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ONE-OF-A-KIND HOME WITH INCREDIBLE FLEXIBILITY! This custom all-brick Winchester home offers a layout you simply don't find every day—4 bedrooms, 4 full baths, two main-level bedrooms, flexible private living spaces, a detached 2-car garage and NO HOA! Step inside to a bright, welcoming floor plan featuring beautiful hardwood floors, abundant natural light, custom built-ins and a cozy gas fireplace. The spacious gourmet kitchen offers granite countertops, stainless steel appliances, generous pantry space and a large breakfast area that flows easily into the dining and living spaces—perfect for everyday living and entertaining. One of this home's standout features is its main-level living potential. The primary suite is conveniently located on the main floor with a private bath and walk-in closet, while a second main-level bedroom and nearby full bath provide exceptional flexibility for guests, a home office or additional living space. Main-level laundry with a utility sink adds even more convenience. Upstairs, you'll discover a private and versatile living area with its own main-level entrance, sitting/living space, two additional bedrooms and a full bath—creating an ideal setup for extended stays, guests, work-from-home needs or anyone wanting additional privacy and separation. And there's even more! The detached two-car garage includes additional finished living space above, complete with a bedroom, full bath and kitchen/living area—opening the door to an incredible variety of possibilities. Outside, enjoy multiple parking options with front and rear driveways, an attached covered carport, detached garage and additional street parking. All of this is tucked into an established Winchester neighborhood convenient to downtown Winchester, Route 7, shopping, dining, medical facilities and major commuter routes. All brick. Four full baths. Two main-level bedrooms. Flexible living spaces. Detached garage. No HOA. This isn't your typical Winchester home—come see just how many possibilities 687 Woodland Avenue has to offer.

4 Beds ⋅ 4 Baths

ONE-OF-A-KIND HOME WITH INCREDIBLE FLEXIBILITY! This custom all-brick Winchester home offers a layout you simply don't find every day—4 bedrooms, 4 full baths, two main-level bedrooms, flexible private living spaces, a detached 2-car garage and NO HOA! Step inside to a bright, welcoming floor plan featuring beautiful hardwood floors, abundant natural light, custom built-ins and a cozy gas fireplace. The spacious gourmet kitchen offers granite countertops, stainless steel appliances, generous pantry space and a large breakfast area that flows easily into the dining and living spaces—perfect for everyday living and entertaining. One of this home's standout features is its main-level living potential. The primary suite is conveniently located on the main floor with a private bath and walk-in closet, while a second main-level bedroom and nearby full bath provide exceptional flexibility for guests, a home office or additional living space. Main-level laundry with a utility sink adds even more convenience. Upstairs, you'll discover a private and versatile living area with its own main-level entrance, sitting/living space, two additional bedrooms and a full bath—creating an ideal setup for extended stays, guests, work-from-home needs or anyone wanting additional privacy and separation. And there's even more! The detached two-car garage includes additional finished living space above, complete with a bedroom, full bath and kitchen/living area—opening the door to an incredible variety of possibilities. Outside, enjoy multiple parking options with front and rear driveways, an attached covered carport, detached garage and additional street parking. All of this is tucked into an established Winchester neighborhood convenient to downtown Winchester, Route 7, shopping, dining, medical facilities and major commuter routes. All brick. Four full baths. Two main-level bedrooms. Flexible living spaces. Detached garage. No HOA. This isn't your typical Winchester home—come see just how many possibilities 687 Woodland Avenue has to offer.

687 Woodland Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$3,175,000

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

6 Beds ⋅ 7 Baths

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

730 Merrimans Ln, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,239,000

This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy. Inside, you will find a stunning kitchen with top-of-the-line appliances and pull-out drawers throughout the cabinets. The great room is a 2 story ceiling and fireplace leading to the deck and wet bar with ice machine and wine racks. The main level office has a full bath attached if you would like to use it as a main level bedroom. The living and dining rooms are open to each other leading to a sunroom off the deck. The primary bedroom as a gas fireplace, a balcony , 2 walk in closets and an updated spa like bathroom. The second bedroom has it's own bath and the 3rd and 4th bedrooms share a full bath with updated tile and floors. The basement also has a fireplace, a full bath, exercise room and plenty of storage. The pool room (in the basement leading to the pool) has a refrigerator, storage for towels and a 1/2 bath. The 3 car garage has a ton of storage, as the original kitchen cabinets are on the wall...This home is truly a showcase!

