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$1,550
Total Monthly Price12 Month Lease Term
Studio Apartment Available Dec 1Total Monthly Price
Base Rent
$1,550
Total Monthly Price
$1,550
219 Washington St, Unit 8
219 Washington StWinchester, MA 01890
Cheap Apartments for Rent in Winchester, MA from $1,100 (42 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.
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$1,150 - $2,850
Total Monthly Price12 Month Lease Term
2 to 4 Bedroom Apartment Available NowTotal Monthly Price
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$1,150 - $2,850
Total Monthly Price
$1,150 - $2,850
2218 Mystic Valley Pky
2218 Mystic Valley PkyMedford, MA 02155
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$1,395
Total Monthly Price9 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,395
Total Monthly Price
$1,395
34 Capen St, Unit 2
34 Capen StMedford, MA 02155
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$1,695 - $2,525
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowLeisure Lane Apartments
100 Leisure LnStoneham, MA 02180
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$1,800 - $2,300
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowBrattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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$1,800
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,800
Total Monthly Price
$1,800
147 Pleasant St, Unit 4
147 Pleasant 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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$1,850 - $2,600
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowOld Colony Apartments
1-17 Old Colony LnArlington, MA 02476
7 Old Colony Ln
ArlingtonMA02476
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$1,895
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,895
Total Monthly Price
$1,895
7 Court St, Unit 1
7 Court StWoburn, MA 01801
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$1,950 - $2,350
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
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$1,950
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,950
Total Monthly Price
$1,950
8 Eastern Ave, Unit Thirdfloor
8 Eastern AveWoburn, MA 01801
4 Colonial Village Dr
ArlingtonMA02474
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.
455 Main St
StonehamMA02180
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$2,000
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Nov 1Total Monthly Price
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$2,000
Total Monthly Price
$2,000
26 Grove St, Unit 6
26 Grove StArlington, MA 02476
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$2,000
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$2,000
Total Monthly Price
$2,000
143 Pleasant St, Unit 1-J
143 Pleasant StWoburn, MA 01801
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$2,000
Plus Fees
Studio Apartments Available Now385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
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$2,050
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,050
Total Monthly Price
$2,050
11 Brattle St, Unit apt 2
11 Brattle StArlington, MA 02476
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4 Old Colony Ln
ArlingtonMA02476
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & 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.
121 Franklin St
StonehamMA02180
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$2,100 - $2,250
Plus Fees
Studio Apartments Available Now119 Pleasant St
119 Pleasant StArlington, MA 02476
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276 Massachusetts Ave
ArlingtonMA02474
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$2,195 - $3,295
Plus Fees
1 to 2 Bedroom Apartments Available NowTudor Glen Village
111 Locust StWoburn, MA 01801
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$2,200 - $2,400
Plus Fees
1 Bedroom Apartments Available Now840 Massachusetts Ave
840 Massachusetts AveArlington, MA 02476
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$2,200
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
4 Colonial Village Dr, Unit 4
4 Colonial Village DrArlington, MA 02474
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$2,200
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Dec 1Arlington Gardens Apartments
130 Everett StArlington, MA 02474
Explore Like a Local: The Insider's Guide to Boston
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$2,200
Plus Fees
1 Bedroom Apartments Available Nov 12898 Massachusetts Ave
898 Massachusetts AveArlington, MA 02476
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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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Showing Results 1-42, 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 | $2,221 | $1,550 | $2,829 |
| Cheap Winchester 1 Bedroom Apartments | $2,659 | $1,395 | $4,195 |
| Cheap Winchester 2 Bedroom Apartments | $3,225 | $2,000 | $5,999 |
| Cheap Winchester 3 Bedroom Apartments | $3,697 | $2,600 | $6,900 |
| Cheap Winchester 4 Bedroom Apartments | $4,575 | $1,150 | $8,000 |
| Winchester 5 Bedroom Apartments | $6,119 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,097 | $5,945 | $8,450 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
See all Apartments in WinchesterExplore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Winchester Apartments for Rent
The cheapest available apartment rental in Winchester, MA is a 1 Bed 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 $1,850. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Leisure Lane Apartments | small 1 bedroom | 1BR,1BA | $1,695 |
| Old Colony Apartments | Studio | Studio,1BA | $1,850 |
| Mass Ave 333-Allen Street Apartments | 1 Bed 1 Bath 650sf | 1BR,1BA | $1,950 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| Brattle Drive Apartments | One Bedroom | 1BR,1BA | $1,950 |
Best Value Apartments for Rent in Winchester, MA
As of October 24, 2025 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 $2,975. The second greatest value Winchester apartment is the 96 Conwell Ave Model at 96 Conwell Ave, Unit 1 starting at $3,000 with a $0.30 price per square foot in the Strawberry Hill 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 |
| 96 Conwell Ave, Unit 1 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 96 Conwell Ave, Unit 2 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 96 Conwell Ave, Unit 1 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.26 |
| 1 Victoria St, Unit #1A | 1 Victoria St | 2BR,1BA | $0.30 |
| 79 Capen St, Unit 1 | 79 Capen St | 2BR,1BA | $0.27 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.26 |
| 29 Capen St, Unit #2 | 29 Capen St | 2BR,1.5BA | $0.30 |
| 8 Cross St, Unit 1 | 8 Cross St | 3BR,1.5BA | $0.30 |
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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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.
Read ArticleDon'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 ArticleThe 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.
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
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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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Getting Around Winchester, MA
Walk Score®
71 / 100
Very Walkable
Most errands can be accomplished on foot
Bike Score®
67 / 100
Bikeable
Some bike infrastructure
Transit Score®
1 / 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 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 $1,750.
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,695 at Leisure Lane Apartments.
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 $2,195 at Leisure Lane 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.
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.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
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.