Set within the gated waterfront enclave of Bayberry Hill, this distinctive waterfront residence with waterside pool offers an exceptional combination of architectural character, wooded privacy, and sweeping water views. Tucked beneath a mature tree canopy, the property feels wonderfully secluded while opening dramatically toward the water, creating a peaceful retreat designed around the Annapolis waterfront lifestyle. A picturesque approach leads through lush landscaping, pond with water feature and across a charming footbridge to the inviting entrance. Inside, soaring wood-clad ceilings, skylights, expansive windows, and impressive stonework create a warm, contemporary aesthetic. The dramatic great room is anchored by a striking floor-to-ceiling stone fireplace, while walls of glass throughout the home bring the surrounding natural beauty indoors. Multiple living spaces offer exceptional versatility for everyday living and entertaining. A glass-enclosed waterside family room adjacent to the gourmet kitchen captures beautiful views and opens to the expansive deck, creating a seamless connection between indoors and out. A beautifully designed wine cellar with custom wood storage, stone accents, and a tasting area adds another distinctive element. The spacious primary suite is a private retreat with vaulted ceilings, a sitting area, dedicated workspace, private side patio and access to the waterside deck. The spa-inspired bath features dual vanities, an oversized soaking tub positioned beneath windows overlooking the water, and a large walk-in shower. The lower level is designed for entertaining with a spacious recreation and game room featuring a fireplace, custom finishes, and sliding doors opening directly to the poolside deck and hot tub. Two bedrooms with ensuite baths, large closets and spectacular pool and water views create an ideal getaway for family or guests. Outside, a series of decks and terraces cascade toward the shoreline, offering multiple places to relax and take in the views. The waterside swimming pool is surrounded by a generous deck beneath the mature trees, while a separate hot tub provides another peaceful vantage point. At the shoreline, a private pier with multiple slips and boat lifts provides effortless access for boating, paddling, and days on the water. Bayberry Hill offers the privacy of a gated waterfront community with water access and tennis/pickleball courts, all within convenient reach of Downtown Annapolis, BWI, major commuting routes, and Washington, D.C. A truly distinctive waterfront retreat where architecture, privacy, and the natural landscape come together beautifully. Welcome Home!