
Homes for Rent in Winchester, MA (307 Rentals) Page 6 of 7


9 Woodland Ave

15 Piggott Rd

71 Montvale Ave

144 Marble St

157 Franklin St

200 Ledgewood Dr

67 Greenleaf Ave

72 Marshall St

100 High St

78 Orchard St

21A Mystic River Rd

77 Adams St

59 Quincy St

483 Broadway

165 Gaston St

38 Norwich Cir

169 George St

15 Taylor St

28 Webster St

12 Wright St

49 Ripley Rd

33 Ashcroft Rd

478 Fulton St

76 Orchard St

90 Monument St

159 Allston St

87 College Ave

136 Burget Ave

357 Boston Ave

23 Winter St

120 Jerome St

5 Curve St

46 Lowell St

28 Theresa Ave

17 Circle Rd

101 Richmond Rd

135 Maple St

15 Trotting Horse Dr

162 E Emerson Rd

127 Lowell St

75 Woodfall Rd

30 Whipple Rd

23 Thoreau Rd

65 Woods Ave

94 North St

44-46 Woods Ave

56 Gordon St

14 Dow St

4 Old Colony Ln
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 | $2,919 | $2,175 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,681 | $2,800 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $5,010 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,565 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,124 | $6,200 | $10,000+ |
Browse Top Homes for Rent in Winchester
Explore Winchester
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 486 Apartments for Rent in Winchester, MA with pricing that ranges from $1,000 to $9,300. There are also 314 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,500 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 $1,500 to $40,000 with an average monthly rent of $4,480.
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 $2,500 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $1,000.
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

How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!