Winchester VA Real Estate & Homes for Sale

This handsome Colonial enjoys a rare spacious location in the heart of Winchester near Handley High School. Beautifully landscaped, it is the perfect setting for large covered porches and a substantial patio. Generously sized rooms feature hardwood throughout, a Main Floor ensuite Primary Bedroom, Gourmet Kitchen, four additional bedrooms plus multiple venues to enjoy life on a grand scale.

One level living and a nice flat yard in Winchester City with recent upgrades make this home a win-win. This 3 bed, 1.5 bath rancher boasts new windows, new HVAC and refinished hardwood floors. Located within walking distance of retails shops and restaurants and just a quick trip to medical services and all local major commuter routes will have you saying, "Location. Location. Location."

This comfortable Cape Cod is recently renovated and move-in ready. You'll enjoy refinished REAL hardwood floors and fresh paint throughout. With a primary bedroom and full bath, including tile shower and glass shower door on the main floor and 2 large bedrooms and a full bath on the second floor this floorplan is highly functional. A shady back patio is the perfect place to relax and the level yard is great for recreation. You'd never guess this home is within walking distance to retail shops and restaurants!

This classic home built in 1930 sits on Winchester's next up & coming street! Located within walking distance of Old Town, the property features a unique 24x24 garage & conditioned workshop built in 2020. Currently used as a print shop, the possibilities are endless with one wall of vintage glass allowing natural light to flow in. The building has a standing seam metal roof and allows for off street parking. The stucco/pebble dash & shake home itself has many substantial updates. Circa 2010, the heat was converted to electric heat pump with gas backup, all the plumbing was redone and the first floor was wired for modern 200 amp service. The standing seam metal roof and half round gutters were installed around 2005 and have decades of life left in them. The new owner may want to make some cosmetic improvements, but most of the heavy lifting has already been done! Covered front porch features tongue & groove floor and quaint vestibule greats visitors at the front door. Main floor offers large rooms, charming nook, window seat and wood floors. Fenced backyard oasis is a dream come true. Don't miss this opportunity to invest in one of Winchester's best kept secrets - East Piccadilly Street! Sale subject to seller finding home of choice or flexible rent back.

Don't miss this 3 bedroom, 1.5 bathroom interior townhouse in the city limits, perfectly poised to meet the needs of both investors and first-time buyers alike. Featuring luxury vinyl tile flooring throughout the main level; also on the upper level in the primary bedroom and full bath. The kitchen features an island with ample counter & cabinet space, plus stainless steel appliances. New backyard fencing installed in 2/2024. Located in a desirable area, this home offers easy access to shopping, dining, entertainment, and transportation options, ensuring that everything you need is just minutes away. Don't miss your chance to make it yours!

This four-bedroom, three-bath home in downtown Winchester is a lesson in how to make an old home contemporary and hip. A bold, handsome exterior greets you first, offering a preview for an attractive, refreshing interior design with neutrals and bold color choices, an open floor plan, and lots of natural light. The common area is anchored on one side by a brick fireplace and a handsome built-in on another. Configure how you like for relaxing and dining. The kitchen shines between the chic gray cabinets, a bold backsplash, the stainless farmhouse sink, and a Samsung Smart Fridge. An island adds more counter and storage space with a raised area for casual dining or working. Exit the kitchen into a space easily usable as a main floor ownerâs suiteâor perfect for a den, office, or reading nook. Big sliding glass doors bring in the light. Turn the corner into a hallway containing a full bath with a luxurious, state-of-the-art shower and wet spa, plus an exterior entry with cabinet storage (if not used as a bedroom, this could be a mudroom area). Heading upstairs, pass a whimsical stained-glass window to the second level, where three large bedrooms, a full bath, and laundry facilities await. A spiral staircase leads to a loft ideal as a bedroomâbut really anything such as recreation, lounging or officeâas it contains a bar with a sink, mini-fridge, and cabinets plus another full bath with one of those dreamy combination wet spa showers. Heading outside, a chic, hardscaped patio with plenty of room for seating, eating, and entertaining looks out over the lawn and garden in this backyard oasis, surrounded by fencing and leading to a gravel parking area containing a large shed. Thereâs already so much to love about this stylishly renovated home, but itâs also in a terrific location, close to the walking mall and all the places that make living downtown desirable.

