21 Royall St, Unit 3B1B on 2nd FL
21 Royall St
MedfordMA02155
Homes for Rent in Winchester, MA (261 Rentals) Page 2 of 6
2500 Mystic Valley Pky, Unit 805
2500 Mystic Valley Pky
MedfordMA02155
52 Clark St, Unit 1
52 Clark St
MedfordMA02155
245 Boston Ave, Unit 3
245 Boston Ave
MedfordMA02155
258 Boston Ave
MedfordMA02155
31 Lyman Ave
MedfordMA02155
106 Boston Ave
MedfordMA02155
280 Boston Ave
MedfordMA02155
30 Touro Ave, Unit 30
30 Touro Ave
MedfordMA02155
21 Jerome St
MedfordMA02155
Explore Like a Local: The Insider's Guide to Boston
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
112 College Ave, Unit 1##
112 College Ave
MedfordMA02155
841 Fellsway W
MedfordMA02155
130 Capen St, Unit 130
130 Capen St
MedfordMA02155
14 Sturtevant Ter
MedfordMA02155
34 Hume Ave, Unit 2
34 Hume Ave
MedfordMA02155
10 Greenleaf Ave, Unit 1
10 Greenleaf Ave
MedfordMA02155
217 Arlington St
MedfordMA02155
479 Fulton St
MedfordMA02155
120 Jerome St, Unit 1
120 Jerome St
MedfordMA02155
140 Jerome St
MedfordMA02155
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
230 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
82 Sharon St
MedfordMA02155
177 Central St
StonehamMA02180
64 Newcomb Rd
StonehamMA02180
45 Wellesley Rd
BelmontMA02478
14 Massachusetts Ave
LexingtonMA02420
14 Irvington Rd, Unit 14 Irvington Road
14 Irvington Rd
SomervilleMA02144
333 Alewife Brook Pky, Unit 2
333 Alewife Brook Pky
SomervilleMA02144
42 Belknap St
SomervilleMA02144
Neighborhood & Market Insights: How to Choose the Right Area to Rent
Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.
88 North St
SomervilleMA02144
56 Gordon St, Unit 1
56 Gordon St
SomervilleMA02144
3 Hamilton Rd
SomervilleMA02144
62 Woods Ave, Unit 2##
62 Woods Ave
SomervilleMA02144
8 Hamilton Rd
SomervilleMA02144
11 Raymond Ave
SomervilleMA02144
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$7,0005 Bedroom Apartments Available Now
14 Sturtevant Terrace, Unit 1
14 Sturtevant TerraceMedford, MA 02155
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$2,3001 Bedroom Apartments Available Oct 2
1 Brattle Dr, Unit 6
1 Brattle DrArlington, MA 02474
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$20,951
Total Monthly Price
5 Bedroom Apartments Available Oct 22Total Monthly Price
Base Rent
$19,884
Required Monthly Fees
$1,067
Total Monthly Price
$20,951
64 Newcomb Rd, Unit SI FL4-ID1586668P
64 Newcomb RdStoneham, MA 02180
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$2,6002 Bedroom Apartments Available Now
66 Mill St, Unit 8
66 Mill StWoburn, MA 01801
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.
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$2,7501 Bedroom Apartments Available Now
32 Walnut St
32 Walnut StArlington, MA 02476
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$5,4976 Bedroom Apartments Available Now
36 Gould St
36 Gould StStoneham, MA 02180
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$2,5002 Bedroom Apartments Available Now
50 Mill St, Unit 5
50 Mill StWoburn, MA 01801
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$2,4501 Bedroom Apartments Available Now
385 Massachusetts Ave, Unit 1
385 Massachusetts AveArlington, MA 02474
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$9,054
Total Monthly Price
5 Bedroom Apartments Available Jan 15, 2027Total Monthly Price
Base Rent
$8,609
Required Monthly Fees
$445
Total Monthly Price
$9,054
3 Chapel Way, Unit SI ID1387521P
3 Chapel WayStoneham, MA 02180
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$2,5002 Bedroom Apartments Available Now
62 Mill St, Unit 6
62 Mill StWoburn, MA 01801
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$2,7501 Bedroom Apartments Available Now
898 Massachusetts Ave, Unit 31
898 Massachusetts AveArlington, MA 02476
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$2,5002 Bedroom Apartments Available Now
68 Mill St, Unit 11
68 Mill StWoburn, MA 01801
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$2,5001 Bedroom Apartments Available Sep 2
898 Massachusetts Ave, Unit 23
898 Massachusetts AveArlington, MA 02476
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$4,2004 Bedroom Apartments Available Sep 1
53 Oakland St, Unit #2
53 Oakland StMedford, MA 02155
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.
Showing Results 51-100, Page 2 of 6
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 | $3,100 | $2,400 | $4,250 |
| Winchester 3 Bedroom Homes for Rent | $4,059 | $2,700 | $7,000 |
| Winchester 4 Bedroom Homes for Rent | $5,517 | $2,800 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $9,074 | $5,000 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,293 | $5,995 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 404 Apartments for Rent in Winchester, MA with pricing that ranges from $1,450 to $20,951. There are also 258 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,050 to $20,000.
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 $20,000 with an average monthly rent of $5,021.
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 $5,994, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,700 to $7,000. Four Bedroom Single-Family rentals are also available starting from $2,800 and Four Bedroom Apartments start at $2,700.
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.
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Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
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There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
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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.