luxury houses for sale Saint Leonard, United States

Rare Waterfront Opportunity! Discover the potential of this rare 1.3-acre waterfront property nestled along the deep, navigable waters of Cuckold Creek in Hollywood, Maryland. Offering the perfect canvas for your vision, this property presents an incredible opportunity to renovate the existing home or build the custom waterfront retreat you've always imagined. With deep water access from your private pier, enjoy fishing, boating, kayaking, paddleboarding, and a variety of water sports right from your own backyard, with easy access to the Patuxent River and the Chesapeake Bay. Few properties offer this combination of location, lifestyle, and opportunity. The existing home needs renovations, including a complete kitchen. Adding to the property's potential is an existing 20 by 40 in-ground pool, a rare feature for waterfront properties in the area. With both the home and pool needing renovations and repairs, both are being sold strictly As-Is. There is also an additional .16 acres of land known as a fourteen-foot right-of-way and conveys as an additional parcel with its own shoreline. Whether you choose to restore or build new, opportunities like this are increasingly hard to find in this highly desirable Southern Maryland location. If you've been searching for a private waterfront setting with deep water, generous acreage, and endless possibilities to create something truly special, this exceptional property is ready for its next chapter.

Discover an extraordinary opportunity for waterfront living on the Patuxent River. This stunning brick-front residence offers 7 bedrooms, 4 full bathrooms, and a private 2-bedroom guest apartment with full kitchen and separate entry. Designed with comfort and accessibility in mind, the home features an elevator serving all three levels, expansive entertaining areas, and a sparkling pool with maintenance-free decking. An oversized 3-car garage, multiple sheds, and two laundry rooms provide outstanding functionality. The outdoor amenities are unmatched — a private paved access road leads to the shoreline with deep-water pier, dual boat lifts, and jet ski lift, ideal for boating enthusiasts. Additional highlights include an all-seasons room, wood-burning fireplace, new roof (2022), new hot water heater (2023), new septic system with nitrogen removal (2023), new well (2024), and a brand-new pool liner (2024). With panoramic river views, modern upgrades, and an incomparable setting, this property offers the perfect blend of luxury, versatility, and privacy — all just minutes from major commuter routes.

Welcome to this bright and airy end-unit townhome in the Richfield Station community of Chesapeake Beach. Sun-filled living spaces include a beautiful kitchen with an island and stainless-steel appliances that opens to the dining area and a spacious living room. The home backs onto serene, mature trees, filling the interior with abundant natural light through multiple windows and doors that lead to the deck. Located on a quiet, non-through street with minimal traffic, this residence offers peaceful everyday living. Condo association fees offer true low-maintenance convenience, covering trash service, lawn maintenance, and exterior maintenance. The roof was replaced in 2026. Richfield Station residents enjoy direct access to the Chesapeake Beach Railway Trail system and the Fishing Creek Boardwalk. You are just minutes from the Chesapeake Bay, its scenic boardwalk, beaches, restaurants, and the full "Bay Life" lifestyle. Calvert County provides convenient access to the region's major metropolitan areas, including Washington, D.C., Annapolis, Northern Virginia, and Ronald Reagan Washington National Airport.

Adorable waterfront cottage nestled along the peaceful shores of Hudson Creek., This charming 2-bedroom, 1-bath home features an open-concept kitchen, dining, and living area designed to maximize comfort and showcase beautiful waterfront views and amazing sunsets. Additional features include front and back porches, firepit, fresh paint throughout and a detached storage shed for all your outdoor gear, Experience Eastern Shore waterfront living and spend your days fishing or crabbing from your private pier, launch your kayaks for an afternoon on the creek, or simply unwind on the deck while taking in the spectacular sunsets. This low-maintenance property has been successfully operated as an income generating vacation rental, making it an excellent opportunity as a personal getaway, investment property, or both. The home is being sold fully furnished, including two kayaks, a BBQ grill and deck furniture

Endless westerly vistas stretch across Madison Bay, delivering breathtaking sunsets that feel like a private showing each and every evening. This is more than a home-it's a waterfront sanctuary designed for those who expect their lifestyle to be as elevated as their surroundings. Welcome to Saltmarsh, an extraordinary 8.5-acre estate where luxury, privacy, and coastal beauty converge. With 5 bedrooms (plus a bonus room that could be considered a 6th) and 3 full bathrooms, this property effortlessly transitions between an exceptional full-time residence and the ultimate weekend retreat for unforgettable gatherings with friends and family. Spanning over 5,000 square feet, the home is thoughtfully designed to maximize both space and scenery, with walls of windows that flood the interior with natural light and showcase those sweeping bay views from nearly every room. The main level is nothing short of an entertainer's masterpiece-an open-concept layout anchored by a stunning great room, seamlessly flowing into a chef's gourmet kitchen and sun-drenched sunroom on one side, while the opposite wing reveals a full-scale game room complete with a pool table and custom bar built for hosting on any scale. Step outside and the experience only gets better. Multiple expansive decks offer the perfect setting for everything from quiet mornings to lively evenings, all framed by panoramic water views. At the private dock, every detail has been accounted for-featuring water and electric, two jet ski lifts, and a 10,000-pound boat lift-creating a true waterfront playground. The oversized 3-bay garage provides ample space for all your water toys, equipment, and more-because a property like this is meant to be enjoyed without compromise. Offered fully furnished, Saltmarsh is completely turnkey-allowing you to step right into an effortless, elevated coastal lifestyle from day one. This is not just a home-it's a statement.

