29 Devereaux St
ArlingtonMA02476
Luxury Homes for Rent in Winchester, MA (241 Rentals) Page 5 of 5
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
61 Warren St
MedfordMA02155
334 Mystic St
ArlingtonMA02474
3 Hamilton Rd, Unit 2
3 Hamilton Rd
SomervilleMA02144
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$6,3007 Bedroom Apartments Available Sep 15
15 Bartlett Ave, Unit TH
15 Bartlett AveArlington, MA 02476
120 Jerome St, Unit 1
120 Jerome St
MedfordMA02155
57 Spy Pond Ln
ArlingtonMA02474
3 Day Cir
WoburnMA01801
24 Chetwynd Rd, Unit 2
24 Chetwynd Rd
SomervilleMA02144
82 Arlmont St
ArlingtonMA02476
3 Day Cir
WoburnMA01801
82 Arlmont St
ArlingtonMA02476
21 Franklin St
ArlingtonMA02474
52 Hillsdale Rd
MedfordMA02155
80 Curtis St
SomervilleMA02144
322 Lowell St
LexingtonMA02420
16 Chetwynd Rd
SomervilleMA02144
232 Fulton St, Unit 2
232 Fulton St
MedfordMA02155
4 High St, Unit 1
4 High St
SomervilleMA02144
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$7,0005 Bedroom Apartments Available Jul 1
14 Sturtevant Terrace, Unit 1
14 Sturtevant TerraceMedford, MA 02155
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$7,2006 Bedroom Apartments Available Now
16 Curtis Ave, Unit 2
16 Curtis AveSomerville, MA 02144
120 Jerome St
MedfordMA02155
11 Garrison Rd
ArlingtonMA02474
108 Radcliffe Rd
BelmontMA02478
3 Hamilton Rd, Unit 2
3 Hamilton Rd
SomervilleMA02144
15 Campbell Rd
ArlingtonMA02476
15 Campbell Rd
ArlingtonMA02476
65 Lancaster Rd
ArlingtonMA02476
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$8,0007 Bedroom Apartments Available Jun 1, 2027
35 Conwell Ave
35 Conwell AveSomerville, MA 02144
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$8,4006 Bedroom Apartments Available Jul 1
14 Sturtevant Terrace, Unit 2
14 Sturtevant TerraceMedford, MA 02155
45 Wellesley Rd
BelmontMA02478
45 Wellesley Rd
BelmontMA02478
12 Windermere Ave
ArlingtonMA02476
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$11,000
Total Monthly Price
5 Bedroom Apartments Available Aug 10Total Monthly Price
Base Rent
$10,464
Required Monthly Fees
$536
Total Monthly Price
$11,000
3 Chapel Way, Unit SI ID1387521P
3 Chapel WayStoneham, MA 02180
10 Blodgett Rd
LexingtonMA02420
75 Woodfall Rd
BelmontMA02478
12 Summit Rd
LexingtonMA02421
30 Whipple Rd
LexingtonMA02420
7 Whipple Rd
LexingtonMA02420
64 Newcomb Rd
StonehamMA02180
23 Thoreau Rd
LexingtonMA02420
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.
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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
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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
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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.
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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
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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.