5 Bedroom Homes for Rent in Winchester, MA (72 Rentals)

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property at 32 Surrey Rd

32 Surrey Rd

WinchesterMA01890
property at 148 Forest St

148 Forest St

WinchesterMA01890
property at 7 Thornberry Rd

7 Thornberry Rd

WinchesterMA01890
property at 74 Sharon St

74 Sharon St

MedfordMA02155

Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

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property at 62 Woods Ave

62 Woods Ave

SomervilleMA02144
property at 123 Winthrop St

123 Winthrop St

MedfordMA02155
property at 476 Fulton St

476 Fulton St

MedfordMA02155
property at 476 Fulton St

476 Fulton St

MedfordMA02155
property at 476 Fulton St

476 Fulton St

MedfordMA02155
property at 76 Curtis St

76 Curtis St, Unit 1

76 Curtis St
SomervilleMA02144
property at 76 Curtis St

76 Curtis St, Unit 1

76 Curtis St
SomervilleMA02144
property at 14 Fairmount St

14 Fairmount St

MedfordMA02155
property at 14 Fairmount St

14 Fairmount St

MedfordMA02155
property at 76 Curtis St

76 Curtis St

SomervilleMA02144
property at 24 Chetwynd Rd

24 Chetwynd Rd

SomervilleMA02144
property at 76 Curtis St

76 Curtis St, Unit 1

76 Curtis St
SomervilleMA02144
Showing Results 1-50, Page 1 of 2

Winchester, MA Local Guide

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Frequently Asked Questions about Winchester

What type of rentals are currently available in Winchester?

There are currently 1000 Apartments for Rent in Winchester, MA with pricing that ranges from $1,100 to $10,400. There are also 560 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,725 to $25,000.

What is the current price range for Rental Homes in Winchester?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $1,725 to $25,000 with an average monthly rent of $4,810.

How much are larger Three and Four Bedroom Rentals in Winchester?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,600 to $7,135, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $7,200. Four Bedroom Single-Family rentals are also available starting from $3,100 and Four Bedroom Apartments start at $3,249.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

The 10 Best Affordable Neighborhoods in Boston, MA

Written by: Amelia Ramstead

Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

decorative image for Renting Smart: Lease Basics Every Renter Needs article

Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

decorative image for Battling the Butts: Your Guide to the Reality of Smoke-Free Renting article

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

decorative image for Understanding Amenity Fees: Know Where You Might Be Able to Save Money article

Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.