
Homes for Rent in Winchester, MA (273 Rentals) Page 5 of 6


31-33 Raymond Ave. Unit 33-2, Unit 33-2

31-33 Raymond Ave. Unit 33-2, Unit 33-2

16 Kilby St

62 Newport St

15 Taylor St, Unit 1

4 Brattle Dr, Unit 3

4 Brattle Dr, Unit 6

77 Fairfax St, Unit B

1 Colonial Village Dr, Unit 3

74 Beach St

124 Washington St

80 N Warren St

121 Cambridge Rd

39 Franklin St

4 Kilby St

6 Stratton Dr

9 Gregg St

380 Place Ln

212 Cambridge Rd

99 Garfield Ave

3 Day Cir

71 Grove St

12 Colonial Village Dr

26 Heath Rd

5 Viking Ct

1 Colonial Village Dr

11 Heath Rd

1 Viking Ct

4 Colonial Village Dr

34 Hamilton Rd

47 Mystic St

18 Hamilton Rd

37 Hilton St

23 Menotomy Rd

11 Woodbury St

83 Orient Ave

334 Mystic St

37 Beverly Rd

15 Piggott Rd

52 Cotting St

37 South St

275 Boston Ave

30 High St

288 Boston Ave

123 Winthrop St

478 Fulton St

87 College Ave

120 Jerome St

71 Montvale Ave
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 | $3,001 | $2,299 | $4,900 |
| Winchester 3 Bedroom Homes for Rent | $4,160 | $2,600 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $4,928 | $3,300 | $7,950 |
| Winchester 5 Bedroom Homes for Rent | $7,323 | $1,275 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,488 | $5,497 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $12,000 | $10,000 | $10,000+ |
Browse Top Homes for Rent in Winchester
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 480 Apartments for Rent in Winchester, MA with pricing that ranges from $1,110 to $17,921. There are also 268 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,275 to $28,000.
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 $1,275 to $28,000 with an average monthly rent of $5,511.
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 $6,034, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $16,000. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $1,150.
Expert Rental Resources
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.
Helpful Local Expert Guides

The 10 Best Affordable Neighborhoods in Boston, MA
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.