
Pet Friendly Luxury Apartments for Rent in Winchester, MA (83 Rentals)
Pet Friendly Winchester Rentals.
Higher End Luxurious Apartments in Winchester.


Sanctuary Winchester North

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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
What It Really Costs to Live in Boston: A Local Renter’s Guide
Thinking of moving to Boston? Discover the real cost of living in the city. Our local expert guide breaks down rent, hidden utility costs, transportation tips, and neighborhood tradeoffs to help you budget smarter.

Mill Street Heights

69 Raymond Ave

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Arlington 360

Mill Street Gardens

Brattle Drive Apartments

483 Summer Street

14 Belknap St

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37 Fowle St

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11 Garrison Rd, Unit NA

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48 Nashua St, Unit 2
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
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16 Appleton Place

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17 Tesla Ave, Unit B1

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286 Main St, Unit 3

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142 W Adams St, Unit 1

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97 W Quincy St, Unit 1

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81 Conwell Ave, Unit 79 Conwell Avenue

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81 Conwell Ave, Unit 3

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91 Burget Ave, Unit 2

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28 Boston Ave, Unit Modern two floor apartment with old charm

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127 Hillsdale Rd, Unit APT2
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.

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89 Burget Ave, Unit 2

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287 Alewife Brook Pky, Unit 2

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210 Powder House Blvd, Unit 1

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1 Victoria St, Unit 1A

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30 Touro Ave, Unit 1

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35 Whitfield Rd, Unit #3

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69 Conwell Ave

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41 Belknap St, Unit 2

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54 Englehutt Rd, Unit 2

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82 Quincy St, Unit 2
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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.

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22 Bradlee Rd, Unit 405

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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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1 Victoria St

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35 College Ave, Unit 1

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96 Conwell Ave, Unit 1

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96 Conwell Ave, Unit 1

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79 Conwell Ave, Unit 1

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3 Hamilton Rd, Unit 1
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.
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 | $2,437 | $1,650 | $3,350 |
| Winchester 1 Bedroom Apartments | $2,688 | $1,695 | $4,170 |
| Winchester 2 Bedroom Apartments | $3,361 | $2,200 | $5,440 |
| Winchester 3 Bedroom Apartments | $3,663 | $2,600 | $5,994 |
| Winchester 4 Bedroom Apartments | $4,375 | $3,300 | $6,000 |
| Winchester 5 Bedroom Apartments | $6,926 | $4,450 | $10,000+ |
Browse Top Apartments in Winchester
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Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
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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 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 $3,798.
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 2,466 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

What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.

Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!

Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!

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

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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.