Cheap Apartments for Rent in the Winchester Town Center Neighborhood of Winchester, MA from $1,800 (30 Rentals)

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

property at 343 Washington St

343 Washington St

WinchesterMA01890

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

property at 200 Swanton St

200 Swanton St

WinchesterMA01890
property at 200 Swanton St

200 Swanton St

WinchesterMA01890
property at 200 Swanton St

200 Swanton St

WinchesterMA01890
property at 6 Skillings Rd

6 Skillings Rd

WinchesterMA01890

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.

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.

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The Artemis at Arlington Heights
Rent Specials
$2,252 - $4,950
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,252 - $4,950

Total Monthly Price
$2,252 - $4,950
Studio to 3 Bedroom Apartments Available Now

The Artemis at Arlington Heights

1163 Massachusetts AveArlington, MA 02476
Affordability
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220 Hancock St, Unit 1
$2,350
Total Monthly Price10 Month Lease Term

Total Monthly Price

Base Rent
$2,350

Total Monthly Price
$2,350
2 Bedroom Apartment Available Now

220 Hancock St, Unit 1

220 Hancock StStoneham, MA 02180
  • Smoke Free
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The Mave
Rent Specials
$2,465 - $4,685
Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,465 - $4,685

Total Monthly Price
$2,465 - $4,685
1 to 2 Bedroom Apartments Available Now

The Mave

225 Fallon RdStoneham, MA 02180
Pet Friendly
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17 Columbus Rd
$2,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500
1 Bedroom Apartment Available Nov 15

17 Columbus Rd

17 Columbus RdWoburn, MA 01801
  • Smoke Free

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.

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8 Cross St, Unit 1
$2,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500
3 Bedroom Apartment Available Now

8 Cross St, Unit 1

8 Cross StWoburn, MA 01801
Cost Per Sq.Ft.

Winchester Town Center, Winchester, MA Local Guide

Cheapest Available Winchester Town Center Apartments for Rent

 

The cheapest available apartment rental in the Winchester Town Center area of Boston, MA is a Studio unit found at Old Colony Apartments priced from $1,850. Tudor Glen Village has the second lowest priced unit, which is a 1 Bed apartment currently listed from $2,195. Here are the most affordable Winchester Town Center apartments for rent in Boston, MA:

Apartment ListingModel NameBed/BathPriced From
Old Colony ApartmentsStudioStudio,1BA$1,850
Tudor Glen VillageThe Cherry1BR,1BA$2,195
Sanctuary Winchester WestA101BR,1BA$2,358

Best Value Apartments for Rent in Winchester Town Center, MA

As of November 03, 2025 the best value apartment in the Winchester Town Center area is the $0.25 price per square foot 8 Cross St Model at 8 Cross St, Unit 1 in the in the Walnut Hill neighborhood starting from $2,500. The second greatest value Winchester Town Center apartment is the 8 Cross St Model at 8 Cross St starting at $2,800 with a $0.28 price per square foot in the Walnut Hill neighborhood. Here is today’s list of the best values for Winchester Town Center apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
8 Cross St, Unit 18 Cross St3BR,1.5BA$0.25
8 Cross St8 Cross St3BR,2BA$0.28
19 Shirley Rd, Unit 1919 Shirley Rd4BR,5BA$1.78
128 Monument St128 Monument St6BR,5BA$2.23
11 Garfield Ave, Unit 111 Garfield Ave4BR,3BA$2.20
224 Arlington St224 Arlington St3BR,2.5BA$1.88
8 Madison St, Unit 18 Madison St2BR,1BA$2.00
286 Main St, Unit 3286 Main St2BR,2BA$2.36
9 Irving St, Unit 29 Irving St3BR,1BA$2.33
220 Hancock St, Unit 1220 Hancock St2BR,1BA$2.14

Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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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.

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The 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.

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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 Town Center, Winchester, MA

Ranked #3

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

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Getting Around the Winchester Town Center Neighborhood in Winchester, MA

Walk Score®

75 / 100

Very Walkable

Most errands can be accomplished on foot

Bike Score®

68 / 100

Bikeable

Some bike infrastructure

Transit Score®

1 / 100

Minimal Transit

It may be possible to get on a bus

Frequently Asked Questions about Cheap Winchester Town Center Apartments

What is the Cheapest Studio apartment in Winchester Town Center?

Currently the most affordable Cheap Studio Apartment in Winchester Town Center is at Old Colony Apartments listed at $1,850.

How much is rent for a Cheap One Bedroom Winchester Town Center Apartment?

The lowest price for a Cheap One Bedroom Winchester Town Center Apartment is $2,195 at Tudor Glen Village.

What is the lowest price for a Cheap Two Bedroom Winchester Town Center Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Winchester Town Center is starting from $2,600 at Old Colony Apartments.

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.

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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.