
Homes for Rent in Winchester, MA (309 Rentals) Page 3 of 7


1 Victoria St

1 Victoria St

88 North St

14 Belknap St, Unit 1

2 High St, Unit 1

32 Irvington Rd

56 Gordon St, Unit 1

52 Raymond Ave, Unit 1

127 Hillsdale Rd, Unit 2

3 Hamilton Rd

50 Curtis Ave

62 Woods Ave, Unit 2##

8 Hamilton Rd

6 Hamilton Rd, Unit 2

62 Woods Ave

14 Hamilton Rd, Unit 14

2 Osgood St, Unit 1

33 Raymond Ave

33 Raymond Ave, Unit 3

301 Alewife Brook Pky

301 Alewife Brook Pky

64 Chetwynd Rd, Unit 1

31 Raymond Ave

76 Curtis St, Unit 1

19 Sunset Rd

3 Hamilton Rd, Unit 2

24 Chetwynd Rd, Unit 2

80 Curtis St

16 Chetwynd Rd

4 High St, Unit 1

3 Hamilton Rd, Unit 2

14 Sturtevant Terrace, Unit 1

15 Bartlett Ave, Unit TH

36 Gould St

286 Main St, Unit 206

92 Sylvia St

182 Central St, Unit 1

19 Adams St

7 Totman Dr, Unit 1

286 Main St, Unit 209

385 Massachusetts Ave, Unit 75

2 Brattle Dr, Unit 7

53 Oakland St, Unit #2

385 Massachusetts Ave, Unit 56

50 Mill St, Unit 11

8 Brattle Dr, Unit 2

0 Brattle Dr, Unit 6

15 Taylor St, Unit #A

898 Massachusetts Ave, Unit 33
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 | $3,178 | $2,150 | $4,500 |
| Winchester 3 Bedroom Homes for Rent | $4,164 | $2,500 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $5,196 | $1,350 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $8,406 | $4,325 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,756 | $6,200 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $12,133 | $5,300 | $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 428 Apartments for Rent in Winchester, MA with pricing that ranges from $900 to $11,104. There are also 301 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,220 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 $1,220 to $28,000 with an average monthly rent of $5,874.
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 $950 to $6,300, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $10,000. Four Bedroom Single-Family rentals are also available starting from $1,350 and Four Bedroom Apartments start at $2,975.
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

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Articles, How-To's, and Tips

Pet-Friendly Renting: Everything You Need to Know Before You Move
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For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
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I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.