4 Beds ⋅ 8 Baths

This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy. Inside, you will find a stunning kitchen with top-of-the-line appliances and pull-out drawers throughout the cabinets. The great room is a 2 story ceiling and fireplace leading to the deck and wet bar with ice machine and wine racks. The main level office has a full bath attached if you would like to use it as a main level bedroom. The living and dining rooms are open to each other leading to a sunroom off the deck. The primary bedroom as a gas fireplace, a balcony , 2 walk in closets and an updated spa like bathroom. The second bedroom has it's own bath and the 3rd and 4th bedrooms share a full bath with updated tile and floors. The basement also has a fireplace, a full bath, exercise room and plenty of storage. The pool room (in the basement leading to the pool) has a refrigerator, storage for towels and a 1/2 bath. The 3 car garage has a ton of storage, as the original kitchen cabinets are on the wall...This home is truly a showcase!

1022 Heth Pl, Winchester

Listing courtesy of Samson Properties. Contact:

$899,000

Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

3 Beds ⋅ 4 Baths

Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

466 Merrimans Ln, Winchester

Listing courtesy of Colony Realty. Contact:

$499,900

Welcome to 110 Russellcroft Road, a beautifully updated 4-bedroom, 3-full-bath ranch-style home in the established Cedarmeade community of Winchester, VA. Offering approximately 3,000 square feet of finished living space including the finished lower level, this home combines comfortable everyday living with the flexibility today's buyers are looking for. The main level features warm hardwood floors, abundant natural light, and an inviting layout centered around an updated kitchen with a large island, pantry, recessed lighting, and easy access to the dining area. Two brick fireplaces add timeless character and create welcoming spaces for gathering, relaxing, or entertaining. The finished lower level is where this home truly stands out, providing an expansive recreation area, built-in bar, full bathroom, garage access, and a separate exterior entrance. Use the additional space as a family room, home office, gym, media room, guest area, game room, or entertaining space—the possibilities are endless. Outside, the nearly half-acre lot provides plenty of room to enjoy the outdoors, with a spacious backyard, mature surroundings, and a welcoming front porch. The attached 2-car garage provides additional convenience and storage. Located in Cedarmeade within Winchester City, this home offers convenient access to schools, parks, shopping, dining, major commuter routes, and all that downtown Winchester has to offer. If you're searching for an updated Winchester, VA ranch home with 4 bedrooms, 3 full baths, a finished basement, substantial living space, and a generous lot, 110 Russellcroft Road deserves a look.

4 Beds ⋅ 3 Baths

Welcome to 110 Russellcroft Road, a beautifully updated 4-bedroom, 3-full-bath ranch-style home in the established Cedarmeade community of Winchester, VA. Offering approximately 3,000 square feet of finished living space including the finished lower level, this home combines comfortable everyday living with the flexibility today's buyers are looking for. The main level features warm hardwood floors, abundant natural light, and an inviting layout centered around an updated kitchen with a large island, pantry, recessed lighting, and easy access to the dining area. Two brick fireplaces add timeless character and create welcoming spaces for gathering, relaxing, or entertaining. The finished lower level is where this home truly stands out, providing an expansive recreation area, built-in bar, full bathroom, garage access, and a separate exterior entrance. Use the additional space as a family room, home office, gym, media room, guest area, game room, or entertaining space—the possibilities are endless. Outside, the nearly half-acre lot provides plenty of room to enjoy the outdoors, with a spacious backyard, mature surroundings, and a welcoming front porch. The attached 2-car garage provides additional convenience and storage. Located in Cedarmeade within Winchester City, this home offers convenient access to schools, parks, shopping, dining, major commuter routes, and all that downtown Winchester has to offer. If you're searching for an updated Winchester, VA ranch home with 4 bedrooms, 3 full baths, a finished basement, substantial living space, and a generous lot, 110 Russellcroft Road deserves a look.

110 Russellcroft Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$324,900

Sellers are motivated and offering incentives. Charming, beautifully maintained all-brick ranch home at 936 Allen Drive! Built in 1965 by Kingsberry Homes using the sought-after Belden model, this special property has been lovingly cared for by one family since its construction and even includes the original architectural floor plans. Inside, the move-in-ready home offers stunning hardwood floors and an enclosed carport seamlessly converted into a spacious family room. The main-level layout features 3 bedrooms and 1.5 baths, including a fully renovated hallway bath with a modern walk-in shower. A full, unfinished basement provides massive storage potential, while the covered rear deck and patio overlook a beautifully landscaped backyard oasis. The sellers have recently invested in numerous proactive improvements, including completed foundation work, radon mitigation, electrical panel optimization, and recent HVAC service (supporting documentation available). Excellent location just minutes from historic downtown Winchester shops and dining, with effortless commuter access to Interstate 81 and Route 50 into Northern Virginia. A wonderful opportunity with important updates already addressed!

