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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.

3 Beds ⋅ 2 Baths

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 St, Winchester

Listing courtesy of Colony Realty. Contact:

$349,900

Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, making meal prep a delight. A generous size family room just off the kitchen. Enjoy the convenience of main-floor laundry and a partially finished basement, perfect for a cozy retreat on gameday, or even possible 3rd bedroom, & couple extra rooms for storage. The attic could also add potential living space.(possible 4th) The inviting outdoor space is ideal for relaxation, Brand New Garage while the driveway provides ample off-street parking. Nestled in a vibrant community, residents benefit from nearby parks, excellent schools, Shenandoah University and convenient public services. Experience the warmth of neighborhood gatherings and the charm of local shops. This home is not just a place to live; it's a place to thrive. Embrace the lifestyle you've been dreaming of!

2 Beds ⋅ 2 Baths

Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, making meal prep a delight. A generous size family room just off the kitchen. Enjoy the convenience of main-floor laundry and a partially finished basement, perfect for a cozy retreat on gameday, or even possible 3rd bedroom, & couple extra rooms for storage. The attic could also add potential living space.(possible 4th) The inviting outdoor space is ideal for relaxation, Brand New Garage while the driveway provides ample off-street parking. Nestled in a vibrant community, residents benefit from nearby parks, excellent schools, Shenandoah University and convenient public services. Experience the warmth of neighborhood gatherings and the charm of local shops. This home is not just a place to live; it's a place to thrive. Embrace the lifestyle you've been dreaming of!

1414 S Braddock St, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$298,900

PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, kitchen has been updated with granite countertops. Full basement partly finished basement, with workshop on a walk out to back yard. The outside shop is ready to set up shop with plenty of room for storage, and it has Electric! Great yard to enjoy all the seasons and relaxing. All this and so much more for $298,900.00.

2 Beds ⋅ 2 Baths

PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, kitchen has been updated with granite countertops. Full basement partly finished basement, with workshop on a walk out to back yard. The outside shop is ready to set up shop with plenty of room for storage, and it has Electric! Great yard to enjoy all the seasons and relaxing. All this and so much more for $298,900.00.

828 Woodland Ave, Winchester

Listing courtesy of Samson Properties. Contact:

How much is your home worth?

How much is your home worth?