Homes for Sale in 21671

Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a

Samantha Jackson Keller Williams Realty

Renovated waterfront living with room for your fleet! Extensively renovated cape cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor master suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

Are you looking for serenity? Tucked away at the end of a picturesque crepe myrtle–lined drive is a breath of fresh air with its peacefully remote surroundings that many people are looking for. 12 miles to St. Michaels, close to Easton and Oxford, This exceptional waterview retreat offers a rare combination of privacy, scenic beauty, and convenience. The property is overlooking Black Walnut

Danny Martin Keller Williams Flagship

The opportunities abound for this waterfront home overlooking the Knapps Narrows. Formally, Maynard Lowery's boat building business, this residentially zoned, single-family home comes with 5 boat slips and unlimited possibilities. Can be easily expanded up to 6 bedrooms and 4 baths. The first level would make an ideal hobby area or additional living area. Handicap Accessible with elevator.

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center

Kim Crouch Ozman Benson & Mangold, LLC

Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting.

Alicia Gannon Dulin Benson & Mangold, LLC

Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor

Cheri Bruce-Phipps TTR Sotheby's International Realty

This historic property known as "The Elms" was built in 1900 and originally used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water and consists of three buildings which are: The original main building, the detached garage and a shed/storage building. The buildings hold virtually no value unless an extensive historic renovation were completed, but the

Monica Penwell TTR Sotheby's International Realty

Kim Crouch Ozman Benson & Mangold, LLC

This charming Tilghman Island cottage was originally built in 1953 and thoughtfully renovated in 2020, including updated plumbing and electric. The home features durable luxury vinyl plank flooring throughout and the roof was replaced with 45-year architectural shingles for added peace of mind. The kitchen offers stainless steel appliances, space for a dining table and flows seamlessly into the

Kim Crouch Ozman Benson & Mangold, LLC

Historic Tilghman Island “W” design home circa 1890 offering classic Eastern Shore character with extensive recent updates. Four bedrooms and two fully renovated baths. Kitchen features updated granite countertops, stove, refrigerator, and dishwasher. Newer flooring and subflooring throughout. Bathrooms include designer tile floors and tiled showers. Recently replaced HVAC system. Main level

Debbie Lipscomb Benson & Mangold, LLC

Charming 2-3BR/2BA coastal cottage with tranquil water views of Black Walnut Cove and the Choptank River - ideal for easy full-time living or a relaxed weekend retreat. Beautiful hardwood floors run throughout, complementing the home’s warm, welcoming character and comfortable scale. The living room, anchored by a wood-burning fireplace, offers a cozy gathering space, while the kitchen is

Laura Carney TTR Sotheby's International Realty