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$2,900
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
49 Conwell Ave, Unit #2
49 Conwell AveSomerville, MA 02144
Luxury Apartments for Rent in Winchester, MA (327 Rentals) Page 2 of 7
The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.
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$2,975
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,975
Total Monthly Price
$2,975
1 Victoria St, Unit 1A
1 Victoria 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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$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
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
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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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
22 Bradlee Rd
22 Bradlee RdMedford, 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
29 Capen St
29 Capen 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
3 Bedroom Apartment Available Nov 1Total 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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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total 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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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
60 Hamilton St, Unit 1
60 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
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
1 Victoria St, Unit #1A
1 Victoria 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
66 North St
66 North StSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
294 Boston Ave, Unit 1
294 Boston AveMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
224 Arlington St
224 Arlington 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
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
9 Irving St, Unit 1
9 Irving StMedford, MA 02155
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
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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
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 NowTotal 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 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 Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
59 Quincy St, Unit 1
59 Quincy 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
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 Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
48 Chester Ave, Unit 1
48 Chester AveMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
293 Boston Ave, Unit 2
293 Boston AveMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Dec 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
48 Summer St, Unit 1
48 Summer StMedford, 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
69 Conwell Ave, Unit 1
69 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
44 Russell Rd, Unit 1
44 Russell RdSomerville, 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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$3,100
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
234 Fulton St, Unit 1
234 Fulton StMedford, MA 02155
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$3,100
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total 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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$3,100
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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$3,100
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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$3,100
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
69 Conwell Ave, Unit 1
69 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
14 Belknap St, Unit 2
14 Belknap 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
14 Belknap St, Unit 3
14 Belknap 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
108 W Quincy St, Unit 1
108 W Quincy 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
108 W Quincy St, Unit 108
108 W Quincy StSomerville, MA 02144
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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
73 Gordon St, Unit 1
73 Gordon StSomerville, MA 02144
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Rent Specials
$3,200
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Now14 Belknap St
14 Belknap StSomerville, MA 02144
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$3,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Dec 1Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
39 Wildwood Ave, Unit 39 Wildwood
39 Wildwood AveArlington, MA 02476
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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
136 Sharon St
136 Sharon StMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
26 Bradlee Rd, Unit 406
26 Bradlee RdMedford, MA 02155
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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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$3,300
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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$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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$3,300
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
89 Hillsdale Rd, Unit 1
89 Hillsdale 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 Luxury Studio Apartments | $2,166 | $1,200 | $2,829 |
| Winchester Luxury 1 Bedroom Apartments | $2,669 | $1,395 | $4,195 |
| Winchester Luxury 2 Bedroom Apartments | $3,230 | $2,195 | $5,999 |
| Winchester Luxury 3 Bedroom Apartments | $3,682 | $2,500 | $6,900 |
| Winchester Luxury 4 Bedroom Apartments | $4,567 | $3,000 | $8,000 |
| Winchester 5 Bedroom Apartments | $6,161 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,089 | $5,945 | $8,450 |
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 104 Studio Apartments in Winchester with rent ranges from $1,200 to $2,829 with an average price of $2,166.
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 $2,669.
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 $5,999. Today's average rental price for Two Bedrooms here is $3,230.
How expensive are Winchester Three Bedroom Apartments?
There are currently 153 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,900 - averaging $3,682 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.