191 old baltimore road

Perched on 2.75 private acres with panoramic valley and mountain views, this extraordinary estate is a true showpiece among Winchester’s finest homes. With over 6,000 finished square feet, a fully fenced backyard adorned with cherry and magnolia trees, and unforgettable outdoor spaces that match the inside of this one-of-kind home, this is luxury living redefined—graceful, timeless, and effortlessly welcoming. From the moment you arrive via the sweeping half-circle paved driveway, you’ll feel the elevated elegance that defines this residence. Wrap-around no maintenance decks, a flat backyard with a fire pit, and a covered stone patio invite year-round entertaining and quiet moments alike—all framed by 365-degree views that capture the beauty of every season. Step inside to soaring ceilings, double crown molding, curved walls, exquisite hand painted wall coverings and surprising details throughout. Unique wood floors, salvaged from a Chinese monastery, add warmth and character, while every bathroom in the home is finished in marble—luxury in every corner. The layout is both grand and inviting, with expansive, light-filled rooms from floor to ceiling windows, designed for both impressive entertaining and comfortable living. The main level features a breathtaking primary suite wing, complete with a generous sitting area, walk-in closet, and spa-like bath with an infinity tub and custom stained glass window. Upstairs, a dramatic curved staircase leads to a spacious central gathering hall and large bedrooms—each with an en suite bath and captivating views from every window. The fully finished lower level offers an additional bedroom, a massive recreation room with oversized windows, and double cinder block construction for peace and durability. Unfinished spaces provide abundant storage or the opportunity to expand. Notable updates include a brand-new roof (April 2025), re-pointed stonework and new backyard patio (2023), and newer HVAC and water heater (2021), among the many others. Best of all, it sits just 10 minutes from Winchester Medical Center and 15 minutes to the heart of downtown. This is truly a rare opportunity to own a home that is as refined as it is welcoming. Grand in scale, yet grounded in comfort—this property makes for an extraordinary setting for celebrating life’s most memorable moments.