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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
505 Main St, Unit 3
505 Main StStoneham, MA 02180
Apartments for Rent in Winchester, MA (651 Rentals) Page 2 of 14
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$5,100
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,100
Total Monthly Price
$5,100
102 W Adams St, Unit 2
102 W Adams 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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$6,375
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,375
Total Monthly Price
$6,375
14 Dow St, Unit 2
14 Dow StSomerville, MA 02144
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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
1 Boline Pl, Unit 1 Boline Place
1 Boline PlWoburn, MA 01801
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$3,150
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
52 Mt Vernon St, Unit 1
52 Mt Vernon StArlington, MA 02476
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
159 Main St
159 Main StStoneham, MA 02180
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, MA 02144
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$3,900
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
185 Powder House Blvd, Unit 1
185 Powder House BlvdSomerville, MA 02144
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$3,900
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
185 Powder House Blvd, Unit 1
185 Powder House BlvdSomerville, MA 02144
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$5,100
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,100
Total Monthly Price
$5,100
102 W Adams St, Unit 2
102 W Adams 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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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
185 Powder House Blvd, Unit 2
185 Powder House BlvdSomerville, MA 02144
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
185 Powder House Blvd, Unit 2
185 Powder House BlvdSomerville, MA 02144
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$2,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
22 Scott St, Unit 1
22 Scott StWoburn, MA 01801
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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
50 Marion Rd, Unit 1
50 Marion RdArlington, MA 02474
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
42 Pinkham Rd, Unit 42
42 Pinkham RdMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, MA 02144
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$5,600
Total Monthly Price24 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,600
Total Monthly Price
$5,600
19 Sunset Rd, Unit 1
19 Sunset RdSomerville, MA 02144
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$6,480
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,480
Total Monthly Price
$6,480
4 High St
4 High StSomerville, MA 02144
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$7,722
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$7,722
Total Monthly Price
$7,722
20 Chetwynd Rd, Unit 2
20 Chetwynd RdSomerville, MA 02144
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$3,100
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
8 Cross St, Unit 1
8 Cross StWoburn, MA 01801
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$3,295
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,295
Total Monthly Price
$3,295
52 Mt Vernon St, Unit 1
52 Mt Vernon StArlington, MA 02476
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
24 Greenleaf Ave, Unit 2
24 Greenleaf AveMedford, MA 02155
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$5,616
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,616
Total Monthly Price
$5,616
24 Chetwynd Rd, Unit 1
24 Chetwynd RdSomerville, MA 02144
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$5,616
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,616
Total Monthly Price
$5,616
24 Chetwynd Rd, Unit 1
24 Chetwynd RdSomerville, MA 02144
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$6,480
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,480
Total Monthly Price
$6,480
4 High St
4 High StSomerville, MA 02144
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$6,885
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,885
Total Monthly Price
$6,885
26 Chetwynd Rd, Unit 2
26 Chetwynd RdSomerville, MA 02144
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$6,885
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,885
Total Monthly Price
$6,885
26 Chetwynd Rd, Unit 2
26 Chetwynd RdSomerville, MA 02144
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$7,128
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$7,128
Total Monthly Price
$7,128
10 High St
10 High StSomerville, MA 02144
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$7,128
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$7,128
Total Monthly Price
$7,128
10 High St
10 High StSomerville, MA 02144
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$7,722
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$7,722
Total Monthly Price
$7,722
20 Chetwynd Rd, Unit 2
20 Chetwynd RdSomerville, MA 02144
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$1,950
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,950
Total Monthly Price
$1,950
8 Eastern Ave, Unit Thirdfloor
8 Eastern AveWoburn, MA 01801
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$2,200
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
4 Colonial Village Dr, Unit 4
4 Colonial Village DrArlington, MA 02474
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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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$5,300
Total Monthly Price24 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,300
Total Monthly Price
$5,300
50 Upland Rd, Unit 2
50 Upland RdSomerville, MA 02144
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$5,600
Total Monthly Price24 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,600
Total Monthly Price
$5,600
19 Sunset Rd, Unit 1
19 Sunset RdSomerville, MA 02144
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$6,250
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,250
Total Monthly Price
$6,250
14 Dow St, Unit 2
14 Dow StSomerville, MA 02144
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$6,750
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,750
Total Monthly Price
$6,750
76 Curtis St, Unit 1
76 Curtis StSomerville, MA 02144
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$1,850
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,850
Total Monthly Price
$1,850
224 Main St, Unit 1B
224 Main StWoburn, MA 01801
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$4,500
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
39 Highland Ave, Unit 2
39 Highland AveArlington, MA 02476
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$3,900
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
89 Hillsdale Rd, Unit 1
89 Hillsdale RdMedford, MA 02155
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$6,000
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,000
Total Monthly Price
$6,000
123 Winthrop St, Unit 1
123 Winthrop StMedford, MA 02155
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$5,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,200
Total Monthly Price
$5,200
29 Chetwynd Rd, Unit 2
29 Chetwynd RdSomerville, MA 02144
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$8,400
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$8,400
Total Monthly Price
$8,400
20 Curtis Ave, Unit 2
20 Curtis AveSomerville, MA 02144
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$2,200
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
7 Boline Pl, Unit 1
7 Boline PlWoburn, MA 01801
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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
110 W Quincy St, Unit 2
110 W Quincy StSomerville, MA 02144
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$2,995
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,995
Total Monthly Price
$2,995
286 Main St, Unit 3
286 Main StWoburn, MA 01801
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Sep 1, 2026Total Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
30 Adams St, Unit 2
30 Adams StMedford, MA 02155
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 | $2,253 | $1,550 | $2,829 |
| Winchester 1 Bedroom Apartments | $2,743 | $1,850 | $4,195 |
| Winchester 2 Bedroom Apartments | $3,222 | $1,995 | $5,050 |
| Winchester 3 Bedroom Apartments | $3,694 | $2,250 | $7,500 |
| Winchester 4 Bedroom Apartments | $4,761 | $3,200 | $5,890 |
| Winchester 5 Bedroom Apartments | $6,023 | $4,000 | $7,500 |
| Winchester 6 Bedroom Apartments | $7,285 | $5,945 | $8,670 |
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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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 102 Studio Apartments in Winchester with rent ranges from $1,550 to $2,829 with an average price of $2,253.
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 $4,195 with an average monthly rent of $2,743.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,995 to $5,050. Today's average rental price for Two Bedrooms here is $3,222.
How expensive are Winchester Three Bedroom Apartments?
There are currently 156 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,250 to $7,500 - averaging $3,694 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.
The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
Kansas Citys Major Employers & the Best Places to Rent Near Them | A Local Expert Guide
Written by: Amber Kanuckel
Hey, there! I’m Amber, your ApartmentHomeLiving.com local expert for Kansas City, and I’m back with my recommendations for top employers in the area.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
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.