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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
Apartments for Rent in Winchester, MA (652 Rentals) Page 7 of 14
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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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$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
24 Chetwynd Rd
24 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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$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
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
50 Hamilton St, Unit 2
50 Hamilton 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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$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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$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 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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$3,325
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,325
Total Monthly Price
$3,325
235 Ashcroft Rd, Unit 1
235 Ashcroft RdMedford, MA 02155
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$3,325
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,325
Total Monthly Price
$3,325
235 Ashcroft Rd, Unit 1
235 Ashcroft RdMedford, 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
258 Boston Ave, Unit 3
258 Boston AveMedford, MA 02155
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$3,325
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,325
Total Monthly Price
$3,325
235 Ashcroft Rd, Unit 1
235 Ashcroft RdMedford, 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
89 Hillsdale Rd, Unit 2
89 Hillsdale RdMedford, MA 02155
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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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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total 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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$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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$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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$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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$4,950
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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$3,100
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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$3,250
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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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
129 Brooks St, Unit 4
129 Brooks StMedford, MA 02155
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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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$6,200
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,200
Total Monthly Price
$6,200
3 Hamilton Rd, Unit 1
3 Hamilton RdSomerville, MA 02144
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$5,450
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,450
Total Monthly Price
$5,450
217 Arlington, Unit 1
217 ArlingtonMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
186 Powder House Blvd, Unit 2
186 Powder House BlvdSomerville, 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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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
14 Cotting St, Unit 3
14 Cotting StMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
67 Orchard St, Unit 1
67 Orchard StMedford, MA 02155
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,600
Total Monthly Price
$4,600
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
79 Conwell Ave, Unit 3
79 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
65 Sterling St, Unit 1
65 Sterling StSomerville, 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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$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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$3,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
373 Boston Ave
373 Boston 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
112 College Ave, Unit 1
112 College AveMedford, MA 02155
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$3,450
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,450
Total Monthly Price
$3,450
141 Hillsdale Rd, Unit 2
141 Hillsdale RdSomerville, MA 02144
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$4,600
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,600
Total Monthly Price
$4,600
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,780
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,780
Total Monthly Price
$4,780
90 Conwell Ave, Unit 2
90 Conwell AveSomerville, 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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$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
43 Teele Ave, Unit 2
43 Teele AveSomerville, 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
24 Curtis Ave
24 Curtis AveSomerville, MA 02144
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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
12 Pinkham Rd, Unit 1
12 Pinkham RdMedford, 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 | $2,752 | $1,850 | $4,195 |
| Winchester 2 Bedroom Apartments | $3,224 | $1,995 | $5,050 |
| Winchester 3 Bedroom Apartments | $3,709 | $2,250 | $7,500 |
| Winchester 4 Bedroom Apartments | $4,754 | $3,200 | $5,890 |
| Winchester 5 Bedroom Apartments | $6,094 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,325 | $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 $2,752.
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 $3,224.
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 $3,709 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.