About This Home

This 3-bedroom, 2-bathroom single family at 338 E PICCADILLY Street in Winchester, VA is listed for $399,900 ($281 per sqft). Built in 1940, the home offers 1,422 sqft of living space on a 0.09 acres lot.

Key Features

  • Built in 1940
  • 0.09 acre lot
  • 3 stories

Property Details

3 stories
2 full
1940
Listing 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.

Monthly Cost Estimate

$2,139/mo

20% down · 6.5% · 30 years

Principal$289
Interest$1,733
Insurance$117

Estimates only. Actual payments may vary.

Location

338 E PICCADILLY Street

Winchester, VA 22601

WINCHESTER CITY

Features & Amenities

Interior Features

Bathroom - Tub ShowerBuilt-InsCeiling Fan(s)Crown MoldingsDining AreaFormal/Separate Dining RoomRecessed LightingUpgraded CountertopsWet/Dry BarWood Floors

Property Details

Construction

Vinyl Siding

Parking

DrivewayOff Street

Heating

Heat Pump (Heating)

Cooling

Ductless

Appliances

WasherDryerDishwasherRefrigeratorOven/Range - ElectricBuilt-In MicrowaveStainless Steel Appliances

Questions & Answers

This 3-bedroom, 2-bathroom single family at 338 E PICCADILLY Street is listed at $399,900 ($281/sqft). The estimated monthly payment is $2,139 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1940, 0.09 acre lot, 3 stories. Interior Features: Bathroom - Tub Shower, Built-Ins, Ceiling Fan(s).

This property is listed by Daniel J Whitacre.

DW

Daniel J Whitacre

License 0225212949

Agent at Colony Realty

Listed by Colony Realty · Broker phone: (540) 662-0323 · View on Broker Site · Broker website

MLS# VAWI2011872· Source: Bright MLS· 7 days on PropertySimple

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.

338 E PICCADILLY Street, Winchester, VA 22601

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