
Pet Friendly Luxury Apartments for Rent in Winchester, MA (117 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
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.

Mill Street Heights

69 Raymond Ave

Brattle Drive Apartments

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Arlington 360

14 Belknap St

174 Summer St

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8 Eastern Ave, Unit 1st floor, Unit 1st floor

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68 Pleasant St, Unit #1, Unit #1

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21 Chetwynd Rd, Unit 1, Unit 1

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7 Marrigan St, Unit 1, Unit 1
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.

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301 Alewife Brook Pky, Unit 2, Unit 2

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286 Main St, Unit 3, Unit 3

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28 Benham St, Unit 2, Unit 2

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16 Kilby St, Unit 3, Unit 3

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57 Greenleaf Ave, Unit 2, Unit 2

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54 Gordon St, Unit 2B, Unit 2B

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43 Winter St, Unit 1, Unit 1

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206 Massachusetts Ave, Unit 8, Unit 8

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210 Massachusetts Ave, Unit 8, Unit 8

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30 Touro Ave, Unit 1, Unit 1
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.

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80 Quincy St, Unit 1, Unit 1

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165 Radcliffe Rd, Unit #169, Unit #169

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123 Winthrop St, Unit 1, Unit 1

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49 Sunset Rd, Unit 49, Unit 49

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45 Adams St, Unit 1, Unit 1

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149 North St

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14 Quincy St

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291 Alewife Brook Pky, Unit 2, Unit 2

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299 Alewife Brook Pky, Unit 2#E, Unit 2#E

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38 George St, Unit 2, 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.

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35 Whitfield Rd, Unit #3, Unit #3

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65 Conwell Ave, Unit 1L, Unit 1L

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69 Raymond Ave, Unit 69, Unit 69

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229 Boston Ave, Unit 2, Unit 2

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73 Gordon St, Unit 1, Unit 1

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69 Conwell Ave, Unit 1, Unit 1

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104 W Quincy St, Unit 1, Unit 1

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26 Bradlee Rd, Unit 05, Unit 05

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120 Jerome St

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54 Upland Rd, Unit 2, Unit 2
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 Studio Apartments | $2,215 | $1,695 | $3,045 |
| Winchester 1 Bedroom Apartments | $2,735 | $1,700 | $4,250 |
| Winchester 2 Bedroom Apartments | $3,330 | $2,200 | $5,440 |
| Winchester 3 Bedroom Apartments | $3,799 | $2,600 | $6,034 |
| Winchester 4 Bedroom Apartments | $4,347 | $3,100 | $5,500 |
| Winchester 5 Bedroom Apartments | $5,886 | $1,110 | $10,000+ |
| Winchester 6 Bedroom Apartments | $6,944 | $4,450 | $8,400 |
Explore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
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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 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 Brattle Drive Apartments listed at $1,725.
How much is the average rent for a Pet Friendly Winchester Apartment?
The average rent for a Pet Friendly Apartment in Winchester is $3,846.
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 $3,200 at 1 Victoria St, Unit 1A.
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 2,053 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

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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.