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$2,2931 Bedroom Apartments Available Now
3 Wainwright Rd, Unit 212
3 Wainwright RdWinchester, MA 01890
Cheap Apartments for Rent in Winchester, MA from $825 (86 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.
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$2,2931 Bedroom Apartments Available Now
3 Wainwright Rd, Unit 203
3 Wainwright RdWinchester, MA 01890
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1 Bedroom Apartments
Elmwood Apartments
2 Elmwood AveWinchester, MA 01890
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$825
Total Monthly Price
Base Rent$825
Total Monthly Price$825
90 North St
90 North StMedford, MA 02155
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$1,600
Total Monthly Price
Base Rent$1,600
Total Monthly Price$1,600
44 Touro Ave, Unit 2
44 Touro AveMedford, MA 02155
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$1,750
Total Monthly Price
Base Rent$1,750
Total Monthly Price$1,750
37 Arlington St, Unit 2F
37 Arlington StWoburn, MA 01801
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$1,795
Total Monthly Price
Base Rent$1,795
Total Monthly Price$1,795
103 Pleasant St, Unit 2
103 Pleasant StWoburn, MA 01801
40 Paul Revere Rd
ArlingtonMA02476
1080 Massachusetts Ave
ArlingtonMA02476
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$1,850
Total Monthly Price
Base Rent$1,850
Total Monthly Price$1,850
21 High St, Unit 2
21 High StSomerville, MA 02144
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$1,850
Total Monthly Price
Base Rent$1,850
Total Monthly Price$1,850
224 Main St, Unit 2
224 Main StWoburn, MA 01801
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$1,895 - $2,585
Total Monthly Price
Base Rent$1,895 - $2,585
Total Monthly Price$1,895 - $2,585
Leisure Lane Apartments
100 Leisure LnStoneham, MA 02180
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Rent Specials
$1,900 - $2,550
Total Monthly Price
Base Rent$1,900 - $2,550
Total Monthly Price$1,900 - $2,550
Brattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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$1,900Studio Apartments Available Oct 7
4 Brattle Dr, Unit 4
4 Brattle DrArlington, MA 02474
993 Massachusetts Ave
ArlingtonMA02476
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Rent Specials
$1,950 - $2,600
Total Monthly Price
Base Rent$1,950 - $2,600
Total Monthly Price$1,950 - $2,600
Mill Street Gardens
57 Mill StWoburn, MA 01801
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$1,950 - $2,375
Total Monthly Price
Base Rent$1,950 - $2,375
Total Monthly Price$1,950 - $2,375
2-15 Winn Park
2-15 Winn ParkWoburn, MA 01801
16 Walnut St
ArlingtonMA02476
80 Cambridge Rd
WoburnMA01801
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$1,995
Total Monthly Price
Base Rent$1,995
Total Monthly Price$1,995
23 Summer St, Unit B
23 Summer 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.
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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
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$2,000 - $2,900
Total Monthly Price
Base Rent$2,000 - $2,900
Total Monthly Price$2,000 - $2,900
HCA - 840-846 Mass Ave
840 Massachusetts AveArlington, MA 02476
167 Summer St
ArlingtonMA02474
80 Cambridge St
WoburnMA01801
6 Wildwood Ln
StonehamMA02180
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$2,100
Total Monthly Price
Base Rent$2,100
Total Monthly Price$2,100
48 Garfield Ave, Unit Woburn Apartment
48 Garfield AveWoburn, MA 01801
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$2,100 - $2,500
Total Monthly Price
Base Rent$2,100 - $2,500
Total Monthly Price$2,100 - $2,500
Old Colony Apartments
1-17 Old Colony LnArlington, MA 02476
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$2,195 - $3,295
Total Monthly Price
Base Rent$2,195 - $3,295
Total Monthly Price$2,195 - $3,295
Tudor Glen Village
111 Locust StWoburn, MA 01801
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$2,200 - $2,400
Total Monthly Price
Base Rent$2,200 - $2,400
Total Monthly PriceVaries
Arlington Gardens
130 Everett StArlington, MA 02474
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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$2,200 - $3,800
Total Monthly Price
Base Rent$2,200 - $3,800
Total Monthly Price$2,200 - $3,800
369 Boston Ave
369 Boston AveMedford, MA 02155
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$2,2001 Bedroom Apartments Available Now
11 Brattle Dr, Unit A
11 Brattle DrArlington, MA 02474
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$2,2001 Bedroom Apartments Available Now
1 Brattle Dr, Unit 12
1 Brattle DrArlington, MA 02474
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$2,2001 Bedroom Apartments Available Nov 1
70 Mill St, Unit 6
70 Mill StWoburn, MA 01801
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$2,2001 Bedroom Apartments Available Now
78 Mill St, Unit 10
78 Mill StWoburn, MA 01801
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$2,2001 Bedroom Apartments Available Nov 3
3 Brattle Dr, Unit 2
3 Brattle DrArlington, MA 02474
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$2,2501 Bedroom Apartments Available Oct 2
1 Brattle Dr, Unit 5
1 Brattle DrArlington, MA 02474
