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$2,0501 Bedroom Apartments Available Now
2 Elmwood Ave, Unit 1
2 Elmwood AveWinchester, MA 01890
Cheap Apartments for Rent in Winchester, MA from $1,000 (44 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.
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$1,000
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,000
Total Monthly Price
$1,000
16 Quincy St, Unit 2
16 Quincy StMedford, MA 02155
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$1,200 - $2,950
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available Now840-846 Massachusetts Ave
840 Massachusetts AveArlington, MA 02476
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$1,350
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,350
Total Monthly Price
$1,350
14 Brogan Rd, Unit 2
14 Brogan RdMedford, MA 02155
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Rent Specials
$1,650 - $2,550
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available Sep 2Brattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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$1,695
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,695
Total Monthly Price
$1,695
58 Campbell St, Unit 2
58 Campbell StWoburn, MA 01801
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$1,695
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,695
Total Monthly Price
$1,695
58 Campbell St, Unit 2
58 Campbell StWoburn, MA 01801
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$1,695
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,695
Total Monthly Price
$1,695
58 Campbell St, Unit 2
58 Campbell StWoburn, MA 01801
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Moving to Boston? Discover how to handle unique rental rules, avoid common moving day pitfalls, and prepare for your first winter in the city
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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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$1,795 - $2,585
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowLeisure Lane Apartments
100 Leisure LnStoneham, MA 02180
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$1,795
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,795
Total Monthly Price
$1,795
7 Mishawum Rd, Unit B
7 Mishawum RdWoburn, MA 01801
19-21-21 Mt Vernon St
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
103 Pleasant St, Unit 2l
103 Pleasant StWoburn, MA 01801
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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
103 Pleasant St, Unit 2
103 Pleasant StWoburn, MA 01801
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$1,900
Total Monthly Price12 Month Lease Term
Studio Apartment Available Aug 15Total Monthly Price
Base Rent
$1,900
Total Monthly Price
$1,900
14 Massachusetts Ave, Unit Studio
14 Massachusetts AveLexington, MA 02420
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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
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
39 Montvale Ave
WoburnMA01801
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$2,0001 Bedroom Apartments Available Now
167-169 Summer St #B, Unit #B
167-169 Summer StArlington, MA 02474
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$2,0001 Bedroom Apartments Available Now
167 Summer St, Unit B
167 Summer StArlington, MA 02474
167 Summer St
ArlingtonMA02474
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$2,050
Plus Fees1 Month Lease Term
Studio Apartments Available Now2-15 Winn Park
2-15 Winn ParkWoburn, MA 01801
80 Cambridge Rd
WoburnMA01801
80 N Warren St
WoburnMA01801
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$2,100
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,100
Total Monthly Price
$2,100
157 Franklin St, Unit #B2
157 Franklin StStoneham, MA 02180
What It Really Costs to Live in Boston: A Local Renter’s Guide
Thinking of moving to Boston? Discover the real cost of living in the city. Our local expert guide breaks down rent, hidden utility costs, transportation tips, and neighborhood tradeoffs to help you budget smarter.
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$2,100 - $3,300
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartment Available NowTotal 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
77 Fairfax StSomerville, MA 02144
40 Dudley St
ArlingtonMA02476
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$2,1501 Bedroom Apartments Available Now
11 Brattle Dr, Unit 5
11 Brattle DrArlington, MA 02474
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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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$2,2001 Bedroom Apartments Available Now
12 Brattle Dr, Unit 6
12 Brattle DrArlington, MA 02474
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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total 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
1 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
11 Old Colony Ln, Unit #7
11 Old Colony LnArlington, MA 02476
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Find your perfect apartment outside Boston. We review Quincy, Braintree, Malden, Somerville, and Lynn, covering local hotspots, commute options, and available rental types.
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$2,2001 Bedroom Apartments Available Now
12 Brattle Dr, Unit 1
12 Brattle DrArlington, MA 02474
18 Salem St
MedfordMA02155
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1 Bedroom Apartments
667 Main St
667 Main StWoburn, MA 01801
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Studio to 2 Bedroom Apartments
109 Oxford St
109 Oxford StArlington, MA 02474
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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
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
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1 to 2 Bedroom Apartments
Shaker Glen Village
241 Lexington StWoburn, MA 01801
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Studio to 2 Bedroom Apartments
Stoneham House
180-222 Central StStoneham, MA 02180
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Studio to 1 Bedroom Apartments
119 Pleasant St
119 Pleasant StArlington, MA 02476
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1 Bedroom Apartments
Mass Ave 333-Allen Street Apartments
333 Massachusetts AveArlington, MA 02474
Showing Results 1-44, Page 1 of 1
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 | $2,434 | $1,650 | $3,350 |
| Cheap Winchester 1 Bedroom Apartments | $2,662 | $1,350 | $4,070 |
| Cheap Winchester 2 Bedroom Apartments | $3,321 | $2,100 | $5,350 |
| Cheap Winchester 3 Bedroom Apartments | $3,749 | $2,600 | $6,063 |
| Cheap Winchester 4 Bedroom Apartments | $4,340 | $3,300 | $6,000 |
| Winchester 5 Bedroom Apartments | $6,872 | $4,350 | $10,000+ |
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
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Cheapest Available Winchester Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 840-846 Massachusetts Ave | 840 - Studio | Studio,1BA | $1,200 |
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
Best Value Apartments for Rent in Winchester, MA
As of August 07, 2026 the best value apartment in the Winchester area is the $0.78 price per square foot 146 W Adams St Model at 146 W Adams St in the in the Strawberry Hill neighborhood starting from $7,800. The second greatest value Winchester apartment is the 10 Pinkham Rd Model at 10 Pinkham Rd, 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. |
|---|---|---|---|
| 146 W Adams St | 146 W Adams St | 6BR,2BA | $0.78 |
| 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 2 | 24 Chetwynd Rd | 5BR,1BA | $0.62 |
| 17 Tesla Ave, Unit #2 | 17 Tesla Ave | 6BR,3BA | $0.81 |
| 282 Boston Ave, Unit 1 | 282 Boston Ave | 4BR,2BA | $0.48 |
| 35 Whitfield Rd, Unit #3 | 35 Whitfield Rd | 2BR,1BA | $0.33 |
| 77 Fairfax St | 77 Fairfax St | 2BR,1BA | $0.33 |
| 124 Forest St, Unit 3R | 124 Forest St | 3BR,1BA | $0.26 |
| 16 Quincy St, Unit 2 | 16 Quincy St | 6BR,2BA | $0.56 |
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.
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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 840-846 Massachusetts Ave listed at $1,200.
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.
What is the most affordable Winchester Three Bedroom Apartment?
The best deal on a cheap Winchester Three Bedroom Apartment rental is at 14 Belknap St and starts from $3,600.
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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