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.
Welcome to this beautifully maintained home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers 3–4 bedroom options, giving you the flexibility to create a home office, playroom, guest space, or additional bedroom to suit your needs. Enjoy the convenience of two full bathrooms, including one privately located off the primary bedroom, while the second is ideally situated off the hallway near the additional bedroom. Upstairs, the full walk-up attic provides an incredible opportunity—easily transform this expansive space into a private third bedroom suite with room for a sitting area, studio, or retreat. ? Highlights You’ll Love: Flexible 3–4 bedroom layout Full walk-up attic with expansion potential Primary bedroom with private bath Eat-in kitchen + formal dining space Charming character throughout This home blends timeless charm with endless possibilities, making it perfect for buyers looking to personalize and grow into their space.
Welcome to this one-of-a-kind property offering a unique and inviting layout designed with a seamless flow from front to back, filled with natural light throughout. Start your mornings on the rear patio enjoying peaceful sunrise views, and unwind in the evenings on the welcoming front porch with beautiful sunsets — the best of both worlds right at home. This home has been thoughtfully updated for peace of mind, featuring a brand-new hot water heater and dishwasher (2026), new HVAC system (2025), and new refrigerator, washer, and dryer (2024). The roof was replaced in 2019, offering added confidence for years to come. Located just a short walk to Winchester's Walking Mall and historic downtown, you’ll love being close to restaurants, shops, the Museum of the Shenandoah Valley (MSV), entertainment, and all of the local Apple Blossom Festival events. Don’t miss your opportunity to enjoy a truly unique home in an unbeatable location!
Unlock the Potential! 3BR/2BA Fixer-Upper in Winchester/Frederick County. Nestled in a quiet Cul De Sac in Frederick County, this 3-bedroom, 2-bath home is bursting with potential and ready for a visionary buyer to bring it back to life. Whether you're looking to renovate and resell or transform this into a charming personal residence, the canvas is yours to create something special. Convenient location with quick access to Route 37, I-81, shopping, and historic downtown Winchester.
Timeless charm meets thoughtful updates in this beautifully maintained all-brick 1958 home, offering effortless one-level living with a warm retro vibe. Freshly painted throughout and enhanced with new quartz countertops, classic subway tile backsplash, updated sink and faucet, and stylish new lighting, this home blends character with modern comfort. The main level is inviting and functional, while the fully finished, light-filled lower level expands your living options with a complete second kitchen, additional bedroom, full bath, and generous living space—ideal for guests, multi-generational living, or potential rental use. A sunroom overlooking the garden offers a peaceful retreat year-round, opening to a beautifully landscaped backyard perfect for relaxing or entertaining. Located just a short stroll to Handley High School and vibrant downtown Winchester, this home offers the best of convenience and community in a truly special setting. Classic, versatile, and full of charm—this is a home that works beautifully for today’s lifestyle while honoring its mid-century roots.
Welcome to this well-maintained one-level rancher tucked away in a quiet cul-de-sac. This home offers easy, comfortable living with a warm and inviting feel throughout. Hardwood floors run through much of the home, complemented by LVP in the living and dining areas. The living room features a cozy fireplace and flows into the dining area and kitchen, where you’ll find stainless steel appliances, tile flooring, and an updated backsplash. Both bathrooms feature beautiful tile finishes, adding to the home’s overall charm. Step outside to a fully fenced backyard complete with a spacious Trex deck and patio, perfect for morning coffee, evenings by the grill, or hosting. Two storage sheds provide plenty of room for tools, hobbies, or extra storage. Paid-off solar panels offer energy efficiency and long-term savings. Conveniently located with quick access to Route 81, downtown, and the Apple Blossom Mall. Enjoy the ease of one-level living in a comfortable and convenient setting.
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.
Timeless soul with modern spirit. Step into a piece of Winchester history, reimagined for the way you live today. From the iconic front porch—perfect for your morning coffee or evening wind-down—to the private, fenced-in backyard, this home is designed for seamless indoor-outdoor living. Renovated top to bottom with classic features such as crown moulding, thick wood banisters, and columns combine with the beautiful neutral LVP flooring creates an open flow in a timeless traditional floorplan, perfect for everyday living and entertaining. The kitchen features all new bright white cabinets and quartz counters, perfectly set with classic stainless steel appliances. Upstairs you'll find four full bedrooms with new carpet and two beautifully renovated bathrooms. Downstairs, the story continues with a mostly finished basement ready for your home gym, theater, family room, or creative studio. Additional storage and laundry are found downstairs. Located just minutes from the vibrant pulse of downtown Winchester, you get the quiet of an established neighborhood with walking distance to dining and shopping at your doorstep.
Sold "As-IS" Nice investment or starter property. Needs a little updating. Hardwoods throughout upstairs and living room downstairs. This price includes 525 Monticello lot. Tax ID #330-02-19. If any questions call listing agent. Agent related to seller.
Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available! ***OFFERING UP TO $12K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level interior unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height. The first level includes a private finished recreation room and possible 4th bedroom with its own full bath and walk in shower, perfect for guests or a home office. Laundry hookups are conveniently located on the third level near the bedrooms. Step outside to a 10X14 maintenance free deck, ideal for relaxing or entertaining. Upgrades throughout make this home truly shine. Come see it for yourself.
