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  1. Building Photo - 3548 N Frederick Pike
    1 BED, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    3548 N Frederick Pike

    3548 N Frederick Pike, Winchester, VA 22603
  2. Building Photo - 209 Winchester Dr
    4 BEDS, 2.5 BATHS
    $2,350
    Total Monthly Price Total Monthly Price New
    Base Rent$2,350
    Required Monthly FeesNone
    Total Monthly Price$2,350

    209 Winchester Dr

    209 Winchester Dr, Winchester, VA 22602
  3. 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
  4. 2 BEDS, 2 BATHS
    $3,100
    Total Monthly Price Total Monthly Price New
    Base Rent$3,100
    Required Monthly FeesNone
    Total Monthly Price$3,100

    210 E Boscawen St Unit 202

    210 E Boscawen St, Winchester, VA 22601
  5. 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

    1016 Franklin St

    1016 Franklin St, Winchester, VA 22601
  6. 3 BEDS, 2.5 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    1970 Cidermill Ln

    1970 Cidermill Ln, Winchester, VA 22601
  7. 4 BEDS, 3.5 BATHS
    $2,300
    Total Monthly Price Total Monthly Price New
    Base Rent$2,300
    Required Monthly FeesNone
    Total Monthly Price$2,300

    174 Munsee Cir

    174 Munsee Cir, Winchester, VA 22602
  8. 3 BEDS, 2.5 BATHS
    $2,195
    Total Monthly Price Total Monthly Price New
    Base Rent$2,195
    Required Monthly FeesNone
    Total Monthly Price$2,195

    104 Reign Wy

    104 Reign Wy, Winchester, VA 22603
  9. 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
  10. 2 BEDS, 2.5 BATHS
    $3,400
    Total Monthly Price Total Monthly Price New
    Base Rent$3,400
    Required Monthly FeesNone
    Total Monthly Price$3,400

    210 E Boscawen St Unit 204

    210 E Boscawen St, Winchester, VA 22601
  11. 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

    1958 Cidermill Ln

    1958 Cidermill Ln, Winchester, VA 22601
  12. 1 BED, 1 BATH
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100

    210 E Boscawen St Unit 203

    210 E Boscawen St, Winchester, VA 22601
  13. 3 BEDS, 2.5 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    290 Sage Cir

    290 Sage Cir, Winchester, VA 22603
  14. 3 BEDS, 2 BATHS
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    105 E Pall Mall St

    105 E Pall Mall St, Winchester, VA 22601
  15. 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
  16. 2 BEDS, 2 BATHS
    $2,200
    Total Monthly Price Total Monthly Price New
    Base Rent$2,200
    Required Monthly FeesNone
    Total Monthly Price$2,200

    21 S Stewart St Unit 4

    21 S Stewart St, Winchester, VA 22601
  17. 2 BEDS, 2 BATHS
    $2,150
    Total Monthly Price Total Monthly Price New
    Base Rent$2,150
    Required Monthly FeesNone
    Total Monthly Price$2,150

    1310 Ramseur Ln

    1310 Ramseur Ln, Winchester, VA 22601
  18. 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
  19. 1 BED, 1 BATH
    $1,299
    Total Monthly Price Total Monthly Price New
    Base Rent$1,299
    Required Monthly FeesNone
    Total Monthly Price$1,299

    3105 Shawnee Dr Unit 7

    3105 Shawnee Dr, Winchester, VA 22601
  20. 2 BEDS, 1 BATH
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    321 N Braddock St

    321 N Braddock St, Winchester, VA 22601
  21. 2 BEDS, 1 BATH
    $1,825
    Total Monthly Price Total Monthly Price New
    Base Rent$1,825
    Required Monthly FeesNone
    Total Monthly Price$1,825

    40 E Piccadilly St Unit 2

    40 E Piccadilly St, Winchester, VA 22601
  22. 3 BEDS, 2 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    200 Canyon Rd

    200 Canyon Rd, Winchester, VA 22602
  23. 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
  24. 3 BEDS, 3.5 BATHS
    $2,250
    Total Monthly Price Total Monthly Price New
    Base Rent$2,250
    Required Monthly FeesNone
    Total Monthly Price$2,250

