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Apartments under $2,000 for Rent in Winchester, VA

267 Rentals
.
  1. Building Photo - 443 Millwood Ave
    2 BEDS, 2 BATHS
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    443 Millwood Ave Unit 2

    443 Millwood Ave, Winchester, VA 22601
  2. Building Photo - 1704 Roberts St
    1 BED, 1 BATH
    $1,124
    Total Monthly Price Total Monthly Price New
    Base Rent$1,124
    Required Monthly FeesNone
    Total Monthly Price$1,124

    1704 Roberts St Unit 1

    1704 Roberts St, Winchester, VA 22601
  3. 2 BEDS, 1 BATH
    $1,450
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450
    Required Monthly FeesNone
    Total Monthly Price$1,450

    224 Kern St

    224 Kern St, Winchester, VA 22601
  4. 2 BEDS, 1 BATH
    $1,810
    Total Monthly Price Total Monthly Price New
    Base Rent$1,810
    Required Monthly FeesNone
    Total Monthly Price$1,810

    137 Fox Dr

    137 Fox Dr, Winchester, VA 22601
  5. 2 BEDS, 1.5 BATHS
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    544 Allston Cir

    544 Allston Cir, Winchester, VA 22601
  6. 4 BEDS, 3 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    603 Panther Dr

    603 Panther Dr, Winchester, VA 22602
  7. 2 BEDS, 1 BATH
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200

    24 W Cecil St

    24 W Cecil St, Winchester, VA 22601
  8. 1 BED, 1 BATH
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200

    553 N Loudoun St Unit 1

    553 N Loudoun St, Winchester, VA 22601
  9. 2 BEDS, 1 BATH
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    108 Martin Dr

    108 Martin Dr, Winchester, VA 22602
  10. 1 BED, 1 BATH
    $1,000
    Total Monthly Price Total Monthly Price New
    Base Rent$1,000
    Required Monthly FeesNone
    Total Monthly Price$1,000

    510 N Kent St Unit 1

    510 N Kent St, Winchester, VA 22601
  11. 2 BEDS, 1 BATH
    $1,450
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450
    Required Monthly FeesNone
    Total Monthly Price$1,450

    208 W Boscawen St Unit 5

    208 W Boscawen St, Winchester, VA 22601
  12. 2 BEDS, 1 BATH
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    228 Opequon Ave

    228 Opequon Ave, Winchester, VA 22601
  13. 2 BEDS, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    378 National Ave

    378 National Ave, Winchester, VA 22601
  14. 1 BED, 1 BATH
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    25 E Boscawen St Unit 301

    25 E Boscawen St, Winchester, VA 22601
  15. 2 BEDS, 1 BATH
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    2645 Valley Ave Unit 30

    2645 Valley Ave, Winchester, VA 22601
  16. 1 BED, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    208 W Boscawen St Unit 12

    208 W Boscawen St, Winchester, VA 22601
  17. 2 BEDS, 1 BATH
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    447 N Loudoun St

    447 N Loudoun St, Winchester, VA 22601
  18. 2 BEDS, 1 BATH
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    434 Fairmont Ave

    434 Fairmont Ave, Winchester, VA 22601
  19. 2 BEDS, 1.5 BATHS
    $1,599
    Total Monthly Price Total Monthly Price New
    Base Rent$1,599
    Required Monthly FeesNone
    Total Monthly Price$1,599

    3107 Shawnee Dr

    3107 Shawnee Dr, Winchester, VA 22601
  20. 1 BED, 1 BATH
    $1,000
    Total Monthly Price Total Monthly Price New
    Base Rent$1,000
    Required Monthly FeesNone
    Total Monthly Price$1,000

    318 S Braddock St

    318 S Braddock St, Winchester, VA 22601
  21. 2 BEDS, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    121 Taft Ave

    121 Taft Ave, Winchester, VA 22601
  22. 1 BED, 1 BATH
    $1,060
    Total Monthly Price Total Monthly Price New
    Base Rent$1,060
    Required Monthly FeesNone
    Total Monthly Price$1,060

    545 N Loudoun St Unit 5

    545 N Loudoun St, Winchester, VA 22601
  23. 2 BEDS, 2 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    110 Brookland Ct

    110 Brookland Ct, Winchester, VA 22602
  24. 2 BEDS, 1 BATH
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    5366 Main St

    5366 Main St, Stephens City, VA 22655
  25. 3 BEDS, 1.5 BATHS
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    225 Nottoway Dr

    225 Nottoway Dr, Stephens City, VA 22655
  26. 3 BEDS, 3 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    129 Schramm Lp

    129 Schramm Lp, Stephens City, VA 22655
  27. 2 BEDS, 2 BATHS
    $1,695
    Total Monthly Price Total Monthly Price New
    Base Rent$1,695
    Required Monthly FeesNone
    Total Monthly Price$1,695

