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$2,000
Total Monthly Price12 Month Lease Term
Studio Apartment Available Jul 1Total Monthly Price
Base Rent
$2,000
Total Monthly Price
$2,000
219 Washington St, Unit 2
219 Washington StWinchester, MA 01890
Cheap Apartments for Rent in Winchester, MA from $900 (42 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.
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1 Bedroom Apartments
Elmwood Apartments
2 Elmwood AveWinchester, MA 01890
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$9503 Bedroom Apartments Available Now
13 Center St, Unit 2
13 Center StWoburn, MA 01801
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$950
Total Monthly Price2 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$950
Total Monthly Price
$950
24 Chetwynd Rd, Unit Apt 2
24 Chetwynd RdSomerville, MA 02144
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$1,065
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,065
Total Monthly Price
$1,065
6 Munroe St, Unit 2
6 Munroe StWoburn, MA 01801
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Rent Specials
$1,650 - $2,550
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available Jul 2Brattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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$1,650 - $3,500
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available Now109 Oxford St
109 Oxford StArlington, MA 02474
568 Main St
WoburnMA01801
Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Get a local expert's guide to Boston's top 5 short-term rental neighborhoods. Essential tips on Fenway, Beacon Hill, Seaport, and Allston/Brighton.
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$1,750 - $2,450
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$1,750 - $2,450
Total Monthly Price
$1,750 - $2,450
48 Nashua St
48 Nashua StWoburn, MA 01801
390 Fellsway W
MedfordMA02155
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$1,750 - $2,500
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowOld Colony Apartments
1-17 Old Colony LnArlington, MA 02476
16 Garden St
MedfordMA02155
48 Warren Ave
WoburnMA01801
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$1,895 - $2,375
Plus Fees12 Month Lease Term
1 Bedroom Apartments Available Sep 15Leisure Lane Apartments
100 Leisure LnStoneham, MA 02180
1080 Massachusetts Ave
ArlingtonMA02476
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$1,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$1,900
Total Monthly Price
$1,900
14 Massachusetts Ave, Unit Lexington studio
14 Massachusetts AveLexington, MA 02420
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
12 Gould St
StonehamMA02180
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Rent Specials
$1,950 - $2,700
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
11 Main St
WoburnMA01801
19 Spring St
StonehamMA02180
21 Spring St
StonehamMA02180
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$2,050
Plus Fees1 Month Lease Term
Studio Apartments Available Now2-15 Winn Park
2-15 Winn ParkWoburn, MA 01801
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$2,095 - $3,295
Plus Fees
1 to 2 Bedroom Apartments Available NowTudor Glen Village
111 Locust StWoburn, MA 01801
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$2,100
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$2,100
Total Monthly Price
$2,100
77 Fairfax St, Unit #B
77 Fairfax StSomerville, MA 02144
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.
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$2,1501 Bedroom Apartments Available Aug 4
11 Brattle Dr, Unit 5
11 Brattle DrArlington, MA 02474
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$2,1501 Bedroom Apartments Available Now
52 Mill St, Unit 11
52 Mill StWoburn, MA 01801
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$2,200Studio Apartments Available Jul 1
89 College Ave, Unit #3
89 College AveMedford, MA 02155
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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 30Total Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
115 Playstead Rd, Unit 2
115 Playstead RdMedford, MA 02155
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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
491 Main St, Unit 2br apartment
491 Main StWoburn, MA 01801
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$2,200 - $3,300
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,200 - $3,300
Total Monthly Price
$2,200 - $3,300
77 Fairfax St
77 Fairfax StSomerville, MA 02144
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$2,2001 Bedroom Apartments Available Aug 1
22 High St, Unit 1
22 High StMedford, MA 02155
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$2,2001 Bedroom Apartments Available Aug 4
0 Brattle Dr, Unit 6
0 Brattle DrArlington, MA 02474
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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$2,200 - $2,400
Total Monthly Price12 Month Lease Term
1 to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,200 - $2,400
Total Monthly Price
Varies
Arlington Gardens
130 Everett StArlington, MA 02474
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1 Bedroom Apartments
667 Main St
667 Main StWoburn, MA 01801
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1 to 2 Bedroom Apartments
411 Main St
411 Main StStoneham, MA 02180
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1 Bedroom Apartments
71-73 Winn St
71-73 Winn StWoburn, MA 01801
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1 to 2 Bedroom Apartments
Brookside Apartments
5-7-10-12 Totman DrWoburn, MA 01801
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1 Bedroom Apartments
Dudley Street Apartments
15-19 Dudley StArlington, MA 02476
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Studio to 1 Bedroom Apartments
119 Pleasant St
119 Pleasant StArlington, MA 02476
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Studio to 2 Bedroom Apartments
Stoneham House
180-222 Central StStoneham, MA 02180
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.