    109 Sequoia Dr

    109 Sequoia Dr, Winchester, VA 22602
  25. 2 BEDS, 2 BATHS
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    115 Brookland Terrace Unit 8

    115 Brookland Terrace, Winchester, VA 22602
  26. 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
  27. 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

    105 N Loudoun St Unit 1

    105 N Loudoun St, Winchester, VA 22601
  28. 3 BEDS, 3.5 BATHS
    $1,999
    Total Monthly Price Total Monthly Price New
    Base Rent$1,999
    Required Monthly FeesNone
    Total Monthly Price$1,999

    102 Metcalf Terrace

    102 Metcalf Terrace, Winchester, VA 22602
  29. 3 BEDS, 3 BATHS
    $2,150
    Total Monthly Price Total Monthly Price New
    Base Rent$2,150
    Required Monthly FeesNone
    Total Monthly Price$2,150

    5252 Mulberry Run Ct

    5252 Mulberry Run Ct, Stephens City, VA 22655
  30. 2 BEDS, 3.5 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    104 Peridot Pl

    104 Peridot Pl, Stephens City, VA 22655
  31. 3 BEDS, 2.5 BATHS
    $2,295
    Total Monthly Price Total Monthly Price New
    Base Rent$2,295
    Required Monthly FeesNone
    Total Monthly Price$2,295

    106 Gossard Wy

    106 Gossard Wy, Stephens City, VA 22655
  32. 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

    112 Jefferson Ct

    112 Jefferson Ct, Stephens City, VA 22655
  33. 4 BEDS, 3.5 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    306 Starry Way Dr

    306 Starry Way Dr, Stephenson, VA 22656
  34. 3 BEDS, 3 BATHS
    $2,399
    Total Monthly Price Total Monthly Price New
    Base Rent$2,399
    Required Monthly FeesNone
    Total Monthly Price$2,399

    127 Heyford Dr

    127 Heyford Dr, Stephenson, VA 22656
  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

    5366 Main St

    5366 Main St, Stephens City, VA 22655
  36. 3 BEDS, 3 BATHS
    $2,325
    Total Monthly Price Total Monthly Price New
    Base Rent$2,325
    Required Monthly FeesNone
    Total Monthly Price$2,325

    219 Patchwork Dr

    219 Patchwork Dr, Stephenson, VA 22656
  37. 3 BEDS, 2.5 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    165 Tigney Dr

    165 Tigney Dr, Stephens City, VA 22655
  38. 3 BEDS, 3.5 BATHS
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500

    105 Domino Ct

    105 Domino Ct, Stephenson, VA 22656
  39. 4 BEDS, 3.5 BATHS
    $2,900
    Total Monthly Price Total Monthly Price New
    Base Rent$2,900
    Required Monthly FeesNone
    Total Monthly Price$2,900

    115 Interlace Wy

    115 Interlace Wy, Stephenson, VA 22656
  40. 3 BEDS, 3 BATHS
    $2,150
    Total Monthly Price Total Monthly Price New
    Base Rent$2,150
    Required Monthly FeesNone
    Total Monthly Price$2,150

    129 Schramm Lp

    129 Schramm Lp, Stephens City, VA 22655
  41. 4 BEDS, 4.5 BATHS
    $2,299
    Total Monthly Price Total Monthly Price New
    Base Rent$2,299
    Required Monthly FeesNone
    Total Monthly Price$2,299

    121 Lindy Wy

    121 Lindy Wy, Stephenson, VA 22656
  42. 3 BEDS, 3 BATHS
    $1,895
    Total Monthly Price Total Monthly Price New
    Base Rent$1,895
    Required Monthly FeesNone
    Total Monthly Price$1,895

    111 Fading Star Ct

    111 Fading Star Ct, Stephenson, VA 22656
Showing 42 of 156 results, Page 3 of 4

Winchester at a Glance

Average Rent

$1,318
(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)

Average Rent in Nearby Cities

(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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