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Two Bedroom Apartments for Rent in Winchester, MA

64 Rentals
  1. Price Drop. $428 Off
    2 BEDS
    $3,572
    Total Monthly Price Total Monthly Price New
    Base Rent$3,572 - $4,087
    Utilities & EssentialsVaries
    Total Monthly Price$3,572 - $4,087

    Sanctuary Winchester West

    416 Cambridge St, Winchester, MA 01890
    (781) 745-3086
  2. Rent Special
    |
    2 BEDS
    $4,023
    Total Monthly Price Total Monthly Price New
    Base Rent$4,023 - $5,457
    Required Monthly FeesNone
    Total Monthly Price$4,023 - $5,457

    Hanover Stoneham

    95 Maple St, Stoneham, MA 02180
    (781) 818-1154
  3. 1 Month Free
    2 BEDS
    $3,300
    Total Monthly Price Total Monthly Price New
    Base Rent$3,300 - $4,930
    Utilities & EssentialsVaries
    Total Monthly Price$3,300 - $4,930
    - 1 Month Lease

    The Mave

    225 Fallon Rd, Stoneham, MA 02180
    (978) 396-2160
  4. 1 Month Free
    2 BEDS
    $3,772
    Total Monthly Price Total Monthly Price New
    Base Rent$3,772 - $4,625
    Utilities & EssentialsVaries
    Total Monthly Price$3,772 - $4,625

    Sanctuary Winchester North

    25-35 River St, Winchester, MA 01890
    (781) 776-5276
  5. Fully Equipped Kitchen with Stainless Steel Appliances Dishwasher and Garbage Disposal - Arlington 360
    2 BEDS
    $4,423
    Total Monthly Price Total Monthly Price New
    Base Rent$4,423 - $4,816
    Utilities & EssentialsVaries
    Total Monthly Price$4,423 - $4,816

    Arlington 360

    4105 Symmes Cir, Arlington, MA 02474
    (781) 678-7526
  6. Building Photo - 63 Holland St
    2 BEDS, 1 BATH
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500

    63 Holland St

    63 Holland St, Winchester, MA 01890
  7. Building Photo - 48 Nashua St
    2 BEDS, 1 BATH
    $2,375
    Total Monthly Price Total Monthly Price New
    Base Rent$2,375
    Required Monthly FeesNone
    Total Monthly Price$2,375
    - 12 Month Lease

    48 Nashua St Unit 2

    48 Nashua St, Woburn, MA 01801
  8. Building Photo - 46 Clewley Rd
    2 BEDS, 1 BATH
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800
    - 12 Month Lease

    46 Clewley Rd Unit 3

    46 Clewley Rd, Medford, MA 02155
  9. 2 BEDS, 1 BATH
    $2,400
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400
    Required Monthly FeesNone
    Total Monthly Price$2,400
    - 12 Month Lease

    3 Colonial Village Dr Unit 10

    3 Colonial Village Dr, Arlington, MA 02474
  10. 2 BEDS, 2 BATHS
    $2,995
    Total Monthly Price Total Monthly Price New
    Base Rent$2,995
    Required Monthly FeesNone
    Total Monthly Price$2,995
    - 12 Month Lease

    286 Main St Unit 3

    286 Main St, Woburn, MA 01801
  11. Building Photo - 1 Colonial Village Dr
    2 BEDS, 1 BATH
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000
    - 12 Month Lease

    1 Colonial Village Dr Unit 10

    1 Colonial Village Dr, Arlington, MA 02474
  12. Building Photo - 32 Pond St
    2 BEDS, 1 BATH
    $2,395
    Total Monthly Price Total Monthly Price New
    Base Rent$2,395
    Required Monthly FeesNone
    Total Monthly Price$2,395
    - 12 Month Lease

    32 Pond St Unit 2

    32 Pond St, Stoneham, MA 02180
  13. 2 BEDS, 1 BATH
    $2,450
    Total Monthly Price Total Monthly Price New
    Base Rent$2,450
    Required Monthly FeesNone
    Total Monthly Price$2,450
    - 12 Month Lease

    25 Arlington Rd Unit Apt #3 6

    25 Arlington Rd, Woburn, MA 01801
  14. 2 BEDS, 1 BATH
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000
    - 12 Month Lease

    36 Century St Unit 1

    36 Century St, Medford, MA 02155
  15. Building Photo - 200 Swanton St
    2 BEDS, 1 BATH
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    200 Swanton St Unit T35

    200 Swanton St, Winchester, MA 01890
  16. Building Photo - 60 Lake St
    2 BEDS, 1.5 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    60 Lake St Unit D

