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$2,950
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,950
Total Monthly Price
$2,950
27 Holton St, Unit 1
27 Holton StMedford, MA 02155
Luxury Apartments for Rent in Winchester, MA (420 Rentals) Page 2 of 9
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
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
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
66 North St
66 North 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
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
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
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
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 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
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
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 Mar 1, 2026Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
321 Alewife Brook Pky, Unit 1
321 Alewife Brook PkySomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 3Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
2 Clark St, Unit 2
2 Clark StWoburn, MA 01801
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$3,060 - $6,857
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,060 - $6,857
Total Monthly Price
$3,060 - $6,857
Arlington 360
4105 Symmes CirArlington, MA 02474
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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
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
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
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
24 Sunset Rd, Unit 2
24 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
83 Conwell Ave, Unit 2
83 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
96 Conwell Ave, Unit 2
96 Conwell AveSomerville, MA 02144
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$3,100
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
86 Orchard St, Unit 3
86 Orchard 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
35 Hilton St, Unit 2
35 Hilton StArlington, MA 02474
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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
12 Fairfax St, Unit 2
12 Fairfax StSomerville, MA 02144
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$3,150
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
63 Newport St, Unit 63 Newport Street
63 Newport StArlington, MA 02476
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$3,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total 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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$3,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
26 Marshall St, Unit 1
26 Marshall StMedford, MA 02155
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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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$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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$3,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
333 Alewife Brook Pkwy, Unit 1
333 Alewife Brook PkwySomerville, 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
12 Pinkham Rd, Unit 1
12 Pinkham RdMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total 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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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
26 Bradlee Rd, Unit 302
26 Bradlee RdMedford, 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
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, 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
294 Boston Ave, Unit A
294 Boston AveMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
167 Allston St, Unit 2
167 Allston 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
167 Allston St, Unit 2
167 Allston StMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
167 Allston St, Unit 2
167 Allston 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
163 Allston St, Unit 2
163 Allston StMedford, 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
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 | $2,272 | $1,550 | $2,914 |
| Winchester Luxury 1 Bedroom Apartments | $2,823 | $1,850 | $4,350 |
| Winchester Luxury 2 Bedroom Apartments | $3,236 | $2,000 | $5,128 |
| Winchester Luxury 3 Bedroom Apartments | $3,681 | $2,250 | $7,500 |
| Winchester Luxury 4 Bedroom Apartments | $4,655 | $3,200 | $6,066 |
| Winchester 5 Bedroom Apartments | $5,988 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,262 | $5,945 | $9,100 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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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 106 Studio Apartments in Winchester with rent ranges from $1,550 to $2,914 with an average price of $2,272.
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 $2,823.
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 $3,236.
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 $3,681 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.
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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
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.