338 E Piccadilly Street
Winchester, VA, 22601 $ 399,900
Bedrooms3 Baths2.0 Sq 1,422 Monthly Estimate*
$ 2,762
for $399,900 with 3 bedrooms and 2 full baths. This 1,422 square foot home was built in 1940 on a lot size of 0.09.
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 spacea 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.
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FeaturesGeneralLiving Area 1422
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Ductless/Mini-Split
Possession Settlement
Appliances Washer Dryer Dishwasher Refrigerator Oven/Range - Electric Built-In Microwave Stainless Steel Appliances
Zoning HR1
Patio/Porch Features Deck(s) Porch(es)
Architectural Style Bungalow
Construction Materials Vinyl Siding
School District WINCHESTER CITY PUBLIC SCHOOLS
Year Built 1940
Levels 3
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County WINCHESTER CITY
New Construction N
Property Type Residential
HOA N
Subdivision Name WINCHESTER CITY
Garage Y/N N
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 2
Status ACTIVE
Directions National Ave to E Piccadilly St.
City WINCHESTER
Disclosures Lead Based Paint - Federal Prop Disclosure
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 3951.00
Tax Annual Amount 2129.0
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 1
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 281.22
Vacation Rental Y/N N
Standard Status Active
Year Built Source Assessor
Tax Lot 15
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InteriorInterior Amenities 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
Heating Fuel Electric
Basement Full Interior Access Sump Pump Unfinished Connecting Stairway
Flooring Hardwood Ceramic Tile
Hot Water Electric
Basement (Y/N) Y
Heating Y/N Y
Above Grade Finished Area 1422
Half Baths 0
Central Air Y/N N
Total Bedrooms 3
Below Grade Finished Area 0
Room Type Living Room Dining Room Primary Bedroom Bedroom 2 Bedroom 3 Kitchen Basement Sun/Florida Room Laundry Full Bath
Main Level Bedrooms 0
Below Grade Finished Area Unit Type Square Feet
Laundry Type Main Floor
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 2
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ExteriorPool No Pool
Fencing Rear
Water Source Public
Type of Parking Off Street Driveway
Foundation Details Concrete Perimeter
Water View Y/N N
Lot Size Acres 0.09
Lot Size Source Assessor
Waterfront Y/N N
Land Assessed Value 40000.00
Navigable Water Y/N N
Water Oriented Y/N N
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* Excluded FeaturesAffordability Calculator
- Monthly Principal & Interest
- $2,762
- Monthly Property Taxes
- $177
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Winchester, VA
Average List Price $550,034
Percent of Sale Price 38%
About Winchester, VA 28,216 Population
20% Since 2002
$ 48,983 Median Income
36.89 Median Age
26% Households with Children
Trends Information provided by ATTOM Data Solutions.
3533429 Elementary School
3533165 Middle School
John Handley High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 10/22/2026 | $399,900 | | Listed Price |