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Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and floor to ceiling windows cascading natural light throughout. The wrap around stairs will wrap around your heart with charm and the thrill to make this glorious mansion your own. Ideal as a single family residence but also zoned B1 for a bed and breakfast or upscale professional offices. Private parking in the rear is another downtown rarity. Includes carriage house. Outstanding residential, commercial, or mixed use investment opportunity, located in the heart of Winchester's Old Town!

6 Beds ⋅ 5 Baths

Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and floor to ceiling windows cascading natural light throughout. The wrap around stairs will wrap around your heart with charm and the thrill to make this glorious mansion your own. Ideal as a single family residence but also zoned B1 for a bed and breakfast or upscale professional offices. Private parking in the rear is another downtown rarity. Includes carriage house. Outstanding residential, commercial, or mixed use investment opportunity, located in the heart of Winchester's Old Town!

217 W Boscawen St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Samson Properties.

$374,900

Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully renovated private bathroom, while another bedroom features direct attic access, ideal for a home office, creative space, or extra storage. One of the bedrooms also offers balcony access overlooking the spacious backyard, adding unique charm to the home. While the property maintains its original hardwood floors and classic character, it has undergone significant improvements, including: • Fully renovated kitchen with quartz countertops, new cabinetry, stainless steel appliances, and backsplash • Upgraded bathrooms, including a new half bath and renovated primary bathroom • Fresh paint throughout • New roof 2025 • Two HVAC systems, One Brand New 2026 and the second HVAC (2023) with zoned heating and cooling. The exterior offers a large fenced backyard with new wire fencing, providing privacy, functionality, and additional convenience. 0.17-acre lot (7,423 sq ft) Long 190-ft deep lot with ALLEY ACCESS. Located just minutes from downtown Winchester, this home offers easy access to shopping, dining, parks, and commuter routes. This property is truly move-in ready and presents a rare opportunity to own a historic home thoughtfully updated with today’s essential upgrades.

4 Beds ⋅ 3 Baths

Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully renovated private bathroom, while another bedroom features direct attic access, ideal for a home office, creative space, or extra storage. One of the bedrooms also offers balcony access overlooking the spacious backyard, adding unique charm to the home. While the property maintains its original hardwood floors and classic character, it has undergone significant improvements, including: • Fully renovated kitchen with quartz countertops, new cabinetry, stainless steel appliances, and backsplash • Upgraded bathrooms, including a new half bath and renovated primary bathroom • Fresh paint throughout • New roof 2025 • Two HVAC systems, One Brand New 2026 and the second HVAC (2023) with zoned heating and cooling. The exterior offers a large fenced backyard with new wire fencing, providing privacy, functionality, and additional convenience. 0.17-acre lot (7,423 sq ft) Long 190-ft deep lot with ALLEY ACCESS. Located just minutes from downtown Winchester, this home offers easy access to shopping, dining, parks, and commuter routes. This property is truly move-in ready and presents a rare opportunity to own a historic home thoughtfully updated with today’s essential upgrades.

317 Gray Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: EXP Realty, LLC.

$205,000

Calling all investors, flippers, and DIY enthusiasts! This 3-bedroom rancher at 1033 Allen Drive in Winchester, VA, is brimming with potential and waiting for your vision to make it shine again. Situated in a fantastic location, this property offers a solid opportunity for your next profitable project, rental property or a home to call your own. Inside, you will find beautiful hardwood floors that are in good shape and ready to be showcased, alongside a spacious basement offering endless possibilities for extra living space, a recreation room, or a workshop. The property boasts a great-sized lot complete with essential off-street parking, a rear deck perfect for outdoor relaxation, and a handy shed for all your outdoor storage needs. If you are ready to bring a little TLC and reap the rewards, this Winchester home is the golden opportunity you’ve been looking for.

3 Beds ⋅ 2 Baths

Calling all investors, flippers, and DIY enthusiasts! This 3-bedroom rancher at 1033 Allen Drive in Winchester, VA, is brimming with potential and waiting for your vision to make it shine again. Situated in a fantastic location, this property offers a solid opportunity for your next profitable project, rental property or a home to call your own. Inside, you will find beautiful hardwood floors that are in good shape and ready to be showcased, alongside a spacious basement offering endless possibilities for extra living space, a recreation room, or a workshop. The property boasts a great-sized lot complete with essential off-street parking, a rear deck perfect for outdoor relaxation, and a handy shed for all your outdoor storage needs. If you are ready to bring a little TLC and reap the rewards, this Winchester home is the golden opportunity you’ve been looking for.

1033 Allen Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Smart Realty, LLC.

$750,000

101 S Loudoun St, Winchester

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

Selling Office: Coldwell Banker Premier.

$450,000

Welcome to 320 Virginia Avenue, where timeless character meets modern sophistication in one of Winchester’s most convenient locations. This beautifully updated home blends historic charm with contemporary finishes, highlighted by designer lighting, exposed brick, custom details, and thoughtful upgrades throughout. From the moment you step inside, the care and craftsmanship are evident. Original features pair seamlessly with modern touches, creating an atmosphere that is both warm and refined. Natural light fills the home, enhancing its well-designed living spaces and distinctive character. Modern conveniences include off-street parking with an oversized single-car garage, a dedicated main-level laundry room, and central air on both levels. Outside, a private backyard provides the perfect setting for relaxing, entertaining, gardening, or simply unwinding at the end of the day. Ideally located just a short walk from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to local restaurants, coffee shops, boutiques, breweries, and community events. The established neighborhood features mature trees, walkable streets, and convenient proximity to commuter routes, schools, parks, and everyday amenities. This is a rare opportunity to own a thoughtfully updated home that captures the best of Winchester living - where character, comfort, and location come together.

3 Beds ⋅ 3 Baths

Welcome to 320 Virginia Avenue, where timeless character meets modern sophistication in one of Winchester’s most convenient locations. This beautifully updated home blends historic charm with contemporary finishes, highlighted by designer lighting, exposed brick, custom details, and thoughtful upgrades throughout. From the moment you step inside, the care and craftsmanship are evident. Original features pair seamlessly with modern touches, creating an atmosphere that is both warm and refined. Natural light fills the home, enhancing its well-designed living spaces and distinctive character. Modern conveniences include off-street parking with an oversized single-car garage, a dedicated main-level laundry room, and central air on both levels. Outside, a private backyard provides the perfect setting for relaxing, entertaining, gardening, or simply unwinding at the end of the day. Ideally located just a short walk from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to local restaurants, coffee shops, boutiques, breweries, and community events. The established neighborhood features mature trees, walkable streets, and convenient proximity to commuter routes, schools, parks, and everyday amenities. This is a rare opportunity to own a thoughtfully updated home that captures the best of Winchester living - where character, comfort, and location come together.

320 Virginia Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Thomas and Talbot Estate Properties, Inc..

$320,000

Fully renovated in 2021 and move-in ready! This charming home is conveniently located just off Route 7 East—perfect for commuters! Enjoy peace of mind with major updates throughout, including brand-new windows, new HVAC, updated electrical system, and all-new appliances, including washer and dryer. The stunning, completely remodeled kitchen features granite countertops, stainless steel appliances, and brand-new cabinetry. Gleaming, refinished hardwood floors flow throughout the home, enhancing its warmth and character. Flexible living spaces include formal living and dining rooms, plus a main-level bedroom or office and a full bath—ideal for guests or remote work. Convenient main-floor laundry adds to the home's functionality. The basement offers excellent storage space, while outside you'll find a huge fenced yard with a shed and outbuilding —perfect for hobbies, storage, or workshop potential. Don't miss this one!

4 Beds ⋅ 2 Baths

Fully renovated in 2021 and move-in ready! This charming home is conveniently located just off Route 7 East—perfect for commuters! Enjoy peace of mind with major updates throughout, including brand-new windows, new HVAC, updated electrical system, and all-new appliances, including washer and dryer. The stunning, completely remodeled kitchen features granite countertops, stainless steel appliances, and brand-new cabinetry. Gleaming, refinished hardwood floors flow throughout the home, enhancing its warmth and character. Flexible living spaces include formal living and dining rooms, plus a main-level bedroom or office and a full bath—ideal for guests or remote work. Convenient main-floor laundry adds to the home's functionality. The basement offers excellent storage space, while outside you'll find a huge fenced yard with a shed and outbuilding —perfect for hobbies, storage, or workshop potential. Don't miss this one!

