200 Swanton St, Unit 310
200 Swanton St
WinchesterMA01890
Condos for Rent in Winchester, MA (138 Rentals)
200 Swanton St
WinchesterMA01890
35 Vine St
WinchesterMA01890
31 Irving St
WinchesterMA01890
60 Lake St
WinchesterMA01890
7 Conant Rd
WinchesterMA01890
8 Richardson St
WinchesterMA01890
22 Grove Pl
WinchesterMA01890
269 Cambridge Rd, Unit undisclosed
269 Cambridge Rd
WoburnMA01801
13 Mill St, Unit 2F
13 Mill St
ArlingtonMA02476
Navigating 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.
333 Massachusetts Ave
ArlingtonMA02474
15 Allen St
ArlingtonMA02474
22 Hamilton Rd
ArlingtonMA02474
34 Hamilton Rd, Unit 206
34 Hamilton Rd
ArlingtonMA02474
1 Watermill Pl, Unit 112
1 Watermill Pl
ArlingtonMA02476
72 Harlow St, Unit 72
72 Harlow St
ArlingtonMA02474
4 Park St, Unit 1
4 Park St
ArlingtonMA02474
62 Newport St, Unit 2
62 Newport St
ArlingtonMA02476
2012 Symmes Cir, Unit 1
2012 Symmes Cir
ArlingtonMA02474
61 Wollaston Ave, Unit 61 Wollaston Ave - 2
61 Wollaston Ave
ArlingtonMA02476
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15 Governors Ave, Unit 17
15 Governors Ave
MedfordMA02155
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
35 Century St, Unit 1
35 Century St
MedfordMA02155
40 Sturges St, Unit 1
40 Sturges St
MedfordMA02155
46 Clewley Rd, Unit 3
46 Clewley Rd
MedfordMA02155
29 Harvard Ave, Unit 33
29 Harvard Ave
MedfordMA02155
245 Boston Ave, Unit 3
245 Boston Ave
MedfordMA02155
260 Boston Ave, Unit 1
260 Boston Ave
MedfordMA02155
258 Boston Ave
MedfordMA02155
258 Boston Ave, Unit 3
258 Boston Ave
MedfordMA02155
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95 Capen St, Unit Apt 1
95 Capen St
MedfordMA02155
207 Boston Ave
MedfordMA02155
227 Boston Ave
MedfordMA02155
7 Greenleaf Ave, Unit 1
7 Greenleaf Ave
MedfordMA02155
124 Forest St, Unit 1
124 Forest St
MedfordMA02155
5 Harris Rd
MedfordMA02155
57 Greenleaf Ave, Unit 3
57 Greenleaf Ave
MedfordMA02155
112 College Ave, Unit 1##
112 College Ave
MedfordMA02155
14 Sturtevant Ter
MedfordMA02155
171 Forest St, Unit SF
171 Forest St
MedfordMA02155
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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49 Oakland St, Unit 2
49 Oakland St
MedfordMA02155
14 Fairmount St
MedfordMA02155
355 Boston Ave, Unit 1
355 Boston Ave
MedfordMA02155
10 Greenleaf Ave, Unit 1
10 Greenleaf Ave
MedfordMA02155
10 Pinkham Rd, Unit 2##
10 Pinkham Rd
MedfordMA02155
17 Tesla Ave
MedfordMA02155
120 Jerome St, Unit 1
120 Jerome St
MedfordMA02155
120 Jerome St
MedfordMA02155
43 Pomeworth St, Unit 34
43 Pomeworth St
StonehamMA02180
11 Raymond Ave
SomervilleMA02144
Explore Like a Local: The Insider's Guide to Boston
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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 | $3,079 | $2,100 | $4,500 |
| Winchester 3 Bedroom Homes for Rent | $4,117 | $2,500 | $8,000 |
| Winchester 4 Bedroom Homes for Rent | $5,153 | $1,350 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $8,904 | $4,325 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $10,901 | $6,200 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,400 | $5,300 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Condos for Rent in Winchester
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Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
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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 Article
Top 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.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
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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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, MA Rentals by Map
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 409 Apartments for Rent in Winchester, MA with pricing that ranges from $950 to $10,993. There are also 289 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,050 to $28,000.
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 $1,050 to $28,000 with an average monthly rent of $5,582.
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 $950 to $6,297, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,350 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
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.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.