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$3,995
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$3,995
Total Monthly Price
$3,995
52 Pleasant St, Unit #2
52 Pleasant StLexington, MA 02421
4 Bedroom Apartments for Rent in Winchester, MA (78 Rentals)
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$5,450
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$5,450
Total Monthly Price
$5,450
29 Chetwynd Rd, Unit 2
29 Chetwynd RdSomerville, MA 02144
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$5,550
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,550
Total Monthly Price
$5,550
24 Chetwynd Rd, Unit 1
24 Chetwynd RdSomerville, MA 02144
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$5,250
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,250
Total Monthly Price
$5,250
14 Dow St, Unit 1
14 Dow StSomerville, MA 02144
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$5,450
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,450
Total Monthly Price
$5,450
24 Chetwynd Rd, Unit 1
24 Chetwynd RdSomerville, MA 02144
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$5,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,650
Total Monthly Price
$5,650
19 Sunset Rd, Unit 19-1
19 Sunset RdSomerville, MA 02144
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$5,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,400
Total Monthly Price
$5,400
14 Dow St, Unit 1
14 Dow StSomerville, MA 02144
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$5,450
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,450
Total Monthly Price
$5,450
29 Chetwynd Rd, Unit 2
29 Chetwynd RdSomerville, MA 02144
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$5,450
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,450
Total Monthly Price
$5,450
24 Chetwynd Rd, Unit 1
24 Chetwynd RdSomerville, MA 02144
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$5,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,650
Total Monthly Price
$5,650
19 Sunset Rd
19 Sunset RdSomerville, MA 02144
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$4,300
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,300
Total Monthly Price
$4,300
190 North St, Unit 2
190 North StSomerville, MA 02144
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Oct 1Total Monthly Price
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$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,300
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,300
Total Monthly Price
$4,300
190 North St, Unit 2
190 North StSomerville, MA 02144
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$5,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,650
Total Monthly Price
$5,650
86 Quincy St, Unit 2
86 Quincy StMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2A
62 Woods AveSomerville, MA 02144
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2T
62 Woods AveSomerville, MA 02144
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$4,300
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,300
Total Monthly Price
$4,300
190 North St, Unit 2
190 North StSomerville, MA 02144
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$4,300
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,300
Total Monthly Price
$4,300
190 North St, Unit 2
190 North StSomerville, MA 02144
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 5 Harris Road
5 Harris RdMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,200
Total Monthly Price
$4,200
40 Orchard St, Unit 1
40 Orchard StMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
190 North St, Unit 2
190 North StSomerville, 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
64 Chetwynd Rd, Unit 2
64 Chetwynd RdSomerville, MA 02144
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$5,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,400
Total Monthly Price
$5,400
86A Quincy St, Unit 2
86A Quincy StMedford, MA 02155
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$5,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$5,200
Total Monthly Price
$5,200
19 Sunset Rd, Unit NA
19 Sunset RdSomerville, MA 02144
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
50 Curtis Ave, Unit 1
50 Curtis AveSomerville, MA 02144
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$6,066
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,066
Total Monthly Price
$6,066
23 Edison Ave, Unit 2
23 Edison AveMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,000
Total Monthly Price
$4,000
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$5,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$5,000
Total Monthly Price
$5,000
86 Orchard St, Unit 1
86 Orchard StMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 2
5 Harris RdMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 2
5 Harris RdMedford, MA 02155
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$5,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,200
Total Monthly Price
$5,200
301 Alewife Brook Pky, Unit #1
301 Alewife Brook PkySomerville, MA 02144
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$4,950
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,950
Total Monthly Price
$4,950
65 Conwell Ave
65 Conwell AveSomerville, MA 02144
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,400
Total Monthly Price
$4,400
75 Summer St, Unit 1
75 Summer StMedford, MA 02155
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$5,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$5,200
Total Monthly Price
$5,200
301 Alewife Brook Pky, Unit 1
301 Alewife Brook PkySomerville, MA 02144
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
82 Quincy St, Unit #2
82 Quincy StMedford, MA 02155
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
50 Curtis Ave, Unit 1
50 Curtis AveSomerville, MA 02144
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$5,300
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,300
Total Monthly Price
$5,300
29 Chetwynd Rd, Unit 2
29 Chetwynd RdSomerville, MA 02144
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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
56 Gordon St, Unit 2
56 Gordon StSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
1 Victoria St, Unit 2
1 Victoria StSomerville, 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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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
12 Barton St, Unit 1
12 Barton StSomerville, 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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$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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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, 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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$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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$5,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,800
Total Monthly Price
$5,800
29 Sunset Rd
29 Sunset RdSomerville, MA 02144
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$5,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,800
Total Monthly Price
$5,800
27 Sunset Rd
27 Sunset RdSomerville, MA 02144
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Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Studio Apartments | $2,270 | $1,550 | $2,914 |
| Winchester 1 Bedroom Apartments | $2,820 | $1,850 | $4,350 |
| Winchester 2 Bedroom Apartments | $3,234 | $2,000 | $5,128 |
| Winchester 3 Bedroom Apartments | $3,680 | $2,250 | $7,500 |
| Winchester 4 Bedroom Apartments | $4,660 | $3,200 | $6,066 |
| Winchester 5 Bedroom Apartments | $6,004 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,280 | $5,945 | $9,100 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
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Winchester, MA Local Guide
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See the most popular apartments and homes in Winchester, MA
Getting Around Winchester, MA
Walk Score®
71 / 100
Very Walkable
Most errands can be accomplished on foot
Bike Score®
67 / 100
Bikeable
Some bike infrastructure
Transit Score®
1 / 100
Minimal Transit
It may be possible to get on a bus
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Winchester
How much are Studio apartments in Winchester?
There are currently 106 Studio Apartments in Winchester with rent ranges from $1,550 to $2,914 with an average price of $2,270.
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 $1,850 to $4,350 with an average monthly rent of $2,820.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,000 to $5,128. Today's average rental price for Two Bedrooms here is $3,234.
How expensive are Winchester Three Bedroom Apartments?
There are currently 168 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,250 to $7,500 - averaging $3,680 for the location.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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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Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
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Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
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Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
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Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.