Downtown Winchester Homes For Sale

305 Amherst St, Winchester

3 Beds ⋅ 3 Baths ⋅ VAWI2009926 MLS ⋅ CLOSED Status

Welcome to a truly special opportunity in the heart of historic downtown Winchester. This inviting three-bedroom, 2.5 bath home offers the rare combination of one-level living, timeless charm, and an unbeatable walkable location. The fully renovated kitchen, completed in 2022, is absolutely gorgeous—featuring bright cabinetry, stunning quartz countertops, brand new appliances, and a fresh, modern feel that perfectly blends style and function. You’re just steps from the vibrant downtown walking mall, moments from the beloved Apple Blossom parade route, and within easy walking distance to Handley High School—perfect for catching a sporting event or enjoying the iconic Handley lawn with your dogs. If you love being social, connected, and part of a welcoming community, this is the place where memories are made. And homes in this location simply do not come up often, which is why they sell so quickly. Inside, you’ll find comfortable main-level living plus a cozy finished basement retreat featuring a family room with a wood-burning fireplace, along with space for a home gym and private office. The basement also provides ample additional space for visiting guests, making it ideal for extended stays or flexible everyday living. In total, the home offers two wood-burning fireplaces, creating warmth and character throughout the seasons. Step outside and the feeling continues. The backyard is your own private retreat, complete with a relaxing hot tub and a charming screened-in porch—perfect for peaceful mornings with coffee or quiet evenings under the stars. Practicality meets convenience with a one-car garage and additional carport, providing flexible covered parking and storage. Meticulously cared for inside and out, this residence reflects pride of ownership at every turn. The home’s mechanical systems have been professionally maintained and remain in pristine condition, the roof was replaced in 2018, and the attic provides valuable additional storage space—offering comfort, function, and peace of mind for years to come. This is more than a home. It’s a lifestyle in one of Winchester’s most treasured locations. Don’t wait—opportunities like this move quickly.

425 Briarmont Drive, Winchester

$270,000

1 Beds ⋅ 2 Baths ⋅ VAWI2007674 MLS ⋅ CLOSED Status

Location-Location-Location. This home offers a 1 bedroom Suite, Sitting Room, Walk-in Closet and Full Bath. Main Level: Offers Large Living Room with Built-in Book Shelves and TV Nook. Dining Room with Built-In China Closet. Kitchen offers Stainless Steel Appliances approximate 2 Years old. Gas Furnace/ Central A/C approximately 2 years old. Covered front porch. Rear yard offers Two stone patios for sitting areas. Has fencing around the home. Property located short walking distance to Old Town Walking Mall to local restaurants and shopping.

129 E Cork Street, Winchester

$362,000

4 Beds ⋅ 2 Baths ⋅ VAWI2007498 MLS ⋅ CLOSED Status

Historic Charm? Check! Modern Amenities? Check! Location? Check! Welcome to 320 S. Cameron Street! Built in 1773, this property will transport you back in time as soon as you arrive! The outside is host to 3 shops/outbuildings; some with power, an English garden, and original horse hitching posts! From the side porch, you will enter a newly renovated kitchen featuring stainless steel appliances and plenty of storage. Around the corner from the kitchen is a large laundry room. Off the kitchen is a stunning dining room with a built in china cabinet and fireplace. The foyer with original woodwork and recently refinished floors opens up to a well-appointed living room with pocket doors and an additional fireplace. A full bathroom has been beautifully renovated on the main level as well! Upstairs you will find 4 spacious, light filled bedrooms, one of which has a private entrance to the upstairs porch! An additional full bathroom finishes off the top floor. Bonus: There is a large, partially finished attic space that could be great for storage, a play room, or extra living space if fully renovated. Some upgrades to note: - Freshly painted throughout - Refinished, original hardwood floors - Renovated Kitchen - Renovated first floor bathroom - Reappointed porches The list goes on and on! Don’t miss this opportunity to own a property that is in walking distance of Downtown Winchester! RB-1 Zoning allows for various uses including residential and some business.

320 S Cameron Street, Winchester

$510,000

3 Beds ⋅ 2 Baths ⋅ VAWI2006182 MLS ⋅ CLOSED Status

This gem in the historical Handley area of Winchester has amazing views of the John Handley High School campus. John Handley High is registered on the National Register of Historic Places, and has a rich history as a privately endowed public school. The side to side front porch overlooks the campus and is across from a grove of historical cherry trees with colorful pink blooms every spring. Stroll over to the walking paths surrounding the campus or enter the trails to the Museum of the Shenandoah Valley at the end of the street. The location of this home is located adjacent to the parade route for the Apple Blossom Festival bringing thousands of spectators to the town each May. The front porch is perfect to watch the 10 K race and with front row seats to watch the annual fireworks as part of the festival. Also it is located within walking distance to the Old Town Walking Mall to enjoy local restaurants, boutiques, museums and more! 253 Jefferson has had only 2 owners since it was built. There have been many mechanical improvements throughout the years leaving the updating and cosmetics to your liking. The backyard is fenced on 2 sides, has a nice shed & all brick covered patio for outdoor entertaining. Come see for yourself the neighborhood and all it's amenities surrounding this all brick, solid bones home!

253 Jefferson Street, Winchester

$350,000

4 Beds ⋅ 2 Baths ⋅ VAWI2004988 MLS ⋅ CLOSED Status

This Home (built in 1773 !!!) has TONS of charm, and boasts so many original features, too plentiful to list!!! Beautiful hardwood floors and high ceilings throughout. The home has generous sized bedrooms, 3 in total, and 2 full baths. The home has a recently updated kitchen. The location is wonderful, within the highly desirable Historic District of Old Town Winchester and a short walk to The Downtown Pedestrian Mall. It is also within walking distance of Handley High School. A walk into the backyard, could be a trip to an Old English Courtyard. Several outbuildings could find an abundance of uses (with electric and gas in some). This is a must see to believe property!!!!

320 S Cameron Street, Winchester

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Downtown Winchester Homes For Sale