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$1,500Studio Apartments Available Now
2 Elmwood Ave, Unit 13
2 Elmwood AveWinchester, MA 01890
Cheap Apartments for Rent in Winchester, MA from $900 (37 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.
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$1,9001 Bedroom Apartments Available Now
2 Elmwood Ave, Unit 22
2 Elmwood AveWinchester, MA 01890
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$2,050Studio Apartments Available Now
2 Elmwood Ave, Unit 53
2 Elmwood AveWinchester, MA 01890
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$2,095
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,095
Total Monthly Price
$2,095
8 Chapin St, Unit #1J, Unit #1J
8 Chapin StWinchester, MA 01890
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$2,095
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$2,095
Total Monthly Price
$2,095
8 Chapin St, Unit 1, Unit 1
8 Chapin StWinchester, MA 01890
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$950
Total Monthly Price3 Month Lease Term
5 Bedroom Apartment Available May 25Total Monthly Price
Base Rent
$950
Total Monthly Price
$950
22 Chetwynd Rd, Unit 2, Unit 2
22 Chetwynd RdSomerville, MA 02144
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$1,110
Total Monthly Price4 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$1,110
Total Monthly Price
$1,110
1011 Massachusetts Ave, Unit 3-room1, Unit 3-room1
1011 Massachusetts AveArlington, MA 02476
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$1,350
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Aug 1Total Monthly Price
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$1,350
Total Monthly Price
$1,350
14 Brogan Rd, Unit 2, Unit 2
14 Brogan RdMedford, MA 02155
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$1,499 - $2,699
Total Monthly Price12 Month Lease Term
1 to 3 Bedroom Apartment Available NowTotal Monthly Price
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$1,499 - $2,699
Total Monthly Price
$1,499 - $2,699
130 Madison Ave
130 Madison AveArlington, MA 02474
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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$1,695 - $2,645
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowLeisure Lane Apartments
100 Leisure LnStoneham, MA 02180
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$1,7001 Bedroom Apartments Available May 15
532 Main St, Unit L
532 Main StWoburn, MA 01801
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$1,700
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
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$1,700
Total Monthly Price
$1,700
111 Boston Ave, Unit B, Unit B
111 Boston AveMedford, MA 02155
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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
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$1,750 - $2,400
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,750 - $2,400
Total Monthly Price
$1,750 - $2,400
48 Nashua St
48 Nashua StWoburn, MA 01801
390 Fellsway W
MedfordMA02155
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$1,780Studio Apartments Available Now
182 Central St, Unit 1
182 Central StStoneham, MA 02180
51 Rangeley Rd
ArlingtonMA02474
48 Warren Ave
WoburnMA01801
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.
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Rent Specials
$1,900 - $2,550
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowBrattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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Rent Specials
$1,950 - $2,600
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
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$1,950Studio Apartments Available Aug 1
15 Governors Ave, Unit 19
15 Governors AveMedford, MA 02155
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$1,9501 Bedroom Apartments Available Jul 2
0 Brattle Dr, Unit 10
0 Brattle DrArlington, MA 02474
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$2,000Studio Apartments Available Now
4 Brattle Dr, Unit 3
4 Brattle DrArlington, MA 02474
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$2,000 - $2,200
Total Monthly Price16 Month Lease Term
1 to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,000 - $2,200
Total Monthly Price
Varies
Arlington Gardens
130 Everett StArlington, MA 02474
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$2,050 - $3,075
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Contact Us For AvailabilityMill Street Heights
59 Mill StWoburn, MA 01801
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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
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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$2,100 - $3,300
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartment Available Jun 1Total Monthly Price
Base Rent
$2,100 - $3,300
Total Monthly Price
$2,100 - $3,300
77 Fairfax St
77 Fairfax StSomerville, MA 02144
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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, Unit #B
77 Fairfax StSomerville, MA 02144
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1 Bedroom Apartments
667 Main St
667 Main StWoburn, MA 01801
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Studio to 2 Bedroom Apartments
Stoneham House
180-222 Central StStoneham, MA 02180
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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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1 Bedroom Apartments
Mass Ave 333-Allen Street Apartments
333 Massachusetts AveArlington, 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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Studio to 1 Bedroom Apartments
119 Pleasant St
119 Pleasant StArlington, MA 02476
Showing Results 1-37, Page 1 of 1
Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cheap Winchester Studio Apartments | $2,188 | $1,500 | $2,825 |
| Cheap Winchester 1 Bedroom Apartments | $2,702 | $1,350 | $4,365 |
| Cheap Winchester 2 Bedroom Apartments | $3,310 | $2,200 | $5,440 |
| Cheap Winchester 3 Bedroom Apartments | $3,907 | $2,699 | $5,950 |
| Cheap Winchester 4 Bedroom Apartments | $4,265 | $3,100 | $5,500 |
| Winchester 5 Bedroom Apartments | $5,684 | $950 | $10,000+ |
| Winchester 6 Bedroom Apartments | $6,908 | $4,450 | $8,400 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
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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 Leisure Lane Apartments in the West Side neighborhood priced from $1,695. 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 |
|---|---|---|---|
| Leisure Lane Apartments | studio | Studio,1BA | $1,695 |
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| Brattle Drive Apartments | Studio | Studio,1BA | $2,000 |
| Mass Ave 333-Allen Street Apartments | 1 Bed 1 Bath 650sf | 1BR,1BA | $2,050 |
| 2-15 Winn Park | Studio | Studio,1BA | $2,050 |
Best Value Apartments for Rent in Winchester, MA
As of May 08, 2026 the best value apartment in the Winchester area is the $0.30 price per square foot 1 Victoria St Model at 1 Victoria St, Unit #1A in the in the Strawberry Hill neighborhood starting from $3,000. The second greatest value Winchester apartment is the 29 Capen St Model at 29 Capen St, Unit #2 starting at $3,000 with a $0.30 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. |
|---|---|---|---|
| 1 Victoria St, Unit #1A | 1 Victoria St | 2BR,1BA | $0.30 |
| 29 Capen St, Unit #2 | 29 Capen St | 2BR,1.5BA | $0.30 |
| 124 Forest St, Unit 2 | 124 Forest St | 3BR,2BA | $0.30 |
| 258 Boston Ave | 258 Boston Ave | 3BR,1BA | $0.37 |
| 10 Pinkham Rd, Unit 2 | 10 Pinkham Rd | 4BR,1BA | $0.40 |
| 1 Victoria St | 1 Victoria St | 4BR,2BA | $0.45 |
| 82 Quincy St, Unit #2 | 82 Quincy St | 4BR,1BA | $0.46 |
| 282 Boston Ave, Unit 2 | 282 Boston Ave | 5BR,2BA | $0.50 |
| 3 Hamilton Rd, Unit #2 | 3 Hamilton Rd | 6BR,4BA | $0.59 |
| 14 Fairmount St, Unit 14.5 | 14 Fairmount St | 5BR,1BA | $0.63 |
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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If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
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Remember the 3 Rules of Real Estate:Location, Location, Location!
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 Leisure Lane Apartments listed at $1,695.
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 Leisure Lane Apartments.
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
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