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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
Luxury Apartments for Rent in Winchester, MA (293 Rentals) Page 3 of 6
The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.
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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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$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
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
77 Fairfax St, Unit #1
77 Fairfax StSomerville, MA 02144
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
41 Belknap St, Unit 2
41 Belknap StSomerville, MA 02144
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
41 Belknap St, Unit 2
41 Belknap StSomerville, MA 02144
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
104 W Quincy St, Unit 1
104 W Quincy StSomerville, MA 02144
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$3,400
Total Monthly Price11 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
7 Patrick St, Unit 2
7 Patrick StArlington, MA 02474
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, MA 02144
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
5 Patrick St, Unit 2
5 Patrick StArlington, MA 02474
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$3,450
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Aug 31, 2026Total Monthly Price
Base Rent
$3,450
Total Monthly Price
$3,450
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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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
59 Quincy St, Unit 1
59 Quincy StMedford, MA 02155
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$3,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
235 Ashcroft Rd
235 Ashcroft RdMedford, MA 02155
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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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$3,500
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
124 Forest St, Unit 1
124 Forest StMedford, MA 02155
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$3,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
43 Orchard St, Unit 1
43 Orchard StMedford, MA 02155
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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
124 Forest St, Unit 1
124 Forest StMedford, MA 02155
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$3,550
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2027Total Monthly Price
Base Rent
$3,550
Total Monthly Price
$3,550
43 Orchard St
43 Orchard StMedford, MA 02155
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$3,573 - $6,605
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,573 - $6,605
Total Monthly Price
$3,573 - $6,605
Arlington 360
4105 Symmes CirArlington, MA 02474
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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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$3,600
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,600
Total Monthly Price
$3,600
112 College Ave
112 College AveMedford, MA 02155
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$3,600
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
Base Rent
$3,600
Total Monthly Price
$3,600
65 Conwell Ave, Unit 3
65 Conwell 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
258 Boston Ave, Unit 2
258 Boston AveMedford, MA 02155
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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
258 Boston Ave, Unit 2
258 Boston AveMedford, MA 02155
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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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$3,750
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,750
Total Monthly Price
$3,750
49 Conwell Ave, Unit 2
49 Conwell AveSomerville, 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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$3,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
165 Radcliffe Rd, Unit #169
165 Radcliffe RdBelmont, MA 02478
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$3,900
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
59 Quincy St
59 Quincy StMedford, MA 02155
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$3,900
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
59 Quincy St
59 Quincy StMedford, MA 02155
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$3,900
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
56 Gordon St, Unit 1
56 Gordon StSomerville, MA 02144
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$3,975
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,975
Total Monthly Price
$3,975
54 Upland Rd, Unit 2
54 Upland RdSomerville, MA 02144
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$3,975
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,975
Total Monthly Price
$3,975
54 Upland Rd, Unit 2
54 Upland RdSomerville, MA 02144
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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
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 Feb 1, 2026Total Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2T
10 Pinkham RdMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
300 Boston Ave, Unit 2
300 Boston AveMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
300 Boston Ave, Unit 2
300 Boston AveMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
300 Boston Ave, Unit 2
300 Boston AveMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
300 Boston Ave, Unit 2
300 Boston AveMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
300 Boston Ave, Unit 2F
300 Boston AveMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
300 Boston Ave, Unit 2
300 Boston AveMedford, 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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$4,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,150
Total Monthly Price
$4,150
290 Boston Ave, Unit 2
290 Boston AveMedford, MA 02155
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$4,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,150
Total Monthly Price
$4,150
290 Boston Ave, Unit 1
290 Boston AveMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2T
62 Woods AveSomerville, MA 02144
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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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$4,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
119 Burget Ave
119 Burget AveMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Feb 1, 2026Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Feb 1, 2026Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2A
62 Woods AveSomerville, 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 | $2,150 | $1,650 | $2,871 |
| Winchester Luxury 1 Bedroom Apartments | $2,599 | $1,295 | $4,195 |
| Winchester Luxury 2 Bedroom Apartments | $3,202 | $2,100 | $4,880 |
| Winchester Luxury 3 Bedroom Apartments | $3,638 | $2,500 | $6,900 |
| Winchester Luxury 4 Bedroom Apartments | $4,312 | $1,000 | $6,375 |
| Winchester 5 Bedroom Apartments | $6,259 | $4,500 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,261 | $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 102 Studio Apartments in Winchester with rent ranges from $1,650 to $2,871 with an average price of $2,150.
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 $1,295 to $4,195 with an average monthly rent of $2,599.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,100 to $4,880. Today's average rental price for Two Bedrooms here is $3,202.
How expensive are Winchester Three Bedroom Apartments?
There are currently 123 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,900 - averaging $3,638 for the location.
Expert Rental Resources
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.
Helpful Local Expert Guides
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.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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.