
Pet Friendly Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (34 Rentals)
Apartments for rent in the Winchester Highlands area of Winchester that love your dogs or cats as much as you do!


Total Monthly Price
219 Washington St, Unit 2

171 Swanton St

60 Lake St

41 Cross St

31 Fells Rd

34 Glen Rd

59 Wedgemere Ave
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.

Elmwood Apartments

Total Monthly Price
The Devon at Weiss Farm

Total Monthly Price
Hanover Stoneham

Total Monthly Price
The Mave

Mill Street Heights

Total Monthly Price
Alta Clara

Mill Street Gardens

Total Monthly Price
286 Main St, Unit 3
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.

Total Monthly Price
16 Kilby St, Unit 3

Total Monthly Price
48 Nashua St

33 Montvale Ave, Unit #3

Total Monthly Price
3 Chapel Way, Unit SI ID1387521P

16 Kilby St

21 Spring St

19 Spring St

568 Main St
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.

6 Philips Rd

80 N Warren St

16 Kilby St

Hillside Gardens

Franklin Condo

Stoneham House

38-50 Washington St

Colonial Court
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.

Lakeside University Apartments

Kilby Manor Apartments
Winchester Highlands, Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands Studio Apartments | $2,362 | $1,700 | $2,700 |
| Winchester Highlands 1 Bedroom Apartments | $3,005 | $1,850 | $4,215 |
| Winchester Highlands 2 Bedroom Apartments | $3,665 | $2,200 | $5,440 |
| Winchester Highlands 3 Bedroom Apartments | $3,931 | $950 | $6,704 |
| Winchester Highlands 4 Bedroom Apartments | $3,550 | $2,900 | $4,000 |
Browse Apartments in this Neighborhood
There are currently 34 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
See all Apartments in WinchesterExplore Winchester
Cheapest Pet Friendly Apartment Rentals in Winchester Highlands
The lowest priced apartment unit that allows pets currently in the Winchester Highlands of Winchester Highlands is the 1 Bedroom, 1 Bath Model at Mill Street Gardens, which is a 1 Bed unit starting from $1,950. The second cheapest Winchester Highlands Pet Friendly apartment is the Studio Studio unit at 2-15 Winn Park starting at $2,050. Here are the most affordable Pet Friendly Winchester Highlands apartments:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Mill Street Gardens | 1 Bedroom, 1 Bath | $1,950 |
| 2-15 Winn Park | Studio | $2,050 |
| 44 Montvale Avenue | Studio | $2,380 |
| The Devon at Weiss Farm | Studio | $2,483 |
| Hanover Stoneham | Ca | $2,563 |
| Alta Clara | 1K1 | $3,061 |
| Sanctuary Winchester North | 1A | $3,187 |
| The Mave | B2AP | $3,530 |
Frequently Asked Questions about Pet Friendly Winchester Highlands Apartments
What is the Cheapest Pet Friendly apartment in Winchester Highlands?
Currently the most affordable Pet Friendly Apartment in Winchester Highlands is at 48 Nashua St listed at $1,750.
How much is the average rent for a Pet Friendly Winchester Highlands Apartment?
The average rent for a Pet Friendly Apartment in Winchester Highlands is $3,298.
What is the largest Pet Friendly Winchester Highlands Apartment for rent?
Today's Pet Friendly apartment with the most square footage in Winchester Highlands is a 1,619 square feet unit starting from $3,187 at Sanctuary Winchester North.
What is the average size for Winchester Highlands Pet Friendly Apartments for rent?
The average size for a Pet Friendly rental in Winchester Highlands is currently at 814 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

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.

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.

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.