
Listing details
100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.
Location
Living in Winchester
City-level context, not this home's school assignment, commute, or tax bill.
Schools
Public schools listed for this area - confirm assignment with the district
- John Handley High School
- Daniel Morgan Middle School
- Quarles Elementary
Commute
Major Routes
I-81, Rt 7, Rt 11, Rt 50, Rt 522
Single Family agents in Winchester
Sorted by how many single-family homes they have sold in Winchester, plus speed, list-to-sold ratio, and price-band fit. Select up to 3 to interview.
Explore local lenders
Based on listed service areas. Explore profiles and choose who you want to work with.
Your path to this home
- 1Select agents who sell this type of home here
- 2Interview, negotiate, and hire your agent online
- 3Explore lender profiles for this area
- 4Choose who to work with and keep your Move together
- 5Manage contract, inspection, appraisal, and closing in one place