Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,100 (35 Rentals)

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

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667 Main St
1 Bedroom Apartments

667 Main St

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

Stoneham House

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

411 Main St

411 Main StStoneham, MA 02180
  • Utilities Included
Showing Results 1-35, Page 1 of 1

Winchester Highlands, Winchester, MA Local Guide

Cheapest Available Winchester Highlands Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
Mill Street Gardens1 Bedroom, 1 Bath1BR,1BA$1,950

Best Value Apartments for Rent in Winchester Highlands, MA

As of June 04, 2025 the best value apartment in the Winchester Highlands area is the $0.48 price per square foot 487 Fulton St Model at 487 Fulton St in the in the Ferryway neighborhood starting from $4,800. The second greatest value Winchester Highlands apartment is the 480 Fulton St Model at 480 Fulton St, Unit 1 starting at $4,995 with a $0.50 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.
487 Fulton St487 Fulton St4BR,4.5BA$0.48
480 Fulton St, Unit 1480 Fulton St4BR,4.5BA$0.50
480 Fulton St, Unit 2480 Fulton St4BR,4.5BA$0.53
482 Fulton St, Unit 1482 Fulton St4BR,4.5BA$0.55
36 Montvale Ave36 Montvale Ave2BR,1BA$0.18
15 Hudson St, Unit R15 Hudson St2BR,1BA$0.31
505 Main St, Unit 1505 Main St3BR,1BA$0.96
30 Pleasant St, Unit 130 Pleasant St1BR,1BA$0.88
75 Church St, Unit #R75 Church St1BR,1BA$1.90
35 Montvale Ave35 Montvale Ave2BR,1BA$1.75

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.

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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

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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 a cheap apartment in Winchester Highlands?

A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Winchester Highlands is under $1,950.

What is the price of a cheap apartment in Winchester Highlands?

The cheapest apartment in Winchester Highlands is Mill Street Gardens which is listed at $1,950, while the average apartment in Winchester Highlands costs $5,295.

What types of apartments are the cheapest in Winchester Highlands?

Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 14 regular apartments in Winchester Highlands that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

How do the prices of cheap apartments compare to the average apartment in Winchester Highlands?

Cheap apartments in Winchester Highlands have an average cost of $460 which is $4,835 cheaper than the average rent for all rentals in Winchester Highlands.

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.

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