314 E Piccadilly St
WinchesterVA22601
Apartments for Rent in the Old Town Neighborhood of Winchester, VA (104 Rentals) Page 2 of 3
312 E Piccadilly St
WinchesterVA22601
619 S Cameron St, Unit 2
619 S Cameron St
WinchesterVA22601
21 S Stewart St
WinchesterVA22601
21 S Stewart St, Unit 4
21 S Stewart St
WinchesterVA22601
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1 Bedroom Apartments
44-48 S Loudoun St
44-48 S Loudoun StWinchester, VA 22601
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2 Bedroom Apartments
25 W Boscawen St
25 W Boscawen StWinchester, VA 22601
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1 Bedroom Apartments
Historic Taylor Apartments
119 N Loudoun StWinchester, VA 22601
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1 Bedroom Apartments
28-30 S Braddock St
28-30 S Braddock StWinchester, VA 22601
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1 Bedroom Apartments
139-141 S Loudoun St
139-141 S Loudoun StWinchester, VA 22601
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Studio Apartments
126 N Braddock St
126 N Braddock StWinchester, VA 22601
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1 Bedroom Apartments
Winchester Towers
200 N Cameron StWinchester, VA 22601
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1 Bedroom Apartments
125 S Braddock St
125 S Braddock StWinchester, VA 22601
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2 Bedroom Apartments
208 N Kent St
208 N Kent StWinchester, VA 22601
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1 Bedroom Apartments
208 W Boscawen St
208 W Boscawen StWinchester, VA 22601
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1 to 2 Bedroom Apartments
317 S Cameron St
317 S Cameron StWinchester, VA 22601
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Studio Apartments
401-403 S Braddock St
401-403 S Braddock StWinchester, VA 22601
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1 Bedroom Apartments
404 S Kent St
404 S Kent StWinchester, VA 22601
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2 Bedroom Apartments
410-412 S Loudoun St
410-412 S Loudoun StWinchester, VA 22601
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1 to 3 Bedroom Apartments
Fort Loudoun Apartments
2-8 Peyton StWinchester, VA 22601
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Studio Apartments
506 S Braddock St
506 S Braddock StWinchester, VA 22601
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Studio to 3 Bedroom Apartments
Winlee Apartments
320-350 Fairmont AveWinchester, VA 22601
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1 Bedroom Apartments
321 Amherst St
321 Amherst StWinchester, VA 22601
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5 Bedroom Apartments
521-525 S Cameron St
521-525 S Cameron StWinchester, VA 22601
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1 to 2 Bedroom Apartments
603 N Cameron St
603 N Cameron StWinchester, VA 22601
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1 to 2 Bedroom Apartments
603-611 S Loudoun St
603-611 S Loudoun StWinchester, VA 22601
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1 Bedroom Apartments
364 National Ave
364 National AveWinchester, VA 22601
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Studio Apartments
450-452 Loudoun St
450-452 Loudoun StWinchester, VA 22601
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1 Bedroom Apartments
378 National Ave
378 National AveWinchester, VA 22601
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2 Bedroom Apartments
721-739 S Kent St
721-739 S Kent StWinchester, VA 22601
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8 Bedroom Apartments
422 W Clifford St
422 W Clifford StWinchester, VA 22601
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1 Bedroom Apartments
24 E Pall Mall St
24 E Pall Mall StWinchester, VA 22601
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Studio Apartments
513 N Loudoun St
513 N Loudoun StWinchester, VA 22601
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Studio Apartments
Old Town Commons
715 S Braddock StWinchester, VA 22601
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2 Bedroom Apartments
517-1/2 N Cameron St
517-1/2 N Cameron StWinchester, VA 22601
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2 Bedroom Apartments
525 Gray Ave
525 Gray AveWinchester, VA 22601
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1 to 2 Bedroom Apartments
540 N Loudoun St
540 N Loudoun StWinchester, VA 22601
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1 to 2 Bedroom Apartments
910-912 S Braddock St
910-912 S Braddock StWinchester, VA 22601
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1 Bedroom Apartments
545 N Loudoun St
545 N Loudoun StWinchester, VA 22601
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2 to 3 Bedroom Apartments
L E Smith
321-337 N Pleasant Valley RdWinchester, VA 22601
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1 Bedroom Apartments
18 N Pleasant Valley Rd
18 N Pleasant Valley RdWinchester, VA 22601
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2 Bedroom Apartments
23-25 N Euclid Ave
23-25 N Euclid AveWinchester, VA 22601
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3 Bedroom Apartments
19-49 West Bond Street
19-49 W Bond StWinchester, VA 22601
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1 to 2 Bedroom Apartments
1110 Valley Ave
1110 Valley AveWinchester, VA 22601
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2 to 3 Bedroom Apartments
715-725 Woodstock Ln
715-725 Woodstock LnWinchester, VA 22601
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2 Bedroom Apartments
Winston Mews
680-696 Smithfield AveWinchester, VA 22601
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2 Bedroom Apartments
Colonial Village Apartments
201 E Whitlock AveWinchester, VA 22601
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2 Bedroom Apartments
1638 S Braddock St
1638 S Braddock StWinchester, VA 22601
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1 to 2 Bedroom Apartments
Cork Street Apartments
506-606 W Cork StWinchester, VA 22601
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1 to 3 Bedroom Apartments
ZeroPak Apartments
570 N Cameron StWinchester, VA 22601
Showing Results 51-100, Page 2 of 3
Old Town, Winchester, VA Local Guide
How much does it cost to rent an apartment in Old Town?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Old Town Studio Apartments | $1,500 | $1,300 | $1,700 |
| Old Town 1 Bedroom Apartments | $1,817 | $1,095 | $2,200 |
| Old Town 2 Bedroom Apartments | $1,977 | $1,150 | $2,600 |
| Old Town 3 Bedroom Apartments | $1,925 | $1,625 | $2,150 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
How much does it cost to rent a home in Old Town?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| 2 Bedroom Homes | $1,543 | $1,250 | $1,900 |
| 3 Bedroom Homes | $1,772 | $1,395 | $2,525 |
| 4 Bedroom Homes | $2,297 | $2,100 | $2,495 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 104 rentals with your search options within a 1 mile radius of the Old Town Neighborhood of Winchester, VA.
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Frequently Asked Questions about Old Town
What is the current pricing and availability for apartments for rent in the Old Town area of Winchester, VA?
As of today, September 08, 2026, there are currently 104 available Old Town apartments priced from $1,095 to $2,600, with an average monthly rent of $1,870.
What is the current price range for One Bedroom Old Town Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Old Town ranges from $1,095 to $2,200 with an average monthly rent of $1,817.
What does renting a Two Bedroom Apartment in Old Town cost?
The monthly rent prices of Two Bedroom Apartments currently available in Old Town range from $1,150 to $2,600. Today's average rental price for Two Bedrooms here is $1,977.
How expensive are Old Town Three Bedroom Apartments?
There are currently 9 Three Bedroom Apartments listings available in Old Town on ApartmentHomeLiving.com. The pricing ranges from $1,625 to $2,150 - averaging $1,925 for the location.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Articles, How-To's, and Tips
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.