
Apartments for Rent in Winchester, MA (471 Rentals)


Sanctuary Winchester North

Total Monthly Price
10 Webster St, Unit 1

Total Monthly Price
3 Glengarry Rd, Unit 3

2 Elmwood Ave, Unit 15

2 Elmwood Ave, Unit 1

10-12-12 Webster St

Washington Crossing Apartments

Total Monthly Price
The Devon at Weiss Farm

Total Monthly Price
The Artemis at Arlington Heights
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.

Total Monthly Price
Hanover Stoneham

Total Monthly Price
Glenbrook Estates

Total Monthly Price
Brigham Square Apartments

Total Monthly Price
The Mave

Townhomes at 285

Tudor Glen Village

Mill Street Heights

Total Monthly Price
The Legacy at Arlington Center

Total Monthly Price
Stonehill Towers

44 Montvale Avenue
Neighborhood & Market Insights: How to Choose the Right Area to Rent
Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

292 Boston Ave

69 Raymond Ave

Brattle Drive Apartments

Mill Street Gardens

Total Monthly Price
Arlington 360

Leisure Lane Apartments

Old Colony Apartments

7-1 Kilby St

49 Summer St

14 Belknap St
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.

Lofts at 307 Main LLC

Total Monthly Price
Arlington Gardens

2-15 Winn Park

840-846 Massachusetts Ave

79 Montvale Ave

Total Monthly Price
51 Russell Rd, Unit NA

Total Monthly Price
25 Arlington Rd, Unit Apt #3 6

Total Monthly Price
63 Newport St, Unit 63 Newport Street

Total Monthly Price
106 Elm St, Unit 106 Elm First Fooor

Total Monthly Price
23 Belknap St, Unit 23
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
125 Hillsdale Rd, Unit 1

Total Monthly Price
125 Hillsdale Rd, Unit First

Total Monthly Price
14 Salem St, Unit 3

Total Monthly Price
27 Orvis Rd, Unit 27 Orvis Rd

Total Monthly Price
159 Main St

Total Monthly Price
286 Main St, Unit 3

Total Monthly Price
66 Cleveland St, Unit 1

Total Monthly Price
56 Gordon St, Unit 2M

Total Monthly Price
16 Kilby St, Unit 3

Total Monthly Price
231 Boston Ave, 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.
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 | $2,272 | $1,650 | $2,825 |
| Winchester 1 Bedroom Apartments | $2,691 | $1,110 | $4,215 |
| Winchester 2 Bedroom Apartments | $3,394 | $1,995 | $5,440 |
| Winchester 3 Bedroom Apartments | $3,814 | $950 | $6,297 |
| Winchester 4 Bedroom Apartments | $4,182 | $2,975 | $5,300 |
| Winchester 5 Bedroom Apartments | $6,024 | $4,500 | $10,000+ |
| Winchester 6 Bedroom Apartments | $6,295 | $950 | $8,400 |
Browse Top Apartments in Winchester
Explore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.
Read Article18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.
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 Winchester
How much are Studio apartments in Winchester?
There are currently 105 Studio Apartments in Winchester with rent ranges from $1,650 to $2,825 with an average price of $2,272.
What is the current price range for One Bedroom Winchester Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $1,110 to $4,215 with an average monthly rent of $2,691.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,995 to $5,440. Today's average rental price for Two Bedrooms here is $3,394.
How expensive are Winchester Three Bedroom Apartments?
There are currently 78 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $950 to $6,297 - averaging $3,814 for the location.
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.

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.

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.