"Best on Barr" - If you are looking for a beautifully kept mid-century modern home in a sought after neighborhood in the city to make your own, this is it! This 1961 brick split foyer home has been shown lots of love, but the mid-century charm remains intact! Beautiful solid oak floors throughout the main living area, a wood burning fireplace, subway tile in the bathrooms, and Frank Lloyd Wright light fixtures. The downstairs is completely finished and boasts a spacious family area with a beautiful wood burning stove. What a warm cozy environment for family movie nights or Super Bowl parties! The garage was converted into a large bedroom with a walk-in closet and doors that lead straight to the driveway if you have loved ones that need to have direct access. The laundry area has plenty of storage cabinets, a sink and a stackable washer and dryer. The well-manicured backyard and brick patio can be accessed from the French doors in the dining area or the family room on the lower level. This home is walkable to downtown, the Green Circle and the MSV trails. Make your showing appointment now, it won't last long!

Lovely brick town home with prime location. This end unit shows exceptionally well. Located right off of Valley Ave in a charming subdivision. Newer carpets upstairs . New vinyl plank flooring on the main level. Newer dishwater and disposal. 2 parking spots. Long term tenant has a lease that expires end of May. Would love to stay if possible.

ONE LEVEL LIVING AT IS FINEST! CUL-DE-SAC LOCATION, CLOSE TO THE HEART OF WINCHESTER, NEW SANDED AND POLYURETHANE (2 COATS), NEW CARPET IN ALL BEDROOMS, FRESHLY PAINTED THE WHOLE HOME, NEW PANTRY DOORS, IT'S A GEM! IMAGINE SITTING ON THE BACK DECK ENJOYING THE SPRING AND SUMMER NIGHTS, FULLY FENCED BACK YARD, GREAT FOR YOUR PETS, SHOPPING LESS THEN A MILE AWAY, CEILING FANS ALL THROUGH HOME, W/D IN FAMILY ROOM, HUGE FAMILY ROOM WITH GAS FIREPLACE, PLENTY OF BRIGHT SUNLIGHT, COME SEE FOR YOURSELF. TV IN BEDROOM 2 CONVEYS

NEW PRICE! Perched atop a quiet cul-de-sac in desirable Rolling Hills Estates, this stunning five bedroom home has space for all of your needs! The gourmet kitchen is a chef's dream. It offers a large island, granite countertops, extensive counterspace, upgraded cabinetry, updated light fixtures and a tile backsplash. The added space of the morning room extends the kitchen and provides a bright and open feeling. Coffee bar/butlers pantry lies between the kitchen and dining room. The split staircase is an attractive focal point upon entering the vaulted foyer. Wood flooring, crown molding, shadow box trim adorn the formal living and dining areas. Large family room with gas fireplace sits between the kitchen and office. Upstairs the luxurious primary suite offers sitting room, double closets, soaking tup, separate showers, and dual sinks. Two bedrooms are joined by a Jack and Jill bathroom, while two other bedrooms share a full hall bath. All floors have 9' ceilings. The walkout basement is ready for your finishing touches! It has rough plumbing for a bathroom as well as a sink for a wet bar. Incredible Trex deck offers outdoor entertaining space and back yard is fully fenced. Enjoy walks to Kernstown Battlefield and Creekside Shopping Center.

NEW CONSTRUCTION! This Upton II is well appointed, this home has stainless steel appliances, quartz countertop, upgraded cabinets in the kitchen and so much more. Where relaxed living meets friendly, historic charm with Lofts at Creekside located just 10 minutes away from Old Town Winchester and steps away from Creekside Station, the only place in Winchester where specialty shops and chic national retailers are right around the corner. Lofts at Creekside is conveniently located minutes from I-81 and Route 7, perfect for commuting. This amazing location has it all from city sophistication to mountainside relaxation. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

NEW CONSTRUCTION! This Upton II is well appointed, this home has stainless steel appliances, quartz countertop, upgraded cabinets in the kitchen and so much more. Where relaxed living meets friendly, historic charm with Lofts at Creekside located just 10 minutes away from Old Town Winchester and steps away from Creekside Station, the only place in Winchester where specialty shops and chic national retailers are right around the corner. Lofts at Creekside is conveniently located minutes from I-81 and Route 7, perfect for commuting. This amazing location has it all from city sophistication to mountainside relaxation. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