1044 Orchard Ave, Winchester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Samson Properties.

$480,000

Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry room. the finished lower level expands the living space with a second fireplace, a wet bar, and a large recreation area ideal for a pool table, ping-pong, or game nights with family and friends. Additional features include a one-and-a-half-car garage, providing excellent storage and parking options, along with additional off-street parking. Enjoy outdoor living on the rear deck overlooking a great backyard—perfect for relaxing or entertaining. Located on a quiet street within walking distance to downtown and convenient to the hospital, this home offers both privacy and accessibility in a desirable setting.

3 Beds ⋅ 3 Baths

Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry room. the finished lower level expands the living space with a second fireplace, a wet bar, and a large recreation area ideal for a pool table, ping-pong, or game nights with family and friends. Additional features include a one-and-a-half-car garage, providing excellent storage and parking options, along with additional off-street parking. Enjoy outdoor living on the rear deck overlooking a great backyard—perfect for relaxing or entertaining. Located on a quiet street within walking distance to downtown and convenient to the hospital, this home offers both privacy and accessibility in a desirable setting.

308 Ridge Ave, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Samson Properties.

$326,000

Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find updated flooring and an open-concept main living area designed for today's lifestyle. The heart of the home is the stunning kitchen, featuring granite countertops, white cabinetry, updated fixtures, and a spacious center island with barstool seating—perfect for casual dining, entertaining, or gathering with family and friends. All four bedrooms are generously sized with ample closet space, while both bathrooms have been tastefully updated with modern finishes. Outside, enjoy a large backyard with plenty of room to relax, play, or entertain. The one-car garage is complemented by an oversized driveway that easily accommodates 3–4 additional vehicles, providing exceptional convenience for guests and everyday living. Stylish updates, spacious living areas, and a move-in-ready condition make this home one you won't want to miss.

4 Beds ⋅ 2 Baths

Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find updated flooring and an open-concept main living area designed for today's lifestyle. The heart of the home is the stunning kitchen, featuring granite countertops, white cabinetry, updated fixtures, and a spacious center island with barstool seating—perfect for casual dining, entertaining, or gathering with family and friends. All four bedrooms are generously sized with ample closet space, while both bathrooms have been tastefully updated with modern finishes. Outside, enjoy a large backyard with plenty of room to relax, play, or entertain. The one-car garage is complemented by an oversized driveway that easily accommodates 3–4 additional vehicles, providing exceptional convenience for guests and everyday living. Stylish updates, spacious living areas, and a move-in-ready condition make this home one you won't want to miss.

629 National Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$332,500

Welcome to 16 S Pleasant Valley Rd, a beautifully maintained home offering a bright and inviting layout filled with natural light throughout. Enjoy your morning coffee on the rear patio and unwind in the evenings on the welcoming front porch while taking in the sunset views. The private fenced backyard provides the perfect space for relaxing, entertaining, or gathering around a fire pit with friends and family. For buyers seeking additional parking, a section of the fence could easily be removed to expanded parking options. This home has been thoughtfully updated for peace of mind, featuring a new HVAC system (2025), new hot water heater and dishwasher (2026), and new refrigerator, washer, and dryer (2024). The roof was replaced in 2019, offering added confidence for years to come. Conveniently located just minutes from Historic Downtown Winchester, the Walking Mall, restaurants, shops, the Museum of the Shenandoah Valley, and Apple Blossom Festival events. Outdoor enthusiasts will love being close to Jim Barnett Park, one of Winchester's premier recreation destinations featuring indoor and outdoor pools, pickleball and tennis courts, walking trails, disc golf, sports fields, playgrounds, a dog park, skate park, and year-round recreational activities. Offering comfort, convenience, and an exceptional location, this home is a wonderful opportunity to enjoy everything Winchester has to offer.

3 Beds ⋅ 3 Baths

Welcome to 16 S Pleasant Valley Rd, a beautifully maintained home offering a bright and inviting layout filled with natural light throughout. Enjoy your morning coffee on the rear patio and unwind in the evenings on the welcoming front porch while taking in the sunset views. The private fenced backyard provides the perfect space for relaxing, entertaining, or gathering around a fire pit with friends and family. For buyers seeking additional parking, a section of the fence could easily be removed to expanded parking options. This home has been thoughtfully updated for peace of mind, featuring a new HVAC system (2025), new hot water heater and dishwasher (2026), and new refrigerator, washer, and dryer (2024). The roof was replaced in 2019, offering added confidence for years to come. Conveniently located just minutes from Historic Downtown Winchester, the Walking Mall, restaurants, shops, the Museum of the Shenandoah Valley, and Apple Blossom Festival events. Outdoor enthusiasts will love being close to Jim Barnett Park, one of Winchester's premier recreation destinations featuring indoor and outdoor pools, pickleball and tennis courts, walking trails, disc golf, sports fields, playgrounds, a dog park, skate park, and year-round recreational activities. Offering comfort, convenience, and an exceptional location, this home is a wonderful opportunity to enjoy everything Winchester has to offer.

16 S Pleasant Valley Rd, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Nest Realty Harrisonburg.

$825,000

Distinctive home on the historic register, Winchester walking tour, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester; restaurants, festivals, shopping! Gorgeous inside and out. Fully renovated, 4 levels with a two-story log cabin (the blue building) likely built with timber from Fort Loudoun) , gourmet emodeled kitchen with gas cooking, large pantry, eat-in space by the window. All three full and two half baths renovated. The red building offers a more formal living space with high ceilings in the large living room and dining room, and fireplaces. This was added onto the blue building in the late 1700's. Beautiful wide plank, old flooring exists throughout this section of the home. The turned staircase in the hallway leads to two upper levels, three bedrooms, and a huge bonus room/closet or flex space. The lower level is a finished basement with side entrance to the driveway with spacefor 4 cars. The blue side of the home consists of the kitchen addition behind the log cabin section wich has knotty pine built-in bookshelves and fireplace with pellet stove, an upper level room currently used as an office and a half bath. There is a n unfinished cellar with wonderful access to the front sidewalk - and crawl space under the kitchen. 7 fireplaces ( two with pellet stoves - the other 5 are "as-is") . 10' ceilings, gorgeous authentic wood paneling. Outside, you will be amazed -- the lot is deep affording privacy in the rear. The "dollhouse' shed with water and electric is a great workshop/storage area. Two porticos, planting beds, a koi pond, patio all add pleasure for outdoor living. Take your place in history as owner of this incredible home!

4 Beds ⋅ 4 Baths

Distinctive home on the historic register, Winchester walking tour, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester; restaurants, festivals, shopping! Gorgeous inside and out. Fully renovated, 4 levels with a two-story log cabin (the blue building) likely built with timber from Fort Loudoun) , gourmet emodeled kitchen with gas cooking, large pantry, eat-in space by the window. All three full and two half baths renovated. The red building offers a more formal living space with high ceilings in the large living room and dining room, and fireplaces. This was added onto the blue building in the late 1700's. Beautiful wide plank, old flooring exists throughout this section of the home. The turned staircase in the hallway leads to two upper levels, three bedrooms, and a huge bonus room/closet or flex space. The lower level is a finished basement with side entrance to the driveway with spacefor 4 cars. The blue side of the home consists of the kitchen addition behind the log cabin section wich has knotty pine built-in bookshelves and fireplace with pellet stove, an upper level room currently used as an office and a half bath. There is a n unfinished cellar with wonderful access to the front sidewalk - and crawl space under the kitchen. 7 fireplaces ( two with pellet stoves - the other 5 are "as-is") . 10' ceilings, gorgeous authentic wood paneling. Outside, you will be amazed -- the lot is deep affording privacy in the rear. The "dollhouse' shed with water and electric is a great workshop/storage area. Two porticos, planting beds, a koi pond, patio all add pleasure for outdoor living. Take your place in history as owner of this incredible home!

