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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 Fairmount St, Unit 14.5
14 Fairmount StMedford, MA 02155
Apartments for Rent in Winchester, MA (559 Rentals) Page 5 of 12
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$3,600
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,600
Total Monthly Price
$3,600
68 North St
68 North StSomerville, MA 02144
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$3,700
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,700
Total Monthly Price
$3,700
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, 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 Fairmount St, Unit 14.5
14 Fairmount StMedford, MA 02155
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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
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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$3,700
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,700
Total Monthly Price
$3,700
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, MA 02144
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Dec 1Total 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 Dec 1Total 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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$7,000
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$7,000
Total Monthly Price
$7,000
59 Sunset Rd, Unit 2
59 Sunset RdSomerville, MA 02144
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$7,700
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$7,700
Total Monthly Price
$7,700
174 Fulton St
174 Fulton 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
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$2,950
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,950
Total Monthly Price
$2,950
50 Hamilton St, Unit 2
50 Hamilton StMedford, MA 02155
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$2,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
110 W Quincy St, Unit 1
110 W Quincy StSomerville, MA 02144
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$3,700
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,700
Total Monthly Price
$3,700
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
258 Boston Ave, Unit 3
258 Boston AveMedford, MA 02155
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$2,500
Total Monthly Price9 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
110 W Quincy St, Unit 1
110 W Quincy StSomerville, MA 02144
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$2,600
Total Monthly Price10 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
69 Raymond Ave, Unit 1
69 Raymond AveSomerville, MA 02144
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$3,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
108 W Quincy St, Unit 108
108 W Quincy StSomerville, MA 02144
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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
44 Greenleaf Ave, Unit 1
44 Greenleaf AveMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
303 Boston Ave, Unit 3
303 Boston AveMedford, 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
96 Conwell Ave, Unit 2
96 Conwell AveSomerville, MA 02144
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$4,050
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,050
Total Monthly Price
$4,050
117 Burget Ave, Unit 1
117 Burget AveMedford, MA 02155
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$4,050
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,050
Total Monthly Price
$4,050
117 Burget Ave, Unit 1
117 Burget AveMedford, 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
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
96 Conwell Ave, Unit 3
96 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
96 Conwell Ave, Unit 2
96 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
96 Conwell Ave, Unit 2
96 Conwell AveSomerville, MA 02144
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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
9 Irving St, Unit 1
9 Irving StMedford, MA 02155
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$3,800
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,800
Total Monthly Price
$3,800
48 Raymond Ave, Unit 3
48 Raymond 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
14 Barton St, Unit 2
14 Barton StSomerville, MA 02144
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$3,100
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
34 Sunset Rd, Unit 2
34 Sunset RdSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
79 Conwell Ave, Unit 2
79 Conwell AveSomerville, MA 02144
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$3,500
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
14 Belknap St, Unit 2
14 Belknap StSomerville, MA 02144
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$4,950
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,950
Total Monthly Price
$4,950
65 Conwell Ave, Unit 1
65 Conwell AveSomerville, MA 02144
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$3,250
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,250
Total Monthly Price
$3,250
26 Bradlee Rd, Unit 3
26 Bradlee RdMedford, MA 02155
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$3,100
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
34 Sunset Rd, Unit 2
34 Sunset RdSomerville, MA 02144
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$5,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,500
Total Monthly Price
$5,500
132 George St, Unit 2
132 George StMedford, MA 02155
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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
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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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
186 Powder House Blvd, Unit 2
186 Powder House BlvdSomerville, MA 02144
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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
67 Orchard St, Unit 1
67 Orchard StMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
30 Adams St, Unit 1
30 Adams StMedford, MA 02155
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
65 Sterling St, Unit 1
65 Sterling StSomerville, MA 02144
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$6,640
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,640
Total Monthly Price
$6,640
76 Curtis St, Unit 1
76 Curtis StSomerville, MA 02144
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$5,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,500
Total Monthly Price
$5,500
141 George St, Unit 1
141 George StMedford, MA 02155
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
79 Conwell Ave, Unit 1
79 Conwell AveSomerville, MA 02144
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$4,900
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,900
Total Monthly Price
$4,900
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$5,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,000
Total Monthly Price
$5,000
104 W Adams St, Unit 2
104 W Adams StSomerville, MA 02144
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$8,437
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$8,437
Total Monthly Price
$8,437
80 Curtis St, Unit 1
80 Curtis StSomerville, MA 02144
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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
59 Quincy St, Unit 1
59 Quincy 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 | $2,138 | $1,200 | $2,829 |
| Winchester 1 Bedroom Apartments | $2,635 | $1,395 | $4,195 |
| Winchester 2 Bedroom Apartments | $3,241 | $2,195 | $5,500 |
| Winchester 3 Bedroom Apartments | $3,654 | $2,500 | $6,900 |
| Winchester 4 Bedroom Apartments | $4,468 | $3,000 | $8,000 |
| Winchester 5 Bedroom Apartments | $6,144 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,147 | $5,945 | $8,437 |
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 105 Studio Apartments in Winchester with rent ranges from $1,200 to $2,829 with an average price of $2,138.
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 $1,395 to $4,195 with an average monthly rent of $2,635.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,195 to $5,500. Today's average rental price for Two Bedrooms here is $3,241.
How expensive are Winchester Three Bedroom Apartments?
There are currently 144 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,900 - averaging $3,654 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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
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.