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21 S Stewart St
21 S Stewart St, Winchester, VA 22601, USA

Apartment for rent
Monthly rent
$1,500–$2,200
Beds2
Baths1–2
Sqft1,100–1,600
modified
5+ Days Ago

Highlights

  • in-unit laundry
  • spacious bedrooms
  • convenient downtown location
  • generous storage space
  • no smoking

Units

21 S Stewart St Winchester, VA

Available

2

2 Beds

1 Bath

$1,500

Listed on 03/14/2026
Listed by Frank Armstrong IV
Days on market: 49
Property Status: Active 2 Bedroom Apartment for Rent - Downtown Winchester Great 2nd-floor apartment located in downtown Winchester with 2 bedrooms and 1 bathroom. This home is just a short walk from Old Town Winchester, giving you easy access to local restaurants, shops, and entertainment. The apartment features very spacious bedrooms, a comfortable family room, and a fully enclosed back porch, perfect for relaxing or extra living space. Features: 2 Bedrooms 1 Bathroom Large family room Spacious bedrooms Fully enclosed back porch Convenient downtown location near Old Town Policies: No smoking No vaping No pets Office Phone: (540) 662-0323 Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Available

4

2 Beds

2 Baths

$2,200

Listed on 01/31/2026
Listed by Frank Armstrong IV
Days on market: 91
Property Status: Active Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester! Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard-ideal for relaxing or entertaining. You'll also love the generous storage space throughout. Application fee: $30 (covers background and credit checks). No smoking, no vaping, and no pets permitted. Office Phone: (540) 662-0323 Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Amenities for 21 S Stewart St

Some units at this address have these amenities. View unit details for more information.

Building
  • Outdoor Space
  • On-Site Laundry
  • Storage
Unit Amenities
  • Carpet
  • Dishwasher
  • On-Site Laundry

Policies at 21 S Stewart St

Applicants

Applicants

One-time.

Contact Property

REQUIRED FEES

Security Deposit

One-time. Refundable.

Contact Property

Dog Policy

Not allowed

Cat Policy

Not allowed

No pets allowed.

Questions about this property’s policies and fees?

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About 21 S Stewart St

HomeApartments in Winchester 21 S Stewart St #2, Winchester, VA 22601, USA

Check out this charming colonial-style property located at 21 S Stewart St, Winchester, VA 22601. This intimate 2-unit building offers a spacious 2-bedroom floorplan, with units ranging from 1100 to 1600 square feet. Residents will appreciate the convenient downtown location, just a stone's throw from top-rated schools, including a high school with an A- or higher rating. Enjoy in-unit laundry, generous storage space, and a remodeled 2-bedroom apartment. Additional amenities include a dishwasher, on-site laundry, storage, and outdoor space. Please note that this is a smoke-free and pet-free property, ideal for those looking for a long-term rental. With only 2 units, this property offers a unique and peaceful living experience.

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Address details

Units2
Units available2
City
Zip code22601

Property highlights

We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.

How 21 S Stewart St, Winchester, VA 22601, USA compares to other nearby properties.

Positives

High school nearby
There is a high school 0.5 mile away
More space
The 2-bedroom is 303 sqft larger than other listings nearby
Dishwasher
Kitchens at this address include dishwashers
Extra Storage
Upgraded in-unit features
Images available
There are at least 10 photos of this address
Laundry available on site
Washers and dryers are available in-building or in-unit
Outdoor space
One or more rentals here have easy access to the outdoors

Considerations

Greater distance from grade schools
The nearest elementary school is farther than 1 mile away

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Rent trends in Winchester

If you decide to upgrade your space, you can expect 2-bedrooms at 21 S Stewart St #2 to be 21% more than the average for similarly sized apartments in Winchester.

Median rents as of Apr 25 2026.
Winchester
A table of studio rental data trends in Winchester
MonthMedian Rent
May 2024$972
June 2024$950
September 2024$1,000
October 2024$998
November 2024$980
December 2024$995
January 2025$859
February 2025$898
March 2025$995
April 2025$1,196
May 2025$1,296
June 2025$1,157
July 2025$1,098
August 2025$1,385
September 2025$1,218
October 2025$1,115
November 2025$1,015
December 2025$995
January 2026$995
February 2026$1,007
March 2026$1,008
April 2026$989

Affordability calculator

Can I afford to live at 21 S Stewart St?

Bedrooms

2 bedrooms

Rent-to-income ratio

30%

Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income

$74,000/yr

With your selected rent-to-income ratio, you'd ideally want to make $74,000 annually to afford this 2-bedrooms median monthly rent price of $1,850.
For more information on rent affordability, visit our rent calculator.

Rent history

The increase or decrease in monthly rent compared to the previous listing price.
Check out the past listing prices for monthly rent at 21 S Stewart St, Winchester, VA.
10 months ago$2,4002 bed2 bath
5 years ago$1,0002 bed1 bath
7 years ago$1,1002 bed1 bath

Schools near 21 S Stewart St #2

Jordan Springs Elementary School

no st address

winchester, VA, 22601

PK, K-5Public
B-

John Kerr Elementary School

427 meadow branch ave

winchester, VA, 22601

PK, K-4Public
B
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Getting around Winchester near 21 S Stewart St

Walking

6/10
Grab your reusable bags–many shops and stores are within walking distance.

Driving

8/10
Commuting is easy with multiple accessible routes and plenty of parking.

Cycling

3/10
This is semi-bikeable, but you’ll need another way of getting around.

Transit

3/10
There are a few mass transit options within the area.

Points of interest for 21 S Stewart St, Winchester

Groceries

7/10
At least one supermarket within a 15-minute walk

Shopping

6/10
Several shops within a few minutes’ walk

Cafes

6/10
Some cafés within a few minutes’ walk

Restaurants

6/10
Some restaurants within a few minutes’ walk

Primary schools

4/10
At least one elementary school within a 30-minute walk

High schools

5/10
At least one high school within a 20-minute walk

Nightlife

4/10
Some bars within walking distance

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