
Condos for Rent in Winchester, MA (93 Rentals) Page 2 of 2


333 Massachusetts Ave, Unit 11

15 Governors Ave, Unit 28

898 Massachusetts Ave, Unit 24

15 Governors Ave, Unit 2

49 Broadway, Unit 9

15 Governors Ave, Unit 5

15 Governors Ave, Unit 24
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47 Curtis Ave, Unit 3

15 Governors Ave, Unit 22

47 Curtis Ave, Unit 1

15 Governors Ave, Unit 28

15 Governors Ave, Unit 2

31 Lyman Ave, Unit 1

15 Governors Ave, Unit 5

15 Governors Ave, Unit 24
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380 Place Ln

282 Place Ln

165 Cambridge Rd

9 Ryder St

14 Arizona Terrace

993 Massachusetts Ave

995 Massachusetts Ave

34 Hamilton Rd
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1 Watermill Pl

39-41 Forest St

28 Scituate St

50 Water St

100 High St

2500 Mystic Valley Pkwy

12 Stevens St

7 Hillside Ave
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8 Greenleaf Ave

132 Emerson Gardens Rd

56 Emerson Gardens Rd

661 Lowell St

14 Hamilton Rd

34 Linden St

52 Mt Vernon St, Unit 52

84 Franklin St, Unit 2
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21 Harold St, Unit 2

184 Winthrop St, Unit 2

14 Belknap St, Unit 2
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 Condos for Rent | $3,077 | $2,400 | $4,250 |
| Winchester 3 Bedroom Condos for Rent | $3,635 | $3,200 | $4,600 |
| Winchester 4 Bedroom Condos for Rent | $4,793 | $3,600 | $5,500 |
| Winchester 5 Bedroom Condos for Rent | $5,761 | $5,000 | $7,250 |
| Winchester 6 Bedroom Condos for Rent | $7,307 | $6,495 | $8,700 |
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 399 Apartments for Rent in Winchester, MA with pricing that ranges from $1,650 to $20,951. There are also 263 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,800 to $8,700.
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 $1,800 to $8,700 with an average monthly rent of $4,114.
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 $5,994, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,200 to $4,600. Four Bedroom Single-Family rentals are also available starting from $3,600 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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