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Dana Roach
REALTOR®
(540) 742-9581

338 E Piccadilly Street , Winchester, VA 22601

$399,900
  • 338 E Piccadilly Street , Winchester, VA 22601 Main Photo

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ACTIVE
BEDS3 BATHS2 full SQUARE FEET1,422 MLS#VAWI2011872
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONWINCHESTER CITY SCHOOLWINCHESTER CITY PUBLIC SCHOOLS

Property Description

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.

338 E Piccadilly Street | MLS# VAWI2011872

This single family home located at 338 E Piccadilly Street , Winchester, VA 22601 is currently listed for sale with an asking price of $399,900. This property was built in 1940 and has 3 bedrooms and 2 full baths with 1422 sq. ft. E Piccadilly Street is located in the WINCHESTER CITY subdivision within the WINCHESTER CITY PUBLIC SCHOOLS school district. Search WINCHESTER CITY real estate on danaroach.massanuttenrealty.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Interior Access, Sump Pump, Unfinished, Connecting Stairway
Cooling: Ductless/Mini-Split
Fuel Type: Electric
Heating: Heat Pump(s)
Home Style: Bungalow
Lot Size: 0.09 Acres
Stories: 3.0
Taxes: $2,129
Year Built: 1940

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Oven/Range - Electric, Built-In Microwave, Stainless Steel Appliances
Days on Site: 8
Exterior: Vinyl Siding
Fencing: Rear
Flooring: Hardwood, Ceramic Tile
Interior: Bathroom - Tub Shower, Built-Ins, Ceiling Fan(s), Crown Moldings, Dining Area, Formal/Separate Dining Room, Recessed Lighting, Upgraded Countertops, Wet/Dry Bar, Wood Floors
Lot Dimensions: 0.09 Acre(S)
Rooms: Living Room, Dining Room, Primary Bedroom, Bedroom 2,Bedroom 3,Kitchen, Basement, Sun/Florida Room, Laundry, Full Bath
Sewer: Public Sewer
SQFT Above Finished: 1422
SQFT Total Finished: 1422
Structure Type: Detached
Water: Public

Local Schools

High School: JOHN HANDLEY
School District: WINCHESTER CITY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Colony Realty

Shown By

Agent Name: Dana Roach
Agent Phone: (540) 742-9581
Agency Title: Massanutten Realty

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Estimated Payment

$ 2,212.14 per month $1,918.08 Principal & Interest $177.42 Property Tax $116.64 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 10/30/2026. The listing information on this page last changed on 10/30/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 10/30/2026 12:07:45 AM EST) or CAAR MLS (last updated Thu 10/29/2026 11:10:46 PM EST) or Staunton MLS (last updated Thu 10/29/2026 7:10:44 AM EST) or HRAR MLS (last updated Thu 10/29/2026 11:29:28 PM EST). Real estate listings held by brokerage firms other than Massanutten Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agency License Information: Massanutten Realty, LLC licensed in the Commonwealth of Virginia since 1986


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