
Pet Friendly Apartments for Rent in Winchester, MA (156 Rentals)
Apartments for rent in Winchester that love your dogs or cats as much as you do!


Sanctuary Winchester North

Washington Crossing Apartments

Total Monthly Price
The Devon at Weiss Farm

Total Monthly Price
Hanover Stoneham

Total Monthly Price
The Artemis at Arlington Heights

Brigham Square Apartments

Total Monthly Price
The Mave

Mill Street Heights

Brightly Renovated 4-Bed / 2-Bath • 1,800 sq
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.

Total Monthly Price
Arlington 360

Mill Street Gardens

Brattle Drive Apartments

109 Oxford St

14 Belknap St

Total Monthly Price
32A Highland St, Unit 32A Highland St

Total Monthly Price
131 Madison Ave, Unit 1

Total Monthly Price
2232 Mystic Valley Pky, Unit 2

Total Monthly Price
52 Pleasant St, Unit b

Total Monthly Price
67 Fairfax St
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.

Total Monthly Price
286 Massachusetts Ave, Unit #110

Total Monthly Price
227 Boston Ave, Unit 1

Total Monthly Price
207 Boston Ave, Unit B

Total Monthly Price
14 Park Pl, Unit A

Total Monthly Price
15 Century St, Unit 2L

Total Monthly Price
67 Fairfax St, Unit 1

Total Monthly Price
65 Conwell Ave, Unit 3

Total Monthly Price
26 Bradlee Rd, Unit 303T

Total Monthly Price
67 Fairfax St, Unit 67

Total Monthly Price
286 Main St, Unit 3
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.

Total Monthly Price
229 Boston Ave, Unit 2

Total Monthly Price
207 Boston Ave, Unit A

Total Monthly Price
44 Chetwynd Rd, Unit 2

Total Monthly Price
48 Chester Ave, Unit 1

Total Monthly Price
67 Fairfax St

Total Monthly Price
8 Cross St, Unit 1

Total Monthly Price
136 Sharon St, Unit 136

Total Monthly Price
136 Sharon St, Unit 2

Total Monthly Price
96 Conwell Ave, Unit 1

Total Monthly Price
14 Dow St, Unit 2
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

Total Monthly Price
227 Boston Ave, Unit 2

Total Monthly Price
134 N Union St, Unit 1

Total Monthly Price
26 Bradlee Rd, Unit 05

Total Monthly Price
303 Boston Ave, Unit 3

Total Monthly Price
165 Radcliffe Rd, Unit #169

Total Monthly Price
92 North St, Unit 1

Total Monthly Price
96 Conwell Ave, Unit 1

Total Monthly Price
96 Conwell Ave, Unit 1

Total Monthly Price
14 Dow St, Unit 2M

Total Monthly Price
279 Massachusetts Ave, Unit 1
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.
Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Pet Friendly Studio Apartments | $2,112 | $1,665 | $2,720 |
| Winchester Pet Friendly 1 Bedroom Apartments | $2,601 | $1,850 | $4,195 |
| Winchester Pet Friendly 2 Bedroom Apartments | $3,267 | $2,195 | $5,066 |
| Winchester Pet Friendly 3 Bedroom Apartments | $3,677 | $2,500 | $6,900 |
| Winchester Pet Friendly 4 Bedroom Apartments | $4,405 | $950 | $5,600 |
| Winchester 5 Bedroom Apartments | $5,982 | $4,500 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,285 | $5,945 | $8,437 |
Browse Top Apartments in Winchester
See all Apartments in WinchesterExplore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Pet Friendliest Winchester Apartments for Rent
The Winchester Apartment community with the highest ApartmentHomeLiving.com Lifestyle Score for Pet Friendliness is Brigham Square Apartments in the Arlington Center neighborhood with a Pet Friendliness rating of 4 of 4. Washington Crossing Apartments in the Walnut Hill neighborhood ranks second in Pet Friendliness with a score of 3.8 of 4. Here is today’s list of the most Pet Friendly Winchester apartments for rent:
| Apartment Listing | Pet Rating | Neighborhood | Priced From |
|---|---|---|---|
| Brigham Square Apartments | 4/4 | Arlington Center | $2,286 |
| Washington Crossing Apartments | 3.8/4 | Walnut Hill | $2,395 |
| The Legacy at Arlington Center | 3.8/4 | Arlington Center | $2,800 |
| 109 Oxford St | 3.6/4 | East Arlington | $2,400 |
| Mill Street Gardens | 3.6/4 | Walnut Hill | $1,950 |
| Brightly Renovated 4-Bed / 2-Bath • 1,800 sq | 3.4/4 | Medford Hillside | $4,500 |
| 65 Conwell Ave | 3.4/4 | West Somerville | $3,600 |
| 14 Park Pl, Unit A | 3.2/4 | Arlington Heights | $3,800 |
| 63 Raymond Ave | 3.2/4 | West Somerville | $3,200 |
| Arlington Gardens Apartments | 3.2/4 | East Arlington | $2,000 |
Cheapest Pet Friendly Apartment Rentals in Winchester, MA
The lowest priced Winchester apartment at a property that allows pets is the 1 Bedroom 1 Bed Model at Arlington Gardens Apartments in the East Arlington neighborhood starting from $2,000. The second cheapest Winchester Pet Friendly apartment is the The Cherry Model at Tudor Glen Village, which is a 1 Bed starting at $2,195 in the Turning Mill neighborhood. Here are the most affordable Pet Friendly Winchester apartments.
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Arlington Gardens Apartments | 1 Bedroom | $2,000 |
| Tudor Glen Village | The Cherry | $2,195 |
| The Artemis at Arlington Heights | S1A | $2,252 |
| Brigham Square Apartments | Menotomy | $2,286 |
| Washington Crossing Apartments | Charles 1B1B | $2,395 |
| 109 Oxford St | 2 Bed | $2,400 |
| Hanover Stoneham | Fa | $2,431 |
| Arlington 360 | A1.2R | $3,267 |
| Brightly Renovated 4-Bed / 2-Bath • 1,800 sq | 86 Orchard | $4,500 |
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 ArticleDon'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 ArticleThe 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 ArticleCash 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.
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 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 Pet Friendly Winchester Apartments
What is the Cheapest Pet Friendly apartment in Winchester?
Currently the most affordable Pet Friendly Apartment in Winchester is at 195 Forest St listed at $1,000.
How much is the average rent for a Pet Friendly Winchester Apartment?
The average rent for a Pet Friendly Apartment in Winchester is $3,683.
What is the largest Pet Friendly Winchester Apartment for rent?
Today's Pet Friendly apartment with the most square footage in Winchester is a 9,999 square feet unit starting from $4,500 at 1 Victoria St, Unit 2.
What is the average size for Winchester Pet Friendly Apartments for rent?
The average size for a Pet Friendly rental in Winchester is currently at 2,630 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

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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.