2 Bedroom Homes for Rent in Winchester, MA (69 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
property at 6 Skillings Rd

6 Skillings Rd

WinchesterMA01890
property at 40 Dunster Ln

40 Dunster Ln

WinchesterMA01890
property at 7 Conant Rd

7 Conant Rd

WinchesterMA01890
property at 2 Rangeley Rd

2 Rangeley Rd

WinchesterMA01890
property at 7 Lewis Rd

7 Lewis Rd, Unit 2

7 Lewis Rd
WinchesterMA01890
property at 44 Main St

44 Main St, Unit 504

44 Main St
StonehamMA02180
property at 46 Lowell St

46 Lowell St, Unit 2

46 Lowell St
LexingtonMA02420
property at 14 Cotting St

14 Cotting St, Unit 3

14 Cotting St
MedfordMA02155
property at 1 Brattle Dr

1 Brattle Dr, Unit 9

1 Brattle Dr
ArlingtonMA02474
property at 177 Central St

177 Central St

StonehamMA02180

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

property at 100 Ledgewood Dr

100 Ledgewood Dr, Unit 515

100 Ledgewood Dr
StonehamMA02180
property at 289 Elm St

289 Elm St, Unit 14

289 Elm St
MedfordMA02155
property at 79 Mystic St

79 Mystic St, Unit 2

79 Mystic St
ArlingtonMA02474
property at 28 Rawson Rd

28 Rawson Rd, Unit 1

28 Rawson Rd
ArlingtonMA02474
property at 75 Mystic St

75 Mystic St, Unit 3

75 Mystic St
ArlingtonMA02474
property at 17 Lorne Rd

17 Lorne Rd, Unit 17

17 Lorne Rd
ArlingtonMA02476
property at 24 South St
property at 9 Circuit St

9 Circuit St, Unit 1

9 Circuit St
MedfordMA02155
property at 29 Harvard Ave

29 Harvard Ave, Unit 29

29 Harvard Ave
MedfordMA02155
property at 36 Cambridge Rd

36 Cambridge Rd, Unit #23

36 Cambridge Rd
WoburnMA01801

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street

Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

property at 53 Fairfax St

53 Fairfax St, Unit 1

53 Fairfax St
SomervilleMA02144
property at 139 Hillsdale Rd

139 Hillsdale Rd, Unit 2

139 Hillsdale Rd
SomervilleMA02144
property at 12 Pond Ln

12 Pond Ln, Unit 26

12 Pond Ln
ArlingtonMA02474
property at 26 Bradlee Rd

26 Bradlee Rd, Unit 1

26 Bradlee Rd
MedfordMA02155
property at 4 Golden Ct

4 Golden Ct, Unit 2

4 Golden Ct
MedfordMA02155
property at 44 Winter St

44 Winter St

MedfordMA02155
property at 1 Victoria St

1 Victoria St, Unit 1A

1 Victoria St
SomervilleMA02144
property at 19 Newland Rd

19 Newland Rd, Unit 2

19 Newland Rd
ArlingtonMA02474
property at 269 Alewife Brook Pky

269 Alewife Brook Pky, Unit 1

269 Alewife Brook Pky
SomervilleMA02144
property at 104 Forest St

104 Forest St, Unit 104

104 Forest St
ArlingtonMA02474

Explore Like a Local: The Insider's Guide to Boston

Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.

property at 132 Broadway

132 Broadway, Unit 1

132 Broadway
ArlingtonMA02474
property at 235 Ashcroft Rd

235 Ashcroft Rd

MedfordMA02155
property at 1 Victoria St

1 Victoria St, Unit 1A

1 Victoria St
SomervilleMA02144
property at 1180 Massachusetts Ave

1180 Massachusetts Ave, Unit C

1180 Massachusetts Ave
ArlingtonMA02476
property at 2012 Symmes Cir

2012 Symmes Cir, Unit 1

2012 Symmes Cir
ArlingtonMA02474
property at 7 Lily Pond Ln

7 Lily Pond Ln

LexingtonMA02420

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

property at 3 Colonial Village Dr

3 Colonial Village Dr

ArlingtonMA02474
property at 67 Bow St

67 Bow St

ArlingtonMA02474
property at 29 Hammond Pl

29 Hammond Pl

WoburnMA01801

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

Winchester, MA Local Guide

Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

Read Article
Decorative image

Boston Neighborhood Guide: Living Near UMass, MGH, and State Street

Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

Read Article
Decorative image

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
Decorative image

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

Read Article
Decorative image

Top Neighborhoods Near Boston Colleges and Universities

Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com

Read Article
Decorative image

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

decorative image of people with a giant lease agreement

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winchester, MA Rentals by Map

View Map
Winchester, MA Apartments Map
View Map
Winchester, MA Rental Homes Map

Frequently Asked Questions about Winchester

What type of rentals are currently available in Winchester?

There are currently 530 Apartments for Rent in Winchester, MA with pricing that ranges from $1,200 to $9,300. There are also 338 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 $4,661.

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 $5,521, 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.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

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.