301 Alewife Brook Pky
SomervilleMA02144
Homes for Rent in Winchester, MA (315 Rentals) Page 4 of 7
64 Chetwynd Rd, Unit 1
64 Chetwynd Rd
SomervilleMA02144
33 Raymond Ave, Unit 3
33 Raymond Ave
SomervilleMA02144
70 Curtis St
SomervilleMA02144
76 Curtis St, Unit 1
76 Curtis St
SomervilleMA02144
31 Raymond Ave, Unit 3
31 Raymond Ave
SomervilleMA02144
3 Hamilton Rd, Unit 2
3 Hamilton Rd
SomervilleMA02144
76 Curtis St
SomervilleMA02144
24 Chetwynd Rd, Unit 2
24 Chetwynd Rd
SomervilleMA02144
80 Curtis St
SomervilleMA02144
16 Chetwynd Rd
SomervilleMA02144
16 Chetwynd Rd
SomervilleMA02144
4 High St, Unit 1
4 High St
SomervilleMA02144
80 Curtis St
SomervilleMA02144
5 Hamilton Rd, Unit 2
5 Hamilton Rd
SomervilleMA02144
3 Hamilton Rd, Unit 2
3 Hamilton Rd
SomervilleMA02144
80 Curtis St
SomervilleMA02144
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$2,650
Plus Fees
1 Bedroom Apartments Available Feb 2, 2026385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
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$2,350
Plus Fees
1 Bedroom Apartments Available Now385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
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$3,000
Plus Fees
2 Bedroom Apartments Available Now26-28-28 Howard St
26-28-28 Howard StArlington, MA 02476
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$3,400
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Now7 Patrick St
7 Patrick StArlington, MA 02474
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$3,100
Plus Fees
2 Bedroom Apartments Available Now385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
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$1,900
Plus Fees
Studio Apartments Available Now385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
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$3,200
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Now110 Sharon St
110 Sharon StMedford, MA 02155
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$3,000
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Now186 Powder House Blvd
186 Powder House BlvdSomerville, MA 02144
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$3,300
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Now49 Conwell Ave
49 Conwell AveSomerville, MA 02144
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$4,200
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Jun 1, 2026301-303 Boston Ave Unit #3
301-303 Boston AveMedford, MA 02155
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$3,700
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Jun 1, 202649 Conwell Ave
49 Conwell AveSomerville, MA 02144
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$3,750
Plus Fees
3 Bedroom Apartments Available Jun 1, 2026258 Boston Ave
258 Boston AveMedford, MA 02155
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$4,600
Plus Fees
4 Bedroom Apartments Available Jun 1, 2026288 Boston Ave
288 Boston AveMedford, MA 02155
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$3,600
Plus Fees
3 Bedroom Apartments Available Jun 1, 202643 Orchard St
43 Orchard StMedford, MA 02155
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$6,250
Plus Fees
5 Bedroom Apartments Available Jun 1, 2026260 Boston Ave
260 Boston AveMedford, MA 02155
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$8,100
Plus Fees
6 Bedroom Apartments Available Jun 1, 202616 Curtis Ave
16 Curtis AveSomerville, MA 02144
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$3,000
Plus Fees
2 Bedroom Apartments Available Now186 Powder House Blvd
186 Powder House BlvdSomerville, MA 02144
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$4,400
Plus Fees
4 Bedroom Apartments Available Jun 1, 202656 Gordon St
56 Gordon StSomerville, MA 02144
Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,920 | $2,175 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,672 | $2,800 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $5,007 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,517 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,124 | $6,200 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winchester
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 486 Apartments for Rent in Winchester, MA with pricing that ranges from $1,000 to $9,300. There are also 314 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,500 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 $1,500 to $40,000 with an average monthly rent of $4,471.
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 $2,800 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $1,000.
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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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.
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How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!