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$2,400 - $4,000
Total Monthly Price12 Month Lease Term
2 to 4 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,400 - $4,000
Total Monthly Price
$2,400 - $4,000
369 Boston Ave
369 Boston AveMedford, MA 02155
Apartments for Rent in Winchester, MA (542 Rentals) Page 3 of 11
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
30 Hume Ave, Unit 1
30 Hume AveMedford, MA 02155
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$7,800
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$7,800
Total Monthly Price
$7,800
17 Tesla Ave
17 Tesla AveMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Aug 31Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
1 Victoria St, Unit 1A
1 Victoria StSomerville, MA 02144
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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
282 Boston Ave, Unit 1
282 Boston AveMedford, MA 02155
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$1,850
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Sep 7Total Monthly Price
Base Rent
$1,850
Total Monthly Price
$1,850
21 High St, Unit 2
21 High StSomerville, MA 02144
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$6,750
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$6,750
Total Monthly Price
$6,750
23 Emery St, Unit 23 Emery Street
23 Emery StMedford, MA 02155
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$2,700
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
54 Englehutt Rd, Unit 2
54 Englehutt RdMedford, MA 02155
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
35 Whitfield Rd, Unit #3
35 Whitfield RdSomerville, MA 02144
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$5,200 - $7,200
Total Monthly Price12 Month Lease Term
4 to 6 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$5,200 - $7,200
Total Monthly Price
$5,200 - $7,200
24 Chetwynd Rd
24 Chetwynd RdSomerville, MA 02144
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
136 Burget Ave, Unit 1
136 Burget AveMedford, MA 02155
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$7,200
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$7,200
Total Monthly Price
$7,200
4 High St
4 High StSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
29 Capen St, Unit 2
29 Capen StMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
69 Conwell Ave
69 Conwell AveSomerville, MA 02144
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,600
Total Monthly Price
$4,600
82 Quincy St, Unit 2
82 Quincy StMedford, MA 02155
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
41 Belknap St, Unit 2
41 Belknap StSomerville, MA 02144
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$3,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,250
Total Monthly Price
$3,250
22 Bradlee Rd, Unit 405
22 Bradlee RdMedford, MA 02155
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$2,650
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,650
Total Monthly Price
$2,650
44 Russell Rd, Unit 2
44 Russell RdSomerville, MA 02144
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$2,950
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Aug 31Total Monthly Price
Base Rent
$2,950
Total Monthly Price
$2,950
79 Capen St, Unit 1
79 Capen StMedford, MA 02155
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$7,200 - $7,800
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$7,200 - $7,800
Total Monthly Price
$7,200 - $7,800
107 North St
107 North StMedford, MA 02155
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$5,750
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$5,750
Total Monthly Price
$5,750
123 Winthrop St, Unit 1
123 Winthrop StMedford, MA 02155
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$6,950
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$6,950
Total Monthly Price
$6,950
21 Emery St, Unit 1
21 Emery StMedford, MA 02155
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$1,000
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,000
Total Monthly Price
$1,000
16 Quincy St, Unit 2
16 Quincy StMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$6,300
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Aug 31Total Monthly Price
Base Rent
$6,300
Total Monthly Price
$6,300
3 Hamilton Rd, Unit 2
3 Hamilton RdSomerville, MA 02144
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$6,250
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$6,250
Total Monthly Price
$6,250
14 Fairmount St, Unit 1
14 Fairmount StMedford, MA 02155
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$6,150
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,150
Total Monthly Price
$6,150
24 Chetwynd Rd, Unit 2
24 Chetwynd RdSomerville, MA 02144
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$3,810
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$3,810
Total Monthly Price
$3,810
77 Lyman Ave, Unit 2
77 Lyman AveMedford, MA 02155
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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
14 Irvington Rd, Unit 1
14 Irvington RdSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
288 Boston Ave, Unit 3