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Studio to 2 Bedroom Apartments
Mass Ave, 385
385 Massachusetts AveArlington, MA 02474
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1 Bedroom Apartments
Mass Ave 333-Allen Street Apartments
333 Massachusetts AveArlington, MA 02474
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Winchester, MA Local Guide
How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cheap Winchester Studio Apartments | $2,325 | $1,650 | $3,500 |
| Cheap Winchester 1 Bedroom Apartments | $2,762 | $1,750 | $4,215 |
| Cheap Winchester 2 Bedroom Apartments | $3,409 | $1,900 | $5,440 |
| Cheap Winchester 3 Bedroom Apartments | $3,813 | $950 | $6,704 |
| Cheap Winchester 4 Bedroom Apartments | $4,232 | $2,900 | $5,500 |
| Winchester 5 Bedroom Apartments | $6,228 | $4,200 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Winchester, MA Local Guide
- Winchester Neighborhoods
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Cheapest Available Winchester Apartments for Rent
The cheapest available apartment rental in Winchester, MA is a Studio unit found at 109 Oxford St in the East Arlington neighborhood priced from $1,650. Old Colony Apartments in the Rock Meadow neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,750. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 109 Oxford St | Studio, 1 bath | Studio,1BA | $1,650 |
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| 2-15 Winn Park | Studio | Studio,1BA | $2,050 |
| Tudor Glen Village | The Cedar | 1BR,1BA | $2,095 |
| Arlington Gardens | 1B1G | 1BR,1BA | $2,200 |
Best Value Apartments for Rent in Winchester, MA
As of June 22, 2026 the best value apartment in the Winchester area is the $0.64 price per square foot 14 Dow St Model at 14 Dow St, Unit 2 in the in the Strawberry Hill neighborhood starting from $6,350. The second greatest value Winchester apartment is the 56 Gordon St Model at 56 Gordon St, Unit 2 starting at $4,000 with a $0.40 price per square foot in the North Medford neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 14 Dow St, Unit 2 | 14 Dow St | 5BR,2BA | $0.64 |
| 56 Gordon St, Unit 2 | 56 Gordon St | 4BR,1BA | $0.40 |
| 77 Fairfax St | 77 Fairfax St | 2BR,1BA | $0.33 |
| 43 Martin St, Unit 1 | 43 Martin St | 4BR,2BA | $0.44 |
| 124 Forest St, Unit 3B | 124 Forest St | 3BR,1BA | $0.27 |
| 19 Adams St, Unit 2A | 19 Adams St | 3BR,2BA | $0.40 |
| 19 Adams St, Unit 2R | 19 Adams St | 3BR,2BA | $0.40 |
| 10 Pinkham Rd, Unit 2 | 10 Pinkham Rd | 4BR,1BA | $0.40 |
| 1 Victoria St | 1 Victoria St | 4BR,2BA | $0.45 |
| 24 Chetwynd Rd, Unit Apt 2 | 24 Chetwynd Rd | 6BR,2BA | $0.68 |
Boston Neighborhood Guide: Living Near UMass, MGH, and 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.
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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.
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.
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Explore Winchester, MA Rentals by Map
See the most popular apartments and homes in Winchester, MA
Frequently Asked Questions about Cheap Winchester Apartments
What is the Cheapest Studio apartment in Winchester?
Currently the most affordable Cheap Studio Apartment in Winchester is at 109 Oxford St listed at $1,650.
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,950 at Mill Street Gardens.
What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $2,250 at Mill Street Gardens.
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.
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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
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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
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Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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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.
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