510 S Loudoun St, Winchester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Keller Williams Realty.

$249,500

Welcome home to this beautifully updated 2-bedroom, 1-bath single-family residence offering charm, comfort, and modern upgrades throughout. From the inviting front porch to the spacious fenced backyard, this move-in ready home combines classic character with thoughtful renovations. Inside, you’ll find brand new LVP flooring on both levels and a completely renovated kitchen featuring ceramic tile flooring, stone countertops, custom backsplash, updated fixtures, and stainless steel appliances. The fully remodeled bathroom includes ceramic tile, a tiled shower, dual vanity, and an LG washer and dryer for added convenience. Comfort is customized year-round with a new 4-zone mini split HVAC system, including individual units in each bedroom, the living room, and dining room. Additional highlights include: Large fenced backyard Cozy covered front porch Two rear porches offering flexible bonus space for dining, office, playroom, or relaxation Newer siding, windows, and doors Durable metal roof Move-in ready condition Perfectly located less than 5 minutes from historic Old Town Winchester, shopping, restaurants, and entertainment. Convenient to Jim Barnett Park, schools, medical centers, and commuter routes including Route 7, Route 50, and I-81. Owner is a licensed Real Estate Agent in Virginia.

2 Beds ⋅ 1 Baths

Welcome home to this beautifully updated 2-bedroom, 1-bath single-family residence offering charm, comfort, and modern upgrades throughout. From the inviting front porch to the spacious fenced backyard, this move-in ready home combines classic character with thoughtful renovations. Inside, you’ll find brand new LVP flooring on both levels and a completely renovated kitchen featuring ceramic tile flooring, stone countertops, custom backsplash, updated fixtures, and stainless steel appliances. The fully remodeled bathroom includes ceramic tile, a tiled shower, dual vanity, and an LG washer and dryer for added convenience. Comfort is customized year-round with a new 4-zone mini split HVAC system, including individual units in each bedroom, the living room, and dining room. Additional highlights include: Large fenced backyard Cozy covered front porch Two rear porches offering flexible bonus space for dining, office, playroom, or relaxation Newer siding, windows, and doors Durable metal roof Move-in ready condition Perfectly located less than 5 minutes from historic Old Town Winchester, shopping, restaurants, and entertainment. Convenient to Jim Barnett Park, schools, medical centers, and commuter routes including Route 7, Route 50, and I-81. Owner is a licensed Real Estate Agent in Virginia.

323 Fairview Ave, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Samson Properties.

$615,000

Discover the charm of this stunning Colonial home nestled in the desirable Harvest Ridge community. With 4 spacious bedrooms and 3.5 bathrooms, this residence offers an impressive 3,944 square feet of meticulously maintained living space, perfect for both relaxation and entertaining. Step inside to find a beautifully designed interior that exudes warmth and sophistication. The open floor plan seamlessly connects the gourmet kitchen, complete with upgraded countertops and a breakfast area, to the inviting family room, where a cozy gas fireplace awaits. Elegant crown moldings and chair railings add a touch of class, while hardwood and ceramic tile flooring enhance the home's aesthetic appeal. The primary suite is a true retreat, featuring a luxurious soaking tub and a walk-in shower, ensuring a spa-like experience at home. The fully finished basement provides additional living space, ideal for a game room, home theater, or gym. With thoughtful features like recessed lighting, window treatments, and a wet/dry bar, this home is designed for modern living. Outside, the property boasts beautifully landscaped grounds on a generous 0.28-acre lot. Enjoy the fresh air on your deck or porch, perfect for morning coffee or evening gatherings. The attached garage and ample driveway space provide convenience for you and your guests. Located in the heart of Harvest Ridge, this home is surrounded by a vibrant community that values connection and convenience. The neighborhood is known for its friendly atmosphere and well-maintained sidewalks, making it perfect for evening strolls or morning jogs. Additionally, the community is well-served by public services, providing peace of mind and ease of living. This exceptional property combines modern amenities with a welcoming community spirit, making it the perfect place to call home. Don't miss your chance to experience the best of Harvest Ridge living!

4 Beds ⋅ 4 Baths

Discover the charm of this stunning Colonial home nestled in the desirable Harvest Ridge community. With 4 spacious bedrooms and 3.5 bathrooms, this residence offers an impressive 3,944 square feet of meticulously maintained living space, perfect for both relaxation and entertaining. Step inside to find a beautifully designed interior that exudes warmth and sophistication. The open floor plan seamlessly connects the gourmet kitchen, complete with upgraded countertops and a breakfast area, to the inviting family room, where a cozy gas fireplace awaits. Elegant crown moldings and chair railings add a touch of class, while hardwood and ceramic tile flooring enhance the home's aesthetic appeal. The primary suite is a true retreat, featuring a luxurious soaking tub and a walk-in shower, ensuring a spa-like experience at home. The fully finished basement provides additional living space, ideal for a game room, home theater, or gym. With thoughtful features like recessed lighting, window treatments, and a wet/dry bar, this home is designed for modern living. Outside, the property boasts beautifully landscaped grounds on a generous 0.28-acre lot. Enjoy the fresh air on your deck or porch, perfect for morning coffee or evening gatherings. The attached garage and ample driveway space provide convenience for you and your guests. Located in the heart of Harvest Ridge, this home is surrounded by a vibrant community that values connection and convenience. The neighborhood is known for its friendly atmosphere and well-maintained sidewalks, making it perfect for evening strolls or morning jogs. Additionally, the community is well-served by public services, providing peace of mind and ease of living. This exceptional property combines modern amenities with a welcoming community spirit, making it the perfect place to call home. Don't miss your chance to experience the best of Harvest Ridge living!

926 Meadow Ct, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$410,000

Well-maintained 3 bed/2 bath rancher just blocks from Jim Barnett Park and close to schools, shopping, dining, and entertainment. Hardwood flooring throughout the main level. Spacious eat-in kitchen with a skylight , featuring Corian countertops, center island, pantry, and additional storage closet. Separate formal dining room. Relax on the 20x6 covered front porch or the 12x16 covered rear deck overlooking the fenced backyard. Property also includes a 14x22 one-car garage and a 12x12 storage shed. The finished lower level offers additional living space with a family room, den, full bath, storage area, and laundry room with utility sink and storage closets. Major updates include roof and shed roof replaced in 2025, HVAC/furnace/heat pump 2020, water heater 2017, gutter guards and updated porch roof 2024, basement LVP flooring 2022, refrigerator 2025, microwave 2024, dishwasher 2019, and replacement windows 2003. Driveway sealed in 2020 and HVAC last serviced 4/2026. Check out the attached 3-D tour!

3 Beds ⋅ 2 Baths

Well-maintained 3 bed/2 bath rancher just blocks from Jim Barnett Park and close to schools, shopping, dining, and entertainment. Hardwood flooring throughout the main level. Spacious eat-in kitchen with a skylight , featuring Corian countertops, center island, pantry, and additional storage closet. Separate formal dining room. Relax on the 20x6 covered front porch or the 12x16 covered rear deck overlooking the fenced backyard. Property also includes a 14x22 one-car garage and a 12x12 storage shed. The finished lower level offers additional living space with a family room, den, full bath, storage area, and laundry room with utility sink and storage closets. Major updates include roof and shed roof replaced in 2025, HVAC/furnace/heat pump 2020, water heater 2017, gutter guards and updated porch roof 2024, basement LVP flooring 2022, refrigerator 2025, microwave 2024, dishwasher 2019, and replacement windows 2003. Driveway sealed in 2020 and HVAC last serviced 4/2026. Check out the attached 3-D tour!

1115 Opequon Ave, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Corcoran McEnearney.

$358,000

Buyers financing fell through. No fault of sellers. HUGE PRICE CUT!. Seller is motivated and open to offers. Explore 433 Beechcroft Road, located in the desirable Cedarmeade community. This lovely one-level ranch home features hardwood flooring throughout and offers 4 bedrooms, 2 full baths, and a spacious combined living and dining area. The kitchen is equipped with custom cabinetry, Corian countertops, and updated appliances, including a refrigerator and dishwasher (2019) and a range and microwave (2024), hot water heater (2026) Enjoy outdoor living on the covered porch overlooking a private, partially fenced rear yard. The property also includes a detached, oversized two-car garage needs touch up to complete, ideal for parking and additional storage. Recent improvements include a new roof on both the home and garage (2018), new gutters on the home (2018), new garage windows (2019), and vinyl siding installed on two sides of the garage (2023).

