Homes for Rent in Winchester, MA (335 Rentals) Page 5 of 7

385 Massachusetts Ave

12 Quincy St

110 Sharon St

258 Boston Ave

86 Orchard St

301-303 Boston Ave Unit #3

86 Orchard St

288 Boston Ave

260 Boston Ave

186 Powder House Blvd

248 Powder House Blvd

56 Gordon St

50 Upland Rd

76 Curtis St

24 Chetwynd Rd

80 Curtis St

0 Green St

46-48-48 Moulton Rd

27 Heath Rd

6 Harris Cir

69 Grove St

2 Viking Ct

3 Day Cir

9 Woodland Ave

50 Franklin St

71 Montvale Ave

71 Montvale Ave

65 Auburn St

72 Marshall St

98 Edward St ##Front Front

585 Lowell St

48 Warren Ave

12 Colonial Village Dr

9 Ryder St

60 Pleasant St

993 Massachusetts Ave

15 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 | $2,988 | $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.












