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Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on a desirable corner lot, the home features ample driveway parking and presents a variety of opportunities to suit your needs.

3 Beds ⋅ 2 Baths

Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on a desirable corner lot, the home features ample driveway parking and presents a variety of opportunities to suit your needs.

302 Wentworth Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$359,900

Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a seamless connection to the formal dining area—perfect for hosting friends and family. The kitchen is a standout feature, boasting granite countertops, stainless steel appliances, white cabinetry, and designer-inspired finishes that make both cooking and entertaining a pleasure. Each bedroom is generously sized with ample closet space, while the thoughtful layout provides comfort and functionality throughout. Outside, a private cement parking pad adds everyday convenience. Packed with charm, natural light, and updates you'll love, Gray Avenue is the perfect place to call home.

3 Beds ⋅ 2 Baths

Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a seamless connection to the formal dining area—perfect for hosting friends and family. The kitchen is a standout feature, boasting granite countertops, stainless steel appliances, white cabinetry, and designer-inspired finishes that make both cooking and entertaining a pleasure. Each bedroom is generously sized with ample closet space, while the thoughtful layout provides comfort and functionality throughout. Outside, a private cement parking pad adds everyday convenience. Packed with charm, natural light, and updates you'll love, Gray Avenue is the perfect place to call home.

601 Gray Ave, Winchester

Listing courtesy of Samson Properties. Contact:

$265,000

BACK ON THE MARKET -NO FAULT OF THE SELLERS -Step inside this historic home in the heart of Winchester and discover a home that offers far more than you might expect. Generously sized rooms provide plenty of space to relax, or enjoy your favorite hobbies, while a light-filled sunroom creates the perfect spot for morning coffee, reading, plants, or simply slowing down and enjoying the day. Inside, you'll find two comfortable bedrooms, a walk-in closet, beautiful hardwood floors, and the convenience of in home laundry. Step outside and you'll find a backyard filled with possibility. Create the secret garden you've always imagined, grow flowers and vegetables, or simply enjoy having a private green space right in the city. One of this home's greatest features, however, is its location. Leave the car at home and enjoy walking through downtown Winchester—from nearby Handley High School to the shops, restaurants, events, and activities of the Old Town Walking Mall. Living near the Apple Blossom parade route with an easy walk to some of the area's best fireworks and festivities. Whether you're looking for your first home, simplifying to a smaller footprint, or simply drawn to the character and walkability of downtown living, this home offers something increasingly difficult to find: historic charm, comfortable spaces, a private backyard, and the opportunity to make a truly unique home your own. Come discover the possibilities waiting on West Germain Street.

2 Beds ⋅ 1 Baths

BACK ON THE MARKET -NO FAULT OF THE SELLERS -Step inside this historic home in the heart of Winchester and discover a home that offers far more than you might expect. Generously sized rooms provide plenty of space to relax, or enjoy your favorite hobbies, while a light-filled sunroom creates the perfect spot for morning coffee, reading, plants, or simply slowing down and enjoying the day. Inside, you'll find two comfortable bedrooms, a walk-in closet, beautiful hardwood floors, and the convenience of in home laundry. Step outside and you'll find a backyard filled with possibility. Create the secret garden you've always imagined, grow flowers and vegetables, or simply enjoy having a private green space right in the city. One of this home's greatest features, however, is its location. Leave the car at home and enjoy walking through downtown Winchester—from nearby Handley High School to the shops, restaurants, events, and activities of the Old Town Walking Mall. Living near the Apple Blossom parade route with an easy walk to some of the area's best fireworks and festivities. Whether you're looking for your first home, simplifying to a smaller footprint, or simply drawn to the character and walkability of downtown living, this home offers something increasingly difficult to find: historic charm, comfortable spaces, a private backyard, and the opportunity to make a truly unique home your own. Come discover the possibilities waiting on West Germain Street.

11 W Germain St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

$385,000

Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow for indoor-outdoor living and entertaining. Three generously sized bedrooms provide ample closet space, while the unfinished basement offers abundant storage and endless potential for future expansion, a home gym, workshop, or recreation space. Step outside to enjoy the privacy of the fully fenced backyard—ideal for relaxing evenings, pets, gardening, or entertaining guests. Great investment opportunity, tenant in place until 7/14/2026.

3 Beds ⋅ 1 Baths

Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow for indoor-outdoor living and entertaining. Three generously sized bedrooms provide ample closet space, while the unfinished basement offers abundant storage and endless potential for future expansion, a home gym, workshop, or recreation space. Step outside to enjoy the privacy of the fully fenced backyard—ideal for relaxing evenings, pets, gardening, or entertaining guests. Great investment opportunity, tenant in place until 7/14/2026.

540 Bellview Ave, Winchester

Listing courtesy of Samson Properties. Contact:

$439,999

Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious bedrooms and 3 full bathrooms, there’s room for everyone. Situated on a quarter-acre lot with no HOA, you'll enjoy privacy and freedom. The large deck and screened-in porch are perfect for outdoor dining, entertaining, or simply unwinding. Conveniently located close to shopping centers and restaurants — everything you need is just minutes away!

