Winchester, VA Homes for Sale under $300,000

Welcome home to 208 Shenandoah Ave in Winchester, VA! This updated ranch home offers the coveted simplicity of easy, one-level living and is perfectly situated in a prime, convenient Winchester location. Featuring 3 bedrooms and 1 full bath, the interior is turn-key with newer flooring and fresh paint throughout. The living spaces are bright and inviting with lots of natural light, creating a

Dan Whitacre Colony Realty

Welcome home to this charming 4-bedroom, 1-bath colonial perfectly situated with walking distance from downtown Winchester. Warm hardwood floors flow throughout the home, complemented by a large covered front porch and a spacious rear deck—ideal for morning coffee or evening gatherings. Recent updates include a new water heater (2025), new water tank (2025), and an updated furnace and bath for

Laura White ERA Oakcrest Realty, Inc.

Adorable and fully renovated 2-bedroom, 1-bath bungalow just minutes from Winchester Medical Center! You’ll love the spacious open layout that connects the living room and kitchen, complete with brand-new stainless steel appliances and beautiful LVP flooring throughout. The large bedrooms offer plenty of space to relax, and the laundry/mudroom adds extra convenience. The bright bathroom features

Amy Emerson-Kerns Cambridge Premier Realty, LLC.

239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home convenient to shopping,schools and parks. A little TLC will go a long way "Come see the possibilities"

William Wertz Wildhawks Realty LLC

"A Slice Of Apple Pie" This 2-bedroom, 1 full bath ranch style home is ready for it's next owner! With modern updates the open style floorplan is perfect for everyday living. Beautiful kitchen with new quartz countertops, new cabinets and stainless-steel appliances. Updated bathroom with a new toilet, new vanity and tile surrounding the new tub/shower. Loft area with new carpet! Home has been

Matt Kilmer Samson Properties

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.

Welcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 full bath. Hardwood floors, no carpet! Attached carport. Brand new shed in the backyard. Backs to common area. Deck off the back of the home. Newer windows. New Roof. Large kitchen. Laundry room off the kitchen. This home is within the city limits of Winchester City School System. Within walking distance to school and

Linda DeFelice Samson Properties

Charming 3 bedroom, 1.5 bath colonial just blocks from downtown Winchester! Enjoy a covered front porch perfect for relaxing and a spacious rear deck for entertaining. Inside, you’ll find inviting spaces with newer windows throughout. Conveniently located near shopping, restaurants, entertainment, the local library, and Jim Barnett Park—this home offers both comfort and an unbeatable location!

Sheila Pack RE/MAX Roots

ONE LEVEL LIVING in a quiet and peaceful setting ! Enjoy the custom open floor plan joining the large country kitchen (with direct access to a full bath, laundry and entertaining deck) to the inviting living room featuring a brick fireplace with wood burning stove and bay window. In addition, there is a light filled family room with exterior access, two bedrooms and a second full bath located in

Wayne Wilson Thomas and Talbot Estate Properties, Inc.

Motivated sellers, Price Reduced!!! Need your Own Space? or you're looking to Downsize or Just Starting Out, Come Checkout this 1–2-bedroom 2 full bath home on 3 Levels Updated Kitchen with Stainless Steel Appliances, a Living room Dining room or Main level Bedroom with a Full bath attached., Washer & Dryer in the shed convey. 2nd Level has a Bedroom Full bathroom and a loft area. Theres a

Richard Kozlowski Long & Foster Real Estate, Inc.

*Investor Opportunity, current tenants have a lease until May of 2027* Welcome to your new home! This beautifully maintained 3 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half

Amber Jenkins Century 21 Redwood Realty

Penthouse condo in excellent condition and move in ready. The cathedral ceilings and skylights in the living room provide for a bright, cheerful space, while the gas fireplace provides a cozy feel. . Sliding glass doors to a charming balcony with some mountain views provide additional enjoyable space. The interior of the unit includes a dining area, kitchen with electric range, dishwasher,

Darcy Amburn Colony Realty

Welcome to your new home! This beautifully maintained 2 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half bath. Upstairs you will find two generously sized bedrooms with large

Amber Jenkins Century 21 Redwood Realty

Top-Floor Gem with Vaulted Ceilings & Modern Upgrades! Welcome home to this bright and airy 2-bedroom, 2-bath top-level condo that perfectly blends comfort, style, and convenience. Step inside and be greeted by soaring vaulted ceilings and abundant natural light streaming through multiple skylights, creating an inviting and open atmosphere.The spacious kitchen is a chef’s delight, featuring sleek

Becky Green Samson Properties

Move in ready 3 bedroom 2 full baths home nestled in the woods that comes with additional lots(2) that can be built on or kept as a privacy buffer and equates to an acre or so. House features hardwood flooring and lots of knotty pine for that rustic look. Living room features a wood burning fireplace that is capable of heating the entire house and there is plenty of free down wood on the lot

James Amick RE/MAX Roots

Coming April 2026. Blue Ocean Modulars introduces The Laurel, a new modular home to be located at Lots 10 & 11, 600 block, Opossum Trail in Wilde Acres. Nestled against a forested backdrop and built with high-quality workmanship, this residence showcases modern modular construction designed for durability, comfort, and long-term value. The home features Insul-Stud framing, a cutting-edge system

Rebecca McTavish Long & Foster Real Estate, Inc.

CLASSIC CHARM MEETS CONTEMPORARY COMFORT IN THIS FANTASTIC DUPLEX UNIT! This charming Winchester duplex unit seamlessly blends timeless character with modern conveniences, offering the perfect balance of historic flair and contemporary living. Nestled just minutes from the vibrant heart of downtown Winchester, this inviting property combines an unbeatable location with a thoughtfully-updated

Kristin Crosby Samson Properties

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.