
Homes for Rent in Winchester, MA (335 Rentals) Page 2 of 7


116 Medford St, Unit 1

1180 Massachusetts Ave, Unit C

91 Williams St, Unit 91

47 Webster St, Unit 47

40 Brattle St

2012 Symmes Cir, Unit 1

13 Garfield Ave

271 Ridge St

22 James St

22 James St

35 Bowdoin St, Unit 35

40 Brattle St

3 Day Cir

14 Brattle Ln

6 Boston Ave

422 High St, Unit 10

14 Cotting St, Unit 3

177 Central St

289 Elm St, Unit 14

100 Ledgewood Dr, Unit 515

9 Circuit St, Unit 1

24 South St, Unit 2b 2b Medford Square Apt

17 Usher Rd, Unit 3

50 Gould St, Unit 1

4 Golden Ct, Unit 2

12 Pinkham Rd, Unit 1

26 Bradlee Rd, Unit 1

44 Winter St

165 Sharon St

258 Boston Ave, Unit 3

112 College Ave, Unit U1

258 Boston Ave, Unit #3

235 Ashcroft Rd

258 Boston Ave, Unit 3

258 Boston Ave, Unit 3

227 Boston Ave, Unit 1

21 Jerome St

46 Winter St, Unit 2

5 Harris Rd, Unit 1

293 Boston Ave, Unit 2

59 Quincy St, Unit 59

59 Quincy St

10 Pinkham Rd, Unit 2

148 George St, Unit 2

10 Pinkham Rd, Unit 2

75 Summer St, Unit 1

5 Harris Rd, Unit 2

5 Harris Rd

5 Harris Rd
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 | $2,988 | $2,075 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,925 | $1,200 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $5,140 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,884 | $4,300 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,479 | $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 534 Apartments for Rent in Winchester, MA with pricing that ranges from $1,200 to $9,300. There are also 335 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,100 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 $1,100 to $40,000 with an average monthly rent of $4,678.
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 $1,200 to $20,000. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $3,000.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

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!

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.