Winchester, VA Homes for Sale under $300,000

Welcome to this charming 2-bedroom, 1.5-bath home in Winchester! Featuring a recently replaced roof (2024) and double-hung windows, this home combines character and functionality. The main floor offers a bedroom with half bath, perfect for guests or home office use, while upstairs boasts a large bedroom with full bath. Enjoy cozy evenings by the brick wood-burning fireplace and the beautiful

Michele Gibson Samson Properties

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

Welcome Home to this Spacious and Upgraded Townhome! Located in a highly desirable commuter location with easy access to major routes, this 2-bedroom, 1.5-bath townhome is a true gem. Step inside to find stunning refinished hardwood floors that flow throughout the main living areas. The heart of the home is the upgraded kitchen, featuring beautiful granite countertops—perfect for cooking and

LESLIE WEBB Long & Foster Real Estate, Inc.

Charming and completely updated! This beautiful home features a brand-new kitchen with new appliances, an updated bathroom, newly installed HVAC system, and a new water heater. Truly move-in ready and waiting for its next owner!

Yoselin Mejia The Vasquez Group LLC

Unwind on the covered front porch of this charming stone Cape Cod, ideally located on a spacious corner lot with sidewalks and a large, fenced backyard. Inside, the inviting living room features hardwood floors and a brick gas-log fireplace—perfect for cozy evenings. Hardwood flooring continues throughout the home, complemented by a convenient kitchen and dining combination. Two bedrooms are

Susan Caulfield Pearson Smith Realty, LLC

Welcome to this cozy 3-bedroom, 1.5-bath ranch home in Shawneeland. Featuring hardwood floors and an open floorplan, this home offers comfortable one-level living. The wood-burning fireplace is currently sealed but adds character and future potential. Enjoy outdoor living with both front and rear decks overlooking the approximately .25-acre lot. Comcast internet available.Community amenities

Amy Longerbeam RE/MAX Roots

Tudor Square Townhouse. Great location to Interstate I-81, Rt.37 By-Pass and Rt. 522 N. Walking Distance to Martins Shopping Center. Valley Health Winchester Medical Center Approximately 3 miles. Near Winchester Downtown Area. Two large bedrooms, 1 I/2 baths offers Large Kitchen Eat-in, Luxury Vinyl Flooring and Dining with Stainless Steel Appliances. Large Living Room with Bay Window and

George Johnson Jim Barb Realty Inc.

Investors dream!!! Or perfect for someone wanting to buy into instant equity and put their own finishing touches!! Welcome to 632 Watson Avenue. Ideally located in the Orchard Terrace subdivision just minutes to the quaint town of Winchester, this 3 bedroom, 2 full bath single family home with 1,600 square feet of living space is nestled on a non-thru street for quiet and peace of mind. The

Tien Cotter Pearson Smith Realty, LLC

Newly remodeled 2-bedroom, 1-bath rancher just minutes from Winchester! This charming home features covered front and side porches, a gravel driveway, and a storage building, all situated on a .29-acre lot that backs to trees for added privacy. Inside, you’ll find luxury vinyl plank flooring throughout, stainless steel appliances, and a modern walk-in shower. Enjoy easy one-level living with

Sheila Pack RE/MAX Roots

Nestled in the charming Hillcrest neighborhood, this delightful Craftsman-style home, built in 1950 and set to shine with major renovations in 2024, offers a perfect blend of classic character and modern convenience. With two spacious bedrooms and two full bathrooms, this residence is designed for comfort and functionality. The heart of the home features a well-appointed kitchen equipped with

Channing Sherfey Hoffman Realty

Coming April 2026. Blue Ocean Modulars introduces The Laurel, a new modular home to be located at 603 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 that enhances

Rebecca McTavish Long & Foster Real Estate, Inc.

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

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.

Spacious doublewide home offering endless potential, situated on 2.47 unrestricted acres in a prime Frederick County area. This 3-bedroom, 2 full bath home features a full unfinished basement, providing abundant space for storage, a workshop, or future expansion as some rooms are already framed in. The basement also includes a one-car garage, adding convenience and functionality. The home boasts

Andrew Fultz 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.