
Condos for Rent in Winchester, MA (182 Rentals)


6 Skillings Rd

7 Conant Rd

2 Rangeley Rd

200 Swanton St

200 Swanton St

200 Swanton St

7 Lewis Rd, Unit 2

44 Main St, Unit 504

46 Lowell St, Unit 2
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & 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.

13 Mill St, Unit 1F

339 Massachusetts Ave, Unit 10

3 Brattle Dr, Unit 3

310 Massachusetts Ave, Unit 11

314 Massachusetts Ave, Unit 11

10 Arizona Ter, Unit 4

892 Massachusetts Ave, Unit 50

215 Massachusetts Ave, Unit 47

1 Brattle Dr, Unit 9

79 Mystic St, Unit 2
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28 Rawson Rd, Unit 1

18 Moulton Rd, Unit 2

75 Mystic St, Unit 3

17 Lorne Rd, Unit 17

400 Massachusetts Ave, Unit 4

995 Massachusetts Ave, Unit 403

36 Cambridge Rd, Unit #23

12 Pond Ln, Unit 26

21 Franklin St, Unit 1

37 Westminster Ave, Unit 2
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
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19 Newland Rd, Unit 2

104 Forest St, Unit 104

132 Broadway, Unit 1

116 Medford St, Unit 1

1180 Massachusetts Ave, Unit C

91 Williams St, Unit 91

47 Webster St, Unit 47

2012 Symmes Cir, Unit 1

35 Bowdoin St, Unit 35

422 High St, Unit 10
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

14 Cotting St, Unit 3

177 Central St

289 Elm St, Unit 14

100 Ledgewood Dr, Unit 515

9 Circuit St, Unit 1

24 South St, Unit 2b 2b Medford Square Apt

17 Usher Rd, Unit 3

50 Gould St, Unit 1

4 Golden Ct, Unit 2

12 Pinkham Rd, Unit 1
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
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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 | $2,980 | $2,075 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,969 | $2,600 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $5,143 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,832 | $4,300 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,292 | $5,000 | $10,000+ |
Browse Top Condos for Rent in Winchester
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Winchester, MA Local Guide
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Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
Read ArticleBoston 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 ArticleDon'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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
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 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.
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 530 Apartments for Rent in Winchester, MA with pricing that ranges from $1,200 to $9,300. There are also 342 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,100 to $40,000.
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 $1,100 to $40,000 with an average monthly rent of $4,650.
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 $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $20,000. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $3,000.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

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.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.