
5 Bedroom Homes for Rent in Winchester, MA (69 Rentals)


12-0lde Olde Village Dr

186 Ridge St

74 Sharon St

215 Boston Ave, Unit 2

227 Boston Ave

221 Boston Ave, Unit 2

14 Fairmount St, Unit 14.5

14 Fairmount St, Unit 14.5

52 Woods Ave, Unit 2
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

418 Massachusetts Ave, Unit 2

314 Massachusetts Ave, Unit 2

62 Woods Ave, Unit 2

62 Woods Ave

476 Fulton St

476 Fulton St

123 Winthrop St

76 Curtis St, Unit 1

476 Fulton St, Unit 476

476 Fulton St

477 Fulton St, Unit T

476 Fulton St

476 Fulton St, Unit 476

476 Fulton St

476 Fulton St, Unit #0

476 Fulton St

476 Fulton St

76 Curtis St, Unit 1

76 Curtis St, Unit 1

22 Harris Rd, Unit 2

76 Curtis St

14 Fairmount St

14 Fairmount St

76 Curtis St, Unit #1

76 Curtis St

14 Fairmount St

14 Fairmount St, Unit 14.5

14 Fairmount St, Unit 1

57 Quincy St

76 Curtis St, Unit curtis st

76 Curtis St, Unit 1

24 Chetwynd Rd

136 Burget Ave, Unit 1

57 Quincy St, Unit 1

57 Quincy St

57 Quincy St, Unit 57

57 Quincy St, Unit 1

24 Chetwynd Rd, Unit 2

18 Hamilton Rd, Unit 18

6 Farmer Cir
Winchester, MA Local Guide

How much does it cost to rent a home in Winchester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winchester 2 Bedroom Homes for Rent | $2,956 | $2,300 | $4,200 |
Winchester 3 Bedroom Homes for Rent | $3,914 | $2,800 | $7,200 |
Winchester 4 Bedroom Homes for Rent | $4,864 | $3,200 | $7,360 |
Winchester 5 Bedroom Homes for Rent | $6,597 | $4,200 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $7,892 | $5,500 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $9,487 | $7,975 | $10,000+ |
Browse Top Homes for Rent in Winchester
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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 964 Apartments for Rent in Winchester, MA with pricing that ranges from $1,100 to $11,037. There are also 495 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,750 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 $1,750 to $25,000 with an average monthly rent of $4,997.
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 $11,037, 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 $3,200 and Four Bedroom Apartments start at $3,000.
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.

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.

Know Your Rights - How Discrimination Laws Impact Landlords & Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

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.

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.