Chester, MA Rent-to-Own Homes & Rental Homes | RentToOwn.org

Search Over 300 Listings Near Chester, MA

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Finding rent-to-own homes in Chester, MA is quick and easy with RentToOwn.org. Our database of rental homes and rent-to-own houses in Chester, MA is regularly updated with a variety of single-family homes, condos, townhomes, and more to suit your needs. In addition to Chester, MA 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 Chester, MA rent-to-own homes has never been easier!

Street view of Eagle St North Adams, MA 01247 Rent-To-Own home

North Adams, MA 01247

1,495 Square Feet

Year Built: 1880

Street view of John St Winsted, CT 06098 Rent-To-Own home

Winsted, CT 06098

3 Beds, 2 Baths

1,538 Square Feet

Year Built: 1900

Street view of Dale St Chicopee, MA 01013 Rent-To-Own home

Chicopee, MA 01013

936 Square Feet

Year Built: 1986

Street view of Silver Brook Ln North Granby, CT 06060 MLS home

Silver Brook Ln

North Granby, CT 06060

5 Beds, 4 Baths

4,332 Square Feet

Year Built: 1995

Rent to Own Eligible

Street view of Center St West Hartland, CT 06091 MLS home

West Hartland, CT 06091

4 Beds, 3 Baths

2,582 Square Feet

Year Built: 1987

Rent to Own Eligible

Street view of Hartland, CT 06027 MLS home

Hartland, CT 06027

4 Beds, 3 Baths

2,163 Square Feet

Year Built: 2025

Rent to Own Eligible

Street view of Mill St Riverton, CT 06065 MLS home

Riverton, CT 06065

3 Beds, 3 Baths

1,896 Square Feet

Year Built: 1988

Rent to Own Eligible

Street view of E River Rd Riverton, CT 06065 MLS home

Riverton, CT 06065

5 Beds, 4 Baths

2,464 Square Feet

Year Built: 1825

Rent to Own Eligible

Street view of Applegate Lane Canton, CT 06109 MLS home

Canton, CT 06109

3 Beds, 3 Baths

2,042 Square Feet

Year Built: 2025

Rent to Own Eligible

Street view of Maple Hollow Rd New Hartford, CT 06057 MLS home

Maple Hollow Rd

New Hartford, CT 06057

1,492 Square Feet

Year Built: 1936

Rent to Own Eligible

Street view of Hamilton Rd East Granby, CT 06026 MLS home

East Granby, CT 06026

3 Beds, 2 Baths

1,564 Square Feet

Year Built: 1957

Rent to Own Eligible

Street view of Prospect Hill Rd Windsor, CT 06095 MLS home

Prospect Hill Rd

Windsor, CT 06095

4 Beds, 3 Baths

2,949 Square Feet

Year Built: 1986

Rent to Own Eligible

Street view of Elm St Winsted, CT 06098 MLS home

Winsted, CT 06098

6 Beds, 2 Baths

2,268 Square Feet

Year Built: 1900

Rent to Own Eligible

Street view of Winburton Rd Torrington, CT 06790 MLS home

Torrington, CT 06790

1,236 Square Feet

Year Built: 1979

Rent to Own Eligible

Street view of Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 2 Baths

1,311 Square Feet

Year Built: 1930

Rent to Own Eligible

Street view of Farmstead Ln West Simsbury, CT 06092 MLS home

West Simsbury, CT 06092

3 Beds, 2 Baths

1,631 Square Feet

Year Built: 1957

Rent to Own Eligible

Street view of Norfolk Rd Winsted, CT 06098 MLS home

Winsted, CT 06098

980 Square Feet

Year Built: 1948

Rent to Own Eligible

Street view of Bloomfield, CT 06002 MLS home

Bloomfield, CT 06002

3 Beds, 3 Baths

1,242 Square Feet

Year Built: 1964

Rent to Own Eligible

Street view of Salmon Brook St Granby, CT 06035 MLS home

Salmon Brook St

Granby, CT 06035

3 Beds, 2 Baths

1,915 Square Feet

Year Built: 1934

Rent to Own Eligible

Street view of Deer Hill Rd Colebrook, CT 06021 MLS home

Colebrook, CT 06021

5 Beds, 3 Baths

3,307 Square Feet

Year Built: 1910

Rent to Own Eligible

Street view of Barry Ln Simsbury, CT 06070 MLS home

Simsbury, CT 06070

3 Beds, 2 Baths

1,722 Square Feet

Year Built: 1952

Rent to Own Eligible

