74 Sharon St
MedfordMA02155
Cheap Homes for Rent in Winchester, MA from $795 (22 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
13 Center St
WoburnMA01801
73 Hathaway Cir
ArlingtonMA02476
34 Hume Ave
MedfordMA02155
21 Royall St
MedfordMA02155
6 Boston Ave
MedfordMA02155
200 Swanton St, Unit 240
200 Swanton St
WinchesterMA01890
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
74 Beach St, Unit 5-1
74 Beach St
WoburnMA01801
74 Beach St
WoburnMA01801
200 Swanton St, Unit 708
200 Swanton St
WinchesterMA01890
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
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$1,900Studio Apartments Available Oct 7
4 Brattle Dr, Unit 4
4 Brattle DrArlington, MA 02474
15 Governors Ave, Unit 22
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 22
15 Governors Ave
MedfordMA02155
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.
15 Governors Ave, Unit 22
15 Governors Ave
MedfordMA02155
200 Swanton St
WinchesterMA01890
37 South St
MedfordMA02155
35 Prospect St, Unit 311
35 Prospect St
WoburnMA01801
98 Sharon St
MedfordMA02155
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$2,0001 Bedroom Apartments Available Now
167 Summer St, Unit B
167 Summer StArlington, MA 02474
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$2,0001 Bedroom Apartments Available Now
167-169 Summer St #B, Unit #B
167-169 Summer 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.
33 Montvale Ave
WoburnMA01801
Showing Results 1-22, 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 | $2,996 | $1,000 | $4,750 |
| Winchester 3 Bedroom Homes for Rent | $3,844 | $2,900 | $6,000 |
| Winchester 4 Bedroom Homes for Rent | $5,066 | $3,450 | $8,750 |
| Winchester 5 Bedroom Homes for Rent | $7,976 | $4,000 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $10,450 | $7,500 | $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
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Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
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Best Value Homes for Rent in Winchester, MA
As of September 23, 2026 the best value rental home in the Winchester area is the $0.26 price per square foot 177 Central St Model at 177 Central St in the Nobility Hill neighborhood starting from $2,600. The second greatest value Winchester rental home is the 31 Lyman Ave Model at 31 Lyman Ave in the North Medford neighborhood starting at $3,000 with a $0.30 price per square foot. Here is today’s list of the best values for Winchester homes based on price per square foot:
| Home Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 177 Central St | 177 Central St | 2BR, 1BA | $0.26 |
| 31 Lyman Ave | 31 Lyman Ave | 3BR, 1BA | $0.30 |
| 14 Belknap St, Unit 2 | 14 Belknap St | 3BR, 1BA | $0.33 |
| 4 Park St | 4 Park St | 3BR, 2BA | $0.35 |
| 112 College Ave, Unit 1## | 112 College Ave | 3BR, 1BA | $0.40 |
| 14 Sturtevant Ter, Unit 1 | 14 Sturtevant Ter | 4BR, 2BA | $0.56 |
| 98 Sharon St | 98 Sharon St | 1BR, 1BA | $0.67 |
| 2 Glenbrook Ln | 2 Glenbrook Ln | 3BR, 2.5BA | $1.83 |
| 7 Greenleaf Ave, Unit 1 | 7 Greenleaf Ave | 3BR, 1BA | $1.64 |
| 53 Oakland St, Unit TWO | 53 Oakland St | 3BR, 2BA | $1.67 |
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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Quick Rent Budget Calculator
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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 Winchester
What type of rentals are currently available in Winchester?
There are currently 440 Apartments for Rent in Winchester, MA with pricing that ranges from $825 to $12,539. There are also 280 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $795 to $18,000.
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 $795 to $18,000 with an average monthly rent of $3,905.
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 $2,500 to $7,312, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,450 and Four Bedroom Apartments start at $2,900.
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
Written by: Amelia Ramstead
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.
How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.