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

185 Rentals
.
  1. Building Photo - 104 Windstone Dr
    3 BEDS, 1.5 BATHS
    $1,890
    Total Monthly Price Total Monthly Price New
    Base Rent$1,890
    Required Monthly FeesNone
    Total Monthly Price$1,890
         - 12 Month Lease

    104 Windstone Dr

    104 Windstone Dr, Winchester, VA 22602
  2. Building Photo - 313 Barrington Ln
    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

    313 Barrington Ln

    313 Barrington Ln, Winchester, VA 22601
  3. Building Photo - 301 Sutton Ct
    2 BEDS, 2.5 BATHS
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    301 Sutton Ct

    301 Sutton Ct, Winchester, VA 22601
  4. 1 BED, 1 BATH
    $1,292
    Total Monthly Price Total Monthly Price New
    Base Rent$1,292
    Required Monthly FeesNone
    Total Monthly Price$1,292

    1816 Valley Ave Unit 16

    1816 Valley Ave, Winchester, VA 22601
  5. 2 BEDS, 2 BATHS
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    443 Millwood Ave Unit 3

    443 Millwood Ave, Winchester, VA 22601
  6. 2 BEDS, 2 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    31 E Germain St

    31 E Germain St, Winchester, VA 22601
  7. 2 BEDS, 1 BATH
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    443 N Loudoun St Unit 2

    443 N Loudoun St, Winchester, VA 22601
  8. 3 BEDS, 2 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    553 Highland Ave

    553 Highland Ave, Winchester, VA 22601
  9. 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

    222 Waterford Ln

    222 Waterford Ln, Winchester, VA 22602
  10. 2 BEDS, 1.5 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    311 Willowbrook Ct

    311 Willowbrook Ct, Winchester, VA 22602
  11. 3 BEDS, 1 BATH
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    1112 Opequon Ave

    1112 Opequon Ave, Winchester, VA 22601
  12. 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
  13. 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

    127 Copperfield Ln

    127 Copperfield Ln, Winchester, VA 22602
  14. 3 BEDS, 2.5 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    921 Orchard Hill Dr

    921 Orchard Hill Dr, Winchester, VA 22601
  15. 2 BEDS, 1.5 BATHS
    $1,695
    Total Monthly Price Total Monthly Price New
    Base Rent$1,695
    Required Monthly FeesNone
    Total Monthly Price$1,695

    107 Parkside Dr

    107 Parkside Dr, Winchester, VA 22602
  16. 2 BEDS, 2 BATHS
    $1,575
    Total Monthly Price Total Monthly Price New
    Base Rent$1,575
    Required Monthly FeesNone
    Total Monthly Price$1,575

    26 E Pall Mall St

    26 E Pall Mall St, Winchester, VA 22601
  17. 2 BEDS, 1.5 BATHS
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    527 Gray Ave

    527 Gray Ave, Winchester, VA 22601
  18. 2 BEDS, 1.5 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    255 Waterford Ln

    255 Waterford Ln, Winchester, VA 22602
  19. 2 BEDS, 2 BATHS
    $1,625
    Total Monthly Price Total Monthly Price New
    Base Rent$1,625
    Required Monthly FeesNone
    Total Monthly Price$1,625

    129 Brookland Terrace

    129 Brookland Terrace, Winchester, VA 22602
  20. 3 BEDS, 1.5 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    125 Longstreet Ave

    125 Longstreet Ave, Winchester, VA 22603
  21. 2 BEDS, 1.5 BATHS
    $1,499
    Total Monthly Price Total Monthly Price New
    Base Rent$1,499
    Required Monthly FeesNone
    Total Monthly Price$1,499

    1111 Franklin St

    1111 Franklin St, Winchester, VA 22601
  22. 2 BEDS, 2.5 BATHS
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    104 Eastside Ln

    104 Eastside Ln, Winchester, VA 22602
  23. 3 BEDS, 1.5 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    105 Fay St

    105 Fay St, Winchester, VA 22602
  24. 1 BED, 1 BATH
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    4 W Cork St Unit 1

