
Pet Friendly Luxury Apartments for Rent in Winchester, MA (81 Rentals)
Pet Friendly Winchester Rentals.
Higher End Luxurious Apartments in Winchester.


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

14 Belknap St

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51 Russell Rd, Unit NA

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63 Newport St, Unit 63 Newport Street

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286 Main St, Unit 3
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.

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16 Kilby St, Unit 3

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11 Garrison Rd, Unit 11

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38 Sterling St, Unit 2

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7 Marrigan St, Unit 1

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165 Radcliffe Rd, Unit #169

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210 Powder House Blvd, Unit 1

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88 Park Ave, Unit 308

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52 Raymond Ave, Unit 2

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30 Touro Ave, Unit 1

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1 Victoria St, Unit 1A
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
What are amenity fees and are they optional? This guide breaks down everything you need to know about apartment amenity fees, including when you can opt out and how you might be able to lower your rent.

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190 North St, Unit 2

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26 Bradlee Rd, Unit 05

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79 Conwell Ave, Unit 3

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49 Sunset Rd, Unit 49

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65 Conwell Ave, Unit 1L

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69 Raymond Ave, Unit 69

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69 Conwell Ave

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41 Belknap St, Unit 2

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3 Hamilton Rd, Unit #2

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82 Quincy St, Unit 2
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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22 Bradlee Rd, Unit 405

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5 Hamilton Rd, Unit 2

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79 Capen St, Unit 1

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3 Hamilton Rd, Unit 2

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77 Fairfax St, Unit #1

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56 Gordon St, Unit 2

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1 Victoria St, Unit #1A

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1 Victoria St

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1 Victoria St, Unit 1A

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15 Taylor St
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Find your perfect apartment outside Boston. We review Quincy, Braintree, Malden, Somerville, and Lynn, covering local hotspots, commute options, and available rental types.
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 | $2,248 | $1,650 | $2,832 |
| Winchester 1 Bedroom Apartments | $2,696 | $1,110 | $4,215 |
| Winchester 2 Bedroom Apartments | $3,356 | $1,995 | $5,440 |
| Winchester 3 Bedroom Apartments | $3,790 | $950 | $6,297 |
| Winchester 4 Bedroom Apartments | $4,172 | $2,900 | $5,300 |
| Winchester 5 Bedroom Apartments | $6,088 | $4,200 | $10,000+ |
| Winchester 6 Bedroom Apartments | $6,358 | $950 | $8,400 |
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 Pet Friendly Winchester Apartments
What is the Cheapest Pet Friendly apartment in Winchester?
Currently the most affordable Pet Friendly Apartment in Winchester is at Brattle Drive Apartments listed at $1,650.
How much is the average rent for a Pet Friendly Winchester Apartment?
The average rent for a Pet Friendly Apartment in Winchester is $3,834.
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 $3,100 at 1 Victoria St.
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 1,863 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.