
5 Bedroom Homes for Rent in Winchester, MA (56 Rentals)


211 Forest St

62 Woods Ave

227 Boston Ave

190 North St, Unit 2

190 North St, Unit 2

74 Sharon St

65 Conwell Ave, Unit 1

41 Suffolk St

14 Fairmount St
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

76 Curtis St

76 Curtis St, Unit 1

14 Fairmount St, Unit 14.5

479 Fulton St

123 Winthrop St

76 Curtis St, Unit 1

76 Curtis St, Unit 1
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

6 High St, Unit #2

476 Fulton St, Unit 476

476 Fulton St

477 Fulton St, Unit T

76 Curtis St, Unit 1

20 Chetwynd Rd, Unit 2

26 Chetwynd Rd, Unit #2

14 Fairmount St, Unit 1

14 Fairmount St

76 Curtis St
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

14 Fairmount St, Unit 0

14 Fairmount St

14 Fairmount St

14 Fairmount St, Unit 14.5

14 Fairmount St, Unit 1

76 Curtis St, Unit 1

24 Chetwynd Rd

136 Burget Ave

136 Burget Ave

57 Quincy St, Unit 57

57 Quincy St, Unit 1

57 Quincy St, Unit 1
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

5 Sollys Way

162 E Emerson Rd

62 Woods Ave

190 North St

476 Fulton St

45 Wellesley Rd

1 Mauriello Dr

74 Sharon St

41 Suffolk St

474 Fulton St
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

374 Woburn St
Winchester, MA Local Guide

How much does it cost to rent a home in Winchester?
Bedroom | Average Price | Cheapest Price | Highest Price |
---|---|---|---|
Winchester 2 Bedroom Homes for Rent | $3,251 | $2,350 | $6,550 |
Winchester 3 Bedroom Homes for Rent | $3,781 | $2,850 | $6,500 |
Winchester 4 Bedroom Homes for Rent | $4,969 | $3,425 | $8,800 |
Winchester 5 Bedroom Homes for Rent | $6,236 | $4,200 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $8,277 | $5,995 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $8,372 | $6,995 | $9,750 |
Browse Top Homes for Rent in Winchester
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Winchester, MA Local Guide
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Quick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Remember the 3 Rules of Real Estate:Location, Location, Location!
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See the most popular apartments and homes in Winchester, MA
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 663 Apartments for Rent in Winchester, MA with pricing that ranges from $900 to $9,300. There are also 460 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,000 to $40,000.
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 $1,000 to $40,000 with an average monthly rent of $4,877.
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 $2,250 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,850 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,425 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.

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.