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 Evergreen Dr Holyoke, MA 01040 Rent-To-Own home

Holyoke, MA 01040

4 Beds, 2 Baths

1,696 Square Feet

Year Built: 1965

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 Mandalay Rd Springfield, MA 01118 Rent-To-Own home

Springfield, MA 01118

4 Beds, 2 Baths

1,800 Square Feet

Year Built: 1870

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 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 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 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 Fox Brook Rd East Hartland, CT 06027 MLS home

East Hartland, CT 06027

1,056 Square Feet

Year Built: 1976

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 Duncaster Rd Bloomfield, CT 06002 MLS home

Bloomfield, CT 06002

2 Beds, 3 Baths

2,115 Square Feet

Year Built: 1940

Rent to Own Eligible

Street view of Margerie St Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 2 Baths

1,560 Square Feet

Year Built: 1927

Rent to Own Eligible

Street view of N Main St Suffield, CT 06078 MLS home

Suffield, CT 06078

5 Beds, 4 Baths

4,816 Square Feet

Year Built: 1892

Rent to Own Eligible

Street view of Curtice St Winsted, CT 06098 MLS home

Winsted, CT 06098

1,248 Square Feet

Year Built: 1908

Rent to Own Eligible

Street view of Gretel Ln Simsbury, CT 06070 MLS home

Simsbury, CT 06070

4 Beds, 3 Baths

2,444 Square Feet

Year Built: 1964

Rent to Own Eligible

Street view of Gillette Rd New Hartford, CT 06057 MLS home

New Hartford, CT 06057

3 Beds, 2 Baths

1,615 Square Feet

Year Built: 1965

Rent to Own Eligible

Street view of Stockade Rd West Simsbury, CT 06092 MLS home

West Simsbury, CT 06092

5 Beds, 4 Baths

3,194 Square Feet

Year Built: 1973

Rent to Own Eligible

Street view of Kearns Cir Granby, CT 06035 MLS home

Granby, CT 06035

5 Beds, 3 Baths

2,701 Square Feet

Year Built: 1952

Rent to Own Eligible

Street view of Meadowlark Rd West Simsbury, CT 06092 MLS home

West Simsbury, CT 06092

4 Beds, 2 Baths

2,266 Square Feet

Year Built: 1985

Rent to Own Eligible

Street view of W Hill Rd New Hartford, CT 06057 MLS home

New Hartford, CT 06057

3 Beds, 2 Baths

2,392 Square Feet

Year Built: 1987

Rent to Own Eligible

Street view of Torrington, CT 06790 MLS home

Torrington, CT 06790

2 Beds, 2 Baths

1,612 Square Feet

Year Built: 1980

Rent to Own Eligible

Street view of Colebrook River Rd Colebrook, CT 06021 MLS home

Colebrook River Rd

Colebrook, CT 06021

1,482 Square Feet

Year Built: 1850

Rent to Own Eligible

Street view of Lionel Dr Simsbury, CT 06070 MLS home

Simsbury, CT 06070

3 Beds, 2 Baths

1,711 Square Feet

Year Built: 1976

Rent to Own Eligible

Street view of Newfield Rd Torrington, CT 06790 MLS home

Torrington, CT 06790

825 Square Feet

Year Built: 1950

Rent to Own Eligible

Street view of Edgewood Dr Torrington, CT 06790 MLS home

Torrington, CT 06790

912 Square Feet

Year Built: 1955

Rent to Own Eligible

Street view of S Stone St West Suffield, CT 06093 MLS home

West Suffield, CT 06093

3 Beds, 2 Baths

1,952 Square Feet

Year Built: 1973

Rent to Own Eligible

Street view of Doman Dr Torrington, CT 06790 MLS home

Torrington, CT 06790

1,152 Square Feet

Year Built: 1988

Rent to Own Eligible

Street view of Newgate Rd West Suffield, CT 06093 MLS home

West Suffield, CT 06093

3 Beds, 2 Baths

1,934 Square Feet

Year Built: 1900

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 W Wakefield Blvd Winsted, CT 06098 MLS home

W Wakefield Blvd

Winsted, CT 06098

4 Beds, 2 Baths

1,781 Square Feet

Year Built: 1904

Rent to Own Eligible

Street view of Cardinal Rd Simsbury, CT 06070 MLS home

Simsbury, CT 06070

4 Beds, 2 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, 2 Baths

2,658 Square Feet

Year Built: 2006

Rent to Own Eligible

Street view of Windsor Ln New Hartford, CT 06057 MLS home

New Hartford, CT 06057

4 Beds, 3 Baths

3,537 Square Feet

Year Built: 2004

Rent to Own Eligible

Street view of Meadow Wood Dr Suffield, CT 06078 MLS home

Suffield, CT 06078

4 Beds, 5 Baths

4,185 Square Feet

Year Built: 1992

Rent to Own Eligible

Street view of Pierce Blvd Windsor, CT 06095 MLS home

Windsor, CT 06095

4 Beds, 3 Baths

3,988 Square Feet

Year Built: 1992

Rent to Own Eligible

Street view of Doman Dr Torrington, CT 06790 MLS home

Torrington, CT 06790

3 Beds, 2 Baths

1,100 Square Feet

Year Built: 1988

Rent to Own Eligible

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

East Granby, CT 06026

3 Beds, 4 Baths

3,692 Square Feet

Year Built: 1978

Rent to Own Eligible

Street view of Enfield, CT 06082 MLS home

Enfield, CT 06082

4 Beds, 2 Baths

1,573 Square Feet

Year Built: 1950

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.