SEIZE THE SUNSET! Enjoy waterfront tranquility right at your back door—and don’t miss this significant price improvement! If you’ve been searching for an immaculate, move-in-ready waterfront home with exceptional first-floor living, this may be the one. Major interior renovations were completed in 2022, and this beautifully updated and meticulously maintained 3-bedroom, 2-bath home offers more than 2,300 square feet of bright, inviting living space designed to showcase the beauty of the Eastern Shore. Panoramic waterfront views greet you from nearly every room, with the living room overlooking the breathtaking vistas of Fishing Creek. Two spacious living areas, each featuring a cozy fireplace, provide plenty of room to relax, entertain, and enjoy the changing seasons.The open gourmet kitchen is the heart of the home, featuring custom finishes, modern updates, and a built-in wine cooler—perfect for preparing meals, gathering with friends, or simply enjoying a quiet evening while taking in the view. Major systems and improvements have already been taken care of, offering peace of mind for the next owner. The roof was replaced in 2018, the HVAC system in 2022, and new thermostats were installed in 2024. An updated sprinkler system, new French gutter drains installed in 2025, and an improved Dry-Zone encapsulated crawl space further enhance the home's efficiency and long-term protection. The crawl space also features a new dehumidifier installed on a raised platform, new insulation, and an indoor monitoring system, all completed in 2026. For additional peace of mind, the home includes transferable USAA flood insurance along with annual Dry-Zone, HVAC, and pest control inspection contracts. Connected to public sewer, this home offers the convenience of simplified ownership from day one.Ideally located just a short distance from historic Cambridge and the Hyatt Regency Chesapeake Bay Golf Resort, with easy access to Easton, Oxford, and St. Michaels. Nature lovers will appreciate the close proximity to Blackwater Wildlife Refuge, where you can explore scenic trails, enjoy kayaking and biking, observe abundant wildlife, and perhaps catch a glimpse of the area's magnificent bald eagles.This is more than a home—it’s an opportunity to embrace the peaceful waterfront lifestyle, spectacular sunsets, and timeless charm of Maryland’s Eastern Shore, with the comfort and confidence of a home where many of the major updates have already been completed.

Your Own Private Island; A 90-Minute Drive from Washington DC Even if our own experience was different, most of us can envision care-free summer days at the shore. Games on the beach, hiking in the forest; only coming back to the house at sunset when it was obvious that we were late for dinner. Now you and your family can create your own summer wonderland with the purchase of an idyllic island located in a sheltered cove of the Chesapeake Bay. Tippity Wichity Island includes a charming and spacious three-bedroom home with a focus on connection to the lush grounds and surrounding water. Each bedroom provides direct outside access. One side of the home features two bedrooms, one of which is the primary, and a full bath. The primary bedroom provides a prominent view of the St. Mary’s River through sliding glass doors giving way to a private porch. The third bedroom and additional full bath are located on the opposite end of the living area for guest privacy. The open “great” room of the home serves as the central gathering place, providing ample space for living, dining, and entertaining. The room is accentuated by a wood-burning fireplace in the center and large windows offering views down the river on one side and access to the back porch, garden, and grounds on the other. While each of the numerous porches offer a unique view and tranquility, the highlight is the screened-in “gazebo” porch. The space welcomes outdoor dining year-round or a shaded respite with the ebb and flow of the river in the background. The Island itself is just under 5 acres highlighted by the dock with boat lift, permitted riprap shoreline and living shoreline with a small beach, soft launch for kayaks/canoes, scenic nature trail and multiple storage structures. The river is clean and temperate, but a heated in-ground swimming pool sits adjacent to the house in its own private garden location. Although much has been written about the erosion of islands in the Chesapeake, Tippity Wichity sits four meters above the high-water line and is protected from all but the most calamitous storms. Mean low water at the boat dock is approximately six feet, which allows for many sail and powerboat options. Nestled squarely in the St. Mary’s River Sanctuary, the Island provides a scenic outpost for nature enthusiasts and the avid outdoorsperson to pursue the abundant wild game and fish down the river, across the mouth of the Potomac, and into the fabled Chesapeake Bay. This incredible property could also serve as a corporate/non-profit retreat or sporting lodge. The property enjoys an easement across farmland on the bank of the River for access to a dock. In addition, the Island itself is just a 5-10 minute boat ride from St. Mary’s College, an historic liberal arts college in St. Mary’s City. In addition to shopping and dining options, the town/College and nearby Leonardtown offer ample opportunities for entertainment, including an outdoor summer concert series and the Governor’s Cup yacht race.

Price reduced SIGNIFICANTLY!! Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ensuite bath with a jetted tub and walk-in shower. Three additional bedrooms—one currently used as a library—share a full hall bath. An attached two-car garage provides convenient parking and storage. Residents of Tilghman on Chesapeake enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available for lease, offering residents an ideal opportunity to enjoy the waterfront lifestyle of Maryland’s Eastern Shore.