For Sale
Single family home for sale at 338 E Piccadilly St, Winchester, VA 22601 | MLS# VAWI2011872 | Listing updated on 2026-10-22
Photo 1 of Single family home for sale at 338 E Piccadilly St, Winchester, VA 22601 | MLS# VAWI2011872 | Listing updated on 2026-10-22
Photo 2 of Single family home for sale at 338 E Piccadilly St, Winchester, VA 22601 | MLS# VAWI2011872 | Listing updated on 2026-10-22
Photo 3 of Single family home for sale at 338 E Piccadilly St, Winchester, VA 22601 | MLS# VAWI2011872 | Listing updated on 2026-10-22
Photo 4 of Single family home for sale at 338 E Piccadilly St, Winchester, VA 22601 | MLS# VAWI2011872 | Listing updated on 2026-10-22
69+
Beds Icon

Street View

$399,900

Monthly Est:$1,990

  • Beds Icon3 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,422sqft

338 E Piccadilly St, Winchester, VA 22601

$1,990/moEst:

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  • Single Family Residence

  • Built in 1940

  • $-- HOA

  • 3,951 sqft lot

  • $281/sq.ft

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.

  • Houzeo last checked: 6 minutes ago
  • Listing updated: October 22, 2026 at 12:41 pm
  • Listing Provided by: Daniel J Whitacre (540) 327-6718 | Colony Realty (540) 662-0323
  • Source: Bright MLS-NJ | MLS#: VAWI2011872 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Winchester City Va County

  • City

    Winchester

  • Neighborhood

    --

  • Year Built

    1940

  • HOA Fees

    -

  • Finished Area

    1,422 sqft

  • Lot Size

    3,951 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    VAWI2011872

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    1

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 2

Interior

  • Interior Features

    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

  • Cooling

    Ductless/mini Split

  • Appliances

    Washer, Dryer, Dishwasher, Refrigerator, Oven/range Electric, Built In Microwave, Stainless Steel Appliances

  • Heating

    Heat Pump(s)

  • Sewer

    Public Sewer

  • Flooring

    Hardwood, Ceramic Tile

Construction

  • Year Built

    Year Built: 1940

  • Home type

    Single Family Residence

  • Architectural Style

    Bungalow

  • Foundation Details

    Concrete Perimeter

  • Construction Materials

    Vinyl Siding

Utilities & Energy

  • Basement

    Full, Interior Access, Sump Pump, Unfinished, Connecting Stairway

  • Water Source

    Public

Other Features

  • Subdivision Name

    Winchester City

  • Patio And Porch Features

    Deck, Porch

Price History

DateEventPrice

10/22/2026

Source: mls_logoBright MLS-NJ #VAWI2011872

Listed for Sale

$399,900 +73.87%

$281/sqft

05/26/2022

Source: mls_logoBright MLS-NJ #VAWI2001680

Sold

$230,000

$162/sqft

Nearby Homes

Based on information from Bright MLS through Oct 29, 2026, 02:15PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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