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$285,000
4 Beds ⋅ 2 Baths ⋅ VAWI2010306 MLS ⋅ CLOSED Status
Priced well below assessed value and sold strictly AS IS — this is the deal investors and renovation buyers have been searching for. This 4-bedroom, 1.5-bath home sits on a generous corner lot in an established Winchester neighborhood, just minutes from historic Old Town, the walking mall, and Shenandoah University. Original hardwood floors hint at the character waiting to be restored, and a flat, usable lot with an outbuilding adds serious versatility — storage, workshop, or a play house. Whether you're flipping, holding as a rental, or building sweat equity, the location and lot size alone make this one a standout. Cash or renovation financing preferred. Bring your contractor — opportunities like this don't come twice.

301 Shawnee Avenue, Winchester
$299,000
2 Beds ⋅ 1 Baths ⋅ VAWI2009102 MLS ⋅ CLOSED Status
Beautiful and affordable Gem in the middle of Winchester City. Private, fully fenced yard with extra parking and storage. Updated A/C and two year old roof.

525 E Cork Street, Winchester
$357,000
3 Beds ⋅ 3 Baths ⋅ VAWI2007344 MLS ⋅ CLOSED Status
WELCOME to this charming, conveniently-located, two-level brick rambler home!! This spacious, well-maintained property has comfortable living spaces inside and out. This cozy home features two finished levels with hardwood floors on the main level and flooring on the basement level as well. The main level features three bedrooms and a nice-sized kitchen. Your outdoor retreat awaits just beyond the back door. Enjoy a large, splendid deck and pleasant backyard area, where you will find abundant outdoor space ideal for both entertaining guests or unwinding in tranquility. There is also a practical storage shed in the back that provides excellent outdoor storage. The lower basement level also comes with newer PVC flooring and has a spacious family/recreation room, a bonus room and is also equipped with a full bathroom for extra convenience. The Laundry room is also conveniently located in the lower level. The driveway adds to your convenience and comfort, providing ample space for parking along with the rear alley access that provides additional parking space in the back of the home. The location is a commuters delight, perfectly situated close to major roads and highways and within short distance distance to public transportation. Close to restaurants and shopping. Take advantage of this wonderful opportunity to own this wonderful home and prime location!

205 Parkway Street, Winchester
$512,552
3 Beds ⋅ 3 Baths ⋅ VAWI2007562 MLS ⋅ CLOSED Status
Picturesque on Parkway - If you’ve been looking for the beauty and bones of an older home that has been updated tastefully, respecting the original charm, look no further. As you step into this immaculate 1940 colonial, you will be greeted with beautiful hardwood floors running throughout the main living area. The living room boasts built in bookshelves that run to the ceiling and tall windows to flood the room with natural light. The kitchen was updated by someone who loves to cook with granite counter tops, gas range, pot filling faucet, exhaust hood, and a double door refrigerator. The dining room is spacious and leads into a cozy sitting room where you could enjoy a cocktail after dinner or your morning coffee. The large high-end composite deck added in 2020 creates a whole outdoor living experience with plenty of room for dining and relaxing, overlooking a fenced in backyard. The fully finished basement is a great place for entertainment or could be used as an in-law suite, as it has a full bathroom with tub and shower, a wet bar, and a separate entrance. The bathroom and laundry room both have ceramic floors. The washer and dryer are brand new high end machines. All renovations took place in 2015, including the roof and all major systems in the home. Located in Winchester City, walkable to Old Town restaurants and shopping and close access to the Green Circle Trail. This move- in ready home was lovingly maintained, thoughtfully updated, and is waiting for its new family!

256 Parkway Street, Winchester
$275,000
3 Beds ⋅ 2 Baths ⋅ VAWI2007590 MLS ⋅ CLOSED Status
INVESTORS SPECIAL Tucked away on a quiet cul-de-sac, this 3-bedroom, 1.5-bath colonial offers 1,152 sq ft of comfortable living space with a flat yard and rear deck—perfect for outdoor gatherings or quiet evenings at home. Just minutes from the charm and conveniences of Old Town Winchester, with easy access to dining, shopping, and commuter routes. A solid choice for investors seeking rental potential or for first-time buyers looking for an affordable entry point into homeownership. This home offers dependable value in a well-established neighborhood.

353 Shawnee Avenue, Winchester
$370,000
4 Beds ⋅ 2 Baths ⋅ VAWI2006634 MLS ⋅ CLOSED Status
This charming single-family home is in a great neighborhood in downtown Winchester, and recent upgrades make this a hot property. The split-level design offers a modern versatility—and the home feels airy with fresh, neutral wall colors and lots of crisp white features offset by hardwood floors. The upstairs leads directly to a large living room benefitting from lots of natural light, plus three sizeable bedrooms and one full bath. The lower level opens to the kitchen and dining rooms, and another bedroom and full bath are down a short hall. The kitchen shines with its ivory cabinets, chic matching counters, new stainless appliances, and even a wine cooler. The adjacent dining area has ample room for seating and extra furniture. Laundry facilities are also on this level, along with access to the backyard in two places. The backyard is huge, offering plenty of room to play, relax, garden, and more. There’s also a storage shed—and alley parking dedicated for your vehicles. With a new roof, updated electrical, flooring, handsome aluminum siding, and so much more, this home feels new and is move-in ready!

