Rent to own Homes in Winchester, MA

Winchester is a town of just over 21,000 residents in Middlesex County, Massachusetts. Located just eight miles north of Boston, Winchester was an important crossroad of trade between Boston and outlying textile mills. The small town grew prosperous as the Middlesex Canal and the Boston and Lowell Railroad brought many people to the area. Today, the town is known for excellent public schools and scenic views of its waterways.

Winchester, MA is a great place for affordable rent-to-own homes! With a median household income of over $173,058 and a median rent of $2,068, the Winchester, MA 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 Winchester, MA. 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 Winchester, MA rent to own homes for sale, which may include auction properties, for sale by owner, and more.
Showing 1 - 44 of 440
6 Whittier Pl
Rent To Own
 
Townhouse/Condo
Boston, MA 02114
2
2
1272 ft2
1964
1 of 37 9 Hawthorne Pl
Rent To Own
West End
Townhouse/Condo
Boston, MA 02114
1
1
828 ft2
1967
126 G ST #2
Rent To Own
Telegraph Hill
Townhouse/Condo
South Boston, MA 02127
2
1
558 ft2
1900
5 Everett Ave #3
Rent To Own
Uphams Corner - Jones Hill
Single Family Home
Boston, MA 02125
2
1
677 ft2
1935
1 of 10 9 COLONIAL VILLAGE DR
Rent To Own
Arlington Heights
Townhouse/Condo
Arlington, MA 02474
1
1
665 ft2
1962
104 POWDER HOUSE BLVD
Rent To Own
Medford Hillside
Townhouse/Condo
Somerville, MA 02144
5
3
3353 ft2
1800
1 of 6 14 Hallmark Gardens, #10
Rent To Own
Havenville
Multifamily (2 - 4 Units)
Burlington, MA 01803
1
1
725 ft2
1970
34 WINDSOR RD
Rent To Own
Somerville
Townhouse/Condo
Somerville, MA 02144
6
4
3619 ft2
1915
1 of 9 41 & 43 Glenwood Road
Rent To Own
Somerville
Multifamily (2 - 4 Units)
Somerville, MA 02145
6
2
2500 ft2
1900
1 of 5 43 MAGNOLIA ST
Rent To Own
Maplewood
Townhouse/Condo
Malden, MA 02148
5
2
1918 ft2
1900
8 Walnut St APT 8
Rent To Own
Glendale
Single Family Home
Everett, MA 02149
1
1
510 ft2
1920
8 WALNUT ST #10
Rent To Own
Glendale
Townhouse/Condo
Everett, MA 02149
1
1
600 ft2
1920
Hot
1 of 46 32 CAMERON ST
Rent To Own
Glendale
Townhouse/Condo
Everett, MA 02149
8
8
3880 ft2
2018
74 PINE HILL CIR
Rent To Own
Piety Corner
Single Family Home
Waltham, MA 02451
3
4
2620 ft2
2018
1 of 18 372 BUNKER HILL ST
Rent To Own
Medford Street - The Neck
Multifamily (2 - 4 Units)
Charlestown, MA 02129
1
1
520 ft2
1999
1 of 12 85 PEARL ST
Rent To Own
Cambridge
Single Family Home
Cambridge, MA 02139
5
2
1926 ft2
1861
92 chapel st
Rent To Own
Nonantum
Multifamily (2 - 4 Units)
Newton, MA 02458
4
3
2079 ft2
1920
1 of 16 111 Hammond Street, Unit 3
Rent To Own
Highlands
Multifamily (2 - 4 Units)
Waltham, MA 02451
2
2
800 ft2
2004
1 of 9 25 WHITTEMORE RD
Rent To Own
Newton Corner
Single Family Home
Newton, MA 02458
4
2
1432 ft2
1940
1 of 27 38A Charter Street
Rent To Own
North End
Multifamily (2 - 4 Units)
Boston, MA 02113
1
1
478 ft2
1 of 25 40 Kenwood Street
Rent To Own
Coolidge Corner
Multifamily (2 - 4 Units)
Brookline, MA 02446
3
2
1370 ft2
1910
15-17 CUSHMAN RD
Rent To Own
St. Elizabeth's
Townhouse/Condo
Brighton, MA 02135
8
3
2600 ft2
1900
1 of 9 51 Hemenway Street, Unit B1
Rent To Own
Fenway - Kenmore - Audubon Circle - Longwood
Multifamily (2 - 4 Units)
Boston, MA 02115
2
1
643 ft2
1900
43 Westland Ave 409
Rent To Own
Fenway - Kenmore - Audubon Circle - Longwood
Townhouse/Condo
Boston, MA 02115
1
1
847 ft2
2014
45 LONGWOOD AVE #107
Rent To Own
Coolidge Corner
Townhouse/Condo
Brookline, MA 02446
2
2
1430 ft2
1968
1 of 11 70 Clarendon Street, #2
Rent To Own
South End
Multifamily (2 - 4 Units)
Boston, MA 02116
2
1
780 ft2
1 of 29 175 COTTAGE ST #615
Rent To Own
Chelsea
Townhouse/Condo
Chelsea, MA 02150
2
2
1166 ft2
2005
416 Massachusetts Ave G
Rent To Own
South End
Townhouse/Condo
Boston, MA 02118
2
2
1574 ft2
1 of 8 15 Mass Ave
Rent To Own
Billerica
Multifamily (2 - 4 Units)
Nutting Lake, MA 01865
3
2
0 ft2
1968
1 of 24 16 Greenough Street, Unit 1
Rent To Own
 