5 Beds ⋅ 3 Baths

Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious bedrooms and 3 full bathrooms, there’s room for everyone. Situated on a quarter-acre lot with no HOA, you'll enjoy privacy and freedom. The large deck and screened-in porch are perfect for outdoor dining, entertaining, or simply unwinding. Conveniently located close to shopping centers and restaurants — everything you need is just minutes away!

419 Summit Ave, Winchester

Listing courtesy of Lifestyle Realty, LLC.. Contact:

$369,000

PRICE REDUCED! BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing or just starting out, or even as an investment property. And there's no HOA! The seller will be installing a new roof and a radon remediation system. The house has replacement windows. Two wood-burning fireplaces. Large living room with a picture window. Formal dining room with a built-in cabinet. Primary bedroom with own bath has a walk-in shower. Central air and a whole house fan. The basement offers a large family room with a pool table, an office/den with built-ins, and a utility room. New vinyl plank flooring in kitchen. Tile floors in the bathrooms. New sinks and toilets. New tub/shower. Updated electric (1994). Public water. Has a 3-bedroom septic, according to health department records. Real estate and personal property sold as-is.

2 Beds ⋅ 2 Baths

PRICE REDUCED! BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing or just starting out, or even as an investment property. And there's no HOA! The seller will be installing a new roof and a radon remediation system. The house has replacement windows. Two wood-burning fireplaces. Large living room with a picture window. Formal dining room with a built-in cabinet. Primary bedroom with own bath has a walk-in shower. Central air and a whole house fan. The basement offers a large family room with a pool table, an office/den with built-ins, and a utility room. New vinyl plank flooring in kitchen. Tile floors in the bathrooms. New sinks and toilets. New tub/shower. Updated electric (1994). Public water. Has a 3-bedroom septic, according to health department records. Real estate and personal property sold as-is.

437 Beechcroft Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

$349,900

Easy, one-level living with thoughtful updates and low-maintenance convenience! Situated on a corner lot in an established 55+ community, 1856 Melvor Lane offers 2 bedrooms, 2 full baths, an open floor plan, and a move-in-ready interior. Step inside to a welcoming living space where cathedral ceilings and natural light create an open, airy feel. Luxury vinyl plank flooring extends through most of the home, complemented by fresh interior paint and updated lighting. The kitchen features granite countertops, a tile backsplash, generous workspace, and an easy flow into the dining and living areas. The primary suite includes a walk-in closet and private full bath, while the second bedroom and additional full bath provide flexible space for a home office, den, hobby room, or additional bedroom. Outside, the corner lot provides a little extra breathing room without the upkeep of a large property. HOA-provided lawn care and snow removal make exterior maintenance easier, while community sidewalks, a neighborhood community center, and HOA activities offer additional ways to enjoy the neighborhood. Conveniently located near shopping, dining, everyday services, Winchester Medical Center, and historic downtown Winchester, this home brings together an updated interior, manageable space, and a low-maintenance lifestyle in a convenient Winchester location.

2 Beds ⋅ 2 Baths

Easy, one-level living with thoughtful updates and low-maintenance convenience! Situated on a corner lot in an established 55+ community, 1856 Melvor Lane offers 2 bedrooms, 2 full baths, an open floor plan, and a move-in-ready interior. Step inside to a welcoming living space where cathedral ceilings and natural light create an open, airy feel. Luxury vinyl plank flooring extends through most of the home, complemented by fresh interior paint and updated lighting. The kitchen features granite countertops, a tile backsplash, generous workspace, and an easy flow into the dining and living areas. The primary suite includes a walk-in closet and private full bath, while the second bedroom and additional full bath provide flexible space for a home office, den, hobby room, or additional bedroom. Outside, the corner lot provides a little extra breathing room without the upkeep of a large property. HOA-provided lawn care and snow removal make exterior maintenance easier, while community sidewalks, a neighborhood community center, and HOA activities offer additional ways to enjoy the neighborhood. Conveniently located near shopping, dining, everyday services, Winchester Medical Center, and historic downtown Winchester, this home brings together an updated interior, manageable space, and a low-maintenance lifestyle in a convenient Winchester location.

1856 Melvor Ln, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$319,000

Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll find a practical and inviting layout featuring 3 bedrooms, 1.5 bathrooms, a spacious kitchen, separate living and dining areas, main-level laundry, and additional storage space. Recent updates add extra peace of mind, including an HVAC system installed in 2020 and a roof recoated in 2021. Outside, the home offers valuable city-living features, including off-street parking and usable outdoor space for relaxing, gardening, pets, or entertaining. The surrounding streetscape is also seeing meaningful improvements, with the street being repaved, sidewalks redone, and new trees expected to be planted along the street. Whether you are searching for a primary residence, a Winchester-area home base, or a potential investment property, this home offers a strong combination of location, utility, and opportunity in an established Winchester neighborhood with quick access to major roadways and the surrounding Shenandoah Valley. Seller offering up to $2,500 towards painting with acceptable offer.