4 Beds ⋅ 2 Baths

Buyers financing fell through. No fault of sellers. HUGE PRICE CUT!. Seller is motivated and open to offers. Explore 433 Beechcroft Road, located in the desirable Cedarmeade community. This lovely one-level ranch home features hardwood flooring throughout and offers 4 bedrooms, 2 full baths, and a spacious combined living and dining area. The kitchen is equipped with custom cabinetry, Corian countertops, and updated appliances, including a refrigerator and dishwasher (2019) and a range and microwave (2024), hot water heater (2026) Enjoy outdoor living on the covered porch overlooking a private, partially fenced rear yard. The property also includes a detached, oversized two-car garage needs touch up to complete, ideal for parking and additional storage. Recent improvements include a new roof on both the home and garage (2018), new gutters on the home (2018), new garage windows (2019), and vinyl siding installed on two sides of the garage (2023).

433 Beechcroft Rd, Winchester

Listing courtesy of United Real Estate Premier. Contact:

Selling Office: NetRealtyNow.com, LLC.

$350,000

Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement provides flexible additional space ideal for a rec room, home office, workout area, or hobby space, along with room for storage. Outside, enjoy the spacious yard, offering plenty of room for outdoor activities, gardening, or simply relaxing. Ideally located close to Old Towne Winchester, shopping, dining, and major commuter routes, providing easy access while still enjoying a neighborhood setting. Come take a tour today!

3 Beds ⋅ 2 Baths

Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement provides flexible additional space ideal for a rec room, home office, workout area, or hobby space, along with room for storage. Outside, enjoy the spacious yard, offering plenty of room for outdoor activities, gardening, or simply relaxing. Ideally located close to Old Towne Winchester, shopping, dining, and major commuter routes, providing easy access while still enjoying a neighborhood setting. Come take a tour today!

113 Christopher Dr, Winchester

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

Selling Office: RE/MAX Allegiance.

$435,000

Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and commuter convenience. Step inside to find a light-filled interior boasting glistening hardwood floors, crisp neutral paint, updated light fixtures, and elegant crown molding throughout. The main level features a comfortable living room and a spacious formal dining room complete with a built-in bar and custom shelving—perfect for hosting dinner parties. The chef-inspired kitchen has been modernized with sleek cabinetry, a stylish backsplash, and stainless steel appliances, while a convenient main-level laundry room and half bath add to the home's practical layout. The upper level is a private retreat, headlined by a primary suite featuring a stunningly renovated ensuite bath with double sinks and a custom-tiled walk-in shower. Two additional generously sized bedrooms and a second updated full bath provide plenty of space for family or guests. For those seeking even more flexibility, the finished lower level offers a versatile space ideal for a home gym, media room, office or play area. Outdoor living is a true highlight here; relax on the rear deck overlooking a meticulously maintained yard and a fully fenced-in backyard, where large mature trees and charming garden beds create a private, picturesque oasis. With off-street parking and every modern finish already in place, 25 W Southwerk St is ready for you to call it home.

3 Beds ⋅ 3 Baths

Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and commuter convenience. Step inside to find a light-filled interior boasting glistening hardwood floors, crisp neutral paint, updated light fixtures, and elegant crown molding throughout. The main level features a comfortable living room and a spacious formal dining room complete with a built-in bar and custom shelving—perfect for hosting dinner parties. The chef-inspired kitchen has been modernized with sleek cabinetry, a stylish backsplash, and stainless steel appliances, while a convenient main-level laundry room and half bath add to the home's practical layout. The upper level is a private retreat, headlined by a primary suite featuring a stunningly renovated ensuite bath with double sinks and a custom-tiled walk-in shower. Two additional generously sized bedrooms and a second updated full bath provide plenty of space for family or guests. For those seeking even more flexibility, the finished lower level offers a versatile space ideal for a home gym, media room, office or play area. Outdoor living is a true highlight here; relax on the rear deck overlooking a meticulously maintained yard and a fully fenced-in backyard, where large mature trees and charming garden beds create a private, picturesque oasis. With off-street parking and every modern finish already in place, 25 W Southwerk St is ready for you to call it home.

25 W Southwerk St, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Re/Max Roots.

$535,000

Beautiful brick split-foyer home tucked away on a quiet dead-end street in the desirable Whittier Acres community. This location is one of Winchester’s best kept secrets! 315 Walker St has nearly 2,900 finished square feet, combining space, flexibility, and a peaceful setting just minutes from Old Town Winchester, Winchester Medical Center, and everyday conveniences. The main level features a functional, flowing layout with spacious living and dining areas, an updated kitchen with stainless steel appliances, refreshed cabinetry, and a modern backsplash. A bright four-season sunroom overlooking the backyard is perfect for morning coffee, a home office, reading space, or an additional dining area. The lower level provides a large recreation area, half bath, and oversized laundry room (15' x 9') with exterior egress and excellent potential for conversion to a 4th bedroom or flex space by relocating the washer/dryer nearby. With full heating and cooling and 8-foot ceilings, the lower level offers a comfortable additional living space ideal for guests, hobbies, or everyday use. Major updates offer peace of mind, including a new roof, two heat pump HVAC systems, and water heater (all 2023), along with updated flooring, lighting, and refreshed interior finishes throughout. Outside, the property sits on a 0.36-acre lot with perennial landscaping, terraced natural stone outcroppings, and a large, established Basswood tree. An inviting front porch enhances curb appeal, while the true two-car side-entry garage and wide driveway provide excellent functionality and privacy. Enjoy the added benefit of being less than a block from Whittier Park, featuring a playground, soccer field, basketball court, and open green space. This home provides a rare opportunity to own a well-maintained, thoughtfully-updated home in one of Winchester’s most convenient neighborhoods.

3 Beds ⋅ 3 Baths

Beautiful brick split-foyer home tucked away on a quiet dead-end street in the desirable Whittier Acres community. This location is one of Winchester’s best kept secrets! 315 Walker St has nearly 2,900 finished square feet, combining space, flexibility, and a peaceful setting just minutes from Old Town Winchester, Winchester Medical Center, and everyday conveniences. The main level features a functional, flowing layout with spacious living and dining areas, an updated kitchen with stainless steel appliances, refreshed cabinetry, and a modern backsplash. A bright four-season sunroom overlooking the backyard is perfect for morning coffee, a home office, reading space, or an additional dining area. The lower level provides a large recreation area, half bath, and oversized laundry room (15' x 9') with exterior egress and excellent potential for conversion to a 4th bedroom or flex space by relocating the washer/dryer nearby. With full heating and cooling and 8-foot ceilings, the lower level offers a comfortable additional living space ideal for guests, hobbies, or everyday use. Major updates offer peace of mind, including a new roof, two heat pump HVAC systems, and water heater (all 2023), along with updated flooring, lighting, and refreshed interior finishes throughout. Outside, the property sits on a 0.36-acre lot with perennial landscaping, terraced natural stone outcroppings, and a large, established Basswood tree. An inviting front porch enhances curb appeal, while the true two-car side-entry garage and wide driveway provide excellent functionality and privacy. Enjoy the added benefit of being less than a block from Whittier Park, featuring a playground, soccer field, basketball court, and open green space. This home provides a rare opportunity to own a well-maintained, thoughtfully-updated home in one of Winchester’s most convenient neighborhoods.

315 Walker St, Winchester

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

Selling Office: Colony Realty.

$459,000

Discover the perfectly updated turnkey home you’ve been searching for in Historic Winchester. This beautifully maintained property offers 3 bedrooms and 2.5 bathrooms, including a spacious primary suite with a full bath and walk‑in closet, convenient main‑level laundry, and a flat, usable backyard with alley access—ideal for a future garage or additional off‑street parking. Gardeners will love the lush lawn, raised beds, mature plantings, and thoughtfully designed greenhouse. Enjoy morning coffee or evening conversations on the welcoming full front porch or the private back deck. Extensive upgrades over the past decade provide both comfort and peace of mind, all within an unbeatable location close to the downtown pedestrian mall, Jim Barnett Park, the Green Circle Trail, and everything Winchester has to offer. Major Improvements Include: • 2016: New electric, dual‑zone HVAC, plumbing, hot water heater, wall & roof insulation, stainless steel appliances, upgraded kitchen & baths, new deck • 2017: New main‑level washer & dryer • 2019: New 30‑year SmartSide siding and double‑hung windows • Additional recent updates: reglazed decorative “9‑light” window, new greenhouse & raised beds, and freshly repainted front and side porches

3 Beds ⋅ 3 Baths

Discover the perfectly updated turnkey home you’ve been searching for in Historic Winchester. This beautifully maintained property offers 3 bedrooms and 2.5 bathrooms, including a spacious primary suite with a full bath and walk‑in closet, convenient main‑level laundry, and a flat, usable backyard with alley access—ideal for a future garage or additional off‑street parking. Gardeners will love the lush lawn, raised beds, mature plantings, and thoughtfully designed greenhouse. Enjoy morning coffee or evening conversations on the welcoming full front porch or the private back deck. Extensive upgrades over the past decade provide both comfort and peace of mind, all within an unbeatable location close to the downtown pedestrian mall, Jim Barnett Park, the Green Circle Trail, and everything Winchester has to offer. Major Improvements Include: • 2016: New electric, dual‑zone HVAC, plumbing, hot water heater, wall & roof insulation, stainless steel appliances, upgraded kitchen & baths, new deck • 2017: New main‑level washer & dryer • 2019: New 30‑year SmartSide siding and double‑hung windows • Additional recent updates: reglazed decorative “9‑light” window, new greenhouse & raised beds, and freshly repainted front and side porches

244 Parkway St, Winchester

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

Selling Office: Samson Properties.

