
Pet Friendly 2 Bedroom Apartments for Rent in Winchester, MA (54 Rentals)


Sanctuary Winchester North

Washington Crossing Apartments

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The Devon at Weiss Farm

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The Artemis at Arlington Heights

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Hanover Stoneham

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Brigham Square Apartments

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The Mave

Townhomes at 285

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The Legacy at Arlington Center
Pet-Friendly Renting: Everything You Need to Know Before You Move
Finding a pet-friendly apartment is with ease. Learn how to navigate the rental process as a pet owner and build trust with your landlord from day one.

Mill Street Heights

69 Raymond Ave

Brattle Drive Apartments

Mill Street Gardens

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Arlington 360

49 Summer St

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Arlington Gardens

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63 Newport St, Unit 63 Newport Street

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286 Main St, Unit 3

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48 Nashua St
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

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26 Grove St, Unit 12

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165 Radcliffe Rd, Unit #169

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1 Victoria St, Unit 1A

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26 Bradlee Rd, Unit 05

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69 Raymond Ave, Unit 69

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69 Conwell Ave

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22 Bradlee Rd, Unit 405

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79 Capen St, Unit 1

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77 Fairfax St, Unit #1

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1 Victoria St, Unit #1A
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.

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1 Victoria St

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1 Victoria St, Unit 1A

153 North St, Unit #1

926 Massachusetts Ave

83 Webster St

49 Newland Rd

53 Fairfax St

Old Medford Condominiums

Trouvaille

Franklin Condo
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

Hillside Gardens

Brookside Apartments

Lakeside University Apartments

Shaker Glen Village

109 Oxford St

174 Summer St

Arlington Minuteman Towers

Capitol Square Apartments

Arlington Minuteman Towers

Millbrook Square
Renting Smart: Lease Basics Every Renter Needs
Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com
Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Studio Apartments | $2,245 | $1,650 | $2,832 |
| Winchester 1 Bedroom Apartments | $2,705 | $1,110 | $4,724 |
| Winchester 2 Bedroom Apartments | $3,352 | $1,995 | $5,440 |
| Winchester 3 Bedroom Apartments | $3,792 | $950 | $6,297 |
| Winchester 4 Bedroom Apartments | $4,182 | $2,900 | $5,300 |
| Winchester 5 Bedroom Apartments | $6,088 | $4,200 | $10,000+ |
Explore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleBoston 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 ArticleTop 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 ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
Read ArticleQuick 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.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, MA Rentals by Map
See the most popular apartments and homes in Winchester, MA
Frequently Asked Questions about 2 Bedroom Winchester Apartments
What is the Cheapest apartment in Winchester with 2 Bedroom?
Currently the most affordable 2 Bedroom in Winchester is at Mill Street Gardens listed at $2,250.
How much is the average rent for a 2 Bedroom Winchester Apartment?
The average rent for a 2 Bedroom Apartment in Winchester is $3,352.
What is the largest available 2 Bedroom Winchester Apartment for rent?
Today's apartment with the most square footage in Winchester is a 1,500 square feet unit starting from $3,095 at Tudor Glen Village.
What is the average size for Winchester 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Winchester is currently 1,898 sq ft.
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

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.

A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!

Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.