3 Beds ⋅ 2 Baths

Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll find a practical and inviting layout featuring 3 bedrooms, 1.5 bathrooms, a spacious kitchen, separate living and dining areas, main-level laundry, and additional storage space. Recent updates add extra peace of mind, including an HVAC system installed in 2020 and a roof recoated in 2021. Outside, the home offers valuable city-living features, including off-street parking and usable outdoor space for relaxing, gardening, pets, or entertaining. The surrounding streetscape is also seeing meaningful improvements, with the street being repaved, sidewalks redone, and new trees expected to be planted along the street. Whether you are searching for a primary residence, a Winchester-area home base, or a potential investment property, this home offers a strong combination of location, utility, and opportunity in an established Winchester neighborhood with quick access to major roadways and the surrounding Shenandoah Valley. Seller offering up to $2,500 towards painting with acceptable offer.

307 E Piccadilly St, Winchester

Listing courtesy of HoneyWay. Contact:

$374,900

This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door. The home looks bright and beautiful from the inside and out. The bathrooms have also gotten a modern makeover, complete with touch mirrors that add a touch of luxury. This one's a must-see!

2 Beds ⋅ 2 Baths

This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door. The home looks bright and beautiful from the inside and out. The bathrooms have also gotten a modern makeover, complete with touch mirrors that add a touch of luxury. This one's a must-see!

711 E Cork St, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact:

$295,000

Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort. Convenient one-level living throughout. Ideally situated just off Berryville Avenue, with quick access to shopping, dining, and major commuter routes, making it a great option for those traveling to Northern Virginia. Don’t miss this opportunity!

3 Beds ⋅ 1 Baths

Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort. Convenient one-level living throughout. Ideally situated just off Berryville Avenue, with quick access to shopping, dining, and major commuter routes, making it a great option for those traveling to Northern Virginia. Don’t miss this opportunity!

608 Dunlap St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$280,000

Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

3 Beds ⋅ 3 Baths

Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

115 S Purcell Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$400,000

Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

4 Beds ⋅ 2 Baths

Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

115 E Monmouth St, Winchester

Listing courtesy of Inmobiliaria De Las Casas LLC. Contact:

$472,000

Listed below recent appraised value. All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, and new carpet in all bedrooms. Tile flooring has been thoughtfully retained in the kitchen, entry, and guest bath. Recessed lighting has been added to the main living area, along with multiple updated light fixtures, creating a bright and welcoming feel. The kitchen features a breakfast nook with a bay window and now includes custom built pantry storage, while the living room has been enhanced with a custom built-in with integrated lighting. A former bar area was removed and replaced with a large storage closet, significantly improving functionality. The primary bathroom has been fully gutted and completely redesigned, featuring a modern walk-in shower, contemporary fixtures, and an aging-in-place–friendly layout with grab bars and improved accessibility. The sunroom has been reconfigured for better flow, with the original sliding doors removed, a new cased opening added, and HVAC extended to the space, allowing it to be enjoyed year-round. A rear deck extends the living space outdoors. Exterior improvements include over $10,000 in rear landscaping designed to buffer Meadow Branch Avenue, featuring Crepe Myrtles, Emerald Green Arborvitae, and Hollies. A crawlspace fan/radon-style ventilation system has also been installed. Situated on a cul-de-sac and conveniently located near hospitals, shopping, dining, fitness facilities, walking trails, coffee shops, and Old Town Winchester. HOA covers lawn maintenance, snow removal, pool, and tennis courts. Not a 55+ community. Homes offering this level of care, thoughtful upgrades, and low-maintenance living in this location are rarely available.

3 Beds ⋅ 2 Baths

Listed below recent appraised value. All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, and new carpet in all bedrooms. Tile flooring has been thoughtfully retained in the kitchen, entry, and guest bath. Recessed lighting has been added to the main living area, along with multiple updated light fixtures, creating a bright and welcoming feel. The kitchen features a breakfast nook with a bay window and now includes custom built pantry storage, while the living room has been enhanced with a custom built-in with integrated lighting. A former bar area was removed and replaced with a large storage closet, significantly improving functionality. The primary bathroom has been fully gutted and completely redesigned, featuring a modern walk-in shower, contemporary fixtures, and an aging-in-place–friendly layout with grab bars and improved accessibility. The sunroom has been reconfigured for better flow, with the original sliding doors removed, a new cased opening added, and HVAC extended to the space, allowing it to be enjoyed year-round. A rear deck extends the living space outdoors. Exterior improvements include over $10,000 in rear landscaping designed to buffer Meadow Branch Avenue, featuring Crepe Myrtles, Emerald Green Arborvitae, and Hollies. A crawlspace fan/radon-style ventilation system has also been installed. Situated on a cul-de-sac and conveniently located near hospitals, shopping, dining, fitness facilities, walking trails, coffee shops, and Old Town Winchester. HOA covers lawn maintenance, snow removal, pool, and tennis courts. Not a 55+ community. Homes offering this level of care, thoughtful upgrades, and low-maintenance living in this location are rarely available.

832 Winder Ct, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: