34 Hume Ave
MedfordMA02155
Cheap Homes for Rent in Winchester, MA from $900 (46 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
74 Sharon St
MedfordMA02155
353 Washington St
ArlingtonMA02474
200 Swanton St
WinchesterMA01890
19-21-21 Mt Vernon St, Unit B
19-21-21 Mt Vernon St
ArlingtonMA02476
9 Ryder St
ArlingtonMA02476
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
15 Governors Ave, Unit 22
15 Governors Ave
MedfordMA02155
35 Prospect St
WoburnMA01801
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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$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
4 Arizona Ter, Unit 5
4 Arizona Ter
ArlingtonMA02474
74 Beach St, Unit 5-1
74 Beach St
WoburnMA01801
98 Sharon St
MedfordMA02155
74 Beach St
WoburnMA01801
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$2,0501 Bedroom Apartments Available Now
2 Elmwood Ave, Unit 1
2 Elmwood AveWinchester, MA 01890
200 Swanton St, Unit 412
200 Swanton St
WinchesterMA01890
14 Arizona Terrace
ArlingtonMA02474
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.
8 Mason St
WinchesterMA01890
1 Brattle Dr, Unit 1
1 Brattle Dr
ArlingtonMA02474
333 Massachusetts Ave
ArlingtonMA02474
333 Massachusetts Ave, Unit 11
333 Massachusetts Ave
ArlingtonMA02474
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$2,1501 Bedroom Apartments Available Now
11 Brattle Dr, Unit 5
11 Brattle DrArlington, MA 02474
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$2,1501 Bedroom Apartments Available Sep 1
9 Arizona Terrace
9 Arizona TerraceArlington, MA 02474
15 Governors Ave, Unit 28
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 2
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 2
15 Governors Ave
MedfordMA02155
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.
15 Governors Ave, Unit 28
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 17
15 Governors Ave
MedfordMA02155
11 Old Colony Ln, Unit 7
11 Old Colony Ln
ArlingtonMA02476
200 Swanton St, Unit 228
200 Swanton St
WinchesterMA01890
426 Main St
StonehamMA02180
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$2,2001 Bedroom Apartments Available Now
12 Brattle Dr, Unit 1
12 Brattle DrArlington, MA 02474
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$2,2001 Bedroom Apartments Available Now
12 Brattle Dr, Unit 6
12 Brattle DrArlington, MA 02474
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$2,2501 Bedroom Apartments Available Now
12 Brattle Dr, Unit 10
12 Brattle DrArlington, MA 02474
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
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
2 Brattle Dr, Unit 7
2 Brattle DrArlington, MA 02474
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$2,2501 Bedroom Apartments Available Now
3 Brattle Dr, Unit 10
3 Brattle DrArlington, MA 02474
898 Massachusetts Ave, Unit 23
898 Massachusetts Ave
ArlingtonMA02476
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
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$2,2501 Bedroom Apartments Available Sep 4
1 Brattle Dr, Unit 8
1 Brattle DrArlington, MA 02474
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$2,3001 Bedroom Apartments Available Oct 2
1 Brattle Dr, Unit 6
1 Brattle DrArlington, MA 02474
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$2,3001 Bedroom Apartments Available Sep 2
2 Brattle Dr, Unit 5
2 Brattle DrArlington, MA 02474
995 Massachusetts Ave
ArlingtonMA02476
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$2,3001 Bedroom Apartments Available Now
8 Brattle Dr, Unit 2
8 Brattle DrArlington, MA 02474
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.
20-22 Emerson St
StonehamMA02180
Showing Results 1-46, Page 1 of 1
Winchester, MA Local Guide
How much does it cost to rent a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $3,101 | $2,300 | $4,750 |
| Winchester 3 Bedroom Homes for Rent | $4,129 | $2,900 | $6,500 |
| Winchester 4 Bedroom Homes for Rent | $5,290 | $2,850 | $9,750 |
| Winchester 5 Bedroom Homes for Rent | $8,751 | $4,900 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,941 | $6,495 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winchester
Explore 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 Studio unit found at 840-846 Massachusetts Ave in the Arlington Center neighborhood priced from $1,200. 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 |
|---|---|---|---|
| 840-846 Massachusetts Ave | 840 - Studio | Studio,1BA | $1,200 |
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
Best Value Apartments for Rent in Winchester, MA
As of August 09, 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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See the most popular apartments and homes in Winchester, MA
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 407 Apartments for Rent in Winchester, MA with pricing that ranges from $1,000 to $20,951. There are also 278 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $985 to $20,000.
What is the current price range for Rental Homes in Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $985 to $20,000 with an average monthly rent of $4,687.
How much are larger Three and Four Bedroom Rentals in Winchester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,600 to $6,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,850 and Four Bedroom Apartments start at $3,300.
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.
Helpful Local Expert Guides
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
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Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!
Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
Articles, How-To's, and Tips
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.