
Condos for Rent in Winchester, MA (158 Rentals) Page 3 of 4


76 Curtis St

24 Chetwynd Rd, Unit 2

16 Chetwynd Rd

80 Curtis St

16 Chetwynd Rd

4 High St, Unit 1

3 Hamilton Rd, Unit 2

5 Hamilton Rd, Unit 2

3 Hamilton Rd

47 Broadway

31-33 Raymond Ave. Unit 33-2

31-33 Raymond Ave. Unit 33-2

4 Brattle Dr

15 Prospect St

1 Colonial Village Dr

38 George St

385 Massachusetts Ave

123 Winthrop St

385 Massachusetts Ave

385 Massachusetts Ave

38 George St

123 Winthrop St

22 Edison Ave

27 Emery St

79 Capen St

24 Chetwynd Rd

10 Colonial Village Dr

995 Massachusetts Ave

71 Grove St

26 Heath Rd

5 Viking Ct

69 Grove St

67 Grove St

11 Heath Rd

74 Beach St

80 N Warren St

34 Hamilton Rd

47 Mystic St

6 Clark St

2 Stratton Dr

1025 Massachusetts Ave

46 Lombard Terrace

15 Piggott Rd

35 Grandview Ave

71 Montvale Ave

150 Main St

20 Marble St

72 Marshall St

30 High 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 | $2,981 | $2,150 | $5,350 |
| Winchester 3 Bedroom Homes for Rent | $4,078 | $2,300 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $5,026 | $3,425 | $7,000 |
| Winchester 5 Bedroom Homes for Rent | $6,526 | $4,325 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,179 | $6,200 | $10,000+ |
Browse Top Condos 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 465 Apartments for Rent in Winchester, MA with pricing that ranges from $1,110 to $19,835. There are also 254 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,500 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 $1,500 to $28,000 with an average monthly rent of $4,386.
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 $2,300 to $5,761, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,300 to $14,500. Four Bedroom Single-Family rentals are also available starting from $3,425 and Four Bedroom Apartments start at $3,300.
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.
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Articles, How-To's, and Tips

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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.

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Renting your next home can feel thrilling and overwhelming at the same time.

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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.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.