    302 Freeton Ct

    302 Freeton Ct, Stephens City, VA 22655
  28. Building Photo - 3105 Shawnee Dr
    1 BED, 1 BATH
    $1,199
    Total Monthly Price Total Monthly Price New
    Base Rent$1,199
    Required Monthly FeesNone
    Total Monthly Price$1,199

    3105 Shawnee Dr Unit 07

    3105 Shawnee Dr, Winchester, VA 22601
  29. Building Photo - 3107 Shawnee Dr
    2 BEDS, 1.5 BATHS
    $1,549
    Total Monthly Price Total Monthly Price New
    Base Rent$1,549
    Required Monthly FeesNone
    Total Monthly Price$1,549

    3107 Shawnee Dr Unit 11

    3107 Shawnee Dr, Winchester, VA 22601
  30. 2 BEDS, 1.5 BATHS
    $1,599
    Total Monthly Price Total Monthly Price New
    Base Rent$1,599
    Required Monthly FeesNone
    Total Monthly Price$1,599

    3107 Shawnee Dr Unit 7

    3107 Shawnee Dr, Winchester, VA 22601
  31. 2 BEDS, 1 BATH
    $1,595
    Total Monthly Price Total Monthly Price New
    Base Rent$1,595
    Required Monthly FeesNone
    Total Monthly Price$1,595

    313 Emily Ln

    313 Emily Ln, Winchester, VA 22602
  32. 2 BEDS, 1.5 BATHS
    $1,995
    Total Monthly Price Total Monthly Price New
    Base Rent$1,995
    Required Monthly FeesNone
    Total Monthly Price$1,995

    402 Tudor Dr

    402 Tudor Dr, Winchester, VA 22603
  33. 3 BEDS, 1 BATH
    $1,695
    Total Monthly Price Total Monthly Price New
    Base Rent$1,695
    Required Monthly FeesNone
    Total Monthly Price$1,695

    211 Sharp St

    211 Sharp St, Winchester, VA 22601
  34. 2 BEDS, 1 BATH
    $1,395
    Total Monthly Price Total Monthly Price New
    Base Rent$1,395
    Required Monthly FeesNone
    Total Monthly Price$1,395

    103 W Germain St

    103 W Germain St, Winchester, VA 22601
  35. 1 BED, 1 BATH
    $1,295
    Total Monthly Price Total Monthly Price New
    Base Rent$1,295
    Required Monthly FeesNone
    Total Monthly Price$1,295

    445 Bryarly Rd

    445 Bryarly Rd, Winchester, VA 22603
  36. 2 BEDS, 1 BATH
    $1,450
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450
    Required Monthly FeesNone
    Total Monthly Price$1,450

    1660 S Braddock St

    1660 S Braddock St, Winchester, VA 22601
  37. 2 BEDS, 1.5 BATHS
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    1815 Henry Ave

    1815 Henry Ave, Winchester, VA 22601
  38. 3 BEDS, 1.5 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    504 Yorktowne Pl

    504 Yorktowne Pl, Winchester, VA 22601
  39. 2 BEDS, 1.5 BATHS
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    1819 Henry Ave

    1819 Henry Ave, Winchester, VA 22601
  41. 2 BEDS, 1 BATH
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    113 W Boscawen St Unit #3

    113 W Boscawen St, Winchester, VA 22601
  42. 3 BEDS, 1 BATH
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    Detached ranch style house

    209 Shenandoah Ave, Winchester, VA 22601
Showing 42 of 88 results, Page 2 of 3

Winchester at a Glance

Average Rent

$1,320
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
4

School Rating

out of 10 Rating
Learn more about
Schools in Winchester
0

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Winchester
39

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Winchester

Renting in Winchester

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Getting Around Winchester

Transportation

48

Car-Dependent

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
39

Somewhat Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
0

Minimal Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Scoreⓘ

Education

GreatSchools Rating
James Wood High

Public High School

Public
Grades 9-12
1,437 Students
GreatSchools Rating
John Handley High

Public High School

Public
Grades 9-12
1,384 Students
GreatSchools Rating
Millbrook High

Public High School

Public
Grades 9-12
1,516 Students
GreatSchools Rating
Admiral Richard E. Byrd Middle

Public Middle School

Public
Grades 6-8
804 Students
GreatSchools Rating
Daniel Morgan Middle

Public Middle School

Public
Grades 7-8
613 Students
GreatSchools Rating
James Wood Middle

Public Middle School

Public
Grades 6-8
803 Students
GreatSchools Rating
Frederick County Middle

Public Middle School

Public
Grades 6-8
751 Students

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

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