    4 W Cork St, Winchester, VA 22601
  25. 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

    235 Millwood Ave

    235 Millwood Ave, Winchester, VA 22601
  26. 3 BEDS, 1.5 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    206 Weathervane Dr

    206 Weathervane Dr, Winchester, VA 22602
  27. 3 BEDS, 1 BATH
    $1,450
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450
    Required Monthly FeesNone
    Total Monthly Price$1,450

    222 E Whitlock Ave

    222 E Whitlock Ave, Winchester, VA 22601
  28. 1 BED, 1 BATH
    $1,150
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150
    Required Monthly FeesNone
    Total Monthly Price$1,150

    29 W Leicester St

    29 W Leicester St, Winchester, VA 22601
  29. 1 BED, 1 BATH
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    116 N Indian Alley Unit 203

    116 N Indian Alley, Winchester, VA 22601
  30. 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

    1057 Foreman Ln

    1057 Foreman Ln, Winchester, VA 22603
  31. 1 BED, 1 BATH
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    116 N Indian Alley Unit 102

    116 N Indian Alley, Winchester, VA 22601
  32. 2 BEDS, 1.5 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    111 Barrington Ln

    111 Barrington Ln, Winchester, VA 22601
  33. 1 BED, 1 BATH
    $995
    Total Monthly Price Total Monthly Price New
    Base Rent$995
    Required Monthly FeesNone
    Total Monthly Price$995

    1816 Valley Ave Unit 2

    1816 Valley Ave, Winchester, VA 22601
  34. 3 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

    8 W Monmouth St

    8 W Monmouth St, Winchester, VA 22601
  35. 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

    204 E Whitlock Ave

    204 E Whitlock Ave, Winchester, VA 22601
  36. 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

    140 Lexington Ct

    140 Lexington Ct, Stephens City, VA 22655
  37. 2 BEDS, 1 BATH
    $1,895
    Total Monthly Price Total Monthly Price New
    Base Rent$1,895
    Required Monthly FeesNone
    Total Monthly Price$1,895

    115 Deer Hill Ct

    115 Deer Hill Ct, Stephens City, VA 22655
  38. 2 BEDS, 1.5 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    219 Surrey Club Ln

    219 Surrey Club Ln, Stephens City, VA 22655
  39. STUDIO, 1 BATH
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    217 Bridgewater Dr

    217 Bridgewater Dr, Stephens City, VA 22655
  40. 3 BEDS, 1.5 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    202 Carroll Dr

    202 Carroll Dr, Stephens City, VA 22655
  41. Building Photo - 1001 S Cameron St
    3 BEDS, 1 BATH
    $1,395
    Total Monthly Price Total Monthly Price New
    Base Rent$1,395
    Required Monthly FeesNone
    Total Monthly Price$1,395

    1001 S Cameron St

    1001 S Cameron St, Winchester, VA 22601
  42. Building Photo - 346 Gray Ave
    3 BEDS, 1 BATH
    $1,395
    Total Monthly Price Total Monthly Price New
    Base Rent$1,395
    Required Monthly FeesNone
    Total Monthly Price$1,395

    346 Gray Ave

    346 Gray Ave, Winchester, VA 22601
Showing 42 of 102 results, Page 2 of 3

Winchester at a Glance

Average Rent

$1,358
(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

Renting in Winchester

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Education

GreatSchools Rating
James Wood High

Public High School

Public
Grades 9-12
1,437 Students
GreatSchools Rating
James Wood High School

Public High School

Public
Grades 9-12
1,437 Students
GreatSchools Rating
Millbrook High School

Public High School

Public
Grades 9-12
1,553 Students
GreatSchools Rating
John Handley High School

Public High School

Public
Grades 9-12
1,361 Students
GreatSchools Rating
Admiral Richard E. Byrd Middle

Public Middle School

Public
Grades 6-8
804 Students
GreatSchools Rating
Admiral Richard E. Byrd Middle School

Public Middle School

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

Public Middle School

Public
Grades 6-8
642 Students
GreatSchools Rating
James Wood Middle

Public Middle School

Public
Grades 6-8
803 Students
GreatSchools Rating
James Wood Middle School

Public Middle School

Public
Grades 6-8
803 Students

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

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