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 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 Center St West Hartland, CT 06091 MLS home

West Hartland, CT 06091

4 Beds, 2 Baths

1,666 Square Feet

Year Built: 1967

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 Dara Ln North Granby, CT 06060 MLS home

North Granby, CT 06060

3 Beds, 2 Baths

1,704 Square Feet

Year Built: 1977

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 Woodlawn Ave Enfield, CT 06082 MLS home

Enfield, CT 06082

3 Beds, 2 Baths

1,665 Square Feet

Year Built: 1945

Rent to Own Eligible

Street view of Cardinal Rd Simsbury, CT 06070 MLS home

Simsbury, CT 06070

4 Beds, 3 Baths

2,343 Square Feet

Year Built: 1967

Rent to Own Eligible

Street view of Glendale Ave Winsted, CT 06098 MLS home

Winsted, CT 06098

1,114 Square Feet

Year Built: 1955

Rent to Own Eligible

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

Canton, CT 06019

4 Beds, 3 Baths

2,246 Square Feet

Year Built: 1976

Rent to Own Eligible

Street view of Stanton Ave Winsted, CT 06098 MLS home

Winsted, CT 06098

1,594 Square Feet

Year Built: 1923

Rent to Own Eligible

Street view of Norfolk Rd Torrington, CT 06790 MLS home

Torrington, CT 06790

4 Beds, 2 Baths

1,810 Square Feet

Year Built: 1981

Rent to Own Eligible

Street view of Bigelow Ave Enfield, CT 06082 MLS home

Enfield, CT 06082

7 Beds, 5 Baths

3,076 Square Feet

Year Built: 1920

Rent to Own Eligible

Street view of Meg Way Windsor Locks, CT 06096 MLS home

Windsor Locks, CT 06096

4 Beds, 4 Baths

2,658 Square Feet

Year Built: 2006

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 Reed St Canaan, CT 06018 MLS home

Canaan, CT 06018

3 Beds, 2 Baths

1,086 Square Feet

Year Built: 1900

Rent to Own Eligible

Street view of Christmas Tree Hl Canton, CT 06019 MLS home

Christmas Tree Hl

Canton, CT 06019

3 Beds, 3 Baths

2,662 Square Feet

Year Built: 1981

Rent to Own Eligible

Street view of Colebrook Rd Winsted, CT 06098 MLS home

Winsted, CT 06098

3 Beds, 2 Baths

1,510 Square Feet

Year Built: 1923

Rent to Own Eligible

Street view of Cardinal Cir Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 3 Baths

2,080 Square Feet

Year Built: 1999

Rent to Own Eligible

Street view of New King St Enfield, CT 06082 MLS home

Enfield, CT 06082

6 Beds, 2 Baths

2,229 Square Feet

Year Built: 1900

Rent to Own Eligible

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

Salmon Brook St

Granby, CT 06035

3 Beds, 3 Baths

2,481 Square Feet

Year Built: 1860

Rent to Own Eligible

Street view of Lynn Ln Windsor Locks, CT 06096 MLS home

Windsor Locks, CT 06096

3 Beds, 2 Baths

1,184 Square Feet

Year Built: 1959

Rent to Own Eligible

Street view of Hopmeadow St Weatogue, CT 06089 MLS home

Weatogue, CT 06089

3 Beds, 4 Baths

2,346 Square Feet

Year Built: 1938

Rent to Own Eligible

Street view of Sunset Ridge Rd Norfolk, CT 06058 MLS home

Sunset Ridge Rd

Norfolk, CT 06058

5 Beds, 2 Baths

2,304 Square Feet

Year Built: 1907

Rent to Own Eligible

Street view of Ridge Blvd East Granby, CT 06026 MLS home

East Granby, CT 06026

4 Beds, 3 Baths

2,662 Square Feet

Year Built: 1995

Rent to Own Eligible

Street view of Carriage Dr Burlington, CT 06013 MLS home

Burlington, CT 06013

4 Beds, 3 Baths

2,399 Square Feet

Year Built: 1977

Rent to Own Eligible

Street view of Windtree St Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 2 Baths

2,107 Square Feet

Year Built: 1973

Rent to Own Eligible

Street view of Musket Trl Simsbury, CT 06070 MLS home

Simsbury, CT 06070

4 Beds, 3 Baths

3,467 Square Feet

Year Built: 1968

Rent to Own Eligible

Street view of Leslie St Windsor Locks, CT 06096 MLS home

Windsor Locks, CT 06096

3 Beds, 2 Baths

1,924 Square Feet

Year Built: 1966

Rent to Own Eligible

Street view of East Granby, CT 06026 MLS home

East Granby, CT 06026

2 Beds, 2 Baths

1,080 Square Feet

Year Built: 1964

Rent to Own Eligible

Street view of Spring St Windsor Locks, CT 06096 MLS home

Windsor Locks, CT 06096

2 Beds, 2 Baths

960 Square Feet

Year Built: 1959

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 Wildwood Rd Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 2 Baths

1,920 Square Feet

Year Built: 1959

Rent to Own Eligible

Street view of Spring St Enfield, CT 06082 MLS home

Enfield, CT 06082

5 Beds, 4 Baths

2,153 Square Feet

Year Built: 1900

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 Winburton Rd Torrington, CT 06790 MLS home

Torrington, CT 06790

1,236 Square Feet

Year Built: 1979

Rent to Own Eligible

Street view of Danbury Quarter Rd Winsted, CT 06098 MLS home

Danbury Quarter Rd

Winsted, CT 06098

4 Beds, 2 Baths

1,999 Square Feet

Year Built: 1800

Rent to Own Eligible

Street view of Oak Meadow Lane Torrington, CT 06791 MLS home

Oak Meadow Lane

Torrington, CT 06791

2 Beds, 4 Baths

2,964 Square Feet

Year Built: 2007

Rent to Own Eligible

Street view of Tarlton St Torrington, CT 06790 MLS home

Torrington, CT 06790

826 Square Feet

Year Built: 1939

Rent to Own Eligible

Street view of Trotters Way Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 3 Baths

1,848 Square Feet

Year Built: 1989

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.