288 Boston AveMedford, MA 02155
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$3,300
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
77 Fairfax St, Unit #1
77 Fairfax StSomerville, MA 02144
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$4,050
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$4,050
Total Monthly Price
$4,050
106 W Adams St, Unit 1
106 W Adams StSomerville, MA 02144
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$4,140
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$4,140
Total Monthly Price
$4,140
29 Chetwynd Rd, Unit 1
29 Chetwynd RdSomerville, MA 02144
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$6,750
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$6,750
Total Monthly Price
$6,750
47 Pearl St, Unit 2
47 Pearl StMedford, MA 02155
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$6,950
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$6,950
Total Monthly Price
$6,950
47 Pearl St, Unit 2
47 Pearl StMedford, MA 02155
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$3,100 - $4,500
Total Monthly Price12 Month Lease Term
2 to 4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100 - $4,500
Total Monthly Price
$3,100 - $4,500
1 Victoria St
1 Victoria StSomerville, MA 02144
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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
115 Playstead Rd, Unit 2
115 Playstead RdMedford, MA 02155
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$4,750
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,750
Total Monthly Price
$4,750
2 Osgood St, Unit 1
2 Osgood StSomerville, MA 02143
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
30 Adams St, Unit 1
30 Adams StMedford, MA 02155
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$3,600
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$3,600
Total Monthly Price
$3,600
68 North St
68 North StSomerville, MA 02144
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$5,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$5,500
Total Monthly Price
$5,500
260 Boston Ave, Unit 2
260 Boston AveMedford, MA 02155
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$3,975
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$3,975
Total Monthly Price
$3,975
38 George St, Unit 1
38 George StMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
86 Conwell Ave, Unit 2
86 Conwell AveSomerville, MA 02144
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$5,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$5,800
Total Monthly Price
$5,800
29 Sunset Rd, Unit 2
29 Sunset RdSomerville, MA 02144
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$3,500
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$3,550
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$3,550
Total Monthly Price
$3,550
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
65 Conwell Ave, Unit 1
65 Conwell AveSomerville, MA 02144
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$3,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
12 Pinkham Rd, Unit 1
12 Pinkham RdMedford, MA 02155
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$7,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$7,500
Total Monthly Price
$7,500
23 Edison Ave, Unit 2
23 Edison AveMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
3 Hamilton Rd, Unit 1
3 Hamilton RdSomerville, MA 02144
Showing Results 101-150, Page 3 of 11
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 | $2,381 | $1,725 | $3,350 |
| Winchester 1 Bedroom Apartments | $2,611 | $825 | $4,070 |
| Winchester 2 Bedroom Apartments | $3,265 | $1,100 | $5,441 |
| Winchester 3 Bedroom Apartments | $3,776 | $2,500 | $6,471 |
| Winchester 4 Bedroom Apartments | $4,651 | $3,200 | $6,750 |
| Winchester 5 Bedroom Apartments | $6,853 | $4,350 | $10,000+ |
| Winchester 6 Bedroom Apartments | $7,195 | $1,000 | $9,600 |
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 is the current pricing and availability for apartments for rent in Winchester, MA?
As of today, August 29, 2026, there are currently 542 available Winchester apartments priced from $825 to $19,900, with an average monthly rent of $3,446.
What Winchester neighborhoods have the most available apartments?
There are 3 neighborhoods in the Winchester area with available listings as of today. The three neighborhoods with the most options are Kendall Square with 5,841 listings, West End Boston with 5,203 listings, and North Station with 4,692 listings.
How much are Studio apartments in Winchester?
There are currently 103 Studio Apartments in Winchester with rent ranges from $1,725 to $3,350 with an average price of $2,381.
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 $825 to $4,070 with an average monthly rent of $2,611.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,100 to $5,441. Today's average rental price for Two Bedrooms here is $3,265.
How expensive are Winchester Three Bedroom Apartments?
There are currently 95 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,471 - averaging $3,776 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.
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