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

238 Rentals
.
  1. Building Photo - 26 Jackson Ave
    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

    26 Jackson Ave

    26 Jackson Ave, Winchester, VA 22601
  2. Building Photo - 311 S Kent St
    2 BEDS, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495

    311 S Kent St

    311 S Kent St, Winchester, VA 22601
  3. 2 BEDS, 1 BATH
    $1,445
    Total Monthly Price Total Monthly Price New
    Base Rent$1,445
    Required Monthly FeesNone
    Total Monthly Price$1,445

    204 E Whitlock Ave

    204 E Whitlock Ave, Winchester, VA 22601
  5. 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

    1839 Henry Ave

    1839 Henry Ave, Winchester, VA 22601
  6. 1 BED, 1 BATH
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    30 W Germain St

    30 W Germain St, Winchester, VA 22601
  7. 1 BED, 1 BATH
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    619 S Cameron St

    619 S Cameron St, Winchester, VA 22601
  8. 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

    203 Dodge Ave

    203 Dodge Ave, Winchester, VA 22602
  9. 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

    523 S Cameron St Unit 3

    523 S Cameron St, Winchester, VA 22601
  10. 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

    523 S Cameron St Unit 1

    523 S Cameron St, Winchester, VA 22601
  11. 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

    1817 Henry Ave

    1817 Henry Ave, Winchester, VA 22601
  12. 3 BEDS, 1.5 BATHS
    $1,925
    Total Monthly Price Total Monthly Price New
    Base Rent$1,925
    Required Monthly FeesNone
    Total Monthly Price$1,925

    1442 Greystone Terrace

    1442 Greystone Terrace, Winchester, VA 22601
  13. 3 BEDS, 1 BATH
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    222 E Whitlock Ave

    222 E Whitlock Ave, Winchester, VA 22601
  14. 2 BEDS, 1 BATH
    $1,295
    Total Monthly Price Total Monthly Price New
    Base Rent$1,295
    Required Monthly FeesNone
    Total Monthly Price$1,295

    307 S Kent St

    307 S Kent St, Winchester, VA 22601
  15. 2 BEDS, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495

    615 S Braddock St

    615 S Braddock St, Winchester, VA 22601
  16. 3 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

    317 Ash Hollow Dr

    317 Ash Hollow Dr, Winchester, VA 22602
  17. 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

    224 East St

    224 East St, Winchester, VA 22601
  18. 1 BED, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495

    2550 Bradford Ct

    2550 Bradford Ct, Winchester, VA 22601
  19. 1 BED, 1 BATH
    $1,395
    Total Monthly Price Total Monthly Price New
    Base Rent$1,395
    Required Monthly FeesNone
    Total Monthly Price$1,395

    2555 Bradford Ct

    2555 Bradford Ct, 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

    808 S Braddock St Unit Apt 1

    808 S Braddock St, Winchester, VA 22601
  23. 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

    109 E Pall Mall St

    109 E Pall Mall St, Winchester, VA 22601
  24. 3 BEDS, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    308 Gainesboro Rd

    308 Gainesboro Rd, Winchester, VA 22603
  25. 2 BEDS, 1 BATH
    $1,375
    Total Monthly Price Total Monthly Price New
    Base Rent$1,375
    Required Monthly FeesNone
    Total Monthly Price$1,375

    412 Diehl St

    412 Diehl St, Winchester, VA 22601
  27. 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

    5340 Water St

    5340 Water St, Stephens City, VA 22655
  28. 2 BEDS, 1 BATH
    $1,525
    Total Monthly Price Total Monthly Price New
    Base Rent$1,525
    Required Monthly FeesNone
    Total Monthly Price$1,525

    1014 Bridle Ct

    1014 Bridle Ct, Stephens City, VA 22655
  29. 4 BEDS, 3.5 BATHS
    $1,995
    Total Monthly Price Total Monthly Price New
    Base Rent$1,995
    Required Monthly FeesNone
    Total Monthly Price$1,995

    247 Crofton Ct

    247 Crofton Ct, Stephenson, VA 22656
Showing 42 of 113 results, Page 3 of 3

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Winchester at a Glance

Average Rent

$1,342
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
5

School Rating

out of 10 Rating
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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
John Handley High

Public High School

Public
Grades 9-12
1,384 Students
GreatSchools Rating
John Handley High School

Public High School

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

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
Admiral Richard E. Byrd Middle School

Public Middle School

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

Public Middle School

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

Public Middle School

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

Public Middle School

Public
Grades 6-8
803 Students
GreatSchools Rating
Jordan Springs Elementary

Public Elementary School

Public
Grades K-5
566 Students

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

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