Street view of Little Brook Rd New Hartford, CT 06057 MLS home

Little Brook Rd

New Hartford, CT 06057

960 Square Feet

Year Built: 1965

Rent to Own Eligible

Street view of Winterset Ln Simsbury, CT 06070 MLS home

Simsbury, CT 06070

4 Beds, 3 Baths

2,445 Square Feet

Year Built: 1972

Rent to Own Eligible

Street view of Eastlawn Dr Torrington, CT 06790 MLS home

Torrington, CT 06790

2 Beds, 2 Baths

1,496 Square Feet

Year Built: 1965

Rent to Own Eligible

Street view of Lakeshore Dr New Hartford, CT 06057 MLS home

New Hartford, CT 06057

3 Beds, 2 Baths

1,146 Square Feet

Year Built: 1976

Rent to Own Eligible

Street view of Canton, CT 06019 MLS home

Canton, CT 06019

4 Beds, 3 Baths

1,720 Square Feet

Year Built: 1960

Rent to Own Eligible

Street view of Old Village Cir Windsor, CT 06095 MLS home

Old Village Cir

Windsor, CT 06095

3 Beds, 3 Baths

1,800 Square Feet

Year Built: 2021

Rent to Own Eligible

Street view of Lewis St Tariffville, CT 06081 MLS home

Tariffville, CT 06081

3 Beds, 2 Baths

1,132 Square Feet

Year Built: 1955

Rent to Own Eligible

Street view of Suffield, CT 06078 MLS home

Suffield, CT 06078

1,388 Square Feet

Year Built: 1900

Rent to Own Eligible

Street view of Shingle Mill Dr Collinsville, CT 06019 MLS home

Shingle Mill Dr

Collinsville, CT 06019

4 Beds, 3 Baths

1,800 Square Feet

Year Built: 1973

Rent to Own Eligible

Street view of Evergreen Rd Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 3 Baths

1,978 Square Feet

Year Built: 1980

Rent to Own Eligible

Street view of W Hill Rd Torrington, CT 06790 MLS home

Torrington, CT 06790

1,464 Square Feet

Year Built: 1958

Rent to Own Eligible

Street view of Westwood Dr Simsbury, CT 06070 MLS home

Simsbury, CT 06070

3 Beds, 2 Baths

1,505 Square Feet

Year Built: 1952

Rent to Own Eligible

Street view of Pratt St Winsted, CT 06098 MLS home

Winsted, CT 06098

4 Beds, 2 Baths

2,239 Square Feet

Year Built: 1901

Rent to Own Eligible

Street view of Sunrise Dr Torrington, CT 06790 MLS home

Torrington, CT 06790

1,392 Square Feet

Year Built: 1958

Rent to Own Eligible

Street view of Colebrook Rd Winsted, CT 06098 MLS home

Winsted, CT 06098

2 Beds, 2 Baths

1,323 Square Feet

Year Built: 1940

Rent to Own Eligible

Street view of Ledge Drive Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 2 Baths

1,612 Square Feet

Year Built: 1976

Rent to Own Eligible

Street view of Crane Pl Simsbury, CT 06070 MLS home

Simsbury, CT 06070

3 Beds, 3 Baths

2,520 Square Feet

Year Built: 1979

Rent to Own Eligible

Street view of Timothy Ter Windsor, CT 06095 MLS home

Windsor, CT 06095

4 Beds, 3 Baths

3,526 Square Feet

Year Built: 1981

Rent to Own Eligible

Street view of Greenridge Rd Torrington, CT 06790 MLS home

Torrington, CT 06790

5 Beds, 2 Baths

1,818 Square Feet

Year Built: 1949

Rent to Own Eligible

Street view of Stebbins Brook Ln Simsbury, CT 06070 MLS home

Stebbins Brook Ln

Simsbury, CT 06070

1,056 Square Feet

Year Built: 1914

Rent to Own Eligible

Street view of E Hill Rd Canton, CT 06019 MLS home

Canton, CT 06019

2 Beds, 2 Baths

1,116 Square Feet

Year Built: 1969

Rent to Own Eligible

Street view of Secret Lake Rd Canton, CT 06019 MLS home

Canton, CT 06019

4 Beds, 4 Baths

2,806 Square Feet

Year Built: 1945

Rent to Own Eligible

Street view of Thompson Ct Enfield, CT 06082 MLS home

Enfield, CT 06082

3 Beds, 2 Baths

1,337 Square Feet

Year Built: 1900

Rent to Own Eligible

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Locations Near Chester

Exploring the rent-to-own real estate market in Chester, MA 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 Chester, MA rent-to-own houses.