NEW CONSTRUCTION! This Upton II is well appointed, this home has stainless steel appliances, quartz countertop, upgraded cabinets in the kitchen and so much more. Where relaxed living meets friendly, historic charm with Lofts at Creekside located just 10 minutes away from Old Town Winchester and steps away from Creekside Station, the only place in Winchester where specialty shops and chic national retailers are right around the corner. Lofts at Creekside is conveniently located minutes from I-81 and Route 7, perfect for commuting. This amazing location has it all from city sophistication to mountainside relaxation. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

NEW CONSTRUCTION! This Upton II is well appointed, this home has stainless steel appliances, quartz countertop, upgraded cabinets in the kitchen and so much more. Where relaxed living meets friendly, historic charm with Lofts at Creekside located just 10 minutes away from Old Town Winchester and steps away from Creekside Station, the only place in Winchester where specialty shops and chic national retailers are right around the corner. Lofts at Creekside is conveniently located minutes from I-81 and Route 7, perfect for commuting. This amazing location has it all from city sophistication to mountainside relaxation. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

NEW CONSTRUCTION! This Upton II is well appointed, this home has stainless steel appliances, quartz countertop, upgraded cabinets in the kitchen and so much more. Where relaxed living meets friendly, historic charm with Lofts at Creekside located just 10 minutes away from Old Town Winchester and steps away from Creekside Station, the only place in Winchester where specialty shops and chic national retailers are right around the corner. Lofts at Creekside is conveniently located minutes from I-81 and Route 7, perfect for commuting. This amazing location has it all from city sophistication to mountainside relaxation. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

Location is Key!! This property is close to everything Winchester has to offer. Just minutes from Old Town Winchester Walking Mall, restaurants, shops, attractions, Jim Barnett Park, Shenandoah University, Daniel Morgan Middle School and Virginia Elementary. The home offers 4 bedrooms, 2 full bathrooms, unfinished basement, eat in kitchen, 3 season rear porch, large front porch, Oak hardwood floors downstairs and pine upstairs. New within the past 10 years: Architectural shingles, double pane vinyl windows, updated bathrooms, privacy fenced yard & walkway, natural gas furnace, freshly painted walls, refinished original hardwood floors, parking pad for 3 vehicles and a Radon mitigation system. Wooden shed with electricity located in the backyard. The backyard also has new privacy fencing and is the perfect spot for summertime entertaining.

Nestled within the serene confines of Rolling Hills Estates, this stunning home boasts five bedrooms and four bathrooms, offering spacious living arrangements including a main floor bedroom and full bathroom for added convenience. The open floorplan seamlessly integrates the gas fireplace, hardwood floors, plush carpet, and engineered wood flooring, creating an inviting atmosphere throughout. A finished basement provides additional living space, while outside, a composite deck overlooks the meticulously landscaped yard with enchanting tree-lined views, perfect for outdoor gatherings or peaceful relaxation. This residence harmoniously blends modern comforts with natural beauty, promising a lifestyle of comfort and tranquility.

Welcome to 316 Walker Street! Solidly built in the 1960's, the brick and bones of this beauty are unmatched in modern construction. The foyer greets visitors with newer engineered hardwood flooring and a mid-century iron railing on the stairs adds distinct character. The large living room offers a functional, wood burning fireplace along with custom built in shelves. Step into the formal dining room with bold but tasteful navy walls and dramatic light fixture. The updated kitchen features stainless steel appliances, a large island with butcher block top and two pantries. The newly rebuilt screened in porch is accessible from the kitchen and is capped with a classic tongue and groove ceiling. The study was once a main floor bedroom, has two closets and could be converted back to a bedroom if needed. There is also a full bathroom on the main level. Upstairs sits four freshly painted bedrooms with brand new LVP flooring. Primary bedroom has unique dressing area, ample closet space and newly remodeled bathroom. Hall bathroom upstairs has also been updated. Enormous basement family room adds even more living space. Ideally located in Whittier Acres, this home sits at the end of quiet street and the fenced yard backs to trees. It is within walking distance of Old Town Winchester, Whittier Park and the Museum of the Shenandoah Valley. It is also minutes from Winchester Medical Center, shopping, entertainment and more!

