Bay Breezes & Beautiful Views: Your Tilghman Island Haven Waterview Living with Room to Breathe on Maryland's Eastern Shore Step into the good life at 5379 Anchor Road, where Chesapeake Bay magic meets everyday comfort. This charming home in Tilghman's friendly beach neighborhood sits just a short stroll from the community beach where neighbors gather and memories are made. Picture yourself unwinding on the deck with morning coffee, watching the sun sparkle across the bay waters. Inside, the welcoming home greets you with warm hardwood floors throughout, two comfortable bedrooms, and two full baths. The kitchen is a joy to cook in—featuring granite countertops, stainless appliances, and beautiful hand-crafted wood cabinets perfect for whipping up fresh seafood dinners or casual breakfasts before heading out to explore the water. What makes this place truly special is the adorable guest cottage built in 2017. This sweet retreat offers a screened porch with more water views, its own heating and cooling, and a half bath—perfect for visiting friends or your own creative escape when you need a moment to yourself. For water lovers, you're in paradise—grab your kayak or paddleboard and launch right from your backyard. Gardening opportunities abound-whether ornamental or the fun of your own fresh summer veggies-the property also includes fruit trees -pies and jams in your future? The practical perks are all here too: a roomy two-car garage with workshop space for projects, outdoor shower for rinsing off sandy feet, beautiful landscaping, plus recent updates including a new roof (2018) and HVAC system (2016) so you can relax knowing the essentials are taken care of. Beyond your doorstep, discover the authentic charm of Tilghman Island. A short, scenic drive connects you to the fabulous restaurants, shops and galleries of St. Michaels, Easton, and Oxford. When you choose this Tilghman Island home, you're investing in more than just real estate—you're gaining a lifestyle where stress melts away with each bay breeze and sunset. Whether you're looking for a full-time home with vacation vibes, a weekend getaway from the city grind, or the perfect spot to eventually retire and watch the osprey soar, this special place offers what so many of us are searching for—a chance to slow down, breathe deeply, and connect with the beauty of the bay. Come see what life on Tilghman time feels like. Your Eastern Shore story is waiting to begin.
Attic, Attic/House Fan, Bathroom - Walk-In Shower, Entry Lvl BR, Pantry, Walk-in Closet(s), Wood Floors
Private, Secure Parking, Paved Driveway, Paved Parking
Covered Parking, Garage - Front Entry, Garage - Side Entry, Garage Door Opener
Bay, Panoramic, Scenic Vista, Water
Built-In Microwave, Built-In Range, Dishwasher, ENERGY STAR Refrigerator, Oven/Range-Gas, Range hood, Stainless Steel Appliances, Washer
Central A/C, Attic Fan, Heat Pump(s), Programmable Thermostat
Extensive Hardscape, Exterior Lighting, Outbuilding Apartment, Outside Shower, Private Beach, Deck(s), Porch-screened
Backs to Trees, Fishing Available, Front Yard, Landscaping, Level, Private, Rear Yard
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Listing information last updated on June 17th, 2025 at 7:15am CDT.