Waterfront Homes for Sale in Saint Leonard, MD

Nestled amongst the trees with a breathtaking view of the waterfront, this stunning contemporary split-level home offers the perfect escape from the city in under an hour or if you're lucky enough you can call Saint Leonard home year round! The only way to describe the feeling of walking the property is a serene, luxury retreat. Take a deep breath and exhale, this is really your new home!

Melinda Brown EXP Realty, LLC

Run!!! Don't Walk!! This exquisite Cape Cod residence, nestled on the Shores of Calvert Beach, offers a harmonious blend of comfort and bay living, perfectly positioned along the banks of the picturesque Chesapeake Bay. With 2,379 square feet of thoughtfully designed living space, this home features four spacious bedrooms and three full bathrooms, ideal for both relaxation and entertaining. Step

Samuel J Thomas Hyatt & Company Real Estate LLC

This 3 Bedroom, 1.5 Bath Rambler with an oversized 1-car detached Garage is located on a quiet street in Long Beach on the Bay (a Chesapeake Bay beach community). Hardwood Floors and Ceramic Tile throughout home. Brand new washing machine (3/2026) and hot water heater (spring/2025). In the rear of the home, there are extra outdoor spaces to enjoy your home. A screened-in Porch is off the Dining

Gail Siegel O'Brien Realty ERA Powered

Welcome to 1650 Parran Road, a remarkable Southern Maryland retreat where timeless charm meets peaceful country living. Nestled in the heart of St. Leonard, this exceptional property offers the perfect blend of privacy, comfort, and natural beauty, creating an idyllic setting for those seeking a more relaxed pace of life without sacrificing convenience. Surrounded by the picturesque landscapes

Michael Hunter Real Broker, LLC

PRICE ADJUSTMENT!!!! Get ready to spend your summer by the water. Welcome to an extraordinary Southern Living–inspired waterfront bungalow offering a rare blend of tranquility, luxury, and charm in pristine condition. Tucked away on a quiet, secluded road with only three homes, this exceptional property is surrounded by water and bordered by 25 acres of protected, unbuildable land, ensuring

Jeannine Wayson Coldwell Banker Realty

STUNNING WATERFRONT! Set on 2.21 private acres along St. Leonard Creek, this exceptional waterfront home offers 4,468 square feet, 4 bedrooms, 4.5 bathrooms, a detached 2-car garage w/ an unfinished storage space above, and a fully finished basement in a setting that feels private, peaceful, and made for everyday luxury. Watch the numerous Bald Eagles and other wildlife and melt away into this

Mark Frisco CENTURY 21 New Millennium

No HOA. Total square footage of 3520. The house's total sq ft is 2400 with 3 bedrooms and 2.5 baths. A 1120 sq ft apartment with 1 bedroom and 1 bath. The Garage has a 1/2 Bath. The property is in the forest management program for reduced taxes. Tucked along the protected waters of Saint Leonard Creek, this is the kind of property you don’t just visit, you settle into. Deep water, nearly 800 feet

Dawn Riley Deep Roots Real Estate

Imagine starting your morning with a walk to the beach, spending the afternoon on the water, and stopping by a local farm stand on your way home for fresh sweet corn and tomatoes. That's everyday life in Calvert Beach, where coastal living and small-town charm come together. Situated on one of the largest lots in the neighborhood, this well-maintained 3-bedroom, 1-bath rambler sits on nearly half

Emily Watts Real Broker, LLC

Welcome to your beach staycation! This charming rambler offers 2 bedrooms and 1 full bathroom, making it an excellent option for a first-time home buyer, downsizer, or anyone looking for a peaceful retreat near the water. Inside, you'll find a spacious living room filled with natural light, a huge kitchen with plenty of cabinet and storage space, and Chesapeake Bay views from the dining area.