This home in the heart of historic Winchester could be yours! This beautifully renovated 1930s gem combines vintage charm with modern luxury. Featuring 3 bedrooms plus a dedicated office space as well as a finished loft! and 3 full baths. Stunning hardwood floors throughout, this home boasts a stylish kitchen with stainless steel appliances and granite countertops. Relax in the spacious living area or entertain in the private backyard. Tons of conditioned storage on the lower level as well as a spacious 2-car garage. Conveniently located near the library, shops, restaurants, and parks, with easy access to just about everything. Don't miss this opportunity to own a piece of Winchester's history! All major systems approximately 2 y.o., roof 10 y.o. Call today for a private showing. #WinchesterHome #HistoricRenovation #ModernLuxury Note: Home is not vacant; pictures reflect the 2022 renovation and living room has been painted.

Completely renovated and remodeled! Come and see this incredible home! Main level remodeled to create open concept living ** Brand new kitchen with stainless steel appliances ** Quartz counter tops ** Working island with room for bar stools White cabinets ** Cozy brick hearth fireplace in living room area ** New windows ** Hardwood floors refinished ** Primary suite includes large primary bath and laundry on main level ** Large secondary bedrooms ** New hall bath ** Lower level includes 2 more bedrooms and new full bath ** Large rec room with kitchenette ** Connections for lower level washer/dryer ** Perfect for multi-generational living ** Plus huge storage room ** New HVAC ** Exterior includes carport, separate shed and a concrete patio behind carport ** Beautiful Home!!

NEW CONSTRUCTION! This Upton II is well appointed, this home has stainless steel appliances, washer and dryer included, upgraded cabinets in the kitchen, quartz countertops and so much more. Where relaxed living meets friendly, historic charm with Lofts at Creekside located just 10 minutes away from Old Town Winchester and steps away from Creekside Station, the only place in Winchester where specialty shops and chic national retailers are right around the corner. Lofts at Creekside is conveniently located minutes from I-81 and Route 7, perfect for commuting. This amazing location has it all from city sophistication to mountainside relaxation. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

NEW CONSTRUCTION! This Upton II is well appointed, this home has stainless steel appliances, quartz countertop, upgraded cabinets in the kitchen and so much more. Where relaxed living meets friendly, historic charm with Lofts at Creekside located just 10 minutes away from Old Town Winchester and steps away from Creekside Station, the only place in Winchester where specialty shops and chic national retailers are right around the corner. Lofts at Creekside is conveniently located minutes from I-81 and Route 7, perfect for commuting. This amazing location has it all from city sophistication to mountainside relaxation. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

Are you ready to embark on your homeownership journey? Look no further than this delightful 2 bedroom, 1 bath townhome perfectly suited for those starting their financial home journey, this residence offers the ideal blend of comfort, convenience, and affordability. Currently occupied and requires a 24 hour notice for viewings, but put this on your schedule. Cozy Living Spaces: Step inside to discover a cozy and inviting interior designed for modern living. With two spacious bedrooms, there's plenty of room for you to personalize and make it your own. Functional Layout: Whether you're enjoying a quiet evening in or entertaining guests, the open layout ensures seamless flow between the living, dining, and kitchen areas, making it perfect for everyday living and hosting gatherings. Convenient Amenities: Say goodbye to the hassle of laundromats with your own in-unit washer and dryer. Plus, a dedicated parking spot ensures convenience for busy lifestyles. Affordable Investment: Why rent when you can invest in your future? This townhome offers an excellent opportunity for young buyers to build equity and establish roots in a thriving community. Don't miss out on this incredible opportunity to own a piece of paradise in town! Schedule your viewing today and take the first step towards making this charming townhome your new home sweet home. Contact us now! Financing of any kind is acceptable and offers are encouraged.

Great location, beautiful neighborhood with no HOA, and a downstairs master, this house has so much to offer. Walk into the beautiful foyer and enjoy the hardwood floors that run throughout the first level. You will find the formal dining room to your left with a pass through to the kitchen for easy entertaining. Walk into the living room complete with high ceilings, and a fireplace. Continue through the living room to the well laid out kitchen. Enjoy making a meal at the center island or enjoy a meal in the eat in area. Walk through the back door and enjoy a meal in the peace of your private backyard. Off the kitchen you will find a laundry for convenience. Don't miss the master bedroom suite on the first floor. This is one level living at its finest. Whether living with your kids or welcoming them home with grandkids, enjoy 3 bedrooms on the second floor. As you walk up the stairs you will find a loft area with built in bookshelves. This would make a wonderful play space or just a nice place to sit and read. The backyard provides a welcome retreat for enjoying the outdoors.