
2 Bedroom Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (45 Rentals)


36 Cross St

343 Washington St

Total Monthly Price
The Devon at Weiss Farm
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

Hanover Stoneham

Total Monthly Price
The Mave

Total Monthly Price
Alta Clara

Mill Street Gardens

Lofts at 307 Main LLC

Total Monthly Price
159 Main St

Total Monthly Price
286 Main St, Unit 3

Total Monthly Price
74 Beach St, Unit #3-3

Total Monthly Price
25 Arlington Rd, Unit Apt 1-1
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.

224 Park St

228 Main St

29 Garfield Ave
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.
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.
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 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 | $2,345 | $1,500 | $2,829 |
| Winchester Highlands 1 Bedroom Apartments | $2,803 | $1,895 | $4,195 |
Winchester Highlands 2 Bedroom Apartments | $3,607 | $2,250 | $4,740 |
| Winchester Highlands 3 Bedroom Apartments | $4,467 | $2,500 | $6,900 |
Browse Apartments in this Neighborhood
There are currently 45 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
See all Apartments in WinchesterExplore Winchester
Winchester Highlands, Winchester, MA Local Guide
- Nearby Winchester neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Largest Available Winchester Highlands 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in the Winchester Highlands area of Boston, MA is found at Lofts at 307 Main LLC and is listed at 1,400 square feet priced from $2,995. Here is today’s list of the largest available 2 Bedroom units in the area:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Lofts at 307 Main LLC | 2BR/1.5BA | 1,400 Sq Ft | $2,995 |
| Sanctuary Winchester North | 2J Den | 1,355 Sq Ft | $4,007 |
| Hanover Stoneham | M | 1,322 Sq Ft | $4,618 |
| Alta Clara | 2H | 1,192 Sq Ft | $3,533 |
| The Mave | B2BP | 1,112 Sq Ft | $3,275 |
Cheapest Available Winchester Highlands 2 Bedroom Apartments
Currently the lowest priced 2 Bedroom apartment unit Winchester Highlands of Boston, MA is the 2 Bedroom Model starting from $2,250 at Mill Street Gardens. The average price for all 2 Bedroom apartments in Winchester Highlands is currently $3,607. Here is today’s list of the cheapest available 2 Bedroom options in the area:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Mill Street Gardens | 2 Bedroom | $2,250 |
| Mill Street Heights | D | $2,850 |
| Lofts at 307 Main LLC | 2BR/1.5BA | $2,995 |
| 48 Pleasant Street | 2BR/1.5BA | $2,995 |
| The Mave | B2AP | $3,085 |
| The Devon at Weiss Farm | 2 Bed 2 Bath | $3,253 |
Don'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 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.
Pet Friendly LifestyleWinchester Highlands, Winchester, MA
Ranked #1
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Getting Around the Winchester Highlands Neighborhood in Winchester, MA
Walk Score®
44 / 100
Car-Dependent
Most errands require a car
Bike Score®
65 / 100
Bikeable
Some bike infrastructure
Transit Score®
5 / 100
Minimal Transit
It may be possible to get on a bus
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about 2 Bedroom Winchester Highlands Apartments
What is the Cheapest apartment in Winchester Highlands with 2 Bedroom?
Currently the most affordable 2 Bedroom in Winchester Highlands is at Mill Street Gardens listed at $2,250.
How much is the average rent for a 2 Bedroom Winchester Highlands Apartment?
The average rent for a 2 Bedroom Apartment in Winchester Highlands is $3,607.
What is the largest available 2 Bedroom Winchester Highlands Apartment for rent?
Today's apartment with the most square footage in Winchester Highlands is a 1,400 square feet unit starting from $2,995 at Lofts at 307 Main LLC.
What is the average size for Winchester Highlands 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Winchester Highlands is currently 2,091 sq ft.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

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.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.




























