21158 N Bayside Rd, Cape Charles, VA 23310

A TIMELESS LEGACY AWAITS. Step back to an era of craftsmanship and enduring style. Built in 1937, this magnificent brick Georgian residence is a rare gem on Virginia’s Eastern Shore, offering an architectural presence and quality that new construction simply cannot replicate. Situated on almost two private acres in charming Cheriton—just minutes from downtown Cape Charles and easy access to both the Chesapeake Bay and the Atlantic Ocean—this estate offers a rich history alongside modern peace of mind. The home welcomes you through its original, oversized wood front door with sidelights and a graceful fanlight into a grand entryway with a sweeping staircase and soaring 10-foot ceilings. Entertain in the formal dining room, prepare meals with the help of a classic butler’s pantry, or relax by the large fireplace in the living room. Historic details abound throughout, including original hardwood floors, a slate roof, keystones over the windows, working wood shutters, original glass doorknobs, French doors, and period-accurate solid brass switch plates. The living space spans three floors with 4 bedrooms, a bonus room, and 2.5 baths (septic rated for 4 bedrooms). The third floor features a charming clawfoot bathtub, while the second floor boasts a walk-out balcony overlooking the private backyard—a front-row seat to the local wildlife along the Atlantic Flyway. While rich in heritage, the infrastructure has been thoughtfully updated. A brand-new high-efficiency HVAC system was professionally installed in 2023 for modern heating and central air (with original radiators preserved). The electrical system features an updated panel with GFI breakers and new 3-prong outlets throughout (keeping the historic touch of solid brass wall plates), plus a dedicated EV charging station outside. The kitchen plumbing has been updated with a new white cast-iron sink and historic chrome bridge faucet. Best of all, the property sits safely above local flood levels, so no flood insurance is required. Outside, the almost two-acre plot includes a garage, shed, covered porte-cochère, and expansive covered front porch, offering endless potential for estate gardens or an outdoor sanctuary. Showings are hosted by private appointment for buyers with a pre-approval letter or proof of funds. Please reach out directly with questions or to arrange your visit.