3 Beds ⋅ 2 Baths

Sellers are motivated and offering incentives. Charming, beautifully maintained all-brick ranch home at 936 Allen Drive! Built in 1965 by Kingsberry Homes using the sought-after Belden model, this special property has been lovingly cared for by one family since its construction and even includes the original architectural floor plans. Inside, the move-in-ready home offers stunning hardwood floors and an enclosed carport seamlessly converted into a spacious family room. The main-level layout features 3 bedrooms and 1.5 baths, including a fully renovated hallway bath with a modern walk-in shower. A full, unfinished basement provides massive storage potential, while the covered rear deck and patio overlook a beautifully landscaped backyard oasis. The sellers have recently invested in numerous proactive improvements, including completed foundation work, radon mitigation, electrical panel optimization, and recent HVAC service (supporting documentation available). Excellent location just minutes from historic downtown Winchester shops and dining, with effortless commuter access to Interstate 81 and Route 50 into Northern Virginia. A wonderful opportunity with important updates already addressed!

936 Allen Dr, Winchester

Listing courtesy of Dream Real Estate. Contact:

$348,000

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:

$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:

$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

Welcome to 1856 Melvor Lane, a beautifully maintained and thoughtfully updated home offering comfort, convenience, and a low-maintenance lifestyle in Winchester's established 55+ community of Willow Lawn Cottages. Step inside and you'll immediately appreciate the cathedral ceilings, abundant natural light, and open floor plan that create a bright, airy, and welcoming atmosphere. Fresh interior paint, updated lighting, and vinyl plank flooring throughout much of the home add to its inviting appeal. The kitchen features granite countertops, a tile backsplash, generous counter space, and a large walk-in pantry, with an open flow into the dining/living areas that's perfect for everyday living and entertaining. The primary suite offers a private full bathroom, walk-in closet, and conveniently located laundry area. A second bedroom and full bathroom provide additional flexibility for guests, a home office, or hobbies. Situated on a corner lot, the home also features a rear patio and attached one-car garage. Enjoy the convenience of HOA-provided lawn maintenance and snow removal, along with neighborhood sidewalks, a community center, and organized activities. Located just minutes from Winchester Medical Center, shopping, dining, and historic downtown Winchester, this delightful home offers a wonderful combination of thoughtful updates, easy living, and everyday convenience. Move right in and enjoy all that this charming home has to offer!

2 Beds ⋅ 2 Baths

Welcome to 1856 Melvor Lane, a beautifully maintained and thoughtfully updated home offering comfort, convenience, and a low-maintenance lifestyle in Winchester's established 55+ community of Willow Lawn Cottages. Step inside and you'll immediately appreciate the cathedral ceilings, abundant natural light, and open floor plan that create a bright, airy, and welcoming atmosphere. Fresh interior paint, updated lighting, and vinyl plank flooring throughout much of the home add to its inviting appeal. The kitchen features granite countertops, a tile backsplash, generous counter space, and a large walk-in pantry, with an open flow into the dining/living areas that's perfect for everyday living and entertaining. The primary suite offers a private full bathroom, walk-in closet, and conveniently located laundry area. A second bedroom and full bathroom provide additional flexibility for guests, a home office, or hobbies. Situated on a corner lot, the home also features a rear patio and attached one-car garage. Enjoy the convenience of HOA-provided lawn maintenance and snow removal, along with neighborhood sidewalks, a community center, and organized activities. Located just minutes from Winchester Medical Center, shopping, dining, and historic downtown Winchester, this delightful home offers a wonderful combination of thoughtful updates, easy living, and everyday convenience. Move right in and enjoy all that this charming home has to offer!

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 fully serviced in 2020 (serviced condenser unit 2026) 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 fully serviced in 2020 (serviced condenser unit 2026) 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:

$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. Motivated seller!!!

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. Motivated seller!!!

115 S Purcell Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$649,500

100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.

3 Beds ⋅ 3 Baths

100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.

112 W Germain St, Winchester

Listing courtesy of RE/MAX Roots. 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:

$465,000

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:

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