# 338 E PICCADILLY Street, Winchester, VA 22601

> **TL;DR:** 3bd/2ba single family, $399,900 ($281/sqft), built 1940, 1,422 sqft. Est. $2,139/mo. Listed 9 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $399,900 |
| Price/sqft | $281 |
| Bedrooms | 3 |
| Bathrooms | 2 full |
| Square Feet | 1,422 |
| Year Built | 1940 |
| Lot Size | 3,951 sqft (0.09 acres) |
| Stories | 3 |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 9 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $2,022 |
| Estimated Insurance | $117 |
| **Total** | **$2,139** |

## Nearby Schools

- **High:** JOHN HANDLEY

## Property Highlights

- Built in 1940
- 0.09 acre lot
- 3 stories

## Description

### Agent 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.

## Location

- **Address:** 338 E PICCADILLY Street, Winchester, VA 22601
- **County:** WINCHESTER CITY
- **Neighborhood:** WINCHESTER CITY
- **Coordinates:** 39.18505, -78.1583
- **Google Maps:** https://www.google.com/maps?q=39.18505,-78.1583

## Listing Agent

- **Name:** Daniel J Whitacre · **License:** 0225212949
- **Brokerage:** Colony Realty
- **Broker Phone:** (540) 662-0323
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/338-E-Piccadilly-St_Winchester_VA_22601_M57695-95033?f=listhub&s=TRENDPA&m=VAWI2011872&c=propsimple)

## Photos

![338 E PICCADILLY Street - Photo 1](http://lh.rdcpix.com/bd663855bfaba3d84cfbce4ea230edeal-f2960152240r.jpg)

![338 E PICCADILLY Street - Photo 2](http://lh.rdcpix.com/bd663855bfaba3d84cfbce4ea230edeal-f3029830112r.jpg)

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---

**MLS#:** VAWI2011872 | **Updated:** 2026-10-27
**Source:** listhub

*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.*

[View on PropertySimple](https://www.propertysimple.ai/listing/338-e-piccadilly-street-winchester-va-22601-9e1c5cad90c942cdadc7bd79b7b8dec7)

---

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