*** ALL OFFERS DUE BY 8PM SUNDAY MARCH 22nd *** Tucked into one of Winchester’s most convenient locations with NO HOA, this 4 Bedroom, 2 Bath home offers the space you need with the setting you’ve been looking for. From the moment you arrive, the classic brick front and welcoming curb appeal set the tone for what’s inside. Step through the door and you’ll find a layout designed for real life with multiple living areas, flexible spaces for gathering or working from home, and room for everyone to spread out comfortably. Natural light fills the home, creating a warm, inviting atmosphere throughout. But what truly sets this home apart is what’s behind it. Backing directly to Friendship Park Pavilion, your backyard becomes an extension of open green space, perfect for morning coffee, evening walks, or simply enjoying the peace and privacy of having no rear neighbors. It’s a rare blend of convenience and calm, just minutes from the energy of Old Town Winchester, Routes 7 and 81, shopping, schools and so much more. Whether you’re hosting, relaxing, or putting your own personal touch on the space over time, this home offers the kind of flexibility and setting that’s hard to find and easy to fall in love with. SINCE 2020: NEW KITCHEN, ROOF, WASHER & DRYER, HVAC, FRESH PAINT, FAUCETS, LIGHT FIXTURES, FRESHLY LANDSCAPED, ELECTRIC PANEL
Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location. This home features 3 bedrooms and 2 full bathrooms, with all bedrooms located on the upper level. At the top of the stairs you’ll find a spacious primary bedroom filled with natural light, creating a bright and inviting retreat. Large windows throughout the home allow sunlight to fill the living spaces, giving the home an airy feel. It also has alley access allowing for off-street parking. The living room offers generous space for relaxing or entertaining, while the kitchen provides a functional layout for everyday cooking. A finished attic space with high ceilings and windows on three sides adds additional flexibility for a home office, hobby space, or reading area. This home has charm of construction with tall ceilings and pocket doors. The walk-out unfinished basement with backyard access provides excellent storage. Outside, the backyard receives great sun exposure and includes a new storage shed for additional convenience. Recent updates include a brand-new roof; March 2026. This includes brand new shingles and metal roofing. Located in a quiet, tree-lined neighborhood with wide sidewalks, this home is just two blocks from Handley Regional Library and within walking distance to shops, dining, and entertainment at the Old Town Winchester Walking Mall. Nearby dining includes Pizzoco Pizza Parlor just around the corner. Enjoy a convenient in-town location close to parks, local amenities, and downtown attractions while still tucked within a peaceful residential setting. Home was once two apartments thus third bedroom is open and owner liked it like that. It was a form living area for upper apt. Home sold as-is.
This 1963 brick ranch is conveniently located off Pleasant Valley Road in Eastview Subdivision and has been the home to one family. Beautiful hardwood floors throughout the main level, and two fireplaces, one on the main level and one in the finished recreation room on the lower level. Most of the windows throughout the home have also been replaced. Oversized two car garage. Roof was replaced in 2023, new air conditioning unit replaced in 2025, and gas boiler installed in 2010. The adjoining lot w/ garage is being sold separately. (Address of adjoining lot being sold separately is 816 Allen Drive.) Home is within walking distance to Daniel Morgan Middle School and Jim Barnett Park. Home being sold "AS-IS".
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.
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 newer HVAC systems (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.
Major Price Reduction! Welcome to this beautifully renovated 2-bedroom, 1-bath ranch-style home nestled in the peaceful, private community of Wild Acres. Surrounded by trees, this cozy 960 sq ft retreat offers the perfect blend of modern updates and natural charm. Inside, you’ll find a bright, refreshed interior with thoughtful updates throughout. Major improvements—including a new well, septic system, and HVAC—offer added value and peace of mind. The open living space flows nicely into the kitchen, creating a comfortable layout for everyday living or entertaining. Step outside to enjoy the charming back deck just off the bedroom—perfect for morning coffee or unwinding in the quiet of nature. Whether you're searching for a full-time home, weekend escape, or investment opportunity, this property offers a relaxed lifestyle in a scenic setting. Additional notes: The property is approved for a one-bedroom septic system, though it is currently configured as two rooms. Some foundation improvements have already been completed, including drainage installation, sealing, and partial block replacement. The home is priced accordingly and being sold as-is, presenting a great opportunity for the next owner to make it their own.
END UNIT Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available! ***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height. The first level includes a private finished recreation room and possible 4th bedroom with its own full bath and walk in shower, perfect for guests or a home office. Laundry hookups are conveniently located on the third level near the bedrooms. Step outside to a 10X14 maintenance free deck, ideal for relaxing or entertaining. Upgrades throughout make this home truly shine. Come see it for yourself.
END UNIT Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available! ***OFFERING UP TO $10K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height, range hood, and wall oven. The first level includes a private finished recreation room and possible 4th bedroom with its own full bath and walk in shower, perfect for guests or a home office. Laundry hookups are conveniently located on the third level near the bedrooms. Step outside to a 10X14 maintenance free deck, ideal for relaxing or entertaining. Upgrades throughout make this home truly shine. Come see it for yourself.
