$3,100,000

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… Read More 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! Read Less

Courtesy of Bradley R Kappel, TTR Sotheby's International Realty 410-280-5600

Listing Snapshot

Days Online

Last Updated

Aug 22, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

4,729

Lot Size

1.27 Acres

Year Built

1985

MLS Number

MDAA2154666

Additional Details

Property Access

Road Responsibility: Private

Appliances & Equipment

Built-In Microwave, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Oven - Wall, Extra Refrigerator/Freezer, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Conditioner - Owned, Water Heater

Basement

Connecting Stairway, Daylight, Partial, Full, Fully Finished, Heated, Improved, Interior Access, Outside Entrance, Rear Entrance, Walkout Level, Windows

Building

Built in 1985, Living area: 4729, Levels: 2, Construction Materials: Combination

Cooling

Central A/C, Ceiling Fan(s), Geothermal, Programmable Thermostat, Ductless/Mini-Split

Accessibility Features

None

Exterior Features

Patio/Porch Features: Deck(s), Patio(s), Porch(es), Extensive Hardscape, Exterior Lighting, Hot Tub, Secure Storage, Stone Retaining Walls, Water Falls, Private Beach

Fireplaces

3 fireplaces, Fireplace - Glass Doors, Stone, Marble

Floors

Ceramic Tile, Hardwood, Luxury Vinyl Plank

Garage

2 spaces

Heating

Forced Air, Programmable Thermostat, Zoned

Home Owner's Association

Association Fee: $2,500, Fee Frequency: Annually, Fee Includes: Trash, Snow Removal, Security Gate, Amenities: Gated Community, Tennis Courts

Interior Features

Bar, Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Butlers Pantry, Cedar Closet(s), Ceiling Fan(s), Combination Dining/Living, Combination Kitchen/Dining, Combination Kitchen/Living, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Pantry, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Skylight(s), Upgraded Countertops, Walk-in Closet(s), Water Treat System, WhirlPool/HotTub, Window Treatments, Wine Storage, Wood Floors

Lot

1.27 acres, Backs to Trees, Landscaping, No Thru Street, Partly Wooded, Poolside, Premium, Pond, Private

Pool

Heated

Property

Other structures: Above Grade, Bay, Creek/Stream, River, Courtyard, Scenic Vista, Water

Security Features

Security System, Smoke Detector, Security Gate

Sewer

Private Septic Tank, On Site Septic

Taxes

Annual Amount: $29,751, Lot: 14, Year: 2025, Zoning: RLD

Utilities

Water Source: Well

Water Features

Water Body Name: Hopkins Creek/Round Bay, Private Dock Site, Sandy Beach

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