    60 Lake St, Winchester, MA 01890
  17. Building Photo - 24 Lebanon St
    2 BEDS, 1 BATH
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500

    24 Lebanon St Unit 1

    24 Lebanon St, Winchester, MA 01890
  18. 2 BEDS, 2 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    666 Main St Unit 208

    666 Main St, Winchester, MA 01890
  19. 2 BEDS, 1.5 BATHS
    $2,600
    Total Monthly Price Total Monthly Price New
    Base Rent$2,600
    Required Monthly FeesNone
    Total Monthly Price$2,600

    16 Lochwan St

    16 Lochwan St, Winchester, MA 01890
  20. 2 BEDS, 1.5 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    7 Ridge St

    7 Ridge St, Winchester, MA 01890
  21. 2 BEDS, 2 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    666 Main St Unit 315-3

    666 Main St, Winchester, MA 01890
  22. 2 BEDS, 1 BATH
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800

    200 Swanton St Unit 705

    200 Swanton St, Winchester, MA 01890
  23. 2 BEDS, 1 BATH
    $2,400
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400
    Required Monthly FeesNone
    Total Monthly Price$2,400

    1357 Massachusetts Ave Unit 1

    1357 Massachusetts Ave, Arlington, MA 02476
  24. 2 BEDS, 1 BATH
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    1 Lincoln St Unit 1

    1 Lincoln St, Stoneham, MA 02180
  25. 2 BEDS, 1 BATH
    $2,575
    Total Monthly Price Total Monthly Price New
    Base Rent$2,575
    Required Monthly FeesNone
    Total Monthly Price$2,575

    32 Century St Unit 1

    32 Century St, Medford, MA 02155
  26. 2 BEDS, 1 BATH
    $2,300
    Total Monthly Price Total Monthly Price New
    Base Rent$2,300
    Required Monthly FeesNone
    Total Monthly Price$2,300

    20-22 Emerson St

    20-22 Emerson St, Stoneham, MA 02180
  27. 2 BEDS, 1 BATH
    $2,950
    Total Monthly Price Total Monthly Price New
    Base Rent$2,950
    Required Monthly FeesNone
    Total Monthly Price$2,950

    18 Wheelwright Rd Unit 18

    18 Wheelwright Rd, Medford, MA 02155
  28. 2 BEDS, 2 BATHS
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    100 Ledgewood Dr Unit 410

    100 Ledgewood Dr, Stoneham, MA 02180
  29. 2 BEDS, 1 BATH
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800

    1 Colonial Village Dr Unit 12

    1 Colonial Village Dr, Arlington, MA 02474
  30. Building Photo - 19-21 Orient Ave
    2 BEDS, 1 BATH
    $2,899
    Total Monthly Price Total Monthly Price New
    Base Rent$2,899
    Required Monthly FeesNone
    Total Monthly Price$2,899

    19-21 Orient Ave Unit 21

    19-21-21 Orient Ave, Arlington, MA 02474
  31. Building Photo - Shaker Glen Village
    2 BEDS
    $2,795
    Total Monthly Price Total Monthly Price New
    Base Rent$2,795
    Required Monthly FeesNone
    Total Monthly Price$2,795

    Shaker Glen Village

    241 Lexington St, Woburn, MA 01801

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Winchester at a Glance

Average Rent

$2,935
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
9

School Rating

out of 10 Rating
Learn more about
Schools in Winchester

Winchester, MA Apartments for Rent

Located 8 miles north of downtown Boston, Winchester combines historic New England character with modern convenience. This charming town, established in 1850, spans just over 6 square miles around the Aberjona River and Mystic Lakes. Winchester's downtown features independent shops and restaurants, while the surrounding neighborhoods offer various apartment options.

Two MBTA Commuter Rail stations connect residents to Boston, making it ideal for commuters who prefer a quieter setting. Nature enthusiasts appreciate the Middlesex Fells Reservation's extensive trail network along the town's eastern border. The median rent for a one-bedroom apartment is $2,933, reflecting Winchester's proximity to Boston and highly rated public schools. Local landmarks include Wedge Pond and Wright-Locke Farm, one of the oldest continuously operating farms in Massachusetts.

Renting in Winchester

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Education

Private University
Private University
Private University
GreatSchools Rating

Public High School

Public
Grades 9-12
1,418 Students
GreatSchools Rating

Public Middle School

Public
Grades 6-8
1,053 Students
GreatSchools Rating

Public Elementary School

Public
Grades K-5
377 Students
GreatSchools Rating

Public Elementary School

Public
Grades K-5
338 Students
GreatSchools Rating

Public Elementary School

Public
Grades K-5
296 Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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