
Apartments for Rent in Winchester, MA (516 Rentals) Page 2 of 11


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25 Arlington Rd, Unit Apt 1-1

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14 Dow St, Unit 2M

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8 Cross St, Unit 1

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227 Boston Ave, Unit 2

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286 Main St, Unit 3

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74 Beach St, Unit #3-3

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165 Radcliffe Rd, Unit #169

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108 W Quincy St, Unit 1

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108 W Quincy St, Unit 1
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

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477 Fulton St, Unit F

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65 Conwell Ave, Unit 3

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92 Sylvia St, Unit 2

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94 North St, Unit 94

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28 Cornell St, Unit 1

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69 Raymond Ave, Unit 69

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34 Capen St, Unit 2

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227 Boston Ave, Unit 2

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20 Stephenson Aman St, Unit 2

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94 North St, Unit 94

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6 Gloucester St, Unit 2 bedrooms

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300 Boston Ave, Unit 2

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69 Raymond Ave, Unit 1R

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24 Chetwynd Rd, Unit 2

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134 N Union St, Unit 1

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300 Boston Ave, Unit 2

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321 Alewife Brook Pky, Unit 1

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14 Dow St, Unit 2

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14 Dow St, Unit 2

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25 Laurel St, Unit 25 Laurel St.

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300 Boston Ave, Unit 2

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14 Dow St, Unit 2

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96 Conwell Ave, Unit 1

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100 W Adams St, Unit 1A

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94 North St, Unit 1

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70 Tufts St, Unit 1

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290 Boston Ave, Unit 2

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4 Colonial Village Dr, Unit 4

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258 Boston Ave, Unit 2

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27 Holton St, Unit 1

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14 Dow St, Unit 2

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14 Dow St, Unit 2F

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43 Orchard St, Unit 1

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14 Dow St, Unit 2

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94 North St, Unit 1

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49 Conwell Ave, Unit 2

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279 Massachusetts Ave, Unit 1

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120 Jerome St, Unit 120 Jerome Street

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108 W Quincy St, Unit 1

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5 Patrick St, Unit 2
Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Studio Apartments | $2,169 | $1,650 | $2,720 |
| Winchester 1 Bedroom Apartments | $2,631 | $1,295 | $4,195 |
| Winchester 2 Bedroom Apartments | $3,219 | $2,195 | $4,835 |
| Winchester 3 Bedroom Apartments | $3,665 | $2,500 | $6,900 |
| Winchester 4 Bedroom Apartments | $4,381 | $1,000 | $6,375 |
| Winchester 5 Bedroom Apartments | $6,286 | $4,500 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,313 | $5,945 | $8,437 |
Browse Top Apartments in Winchester
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Frequently Asked Questions about Winchester
How much are Studio apartments in Winchester?
There are currently 102 Studio Apartments in Winchester with rent ranges from $1,650 to $2,720 with an average price of $2,169.
What is the current price range for One Bedroom Winchester Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $1,295 to $4,195 with an average monthly rent of $2,631.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,195 to $4,835. Today's average rental price for Two Bedrooms here is $3,219.
How expensive are Winchester Three Bedroom Apartments?
There are currently 112 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,900 - averaging $3,665 for the location.
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
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A Local Experts Guide to the Top Boston Neighborhoods for College Renters
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Explore Like a Local: The Insider's Guide to Boston
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Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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Articles, How-To's, and Tips

How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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!