$275,000

**Brand new carpet and paint on main level** Welcome to 2956 Grace Street, this 3-bedroom 1-bath ranch-style home offers a functional layout designed for everyday living, paired with the added benefit of a fullt equipped guest suite. Whether you are accomodating extended family, hosting long-term guests or exploring rental potential, this home provides flexibility to fit a variety of lifestyles. From the moment you step inside, you're welcomed by a light filled living space that creates a warm and inviting atmosphere, with ceramic tile that adds warmth and character to gather or unwind at the end of the day. The main level offers the ease of single level living, with a simple, practical layout supports both comfort and convenience. The kitchen features modern appliences, updated countertops and ample cabinetry, blending style with functionality for everyday use. The adjacent dining and living areas allow for an easy open flow, ideal for both daily routines and entertaining. Each bedroom offers generous space natural light and closet storage and a centrally located full bath provides convenient access from all rooms. Separate laundry and office rooms add to the homes functionality. Step outside to enjoy a private fenced in backyard with a deck, perfect fo relaxing, entertaining or creating your own outdoor retreat. A 20x26 2 car detached garage adds valuable flexibility for storage, workshop or hobbies. Located in Winchester, VA the home is convenient for shopping, dining, schools and major commuter routes. Nearby destinations include, Apple Blossom Mall and Winchester Gateway, along with a variety of lcal shops and restaurants. asy access to U.S Route 7, Route 50 and interstate 81 provdes convenient connections to Northern VA and surrounding areas. Historic Old Town Winchester is just a short drive away, offering local dining boutiques and year round community events while nearby parks and outdoor spaces provide additional opportunities for recreation. 2956 Grace Street combines the ease of one level living with flexible space and a convenient location, ready for you to settle in and make it your own.

4 Beds ⋅ 1 Baths

**Brand new carpet and paint on main level** Welcome to 2956 Grace Street, this 3-bedroom 1-bath ranch-style home offers a functional layout designed for everyday living, paired with the added benefit of a fullt equipped guest suite. Whether you are accomodating extended family, hosting long-term guests or exploring rental potential, this home provides flexibility to fit a variety of lifestyles. From the moment you step inside, you're welcomed by a light filled living space that creates a warm and inviting atmosphere, with ceramic tile that adds warmth and character to gather or unwind at the end of the day. The main level offers the ease of single level living, with a simple, practical layout supports both comfort and convenience. The kitchen features modern appliences, updated countertops and ample cabinetry, blending style with functionality for everyday use. The adjacent dining and living areas allow for an easy open flow, ideal for both daily routines and entertaining. Each bedroom offers generous space natural light and closet storage and a centrally located full bath provides convenient access from all rooms. Separate laundry and office rooms add to the homes functionality. Step outside to enjoy a private fenced in backyard with a deck, perfect fo relaxing, entertaining or creating your own outdoor retreat. A 20x26 2 car detached garage adds valuable flexibility for storage, workshop or hobbies. Located in Winchester, VA the home is convenient for shopping, dining, schools and major commuter routes. Nearby destinations include, Apple Blossom Mall and Winchester Gateway, along with a variety of lcal shops and restaurants. asy access to U.S Route 7, Route 50 and interstate 81 provdes convenient connections to Northern VA and surrounding areas. Historic Old Town Winchester is just a short drive away, offering local dining boutiques and year round community events while nearby parks and outdoor spaces provide additional opportunities for recreation. 2956 Grace Street combines the ease of one level living with flexible space and a convenient location, ready for you to settle in and make it your own.

2956 Grace St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Unrepresented.

$420,000

OPEN HOUSE CANCELED.....UNDER CONTRACT....The perfect old town Winchester location and ready for you to move in......Classic brick “American Foursquare” house in Winchester’s historic district. . This well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front porch with a ceiling fan. This 4 bedroom, 2 bath home is located in the historic Winchester “Potato Hill” neighborhood and just a few blocks from old town’s vibrant Loudoun Street mall. Enjoy numerous locally owned shops, historic attractions, street festivals, city sponsored activities, museums and restaurants. Among the many features are landscaping that emphasizes native trees, shrubs, wildflowers and ferns. See the features list ....your buyer representative will get you a copyThe 16x18 wooden rear garage has electrical service and is on the footprint of the original 1928 garage with a new concrete pad, 2 doors, copper roof, gutters and downspouts. In additon, there is an attached carport over the driveway. Hardwood floors in the living room and dining room, laminate in the remainder of the main level with pine flooring on the 2nd and 3rd floors with some carpeting. There are wooden blinds on most of the 1st and 2nd floor windows along with 7 ceiling fans. The unfinished basement has a concrete block foundation and a concrete floor. An extra commode and utility sink are located in the basement. The interior walls are mostly plaster but also include some drywall, brick and pine paneling. This all-electric home features heating and air conditioning supplied by two high-efficiency inverter heat pumps installed in 2023 and seven mini-split air handlers on the first and second floors. High-efficiency 50-gallon hybrid heat pump water heater was installed in 2023. Stacked washer/dryer (new in 2025) conveys. Internet and TV by GloFiber high speed glass fiber cable. The owners have never used the fireplace. Note that the square footage in the city tax records is less than the actual size according to the seller's records. Buyers should confirm the square footage. THE AMERICAN FOURSQUARE HOME…….From Mail-Order Home to Iconic Architecture Imagine the United States in the late 19th century in the midst of a growing economy and modernization. Urban communities were developing fast with more Americans leaving rural areas to pursue employment opportunities in the cities. It was a time when families moved away from their multi-generational residences and aspired to live in their separate homes.Enter the Foursquare, one of the most popular styles in the U.S. from the mid-1890s through the late 1930s during the economic boom that resulted in a greater demand for housing. Often mistaken for a Colonial home, the Foursquare is considered a variant of the Prairie Style and is sometimes called “Prairie Box.” With its boxy shape and simple design, the Foursquare – so-called because of its typically square footprint – was a reaction against the ornate and dramatic embellishments of other Victorian-era styles of the period.

