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338 E Piccadilly St, Winchester, VA 22601
338 E Piccadilly St, Winchester, VA 22601
338 E Piccadilly St, Winchester, VA 22601
338 E Piccadilly St, Winchester, VA 22601
338 E Piccadilly St, Winchester, VA 22601
338 E Piccadilly St, Winchester, VA 22601
338 E Piccadilly St, Winchester, VA 22601

338 E Piccadilly St Winchester, VA 22601

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$399,900

ACTIVE
Beds
3
Baths
2
Sqft
1,422
Acres
0.09
Year
1940
Days on Site
1 Hour
Property Type
Residential
Sub Type
Per Square Foot
$281
Date Listed
Oct 22, 2026

Description of 338 E Piccadilly St, Winchester, VA 22601

Listing details for 338 E Piccadilly St, Winchester, VA 22601 : Welcome to 338 E Piccadilly Street, a beautifully updated 3-bedroom, 2-bathroom home perfectly positioned in a highly convenient Winchester location. Overflowing with natural light and seamless charm, this move-in ready residence effortlessly blends classic architectural characteristics with high-end modern finishes and thoughtful details throughout. The inviting curb appeal begins with a freshly paved front walkway leading to a covered front porch framed by classic arches and complete with an adorable porch swing. Inside, the bright foyer opens into a warm living room with rich hardwood flooring that flows seamlessly into the beautifully redesigned kitchen. A standout focal point of the main level, it boasts a chic two-tone design with bright white upper cabinetry grounded by sophisticated muted green lowers, accented by a gorgeous backsplash, stainless steel appliances, and upgraded fixtures. Designed with entertaining in mind, the adjacent dining room features custom built-in cabinets, a distinct exposed brick pillar, and a separate wet bar complete with counter space, sink, and wine fridge. Just off the dining area, a dedicated laundry room provides direct access to the rear deck, alongside an updated full bath complete with a new vanity, fresh flooring, and a subway tile tub/shower with a glass surround. Downstairs, an unfinished basement provides excellent additional storage space. Upstairs, you will find three bedrooms, including a primary retreat with an attached light-filled sunroom/bonus space—a fabulous layout for a massive walk-in closet, home office, workout room, or playroom. Two additional bedrooms share this level with a beautifully renovated full bathroom that truly shines, highlighted by a classic clawfoot tub, stylish flooring, and a sleek new vanity. Outside, the private backyard is perfect for relaxing or entertaining, complete with a deck and a newer privacy fence ideal for pets or outdoor gatherings. Convenient off-street parking is provided by a driveway plus a detached storage building with alley access. This home also offers total peace of mind with major upgrades completed in recent years, including a 2-year-old HVAC system with heat pump and 3 mini-splits, an upgraded 200-amp electrical panel, newer supply plumbing, and a newer roof, siding, gutters, and insulation. Combining historic Winchester charm, extensive modern upgrades, and unbeatable proximity to downtown dining, parks, schools, and commuter routes, this exceptional home is truly turn-key living at its finest.
Listing Updated : 10-22-2026 at 9:03 AM EDT

Information Deemed Reliable But Not Guaranteed

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which participates, and is provided by BRIGHT through a licensing agreement.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data last updated: October 17, 2026 3:49 PM UTC

Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. 

Listing Provided By

Daniel J Whitacre, 5403276718, [email protected], Colony Realty

Source

Bright MLS, MLS#: VAWI2011872

For more information on this listing contact us at 703-646-1171

Property History

DateEventPrice
10/22/2026
Listed for sale
$399,900 +73.9%
$281/sqft
Source:Bright MLS #VAWI2011872
5/26/2022
Sold
$230,000
$162/sqft
Source:Bright MLS #VAWI2001680
4/20/2022
Listed for sale
—
Source:Bright MLS #VAWI2001680
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©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or Tesoro Team and EXP Realty. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-09-10T15:58:10.97.

For more information on this listing contact us at 703-646-1171