Beautiful, just like brand new, 3 bedroom 2.5 bath end unit townhome located in The Lofts at Creekside! Walking distance to local restaurants and shopping here in Creekside. Home features large kitchen island, stainless steel appliances, and luxury vinyl plank flooring, private balcony, surrounded by open floor plan which provides for great entertainment. Nice upgrades all throughout the house! Come see this one for yourself!
Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to an extended stone patio, plus enjoy the convenience of a 1-car garage for storage. Recent updates include a new HVAC (2024) and a new roof (2025). Low-maintenance living includes lawn care and snow removal, allowing more time to enjoy the community’s clubhouse, exercise room, game room, and scenic walking paths. Conveniently located near shopping, dining, and healthcare, Winchester Medical Center and close to local attractions, including performances at Shenandoah University Theatre, exhibits at the Shenandoah Valley Discovery Museum, and the galleries at the Museum of the Shenandoah Valley. A wonderful blend of comfort, convenience, and active 55+ community living in the heart of Winchester, Virginia. More photos coming soon!
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 windows in the house (besides the middle front center window) will be replaced with vinyl windows. The back of the house will have new vinyl siding put on and 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
Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main level includes a spacious primary suite with a walk-in closet and beautifully renovated bathroom showcasing a tiled shower with glass doors. An additional generously sized bedroom and full bath complete are also on the first floor. There is also a mud room/laundry area that has brand new flooring and leads out to the backyard. Upstairs you’ll find two more bedrooms plus access to a large attic , providing abundant storage space. The finished basement offers incredible flexibility — ideal for an in-law suite — complete with a full kitchen, spacious living area, two bedrooms, and a full bathroom. Outside, enjoy a long driveway with ample parking, two detached garages, and a sprawling flat yard designed for entertaining. The in-ground pool makes summer living even better!
Welcome to this beautifully-updated brick rancher, a masterclass in blending timeless character with high-end, modern sophistication. From the moment you arrive, the covered front porch and classic silhouette command attention, offering undeniable curb appeal in one of Winchester’s most sought-after locations. Step inside to find a main level bathed in natural light, showcasing gleaming hardwood floors, designer light fixtures, and a fresh, polished aesthetic throughout. The heart of the home is the chef-inspired kitchen, a true showstopper featuring sleek cabinetry in a modern, rich navy, premium upgraded countertops, a chic tile backsplash, and new stainless steel appliances. Three spacious bedrooms—each fitted with new ceiling fans—occupy the main floor, including a private primary retreat with a stylishly renovated half-bath. Beyond the main level, the home offers incredible additional square footage in the finished basement, which has been refreshed with new flooring and paint. This level is anchored by a massive brick wood-burning fireplace, creating an inviting, high-impact focal point for the spacious recreation room—the ultimate backdrop for cozy movie nights, relaxing weekends, and comfortable everyday living. The lower level also features an updated second full bathroom and ample unfinished space for storage and laundry. Outside, the lush, level lawn provides a private oasis for outdoor living, complete with a new dedicated storage shed and an exclusive driveway for seamless off-street parking. Ideally positioned for an effortless lifestyle, this home is just minutes from the Winchester Medical Center and major commuting routes. Beautifully finished, move-in ready, and perfectly located—this is the exceptional Winchester home you have been waiting for.
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. Whether enjoying mint julips on a summer evening, entertaining guests, or impressing clients, fear not, 217 W. Boscawen has arrived! Professional Photos Coming 3.20.26. Asking $1.2M.
Welcome home to this spacious, light filled four bedroom, two and a half bath home in the Westridge subdivision. The traditional main level floor plan offers the perfect separation of spaces which include a formal dining room or potential home office/den, a kitchen that opens into a living area perfect for a casual breakfast table and a cozy sofa in front of the fireplace and a large, more formal living area for relaxation, family and guests. The upper level of the home offers a primary bedroom/bathroom and two separate bedrooms with a shared bathroom. The lower level bedroom which could also be a home office or exercise room has an interior and exterior entrance. The remaining unfinished basement could also be used for additional recreational space, workout area and additional storage. The backyard is perfect for entertaining. Got a green thumb? Garden plots are ready for you to start planting! Recent improvements include a new rear deck and a freshly painted two car garage door. Primary bedroom furniture can convey at no value to buyers. Minutes to downtown Winchester, this home is ready for the next owner. Hurry, this home won't last!
Winchester is located in Virginia. Winchester, Virginia 22601has a population of 28,194. Winchester 22601 is more family-centric than the surrounding county with 28.16% of the households containing married families with children. The county average for households married with children is 26.15%.
The median household income in Winchester, Virginia 22601 is $61,321. The median household income for the surrounding county is $61,321 compared to the national median of $69,021. The median age of people living in Winchester 22601 is 36.6 years.
The average high temperature in July is 85.7 degrees, with an average low temperature in January of 21.3 degrees. The average rainfall is approximately 38.3 inches per year, with 21.9 inches of snow per year.