4 Beds ⋅ 2 Baths

OPEN HOUSE CANCELED.....UNDER CONTRACT....The perfect old town Winchester location and ready for you to move in......Classic brick “American Foursquare” house in Winchester’s historic district. . This well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front porch with a ceiling fan. This 4 bedroom, 2 bath home is located in the historic Winchester “Potato Hill” neighborhood and just a few blocks from old town’s vibrant Loudoun Street mall. Enjoy numerous locally owned shops, historic attractions, street festivals, city sponsored activities, museums and restaurants. Among the many features are landscaping that emphasizes native trees, shrubs, wildflowers and ferns. See the features list ....your buyer representative will get you a copyThe 16x18 wooden rear garage has electrical service and is on the footprint of the original 1928 garage with a new concrete pad, 2 doors, copper roof, gutters and downspouts. In additon, there is an attached carport over the driveway. Hardwood floors in the living room and dining room, laminate in the remainder of the main level with pine flooring on the 2nd and 3rd floors with some carpeting. There are wooden blinds on most of the 1st and 2nd floor windows along with 7 ceiling fans. The unfinished basement has a concrete block foundation and a concrete floor. An extra commode and utility sink are located in the basement. The interior walls are mostly plaster but also include some drywall, brick and pine paneling. This all-electric home features heating and air conditioning supplied by two high-efficiency inverter heat pumps installed in 2023 and seven mini-split air handlers on the first and second floors. High-efficiency 50-gallon hybrid heat pump water heater was installed in 2023. Stacked washer/dryer (new in 2025) conveys. Internet and TV by GloFiber high speed glass fiber cable. The owners have never used the fireplace. Note that the square footage in the city tax records is less than the actual size according to the seller's records. Buyers should confirm the square footage. THE AMERICAN FOURSQUARE HOME…….From Mail-Order Home to Iconic Architecture Imagine the United States in the late 19th century in the midst of a growing economy and modernization. Urban communities were developing fast with more Americans leaving rural areas to pursue employment opportunities in the cities. It was a time when families moved away from their multi-generational residences and aspired to live in their separate homes.Enter the Foursquare, one of the most popular styles in the U.S. from the mid-1890s through the late 1930s during the economic boom that resulted in a greater demand for housing. Often mistaken for a Colonial home, the Foursquare is considered a variant of the Prairie Style and is sometimes called “Prairie Box.” With its boxy shape and simple design, the Foursquare – so-called because of its typically square footprint – was a reaction against the ornate and dramatic embellishments of other Victorian-era styles of the period.

17 E Leicester St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Compass.

$479,000

Welcome to effortless in-town living on Greystone Terrace! This classic all-brick home blends timeless charm with modern comfort in an unbeatable walkable location— to downtown, local coffee shops, parks, and dining. Commuters will love the easy access to major routes, retail, and shopping! Inside, sunlight dances across rich hardwood floors that run throughout. An airy, open-flow layout showcases crisp, upscale finishes like exposed brick, working fireplace, updated lighting, built in cabinetry, and a fully remodeled kitchen. The large first-floor bedroom anchors the main level, adjacent to the full bath—perfect for first-floor living! The second-floor bedrooms and additional full bathroom are ideal for growing families, guests, office, or flex space! Step outside to your oversized back deck—an outdoor living room overlooking a private yard, ideal for grilling, gatherings, or quiet mornings with coffee. A separate carriage garage adds extra storage, hobby space, or a garden shed. Tons of storage in the full basement too! Bonus, an additional lot behind the house is offered for sale too! (is not a residential building lot but ideal for building a large garage, yoga studio, or any type of secondary recreational structure!) Contact Agent for details! Owner/Agent

3 Beds ⋅ 2 Baths

Welcome to effortless in-town living on Greystone Terrace! This classic all-brick home blends timeless charm with modern comfort in an unbeatable walkable location— to downtown, local coffee shops, parks, and dining. Commuters will love the easy access to major routes, retail, and shopping! Inside, sunlight dances across rich hardwood floors that run throughout. An airy, open-flow layout showcases crisp, upscale finishes like exposed brick, working fireplace, updated lighting, built in cabinetry, and a fully remodeled kitchen. The large first-floor bedroom anchors the main level, adjacent to the full bath—perfect for first-floor living! The second-floor bedrooms and additional full bathroom are ideal for growing families, guests, office, or flex space! Step outside to your oversized back deck—an outdoor living room overlooking a private yard, ideal for grilling, gatherings, or quiet mornings with coffee. A separate carriage garage adds extra storage, hobby space, or a garden shed. Tons of storage in the full basement too! Bonus, an additional lot behind the house is offered for sale too! (is not a residential building lot but ideal for building a large garage, yoga studio, or any type of secondary recreational structure!) Contact Agent for details! Owner/Agent

1423 Greystone Ter, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Samson Properties.

$299,900

This 3-bedroom, 1 full bath home is ready for you to move right in! Entire inside has been freshly painted. As you enter, you'll see the spacious living room with LVP flooring. Kitchen with new LVP flooring, new stainless-steel stove, new stainless-steel hood vent, new stainless-steel refrigerator and an eating area. Beautiful full bath with tile shower. 3 great sized bedrooms with LVP flooring. Enjoy relaxing on the covered front porch. Storage shed behind the house, along with room for 2 cars to park (alley behind the house to get to it). All new windows (besides the middle front center window). The back of the house has new vinyl siding that has been painted to match the house. HVAC system (duct work included) was installed roughly 5 years ago. Front porch was redone roughly 5 years ago. Roof/Gutters/Downspouts were redone roughly 5 years ago. The outside of the house was painted roughly 5 years ago. 2 new hose bibs. The city has the year of the house as 1989 but that is not correct (unknown of the correct year). Agent/Owner

3 Beds ⋅ 1 Baths

This 3-bedroom, 1 full bath home is ready for you to move right in! Entire inside has been freshly painted. As you enter, you'll see the spacious living room with LVP flooring. Kitchen with new LVP flooring, new stainless-steel stove, new stainless-steel hood vent, new stainless-steel refrigerator and an eating area. Beautiful full bath with tile shower. 3 great sized bedrooms with LVP flooring. Enjoy relaxing on the covered front porch. Storage shed behind the house, along with room for 2 cars to park (alley behind the house to get to it). All new windows (besides the middle front center window). The back of the house has new vinyl siding that has been painted to match the house. HVAC system (duct work included) was installed roughly 5 years ago. Front porch was redone roughly 5 years ago. Roof/Gutters/Downspouts were redone roughly 5 years ago. The outside of the house was painted roughly 5 years ago. 2 new hose bibs. The city has the year of the house as 1989 but that is not correct (unknown of the correct year). Agent/Owner

126 S Euclid Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$145,000

2 Level Rambler Featuring Spacious Bedrooms and a Functional Layout Perfect for Comfortable Living. Enjoy Quiet Mornings or Evening Relaxation on the Inviting Covered Front Porch, and Take Advantage of the Rear Deck for Outdoor Dining and Entertaining. The Property Also Includes a Walk Out Basement and Storage Shed Providing Extra Space For Tools, Equipment, or Seasonal Items. Situated on a Desirable Lot, This Home Presents a Fantastic Opportunity for Buyers Seeking Value and Potential. With Some Cosmetic Updates and Renovations, This Property Can Truly Shine and be Transformed into a Beautiful Personalized Residence or Investment Opportunity. Sold As-Is

2 Beds ⋅ 1 Baths

2 Level Rambler Featuring Spacious Bedrooms and a Functional Layout Perfect for Comfortable Living. Enjoy Quiet Mornings or Evening Relaxation on the Inviting Covered Front Porch, and Take Advantage of the Rear Deck for Outdoor Dining and Entertaining. The Property Also Includes a Walk Out Basement and Storage Shed Providing Extra Space For Tools, Equipment, or Seasonal Items. Situated on a Desirable Lot, This Home Presents a Fantastic Opportunity for Buyers Seeking Value and Potential. With Some Cosmetic Updates and Renovations, This Property Can Truly Shine and be Transformed into a Beautiful Personalized Residence or Investment Opportunity. Sold As-Is

1124 Conway St, Winchester

Listing courtesy of ANR Realty, LLC. Contact:

Selling Office: Metas Realty Group, LLC.

$549,000

Experience the perfect blend of traditional charm and modern scale in this meticulously maintained residence located in the highly sought-after and established community of Meadow Branch South. The striking exterior, framed by a beautifully manicured lawn and mature landscaping, welcomes you into a soaring two-story foyer anchored by gleaming hardwood floors. The main level is designed for effortless living, featuring a formal living room accented by classic columns and an inviting open-concept layout. The gourmet kitchen is a showstopper, boasting vaulted ceilings, a center island with breakfast bar seating, elegant stone counters, and a custom tile backsplash. This space flows seamlessly into an expansive family room that serves as the true centerpiece of the home; with its cozy fireplace, impressive high ceilings, and wall of windows, it offers a sun-drenched space perfect for quiet evenings or lively gatherings. Retreat to the rare main-level primary suite, a private haven defined by high ceilings and oversized windows that flood the room with natural light. The ensuite bath is a spa-like escape, featuring a dual-sink vanity, a separate shower, and a large soaking tub tucked under a corner window. Functional needs are met with a dedicated main-level laundry room and a convenient half bath, while the upper level hosts two generously sized guest bedrooms and a full bath. For those needing extra room, the massive walk-up basement provides tons of storage space and offers a clean slate ready to be finished into a home gym, workshop, or recreation hub. The outdoor living spaces are truly the crown jewel of this property. The fabulous screened-in porch is an entertainer’s dream, featuring a ceiling fan and ample room for sipping morning coffee or enjoying al fresco dinners while overlooking the lush, fenced-in backyard. Beyond the porch, an additional deck leads down to the verdant lawn, which is bordered by a charming picket fence and privacy-enhancing mature greenery. Complete with an attached two-car garage, this Winchester gem offers a peaceful suburban lifestyle without sacrificing proximity to local amenities.

