Winchester, VA Homes for Sale under $300,000

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.

Affordable and move-in ready ranch-style home on a little more than a half acre. The mature trees, abundant wildlife, and quiet location make this a serene location. Featuring 2 bedrooms and 1 full bath, this home was freshly painted (Nov 2025) and underwent a major renovation in 2017 (roof, HVAC, water heater, floors, fixtures, and more). Enjoy the comfort of 1-level living with plenty of

Eric Kronenwetter RE/MAX Roots

******Price Reduction******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

William Wertz Wildhawks Realty LLC

Great two bedroom ,two bath condo. Very convenient first floor entrance. Zero steps. Great commuter location off Rt. 7

John Scully Colony Realty

*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

Turn Key + Convenience + Outstanding Value! Perfect 2/1 open floorplan single family home on Senseny Road with HUGE backyard! Hardwood floors, newer roof, updated throughout! Best value in Frederick County! Meticulous condition and will go fast! Only $269K!

Gillian Greenfield Coldwell Banker Premier

Tudor Square Townhouse. Great location to Interstate 81, shopping and to Winchester Downtown. Two large bedrooms, 1 I/2 baths offers Large Kitchen Eat-in and dining with Stainless Steel Appliances and Luxury Vinyl Flooring. Large Living Room with Bay Window and Hardwood Floors. Half Bath. Upper level offers Hardwood Floors and Full Bath. Gas Forced Air Heat and Central A/C.Washer and Dryer.

George Johnson Jim Barb 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

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

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

This is a two level house 3 bedrooms 2 full bathrooms good for fist time buyers or investment property, ready to move in , house is sold as is. Thank you for showing.

Virgilio & Maria Vasquez The Vasquez Group LLC

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.

Welcome home to 124 Arrowhead Tr., Winchester, VA, a charming retreat nestled on 1.25 acres in the sought-after Shawnee Land community. This inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort, character, and space to enjoy the outdoors.Step inside to an open-concept living and kitchen area designed for both everyday living and entertaining. The living room is filled with

Lindsay Barnhart NextHome Realty Select

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

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

Great opportunity to own this 2-bed, 1-bath Winchester City charmer that sits just minutes from Shenandoah University and the Old Town walking mall. Main level living with a bright comfortable living area, an eat-in kitchen home that includes a bonus room providing flexible space for an office, playroom, fitness area, or guest room, central air and the convenience of an in-home washer & dryer

Janet Flaherty Keller Williams Realty

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

Top-Floor Gem with Vaulted Ceilings, Modern Upgrades & Quick Seller Move-Out!Welcome home to this bright and airy 2-bedroom, 2-bath top-level condo that perfectly blends comfort, style, and convenience — and offers buyers the advantage of quick seller vacancy for a smooth and flexible closing! Step inside and be greeted by soaring vaulted ceilings and abundant natural light streaming through

Becky Green Samson Properties

Just minutes from the downtown walking mall, this single family home offers three bedrooms, stainless steel appliances and granite countertops, a great yard, off street parking, and a front porch. The home comes with an electric car charger usable for all brands.

Katie Landi Jordan 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.

Stunning Modern Renovation! 2-Level Townhome with Fenced Yard near Rt 81.Step right into modern luxury! This two-level townhome has been fully renovated from top to bottom, offering a sleek, contemporary look and feel. Gleaming hardwood floors flow through the main living areas, leading you to the heart of the home: a huge eat-in kitchen equipped with a huge Kitchen Island and brand-new

Raman Singh Prime Properties DMV, LLC.

This exquisite end-of-row townhouse, underwent a major renovation in 2025, offers a perfect blend of modern luxury and timeless comfort. With two spacious bedrooms and one and a half elegantly appointed bathrooms, this home is designed for both relaxation and entertaining. Step inside to discover a gourmet kitchen that will inspire your culinary adventures. Featuring upgraded granite countertops,

Brandon Pifer Pifer Realty, LLC