Winchester, VA Homes for Sale under $300,000

Adorable ranch home with great potential - TLC needed. 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. Selling as-is. Inspections for informational purposes only. The home is located downtown within close proximity to shopping, restaurants, Jim Barnett Park, and

Renee Waymire Samson Properties

Welcome to 115 Hickory Lane, conveniently located just outside the Winchester city limits, this charming 2-bedroom, 1-bath rancher offers the perfect blend of convenience, comfort, and value. This home features a cozy yet surprisingly spacious floor plan designed for easy everyday living. Enjoy the added potential of an unfinished basement, a great backyard perfect for relaxing or entertaining,

Tiffany Hunter ERA Oakcrest Realty, Inc.

Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large windows that let in plenty

Heloisa Amar Samson Properties

Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or den. Upstairs you will find three bedrooms, full bathroom and

Amy Capitano MarketPlace REALTY

Will Walraven Realty One Group Key Properties

Welcome to this charming ranch-style home situated on a spacious .44-acre corner lot in the desirable Shawneeland community. Thoughtfully updated and well maintained, this home offers comfort, functionality, and modern touches throughout. The kitchen has been enhanced with a newly added pantry (2026) making everyday living and entertaining effortless. The primary bedroom features French doors

Lindsey Gomes Real Broker, LLC

Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of

Jodi Costello ERA Oakcrest Realty, Inc.

Nestled in the charming Brookland Heights community, this delightful Colonial townhouse offers a perfect blend of comfort and style. Built in 1989, this home features a warm and inviting atmosphere, ideal for creating lasting memories. Step inside to discover a cozy interior that boasts a thoughtfully designed kitchen with ample table space, perfect for casual dining or entertaining friends. The

Rebecca Sims Century 21 Redwood Realty

Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painted with new luxury vinyl planking throughout the entire house. Brand new bathroom with tub /shower. Open floor plan with bedrooms on each end of the house for privacy. 2 sheds that convey to store whatever your heart desires. Come out and and enjoy all the open space! Go fishing ,play on the playground, kick

Jacquelyn Rizzari MarketPlace REALTY

APPROVED SHORT SALE!!!!! This diamond in the rough has solid bones and plenty of potential for the right buyer. The HVAC system is only two years old, the water heater is brand new, and both full bathrooms have already been updated. The home could use some fresh paint, and the dishwasher is currently not working, but the major systems are in great shape—making this an excellent opportunity for a

Jamie Cook Treck Realty LLC

2 Bed, 2 bath condominium. New appliances, including water heater and heat pump. Gas fireplace, open concept with separate dining room. Patio/ porch with french doors and skylights in living room allow tons of natural light. Primary suite includes walk-in closet. Conveniently located off rt 7 and 81.

Vicki Broy RE/MAX Roots

4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable.Sold As Is With

Tracy Link Coldwell Banker Premier

Nestled in a peaceful country setting just minutes from Winchester, this property offers an incredible opportunity to enjoy scenic mountain views and beautiful surrounding pasture land on a picturesque half-acre lot. The setting is truly the star here, with open views in the front and mountains stretching across the backdrop. Conveniently located with easy access to shopping, dining, and commuter

Phyllis Guthrie Keller Williams Realty

Nestled in the serene Shawneeland community, this charming ranch-style home offers a perfect blend of comfort and tranquility. Set on a generous 1.92-acre lot, the property features a gently sloping landscape adorned with mature trees, creating a peaceful retreat from the hustle and bustle of everyday life. This 3-bedroom, 1-bathroom home invites you to unwind and make lasting memories. The

Steve DuBrueler Coldwell Banker Premier

Thoughtfully designed for comfortable everyday living, this home offers a warm and inviting feel from the moment you step inside. LVP flooring throughout adds both style and durability, while cathedral ceilings create an open, airy atmosphere in the main living spaces. The kitchen is equipped with seamless appliances for a clean, modern look, and the layout offers flexibility for both daily

Sarah Reynolds Keller Williams Realty

Fully Renovated 2026 | Turnkey 2BR/2BA Condo in Park Place Welcome to 136-8 Brookland Ct—where style, comfort, and convenience come together. This stunning second-floor condo has been completely renovated in 2026, offering a like-new feel without the wait! Step inside to discover all-new flooring, appliances, lighting, fixtures, vanities, doors, and countertops—every detail thoughtfully updated

Amy Longerbeam RE/MAX Roots

This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two

Marisa Varley ERA Oakcrest Realty, Inc.

Welcome to this well-maintained and move-in ready second-floor condo offering comfortable, easy living in a convenient Winchester location. This two-bedroom, two full bath unit features a bright primary suite with windows on two sides, filling the space with natural light. The primary bedroom also includes a walk-in closet and a private bath with a shower. The living area opens to a covered

Katie Landi Jordan Samson Properties

This wonderful cape cod is so charming with its covered, front porch, and it's located just outside Winchester city limits, yet before you get to the Sunnyside shopping area. It's tucked away in a community away from the hustle and bustle of town, and yet easy access to commuter routes. Remodeled in 2023, and then further improved. Recent upgrades include a new metal roof, vapor barrier, new

Natalie Langford ERA Oakcrest Realty, Inc.