3 Beds ⋅ 3 Baths

Experience the perfect blend of traditional charm and modern scale in this meticulously maintained residence located in the highly sought-after and established community of Meadow Branch South. The striking exterior, framed by a beautifully manicured lawn and mature landscaping, welcomes you into a soaring two-story foyer anchored by gleaming hardwood floors. The main level is designed for effortless living, featuring a formal living room accented by classic columns and an inviting open-concept layout. The gourmet kitchen is a showstopper, boasting vaulted ceilings, a center island with breakfast bar seating, elegant stone counters, and a custom tile backsplash. This space flows seamlessly into an expansive family room that serves as the true centerpiece of the home; with its cozy fireplace, impressive high ceilings, and wall of windows, it offers a sun-drenched space perfect for quiet evenings or lively gatherings. Retreat to the rare main-level primary suite, a private haven defined by high ceilings and oversized windows that flood the room with natural light. The ensuite bath is a spa-like escape, featuring a dual-sink vanity, a separate shower, and a large soaking tub tucked under a corner window. Functional needs are met with a dedicated main-level laundry room and a convenient half bath, while the upper level hosts two generously sized guest bedrooms and a full bath. For those needing extra room, the massive walk-up basement provides tons of storage space and offers a clean slate ready to be finished into a home gym, workshop, or recreation hub. The outdoor living spaces are truly the crown jewel of this property. The fabulous screened-in porch is an entertainer’s dream, featuring a ceiling fan and ample room for sipping morning coffee or enjoying al fresco dinners while overlooking the lush, fenced-in backyard. Beyond the porch, an additional deck leads down to the verdant lawn, which is bordered by a charming picket fence and privacy-enhancing mature greenery. Complete with an attached two-car garage, this Winchester gem offers a peaceful suburban lifestyle without sacrificing proximity to local amenities.

1930 Harvest Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Samson Properties.

$275,000

Adorable ranch home ready for new owners! The home has a large family room for entertainment, a rear patio for outside relaxation, and a fully fenced yard. Laminate flooring throughout the home with carpet in the family room. The price has been increased to reflect recent upgrades, including a fully remodeled bathroom, refinished kitchen cabinets, new countertops, fresh interior paint throughout the home, and newly painted exterior wood trim. The home is located downtown within close proximity to shopping, restaurants, Jim Barnett Park, and Shenandoah University. Roof replaced in 2019. Owners are licensed agents.

3 Beds ⋅ 1 Baths

Adorable ranch home ready for new owners! The home has a large family room for entertainment, a rear patio for outside relaxation, and a fully fenced yard. Laminate flooring throughout the home with carpet in the family room. The price has been increased to reflect recent upgrades, including a fully remodeled bathroom, refinished kitchen cabinets, new countertops, fresh interior paint throughout the home, and newly painted exterior wood trim. The home is located downtown within close proximity to shopping, restaurants, Jim Barnett Park, and Shenandoah University. Roof replaced in 2019. Owners are licensed agents.

332 Opequon Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Non Subscribing Office.

$499,000

Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods. Inside, you’ll find nearly 1,800 square feet of living space filled with original details, including stunning hardwood floors with an intricate decorative apple blossom inlay, classic trim, original bedroom door hardware, and the beloved three-over-one Craftsman-style sash windows. The main living areas are graced with built-in colonnades between the living and dining rooms, giving the space warmth and flow. The home has been freshly painted and features a newer roof, along with refreshed flooring in the kitchen, half bath, and butler’s pantry. The kitchen and bathrooms have been thoughtfully updated, including a charming primary bath that’s ready for everyday comfort or weekend relaxation. Even the heating system has been upgraded, with a recent conversion from oil to natural gas for better efficiency and modern living. Upstairs, you'll find a finished attic bedroom—perfect as a guest room, home office, or creative space. And when you step outside, you’re just as charmed: tucked just beyond the main home, you’ll find a charming one-bedroom, one-bath guest cottage—perfect for extended family or visiting friends. This cozy space includes a wet bar and living area, offering privacy and comfort in a picturesque backyard setting. It’s conveniently connected to a two-car carport, providing covered parking and easy access. Whether you use it as a guest retreat, studio, or home office, this cottage adds incredible flexibility and value to an already exceptional property. This truly special home isn’t just move-in ready—it’s a one-of-a-kind opportunity to own a meaningful piece of Winchester’s story. The backyard is thriving with native Virginia perennials and backs up to Town Run and Winchester’s scenic Green Circle Trail, ideal for a morning walk or afternoon bike ride. You’re also just minutes from the lively Old Town Walking Mall, where shops, cafes, and community events bring the city’s rich culture to life and the highly sought-after Shenandoah University. If you're looking for history, charm, and location, you’ll find it all right here—ready and waiting for your next chapter.

4 Beds ⋅ 3 Baths

Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods. Inside, you’ll find nearly 1,800 square feet of living space filled with original details, including stunning hardwood floors with an intricate decorative apple blossom inlay, classic trim, original bedroom door hardware, and the beloved three-over-one Craftsman-style sash windows. The main living areas are graced with built-in colonnades between the living and dining rooms, giving the space warmth and flow. The home has been freshly painted and features a newer roof, along with refreshed flooring in the kitchen, half bath, and butler’s pantry. The kitchen and bathrooms have been thoughtfully updated, including a charming primary bath that’s ready for everyday comfort or weekend relaxation. Even the heating system has been upgraded, with a recent conversion from oil to natural gas for better efficiency and modern living. Upstairs, you'll find a finished attic bedroom—perfect as a guest room, home office, or creative space. And when you step outside, you’re just as charmed: tucked just beyond the main home, you’ll find a charming one-bedroom, one-bath guest cottage—perfect for extended family or visiting friends. This cozy space includes a wet bar and living area, offering privacy and comfort in a picturesque backyard setting. It’s conveniently connected to a two-car carport, providing covered parking and easy access. Whether you use it as a guest retreat, studio, or home office, this cottage adds incredible flexibility and value to an already exceptional property. This truly special home isn’t just move-in ready—it’s a one-of-a-kind opportunity to own a meaningful piece of Winchester’s story. The backyard is thriving with native Virginia perennials and backs up to Town Run and Winchester’s scenic Green Circle Trail, ideal for a morning walk or afternoon bike ride. You’re also just minutes from the lively Old Town Walking Mall, where shops, cafes, and community events bring the city’s rich culture to life and the highly sought-after Shenandoah University. If you're looking for history, charm, and location, you’ll find it all right here—ready and waiting for your next chapter.

720 S Kent St, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: Samson Properties.

$540,000

Welcome to 1300 Caroline Street—where timeless design meets everyday functionality in one of Winchester’s most convenient locations. Perfectly positioned on a spacious 0.32-acre corner lot, this beautifully maintained residence offers 4 bedrooms, 3.5 bathrooms, a finished basement, and a desirable 2-car side-load garage. The main level showcases a thoughtfully renovated kitchen featuring updated appliances, tile flooring, and a seamless flow into the formal dining room. Hardwood floors carry throughout the sun-filled formal living and family rooms, where the inviting family room is anchored by a classic brick-encased wood burning fireplace and custom built-ins—creating a warm, refined gathering space. Upstairs, you’ll find three generously sized guest bedrooms and a well-appointed hall bath. The primary suite offers a peaceful retreat with hardwoods and a private en-suite bath. The finished lower level expands your living space with a second brick-encased fireplace, a full bathroom, and a spacious laundry room complete with built-in cabinetry for exceptional storage. A large unfinished area provides ideal climate-controlled storage, and the walk-up access adds convenience and flexibility. Outdoors, enjoy a lush, green setting designed for entertaining—featuring a spacious deck that flows down to a thoughtfully designed patio, perfect for hosting family, friends, or summer barbecues. Ideally located just moments from major commuter routes i.e., I-81, Rte. 37, 50, and 522 this home offers easy access to everything you need. Enjoy close proximity to downtown Winchester, where you’ll find exceptional local shopping and dining, and just a quick 2-minute drive to The Winchester Medical Center. Set within a community that blends charm, sophistication, and everyday convenience—with the added benefit of no HOA—this is a rare opportunity to experience elevated living in the heart of Winchester Virginia!

