Luxury Homes for Rent in Winchester, MA (441 Rentals)

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The most luxurious Homes in Winchester with high-end amenities, features, and finishes.

property at 7 Thornberry Rd

7 Thornberry Rd

WinchesterMA01890
property at 148 Forest St

148 Forest St

WinchesterMA01890
property at 32 Surrey Rd

32 Surrey Rd

WinchesterMA01890
property at 171 Swanton St

171 Swanton St

WinchesterMA01890
property at 39 Clark St

39 Clark St

WinchesterMA01890

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

property at 10 Cedar St

10 Cedar St

WinchesterMA01890
property at 75 Woodfall Rd

75 Woodfall Rd

BelmontMA02478
property at 80 Curtis St

80 Curtis St, Unit 1

80 Curtis St
SomervilleMA02144
property at 80 Curtis St

80 Curtis St

SomervilleMA02144
property at 16 Chetwynd Rd

16 Chetwynd Rd

SomervilleMA02144
property at 16 Chetwynd Rd

16 Chetwynd Rd

SomervilleMA02144
property at 80 Curtis St

80 Curtis St

SomervilleMA02144
property at 16 Chetwynd Rd

16 Chetwynd Rd

SomervilleMA02144
property at 16 Chetwynd Rd

16 Chetwynd Rd

SomervilleMA02144
property at 31 Marsh St

31 Marsh St

BelmontMA02478
property at 232 Fulton St

232 Fulton St

MedfordMA02155
property at 232 Fulton St

232 Fulton St

MedfordMA02155
property at 232 Fulton St

232 Fulton St

MedfordMA02155
property at 232 Fulton St

232 Fulton St

MedfordMA02155
property at 120 Jerome St

120 Jerome St

MedfordMA02155
property at 120 Jerome St

120 Jerome St

MedfordMA02155
property at 232 Fulton St

232 Fulton St

MedfordMA02155
property at 232 Fulton St

232 Fulton St

MedfordMA02155
property at 120 Jerome St

120 Jerome St

MedfordMA02155
property at 22 Belknap St

22 Belknap St

ArlingtonMA02474
property at 17 Tesla Ave

17 Tesla Ave, Unit 2

17 Tesla Ave
MedfordMA02155

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 926 Apartments for Rent in Winchester, MA with pricing that ranges from $1,400 to $12,069. There are also 491 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,700 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 $1,700 to $25,000 with an average monthly rent of $4,773.

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 $2,700 to $12,069, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $6,200. Four Bedroom Single-Family rentals are also available starting from $3,200 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 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.

decorative image for How Your Move-In Inspection Can Protect Your Security Deposit  article

How Your Move-In Inspection Can Protect Your Security Deposit

Written by: Christine Leonard, Esq.

If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.