336 Parkway Street, Winchester
$269,000
2 Beds ⋅ 1 Baths ⋅ VAWI2006238 MLS ⋅ CLOSED Status
Welcome to this delightful 2-bedroom, 1-bathroom ranch home, ideally situated in the heart of Winchester. This older home has been lovingly maintained and features beautiful hardwood floors throughout. The spacious layout includes a separate dining room, a cozy kitchen, and a comfortable living room, perfect for everyday living. Step outside to enjoy the covered back porch or relax on the deck, which boasts durable Trex decking. The property also offers a concrete driveway with a convenient storage building, providing ample space for your outdoor needs. While the home has received many updates over the years, it still offers the opportunity to add your personal touch and make it truly your own. Don’t miss the chance to own this charming home in a prime location!

301 Shenandoah Avenue, Winchester
$329,000
3 Beds ⋅ 2 Baths ⋅ VAWI2005996 MLS ⋅ CLOSED Status
COMING SOON! Additional Photos will be available soon. Welcome to this beautifully updated 3-bedroom, 2-bathroom home, perfectly situated just a short stroll from the vibrant downtown area, offering an array of shops, restaurants, and entertainment options. Additionally, the scenic Jim Barnett Park is within walking distance, providing ample recreational activities. Step inside to discover a spacious interior freshly painted in a soothing palette, complemented by stylish new light fixtures and elegant vinyl plank flooring throughout. The updated kitchen has brand-new quartz countertops and kitchen cabinets. The bathrooms have been upgraded with new vanities, lights, mirror, and faucets. Practical upgrades include a new roof (2024) new HVAC system (2024). Off street parking in the rear. The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent. **AGENT RELATED TO SELLER**

321 Shenandoah Avenue, Winchester
$379,000
3 Beds ⋅ 2 Baths ⋅ VAWI2006004 MLS ⋅ CLOSED Status
This charming fully renovated cottage is adorable. Minutes to central downtown Winchester. Total renovation by skilled craftsmen completed in late May 2024. Everything new. Total new kitchen - granite counters, stainless steel whirlpool appliances, new cabinets, sink and fixtures. . All newly refinished original wood floors throughout. New double pane insulated windows and storm doors. New light fixtures, 2 charming original 1948 light fixtures were taken down and refinished then reinstalled - lots of care to this lovely old home. The newly built sun room on the back of the house adds additional living space. The upstairs full bath has original clawfoot tub which has been refinished and looks like new. The addition of a second full bath on the first floor is a real plus. The historic walking mall just minutes away as well as Shenandoah University and the Hospital. Fantastic location. A must see. Offer deadline Friday, July 26 5:00pm.

205 Shawnee Avenue, Winchester
$286,000
4 Beds ⋅ 2 Baths ⋅ VAWI2005844 MLS ⋅ CLOSED Status
SO MUCH POTENTIAL! Looking for a project? What are you waiting for? Roll up your sleeves and get to work bringing this spacious 1960s split foyer into the 21st century. This 4-bedroom house in Winchester is an excellent and affordable choice for contractors, flippers, those who are handy or a landlord adding to rental inventory. On a wide street. Near city park, shopping and services. Convenient to downtown and commuter routes 7, 50 and I-81. Two levels total approximately 1,620 square feet. This home features a large lower-level kitchen sometimes found in early split foyers and a main-floor living room above. Hardwood under carpet on the main level. Walkout basement and level back yard with a public alley at the rear. One parking spot behind the house. Price is based on a 2023 appraisal. Real estate and personal property are sold as-is. Dishwasher does not work. Downstairs bathroom is not functional. Cash, bank portfolio or conventional loans are best.

336 Parkway Street, Winchester
$350,000
5 Beds ⋅ 2 Baths ⋅ VAWI2005908 MLS ⋅ CLOSED Status
Discover the charm of downtown living at 213 Parkway Street! This spacious 5-bedroom, 2-bath home is perfectly situated to enjoy all the vibrant amenities Winchester has to offer. Step inside to find stunning hardwood floors that flow throughout, infusing warmth and character into every room. The generous living spaces and bedrooms provide plenty of room for relaxation and entertaining. Outside, the fenced-in backyard offers a private retreat, complete with off-street parking accessible through the rear alley for added convenience. A large storage shed provides ample space for all your storage needs. While the home requires some TLC, it brims with charm and potential, inviting you to make it your own. Don't miss this opportunity to own a delightful home in a prime downtown location. Schedule a showing today and imagine the possibilities!

213 Parkway Street, Winchester
$450,000
5 Beds ⋅ 3 Baths ⋅ VAWI2005402 MLS ⋅ CLOSED Status
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!!

365 Shenandoah Avenue, Winchester
$375,000
4 Beds ⋅ 3 Baths ⋅ VAWI2004328 MLS ⋅ CLOSED Status
NEW PRICE! Where else can you find a single family home with 4 bedrooms, 3 bathrooms, 2 car garage, off street parking, fenced backyard AND be walking distance from Old Town Winchester for under $400,000? Sitting on lovely, wide Parkway Street, this home well located home was renovated in 2015. Outside features include a deck, patio/basketball court, wood fence, mature trees and a private backyard - are rare find downtown! The inside of the home is so much larger than it appears offering a spacious living room, sun room, finished family room/rec room in basement as well as ample storage. There are gorgeous wood floors throughout main level and the home offers two brick fireplaces. Oversized garage opens to backyard as well as front. Finished basement square footage approximate. Seller open to a closing cost credit!

352 Parkway Street, Winchester