Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,400 (28 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.

Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

Read Article
close
View Me
667 Main St
1 Bedroom Apartments

667 Main St

667 Main StWoburn, MA 01801
  • Utilities Included
close
View Me
Stoneham House
1 to 2 Bedroom Apartments

Stoneham House

180-222 Central StStoneham, MA 02180
  • Utilities Included
close
View Me
411 Main St
1 to 2 Bedroom Apartments

411 Main St

411 Main StStoneham, MA 02180
  • Utilities Included
Showing Results 1-28, Page 1 of 1

Winchester Highlands, Winchester, MA Local Guide

Best Value Apartments for Rent in Winchester Highlands, MA

As of April 16, 2025 the best value apartment in the Winchester Highlands area is the $0.18 price per square foot 36 Montvale Ave Model at 36 Montvale Ave in the in the Walnut Hill neighborhood starting from $1,750. The second greatest value Winchester Highlands apartment is the 480 Fulton St Model at 480 Fulton St, Unit Right starting at $5,300 with a $0.53 price per square foot in the Ferryway neighborhood. Here is today’s list of the best values for Winchester Highlands apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
36 Montvale Ave36 Montvale Ave2BR,1BA$0.18
480 Fulton St, Unit Right480 Fulton St4BR,4.5BA$0.53
14 Richardson St, Unit #14x14 Richardson St2BR,1BA$1.60
159 Franklin St, Unit #D3159 Franklin St2BR,1BA$2.27
2 Fremont St, Unit 12 Fremont St2BR,1BA$1.84
15 Church Ave, Unit #215 Church Ave1BR,1BA$2.00
75 Church St, Unit #R75 Church St1BR,1BA$1.90
35 Montvale Ave35 Montvale Ave2BR,1BA$1.75
224 Main St, Unit 2224 Main St1BR,1BA$2.06
24 Arlington Rd, Unit #R24 Arlington Rd1BR,1BA$2.00

Quick 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.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Winchester Highlands, Winchester, MA

Ranked #3

Among neighborhoods in Winchester, MA for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

decorative image of woman handing cat to small boy

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 Cheap Winchester Highlands Apartments

What is the Cheapest Studio apartment in Winchester Highlands?

Currently the most affordable Cheap Studio Apartment in Winchester Highlands is at Hanover Stoneham listed at $2,380.

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.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

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.

decorative image for Understanding Amenity Fees: Know Where You Might Be Able to Save Money article

Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

decorative image for Know Your Rights - How Discrimination Laws Impact Landlords & Tenants article

Know Your Rights - How Discrimination Laws Impact Landlords & Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

decorative image for Renting Smart: Lease Basics Every Renter Needs article

Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.