BE SURE TO WATCH THE VIDEO TOUR TO EXPERIENCE THE PROPERTY AND SETTING. Privacy, a gunite pool, and two acres on Tilghman Island, just 12 miles from St. Michaels. A long, crepe myrtle-lined driveway leads to 4957 Bar Neck Road, surrounded by mature landscaping and expansive lawn with no HOA. The property offers flexibility as a full-time residence, weekend retreat, or potential income-producing short-term rental. Two leaded-glass doors provide separate entrances. The main entrance opens to the foyer, while the second leads to the breezeway and laundry area with a utility sink, storage, and access to a full bath. The main level features hardwood floors, a parlor with built-ins, formal dining room, and family room centered around a wood-burning fireplace. Exposed brick from the fireplace extends upward along the staircase to the second floor, adding warmth and architectural character. Sliding glass doors open directly to the deck, patio, and pool. The kitchen includes granite countertops, stainless steel appliances, light wood cabinetry, and a breakfast bar. Upstairs are three bedrooms, including a spacious primary suite with generous storage and an en-suite bath. A closet-lined passage leads from the bedroom to the bath, which features an oversized jetted tub, double vanity, and abundant natural light. An expansive finished bonus room adds another dimension to the home, with a wood-clad vaulted ceiling, built-in workspace and storage, and a separate mini-split. The space offers tremendous flexibility as an office, den, studio, recreation room, or additional retreat. Outside, the in-ground gunite pool anchors a private outdoor living area surrounded by two acres of open lawn and mature landscaping. A deck, patio, pergola, fire pit, and multiple gathering areas provide plenty of room for relaxing and entertaining. An oversized two-car garage provides additional parking and storage. Improvements include a newer roof, AZEK front decking and steps with vinyl railings, encapsulated crawlspace with concrete floor, tankless water heater, Bosch heating system, and updated primary bath. The home also features two security systems, fire and carbon monoxide detection, and a custom exterior camera system. The property is not located in a flood zone. With two acres, privacy, a gunite pool, generous indoor and outdoor living spaces, and no HOA, 4957 Bar Neck Road offers a distinctive opportunity for year-round living, a second home, or potential short-term rental near St. Michaels and the Chesapeake Bay.