND LN
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
5
4
4949 ft2
2005
1 of 132 442 RAILROAD AVE
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
3
3
2058 ft2
1901
1 of 27 2941 GROVE NECK RD
Rent to Own Eligible
 
Single Family Home
Earleville, MD 21919
3
2
1704 ft2
1997
1 of 26 110 RADAR LN
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
3
3
2211 ft2
2017
1 of 32 202 OVERTURE WAY
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
4
4
2628 ft2
2005
1 of 46 303 SYMPHONY WAY
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
4
3
3056 ft2
2005
1 of 49 309 UPPER MILL CT
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
3
3
2608 ft2
2000
1 of 25 205 LEGION RD
Rent to Own Eligible
 
Single Family Home
Millington, MD 21651
3
2
1092 ft2
1982
1 of 56 120 HERON VIEW DR
Rent to Own Eligible
 
Single Family Home
Centreville, MD 21617
4
3
2434 ft2
1997
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Buying a Home in Chestertown, MD

Chestertown, MD is seeing rapid growth and Chestertown, MD's' housing market remains not optimal with an average home price that is 20% above the 2024 national average. Chestertown, MD is part of Kent 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 Kent is 0.67% which is below the national average, which is 0.99%.

Median Home Price in Chestertown, MD

Median Rent in Chestertown, MD

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