Tannar Jones Samson Properties

Located in Calvert Estates just a short walk from the Chesapeake Bay, this 4 level split level offers a comfortable layout, a quiet established neighborhood, and the kind of location that makes everyday living feel a little easier. The home has over 2,300 square feet of living space with 3 bedrooms, 2.5 baths, multiple living areas, and a finished lower level that gives you extra room for a

Brian Mayer Real Broker, LLC

Deeded Boat Slip Conveys!! Bayside Living! Bayview new construction only a short walk to the private beach & marina! This 2000sqft 3 Bed 2.5 Bath Colonial with an attached 1.5 Car Garage & an Unfinished Basement, has been designed to Maximize the Views while the .91 acre lot maximizes privacy! The primary bedroom & attached balcony will have substantial views of the Chesapeake Bay! This floorplan

Mark Frisco CENTURY 21 New Millennium

Charming rambler offering comfortable one-level living with a partially finished basement and plenty of potential to make it your own. The main level features just under 1,300 square feet of living space, including a spacious primary suite with a large bedroom and private bath, plus two additional bedrooms and a full hall bath.The eat-in kitchen flows directly into the oversized family room,

Crystal Culley Berkshire Hathaway HomeServices PenFed Realty

Nestled in a serene bayblock setting, this exquisite raised ranch, 3 bedroom, 1.5 bath home offers a harmonious blend of modern luxury and timeless comfort. With a major renovation completed in 2026, every corner of this residence has been thoughtfully designed to elevate your lifestyle. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen

Gregory Bennett Jr. Five Star Real Estate

Luxury home on 5 private wooded acres in sought-after Calvert County, Maryland with Chesapeake Bay boating access. Bordered by 121 acres of protected community open space, this property offers rare privacy, natural views, and resort-style amenities. The oversized kitchen features solid cherry cabinetry and expansive prep space ideal for entertaining. Main level includes a dramatic second family

Jeffrey Lewis Berkshire Hathaway HomeServices PenFed Realty

Experience this beautifully renovated, coastal retreat in sought after Calvert Beach, on the Chesapeake Bay. In 2022, the new owners gutted (down to the studs), reconstructed, and redesigned the entire main floor of this three-bedroom, three-bathroom Rambler with full, walk-out Basement. The renovation included all new plumbing, electric, HVAC, and such high-end upgrades as heated floors in two

Gail Siegel O'Brien Realty ERA Powered

Custom built colonial with Water Access, Brand New Roof with a Lifetime Shingle Warranty, and an extremely efficient Geothermal HVAC system! Crafted with precision by the original owner, a skilled custom homebuilder, this stately colonial reflects uncompromising quality with no original detail overlooked. Home does need some updating but bones are extremely strong! With 4 bedrooms and 2.5 baths,

Conor Stueckler Keller Williams Flagship

This one-of-a-kind private peninsula offers panoramic waterfront views on an expansive 5.2-acre homesite. It is conveniently equipped with an included pier and boat lift. These rare characteristics make it a strong investment opportunity. Notably, this peninsula was once a ferry wharf between Calvert and St. Mary’s Counties and was owned by Pulitzer Prize winner Thomas Stokes, who hosted Harry

John Lesniewski RE/MAX United Real Estate

Welcome to the kind of property that rarely comes available and can never truly be replicated.Nestled along the shores of historic Battle Creek, this beloved waterfront retreat has been cherished by the same family for generations. More than a home, it is a place filled with stories, traditions, and memories made on the water.Set on nearly an acre of private waterfront land, the property

Dawn Riley Deep Roots Real Estate

**PERRY POINT ON ST. LEONARD CREEK:** A premier 6.4-acre deep-water sanctuary along the shoreline of St. Leonard Creek. The property is incredibly private, offering placid and protected water. Wildlife is abundant with bald eagles, osprey, herons, and more. Located just an hour from Capitol Hill, the 4,300 SF contemporary-coastal home offers the ultimate year-round Chesapeake lifestyle. Enjoy

Chris McNelis Berkshire Hathaway HomeServices PenFed Realty

Welcome to this beautifully maintained waterfront split-foyer home nestled on 1.15 private acres in a sought-after water-access community. Designed for comfort, leisure, and waterfront living, this property offers the perfect blend of indoor charm and outdoor enjoyment. Step inside to find 4 spacious bedrooms and 3 full bathrooms, including a newly finished lower level featuring a cozy propane

Angela Jewell O'Brien Realty ERA Powered