
Condos for Rent in Winchester, MA (307 Rentals)


247 Washington St, Unit 13

40 Florence St, Unit 2

200 Swanton St

35 Vine St

171 Swanton St

29 Harvard Ave, Unit 33

2500 Mystic Valley Pky, Unit 702

19 Arizona Ter
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.

35 Prospect St, Unit 35 Prospect St # 102

1 Brattle Dr, Unit 1

215 Massachusetts Ave, Unit 47

3 Brattle Dr, Unit 8

7 Arizona Ter, Unit 2

215 Massachusetts Ave, Unit 1

220 Massachusetts Ave, Unit 3

215 Massachusetts Ave, Unit 19
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

79 Mystic St, Unit 2

75 Mystic St, Unit 3

22 Scott St, Unit 1

400 Massachusetts Ave, Unit 4

1180 Massachusetts Ave, Unit C

42 Everett St, Unit #1

12 Pond Ln

10 Pond Ln

12 Pond Ln, Unit 26

37 Westminster Ave, Unit 2

132 Broadway, Unit 1

104 Forest St, Unit 104

116 Medford St, Unit 1
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.

17 Lowell Street Pl, Unit 17 Lowell St Place

91 Williams St, Unit 91

19 Newland Rd, Unit 2

47 Webster St, Unit 47

2012 Symmes Cir, Unit 1

4 Stratton Dr, Unit 205

35 Bowdoin St, Unit 35
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

282 Main St, Unit 2

24 South St, Unit 3

289 Elm St, Unit 14

22 High St, Unit 11

22 High St

190 High St, Unit 109

50 Water St, Unit 25

159 Main St, Unit 37A

9 Circuit St, Unit 1

2500 Mystic Valley Pky, Unit 1106

129 Monument St

17 Usher Rd, Unit 3

349 Boston Ave
Winchester, MA Local Guide

How much does it cost to rent a home in Winchester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winchester 2 Bedroom Homes for Rent | $3,265 | $2,400 | $6,400 |
Winchester 3 Bedroom Homes for Rent | $3,713 | $2,600 | $6,000 |
Winchester 4 Bedroom Homes for Rent | $5,189 | $3,300 | $10,000+ |
Winchester 5 Bedroom Homes for Rent | $6,128 | $975 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $8,107 | $5,995 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $8,372 | $6,995 | $9,750 |
Browse Top Condos for Rent in Winchester
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Winchester, MA Local Guide
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Quick 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.
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 725 Apartments for Rent in Winchester, MA with pricing that ranges from $1,300 to $10,400. There are also 529 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $975 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 $975 to $40,000 with an average monthly rent of $4,938.
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 $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $3,150.
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.

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.