Chestertown, MD Rent-to-Own Homes & Rental Homes | RentToOwn.org

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Finding rent-to-own homes in Chestertown, MD is quick and easy with RentToOwn.org. Our database of rental homes and rent-to-own houses in Chestertown, MD is regularly updated with a variety of single-family homes, condos, townhomes, and more to suit your needs. In addition to Chestertown, MD rent-to-own homes, you can expect to find other sale types, including for sale by owner (FSBO) homes, sherriff sales, REO foreclosures, and pre-foreclosures. Finding affordable Chestertown, MD rent-to-own homes has never been easier!

Street view of S Kent St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

936 Square Feet

Year Built: 1900

Rent to Own Eligible

Street view of N Kent St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,566 Square Feet

Year Built: 1974

Rent to Own Eligible

Street view of Church Aly Chestertown, MD 21620 MLS home

Chestertown, MD 21620

2 Beds, 2 Baths

1,416 Square Feet

Year Built: 1880

Rent to Own Eligible

Street view of Rolling Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

1,202 Square Feet

Year Built: 1961

Rent to Own Eligible

Street view of Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 3 Baths

1,420 Square Feet

Year Built: 2023

Rent to Own Eligible

Street view of N Water St, Unit A Chestertown, MD 21620 MLS home

N Water St, Unit A

Chestertown, MD 21620

787 Square Feet

Year Built: 1886

Rent to Own Eligible

Street view of Pine St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

2,212 Square Feet

Year Built: 1955

Rent to Own Eligible

Street view of Valley Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,886 Square Feet

Year Built: 1978

Rent to Own Eligible

Street view of S Mill St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 4 Baths

2,492 Square Feet

Year Built: 1900

Rent to Own Eligible

Street view of N Kent St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 2 Baths

2,220 Square Feet

Year Built: 1965

Rent to Own Eligible

Street view of Silver Heel Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

5 Beds, 3 Baths

2,615 Square Feet

Year Built: 2023

Rent to Own Eligible

Street view of Chestertown, MD 21620 MLS home

Chestertown, MD 21620

2 Beds, 3 Baths

1,711 Square Feet

Year Built: 1972

Rent to Own Eligible

Street view of Valley Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 2 Baths

2,869 Square Feet

Year Built: 1957

Rent to Own Eligible

Street view of Metcalf Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,280 Square Feet

Year Built: 2023

Rent to Own Eligible

Street view of Landing Lane Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 3 Baths

2,200 Square Feet

Rent to Own Eligible

Street view of Washington Ave Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,224 Square Feet

Year Built: 1949

Rent to Own Eligible

Street view of Metcalf Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,140 Square Feet

Year Built: 2023

Rent to Own Eligible

Street view of Foxview Ct Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 4 Baths

3,000 Square Feet

Year Built: 1999

Rent to Own Eligible

Street view of Birch Run Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 3 Baths

2,672 Square Feet

Year Built: 2007

Rent to Own Eligible

Street view of N Water Street Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 3 Baths

Year Built: 1885

Rent to Own Eligible

Street view of Metcalf Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,140 Square Feet

Year Built: 2023

Rent to Own Eligible

Street view of S College Ave Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,216 Square Feet

Year Built: 1900

Rent to Own Eligible

Street view of Malone Ave Chestertown, MD 21620 MLS home

Chestertown, MD 21620

1,200 Square Feet

Year Built: 1962

Rent to Own Eligible

Street view of Greenwood Ave Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,676 Square Feet

Year Built: 2003

Rent to Own Eligible

Street view of S Meadowview Dr Chestertown, MD 21620 MLS home

S Meadowview Dr

Chestertown, MD 21620

3 Beds, 2 Baths

1,509 Square Feet

Year Built: 2002

Rent to Own Eligible

Street view of Birch Run Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 3 Baths

2,208 Square Feet

Year Built: 1984

Rent to Own Eligible

Street view of Lincoln Dr Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 3 Baths

1,632 Square Feet

Year Built: 1965

Rent to Own Eligible

Street view of Barroll Dr Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,820 Square Feet

Year Built: 1986

Rent to Own Eligible

Street view of Chester Arms Dr Chestertown, MD 21620 MLS home

Chester Arms Dr

Chestertown, MD 21620

3 Beds, 2 Baths

1,140 Square Feet

Year Built: 2022

Rent to Own Eligible

Street view of Adela Way Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 4 Baths

5,576 Square Feet

Year Built: 2008

Rent to Own Eligible

Street view of Lincoln Dr Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

960 Square Feet

Year Built: 1966

Rent to Own Eligible

Street view of Washington Ave Chestertown, MD 21620 MLS home

Chestertown, MD 21620

1,454 Square Feet

Year Built: 1956

Rent to Own Eligible

Street view of E Campus Ave Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,532 Square Feet

Year Built: 1963

Rent to Own Eligible

Street view of N College Ave Chestertown, MD 21620 MLS home

Chestertown, MD 21620

1,152 Square Feet

Year Built: 1900

Rent to Own Eligible

Street view of N Queen St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

5 Beds, 3 Baths

3,240 Square Feet

Year Built: 1900

Rent to Own Eligible

Street view of High St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

1,290 Square Feet

Year Built: 1920

Rent to Own Eligible

Street view of Birch Run Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,588 Square Feet

Year Built: 1980

Rent to Own Eligible

Street view of Birch Run Rd Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 2 Baths

1,961 Square Feet

Year Built: 1979

Rent to Own Eligible

Street view of Radcliffe Dr Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 3 Baths

2,736 Square Feet

Year Built: 2011

Rent to Own Eligible

Street view of High St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

5 Beds, 5 Baths

Year Built: 1900

Rent to Own Eligible

Street view of Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 3 Baths

1,420 Square Feet

Year Built: 2023

Rent to Own Eligible

Street view of N Water St Chestertown, MD 21620 MLS home

Chestertown, MD 21620

4 Beds, 5 Baths

5,195 Square Feet

Year Built: 1800

Rent to Own Eligible

Street view of Landing Ln Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 4 Baths

Year Built: 2024

Rent to Own Eligible

Street view of Hilltop Dr Chestertown, MD 21620 MLS home

Chestertown, MD 21620

3 Beds, 3 Baths

2,733 Square Feet

Year Built: 2001

Rent to Own Eligible

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Locations Near Chestertown

Exploring the rent-to-own real estate market in Chestertown, MD is a great alternative housing option. Whether you have bad credit and need time to repair your scores or simply can't afford a large down payment on a traditional home sale, renting to own allows you to rebuild your credit, save money, and build equity all while living in the home you'll eventually own. If you find a house you love, register with RentToOwn.org so you can gain full access to all price, property, and contact information! We look forward to helping you realize your home ownership dreams with Chestertown, MD rent-to-own houses.