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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
Luxury Apartments for Rent in Winchester, MA (293 Rentals) Page 4 of 6
The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.
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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
100 W Adams St, Unit 1A
100 W Adams StSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
288 Boston Ave, Unit 3
288 Boston AveMedford, MA 02155
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$4,500
Total Monthly Price6 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
70 Tufts St, Unit 1
70 Tufts StArlington, MA 02474
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$4,500
Plus Fees
4 Bedroom Apartments Available NowBrightly Renovated 4-Bed / 2-Bath • 1,800 sq
86 Orchard StMedford, MA 02155
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
215 Boston Ave
215 Boston AveMedford, MA 02155
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$4,545
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Sep 1, 2026Total Monthly Price
Base Rent
$4,545
Total Monthly Price
$4,545
227 Boston Ave, Unit 2
227 Boston AveMedford, 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
50 Curtis Ave, Unit 1
50 Curtis 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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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,600
Total Monthly Price
$4,600
82 Quincy St, Unit #2
82 Quincy StMedford, MA 02155
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$4,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,650
Total Monthly Price
$4,650
299 Alewife Brook Pky, Unit 2
299 Alewife Brook PkySomerville, MA 02144
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$4,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,650
Total Monthly Price
$4,650
299 Alewife Brook Pky, Unit 2
299 Alewife Brook PkySomerville, MA 02144
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$4,750
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,750
Total Monthly Price
$4,750
2 Osgood St, Unit 1
2 Osgood StSomerville, MA 02143
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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
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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
67 Greenleaf Ave, Unit 1
67 Greenleaf AveMedford, MA 02155
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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
288 Boston Ave, Unit 3
288 Boston AveMedford, MA 02155
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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Feb 1, 2026Total Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
112 College Ave, Unit 2T
112 College AveMedford, MA 02155
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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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$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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$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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$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
477 Fulton St, Unit F
477 Fulton StMedford, MA 02155
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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
62 Woods Ave, Unit 2
62 Woods AveSomerville, 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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$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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$5,500
Total Monthly Price5 Month Lease Term
5 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
Base Rent
$5,500
Total Monthly Price
$5,500
282 Boston Ave, Unit 2
282 Boston AveMedford, MA 02155
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$5,729
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,729
Total Monthly Price
$5,729
76 Curtis St, Unit 1
76 Curtis StSomerville, MA 02144
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$5,945
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,945
Total Monthly Price
$5,945
3 Hamilton Rd, Unit #2
3 Hamilton RdSomerville, MA 02144
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$5,945
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,945
Total Monthly Price
$5,945
5 Hamilton Rd, Unit 1
5 Hamilton RdSomerville, MA 02144
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$5,995
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,995
Total Monthly Price
$5,995
3 Hamilton Rd, Unit 2
3 Hamilton RdSomerville, MA 02144
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$6,000
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,000
Total Monthly Price
$6,000
123 Winthrop St, Unit 2
123 Winthrop StMedford, MA 02155
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$6,200
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,200
Total Monthly Price
$6,200
3 Hamilton Rd, Unit #2
3 Hamilton RdSomerville, 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
123 Winthrop St, Unit 1
123 Winthrop StMedford, MA 02155
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$6,250
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal 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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$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
24 Chetwynd Rd, Unit 2
24 Chetwynd 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
14 Dow St, Unit 2
14 Dow StSomerville, MA 02144
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$6,375
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,375
Total Monthly Price
$6,375
14 Dow St, Unit 2
14 Dow StSomerville, MA 02144
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$6,375
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,375
Total Monthly Price
$6,375
14 Dow St, Unit 14 Dow Street
14 Dow StSomerville, 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
14 Dow St, Unit 2
14 Dow StSomerville, 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
14 Dow St, Unit 2
14 Dow StSomerville, MA 02144
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
136 Burget Ave
136 Burget AveMedford, MA 02155
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
57 Quincy St
57 Quincy StMedford, MA 02155
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
136 Burget Ave
136 Burget AveMedford, MA 02155
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
136 Burget Ave
136 Burget AveMedford, MA 02155
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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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$6,650
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,650
Total Monthly Price
$6,650
14 Dow St, Unit 2
14 Dow StSomerville, MA 02144
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$6,750
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,750
Total Monthly Price
$6,750
14 Dow St, Unit 2F
14 Dow StSomerville, MA 02144
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$6,750
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,750
Total Monthly Price
$6,750
14 Dow St, Unit 2
14 Dow StSomerville, MA 02144
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$6,995
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,995
Total Monthly Price
$6,995
120 Jerome St
120 Jerome StMedford, MA 02155
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$7,000
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$7,000
Total Monthly Price
$7,000
24 Chetwynd Rd, Unit Apt 1
24 Chetwynd RdSomerville, 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.