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  3. Building Photo - 148 N Loudoun St
    1 BED
    $1,600+
    2 BEDS
    $1,800+
    Plus Fees

    148 N Loudoun St

    148 N Loudoun St, Winchester, VA 22601
  4. Building Photo - Peppertree VA
    1 BED
    $1,499+
    2 BEDS
    $1,567+
    3 BEDS
    $1,850+
    Plus Fees

    Peppertree VA

    221 Peppertree Ln, Winchester, VA 22601
  5. STUDIO
    $1,600+
    1 BED
    $1,800+
    2 BEDS
    $2,600+
    Plus Fees - 1 Month Lease

    114 N Loudoun St

    114 N Loudoun St, Winchester, VA 22601
    Apply
  7. 2 BEDS, 1 BATH
    $1,975
    Total Monthly Price Total Monthly Price New
    Base Rent$1,975
    Required Monthly FeesNone
    Total Monthly Price$1,975
         - 1 Month Lease

    342 Fairmont Ave Unit Apt 3

    342 Fairmont Ave, Winchester, VA 22601
    Apply

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Winchester at a Glance

Average Rent

$1,342
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
4

School Rating

out of 10 Rating
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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

Winchester, VA Apartments for Rent

Nestled in the scenic Shenandoah Valley, Winchester combines historic character with contemporary living. This northwestern Virginia city, established in 1744, features the Museum of the Shenandoah Valley and the Loudoun Street pedestrian mall, both within walking distance of many apartment communities. With one-bedroom apartments averaging $1,338 monthly, Winchester offers more affordable housing options than Washington D.C., located 75 miles away.

Located along Interstate 81, Winchester provides convenient access to several major highways throughout the region. The city is home to Shenandoah University and Valley Health's Winchester Medical Center. Residents enjoy all four seasons with access to local parks and the Blue Ridge Mountains. Housing options range from apartments in restored historic buildings downtown to newer residential communities throughout the city.

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

Private University
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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