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$2,2502 Bedroom Apartments Available Oct 1
22 High St, Unit 5
22 High StMedford, MA 02155
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$2,2501 Bedroom Apartments Available Now
12 Totman Dr, Unit 9
12 Totman DrWoburn, MA 01801
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$2,2501 Bedroom Apartments Available Now
898 Massachusetts Ave, Unit 23
898 Massachusetts AveArlington, 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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$2,2501 Bedroom Apartments Available Now
1 Brattle Dr, Unit 8
1 Brattle DrArlington, MA 02474
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$2,295
Total Monthly Price
Base Rent$2,295
Total Monthly Price$2,295
628 Main St, Unit 4
628 Main StWoburn, MA 01801
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$2,3001 Bedroom Apartments Available Oct 1
70 Mill St, Unit 2
70 Mill StWoburn, MA 01801
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$2,3001 Bedroom Apartments Available Oct 2
12 Brattle Dr, Unit 5
12 Brattle DrArlington, MA 02474
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$2,3001 Bedroom Apartments Available Now
70 Mill St, Unit 10
70 Mill StWoburn, MA 01801
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$2,300 - $2,350
Total Monthly Price
Base Rent$2,300 - $2,350
Total Monthly Price$2,300 - $2,350
7-1 Kilby St
7 Kilby StWoburn, MA 01801
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$2,3002 Bedroom Apartments Available Now
7 Totman Dr, Unit 1
7 Totman DrWoburn, MA 01801
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$2,3502 Bedroom Apartments Available Now
22 High St, Unit 11
22 High StMedford, MA 02155
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$2,3502 Bedroom Apartments Available Oct 1
22 High St, Unit 4
22 High StMedford, MA 02155
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$2,3752 Bedroom Apartments Available Now
5 Totman Dr, Unit 7
5 Totman DrWoburn, MA 01801
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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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 | $2,362 | $1,875 | $3,322 |
| Cheap Winchester 1 Bedroom Apartments | $2,606 | $825 | $4,315 |
| Cheap Winchester 2 Bedroom Apartments | $3,275 | $2,200 | $5,354 |
| Cheap Winchester 3 Bedroom Apartments | $3,851 | $2,500 | $7,312 |
| Cheap Winchester 4 Bedroom Apartments | $4,753 | $2,900 | $6,750 |
| Winchester 5 Bedroom Apartments | $6,761 | $4,000 | $10,000+ |
| Winchester 6 Bedroom Apartments | $7,822 | $6,300 | $9,600 |
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
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Cheapest Available Winchester Apartments for Rent
The cheapest available apartment rental in Winchester, MA is a 1 Bed unit found at Elmwood Apartments in the Nobility Hill neighborhood priced from $1,900. Mill Street Gardens in the Nobility Hill neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,950. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Elmwood Apartments | Studio 265sf | 1BR, 1BA | $1,900 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR, 1BA | $1,950 |
| 2-15 Winn Park | Studio | Studio, 1BA | $1,950 |
| HCA - 840-846 Mass Ave | Studio | Studio, 1BA | $2,000 |
| Old Colony Apartments | 1 Bedroom | 1BR, 1BA | $2,100 |
| Tudor Glen Village | The Beech | 1BR, 1BA | $2,195 |
Best Value Apartments for Rent in Winchester, MA
As of September 21, 2026 the best value apartment in the Winchester area is the $0.39 price per square foot 89 Hillsdale Rd Model at 89 Hillsdale Rd in the Strawberry Hill neighborhood starting from $3,900. The second greatest value Winchester apartment is the 86 Conwell Ave Model at 86 Conwell Ave, Unit 2 in the Strawberry Hill neighborhood starting at $3,000 with a $0.30 price per square foot. 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. |
|---|---|---|---|
| 89 Hillsdale Rd | 89 Hillsdale Rd | 3BR, 1BA | $0.39 |
| 86 Conwell Ave, Unit 2 | 86 Conwell Ave | 3BR, 1BA | $0.30 |
| 10 Pinkham Rd, Unit 2 | 10 Pinkham Rd | 4BR, 1BA | $0.40 |
| 79 Capen St, Unit 1 | 79 Capen St | 2BR, 1BA | $0.30 |
| 1 Victoria St, Unit 1A | 1 Victoria St | 2BR, 1BA | $0.32 |
| 19 Adams St, Unit 2A | 19 Adams St | 3BR, 2BA | $0.40 |
| 97 W Quincy St, Unit 1 | 97 W Quincy St | 2BR, 1BA | $0.32 |
| 333 Alewife Brook Pky, Unit 3 | 333 Alewife Brook Pky | 3BR, 1BA | $0.29 |
| 158 W Adams St, Unit 2 | 158 W Adams St | 3BR, 1BA | $0.33 |
| 85 Boston Ave, Unit 1 | 85 Boston Ave | 2BR, 1BA | $0.32 |
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 ArticleNavigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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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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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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 2-15 Winn Park listed at $1,950.
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,900 at Elmwood 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 $2,250 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 $3,200.
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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