4 Beds ⋅ 4 Baths

Welcome to 1300 Caroline Street—where timeless design meets everyday functionality in one of Winchester’s most convenient locations. Perfectly positioned on a spacious 0.32-acre corner lot, this beautifully maintained residence offers 4 bedrooms, 3.5 bathrooms, a finished basement, and a desirable 2-car side-load garage. The main level showcases a thoughtfully renovated kitchen featuring updated appliances, tile flooring, and a seamless flow into the formal dining room. Hardwood floors carry throughout the sun-filled formal living and family rooms, where the inviting family room is anchored by a classic brick-encased wood burning fireplace and custom built-ins—creating a warm, refined gathering space. Upstairs, you’ll find three generously sized guest bedrooms and a well-appointed hall bath. The primary suite offers a peaceful retreat with hardwoods and a private en-suite bath. The finished lower level expands your living space with a second brick-encased fireplace, a full bathroom, and a spacious laundry room complete with built-in cabinetry for exceptional storage. A large unfinished area provides ideal climate-controlled storage, and the walk-up access adds convenience and flexibility. Outdoors, enjoy a lush, green setting designed for entertaining—featuring a spacious deck that flows down to a thoughtfully designed patio, perfect for hosting family, friends, or summer barbecues. Ideally located just moments from major commuter routes i.e., I-81, Rte. 37, 50, and 522 this home offers easy access to everything you need. Enjoy close proximity to downtown Winchester, where you’ll find exceptional local shopping and dining, and just a quick 2-minute drive to The Winchester Medical Center. Set within a community that blends charm, sophistication, and everyday convenience—with the added benefit of no HOA—this is a rare opportunity to experience elevated living in the heart of Winchester Virginia!

1300 Caroline St, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

Selling Office: Century 21 Redwood Realty.

$292,500

***Multiple offers have been received. Highest and best offers by Monday, June 8 at 5:00 PM.*** Opportunity awaits at 1004 Allen Dr in the City of Winchester! This all-brick 3-bedroom, 2-bath home is full of potential and ready for your personal touches. Whether you are an investor, first-time buyer, or someone looking to build sweat equity, this home offers a chance to add value from day one. Roll up your sleeves and bring your vision to life. Situated on a great City of Winchester lot, the property features a welcoming covered front porch, spacious front lawn, driveway, fenced backyard, shed with power, and an additional workshop/pantry space just off the kitchen — perfect for storage, hobbies, or future improvements. Conveniently located just minutes from downtown Winchester and Shenandoah University, with easy access to shopping, dining, and commuter routes. Only 57 minutes to Dulles Airport. Winchester, VA continues to be one of the fastest-growing areas in Virginia, making this a great opportunity to buy now and build equity over time. Home needs some work and is priced accordingly.

3 Beds ⋅ 2 Baths

***Multiple offers have been received. Highest and best offers by Monday, June 8 at 5:00 PM.*** Opportunity awaits at 1004 Allen Dr in the City of Winchester! This all-brick 3-bedroom, 2-bath home is full of potential and ready for your personal touches. Whether you are an investor, first-time buyer, or someone looking to build sweat equity, this home offers a chance to add value from day one. Roll up your sleeves and bring your vision to life. Situated on a great City of Winchester lot, the property features a welcoming covered front porch, spacious front lawn, driveway, fenced backyard, shed with power, and an additional workshop/pantry space just off the kitchen — perfect for storage, hobbies, or future improvements. Conveniently located just minutes from downtown Winchester and Shenandoah University, with easy access to shopping, dining, and commuter routes. Only 57 minutes to Dulles Airport. Winchester, VA continues to be one of the fastest-growing areas in Virginia, making this a great opportunity to buy now and build equity over time. Home needs some work and is priced accordingly.

1004 Allen Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Samson Properties.

$305,000

Charming 3-bedroom, 1-bath home featuring a full basement and a large level yard offering plenty of outdoor space for a variety of uses. Inside, you’ll find hardwood floors throughout, a spacious formal dining room, and a large kitchen with ample cabinet and counter space. A versatile bonus room on the main level provides flexibility for a home office, den, hobby room, study area, or additional living space to fit your needs. Conveniently located near schools, shopping, banking, dining, and commuter routes including I-81, Route 7, and Route 50, making travel and daily errands easily accessible. Lot size is approximate.

3 Beds ⋅ 1 Baths

Charming 3-bedroom, 1-bath home featuring a full basement and a large level yard offering plenty of outdoor space for a variety of uses. Inside, you’ll find hardwood floors throughout, a spacious formal dining room, and a large kitchen with ample cabinet and counter space. A versatile bonus room on the main level provides flexibility for a home office, den, hobby room, study area, or additional living space to fit your needs. Conveniently located near schools, shopping, banking, dining, and commuter routes including I-81, Route 7, and Route 50, making travel and daily errands easily accessible. Lot size is approximate.

410 N Pleasant Valley Rd, Winchester

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

Selling Office: Realty FC.

$985,000

This property exudes luxury multigenerational living in Meadowbranch! • Main level bedroom + bath • 6500 sq ft • Wet bar in primary suite • 3-car garage • No HOA • Backing to trees, and more..... Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 7 bedroom/5.5 bath residence features a main-level bedroom and full bath—ideal for an in-law suite. Just off the kitchen, the covered back deck offers the perfect space for entertaining. Inside, you’ll find a kitchen that doesn’t compromise with Jenn-Air appliances, solid cherry cabinetry, and an oversized walk-in pantry, making cooking a joy. Hardwood and tile floors flow throughout the main level, while the lower-level recreation room boasts durable waterproof laminate flooring. The expansive primary suite offers a double-sided gas fireplace and a private wet bar/coffee bar with a sink—ideal for unwinding after a long day. The bedroom-level laundry room is fully equipped with cabinetry and a utility sink for added convenience. A 3-car side entry garage includes a half bath. Modern comforts include multiple furnaces & heat pumps, central vacuum & intercom system, front yard irrigation, an intercom system, and no costly monthly HOA dues. Whether you are seeking multi-generational living or space for a large family, this home blends thoughtful design with timeless upgrades. Recent updates include a new roof (2023), attic HVAC serviced/replaced A coil (2024), basement HVAC replaced A Coil & condenser (2021), and a new water softener (2025). See the virtual tour attached to the listing! One-owner, custom home, thoughtfully built with added upgrades by the builder! One year Home warranty offered with acceptable offer.

7 Beds ⋅ 6 Baths

This property exudes luxury multigenerational living in Meadowbranch! • Main level bedroom + bath • 6500 sq ft • Wet bar in primary suite • 3-car garage • No HOA • Backing to trees, and more..... Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 7 bedroom/5.5 bath residence features a main-level bedroom and full bath—ideal for an in-law suite. Just off the kitchen, the covered back deck offers the perfect space for entertaining. Inside, you’ll find a kitchen that doesn’t compromise with Jenn-Air appliances, solid cherry cabinetry, and an oversized walk-in pantry, making cooking a joy. Hardwood and tile floors flow throughout the main level, while the lower-level recreation room boasts durable waterproof laminate flooring. The expansive primary suite offers a double-sided gas fireplace and a private wet bar/coffee bar with a sink—ideal for unwinding after a long day. The bedroom-level laundry room is fully equipped with cabinetry and a utility sink for added convenience. A 3-car side entry garage includes a half bath. Modern comforts include multiple furnaces & heat pumps, central vacuum & intercom system, front yard irrigation, an intercom system, and no costly monthly HOA dues. Whether you are seeking multi-generational living or space for a large family, this home blends thoughtful design with timeless upgrades. Recent updates include a new roof (2023), attic HVAC serviced/replaced A coil (2024), basement HVAC replaced A Coil & condenser (2021), and a new water softener (2025). See the virtual tour attached to the listing! One-owner, custom home, thoughtfully built with added upgrades by the builder! One year Home warranty offered with acceptable offer.

1020 Breckinridge Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Non Subscribing Office.

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