Multifamily (2 - 4 Units)
Brookline, MA 02445
3
3
2520 ft2
1 of 27 8 AMOS ST
Rent To Own
Tewksbury
Single Family Home
Tewksbury, MA 01876
3
3
2661 ft2
1952
11 CREHORE DR
Rent To Own
Newton Lower Falls
Single Family Home
Newton Lower Falls, MA 02462
5
5
5084 ft2
1952
1 of 2 35-37 HIGH ST
Rent To Own
Newton Upper Falls
Townhouse/Condo
Newton, MA 02464
7
4
4000 ft2
1895
1 of 18 116 N ST
Rent To Own
City Point
Multifamily (2 - 4 Units)
South Boston, MA 02127
2
2
1141 ft2
1910
1 of 33 30 Margin Street
Rent To Own
 
Multifamily (2 - 4 Units)
Lynn, MA 01905
2
3
1430 ft2
1988
44 PARKLAWN RD
Rent To Own
Brook Farm
Single Family Home
West Roxbury, MA 02132
4
2
1716 ft2
1920
11 BELLAIR ST
Rent To Own
Lynn
Townhouse/Condo
Lynn, MA 01902
8
5
4642 ft2
1923
1 of 9 131 A Grew Avenue
Rent To Own
West Street - River Street
Multifamily (2 - 4 Units)
Boston, MA 02053
3
2
1050 ft2
1988
47 GLENWOOD ST
Rent To Own
Lynn
Single Family Home
Lynn, MA 01902
2
2
1226 ft2
1905
1 of 31 16 RIVERVIEW ST
Rent To Own
Riverdale
Single Family Home
Dedham, MA 02026
3
2
1300 ft2
1923
1 of 45 25 APPLEBY RD
Rent To Own
 
Single Family Home
Salem, MA 01970
4
2
2080 ft2
1964
1 of 14 25 MILLSTONE RD
Rent To Own
Readville
Single Family Home
Hyde Park, MA 02136
4
2
1450 ft2
1967
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Buying a Home in Winchester, MA

Winchester, MA is seeing rapid growth and Winchester, MA's' housing market remains not optimal with an average home price that is 345% above the 2024 national average. Winchester, MA is part of Middlesex 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 Middlesex is 1.04% which is above the national average, which is 0.99%.

Median Home Price in Winchester, MA

Median Rent in Winchester, MA

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

Top 6 Reasons to Live in Winchester, MA

Rising home values! The average home value in Winchester is $813,300, up 5.7 percent over the last year. These values are expected to continue to rise in the coming year as well. Winchester Highlands is an affordable neighborhood to look for a rent to own house or a starter home. For more upscale properties, the winding cul de sacs on the west side of Route 3 are filled with lovely, large homes.

Italian restaurants galore! For a small town, Winchester has more than its fair share of great eateries. Italian food lovers are in for a particular treat. From local delis to upscale establishments, Winchester specializes in Italian food. Cafe Piazza Dolce serves up a wide variety of filling paninis, while D'Agostino's Delicatessen is a classic for both hot and cold lunch fare. For a night out, splurge on duck breast prosciutto and rich olive oil cake at A Tavola.

Affordable rents! The average monthly rent in Winchester in 2012 was just $1,393, which is far below the Boston metro area average of $2,200 per month. Stetson Hall on Elm Street is an apartment complex within walking distance from the Commuter Rail station, perfect for getting to and from Boston with ease. A Realtor can guide you to several rental homes on the side streets around Main Street.

Arts and culture! Winchester is home to the Griffin Museum of Photography, a small but impressive rotating collection of photography of all genres and styles. They also host events like book signings, so be sure to check their calendar. The Winchester Historical Society offers programs about architecture and local history at the Sanborn House Historical and Cultural Center, a beaux arts mansion that is currently being restored to its former glory.

Great local shops! In addition to basic grocery stores and pharmacies, Winchester is home to many boutiques and locally-owned small businesses. It's an especially great place for arts-lovers to shop. Mouradian Guitar Co. has both electric and acoustic guitars for sale, and musicians love their years of experience in repairing instruments as well. For crafty types, Another Yarn supplies knitters and crocheters with all the supplies they need to make that next sweater.