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luxury real estate for sale Saint Leonard, United States

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House with pool Saint Leonard (United States)

Welcome to a breathtaking, unparalleled, retreat in Calvert County, Maryland, where luxury meets nature on a remarkable 103-acre estate. Enter through elegant gates and meander up a breathtaking lane that unfolds to reveal a stunning, picturesque setting and the grand main house, a true masterpiece of modern contemporary design. Spanning over 8,000 square feet, this meticulously updated home features a spectacular main family room with soaring 23-foot ceilings, creating an inviting lodge-like atmosphere. If you are looking for lodge-chic, this is the place for you! The spacious kitchen, equipped with high-end appliances, is perfect for culinary enthusiasts and gatherings alike. Enjoy tranquil afternoons in the sunroom or step outside to your private oasis. The expansive outdoor area includes a large pool, exquisite hardscaping, multiple decks, a charming pavilion, an outdoor kitchen, and a cozy fire pit-ideal for entertaining or relaxing under the stars. With 5 well-appointed bedrooms and a large wet bar in the walk-out basement, this residence is perfect for hosting family and friends. A separate guest house, with radiant heated floors, provides an additional accommodation for guests. While the three-car attached garage, 40 x 60 with hydronic heated floor pole barn and detached workshop offer ample storage and functionality. The pole barn has 10x10 doors on each end, extra cabinets, ceiling fans, insulated walls and insulated attic and a 50-Amp outlet for welding. This property is not only a serene escape but also an adventurous playground. Whether you envision a corporate retreat, private hunting grounds, space for horses and livestock, or a family compound, the possibilities are endless. Enjoy the trails that weave through the wooded areas for hiking, trail biking or horseback riding. For those considering investment opportunities, the estate offers the potential for subdivision into three separate parcels. Buyers are responsible to conduct their own due diligence regarding subdivision possibilities. Please, no drive-bys. Appointments to see this wonderful oasis are required. With dual geothermal HVAC systems and heated, radiant flooring, ensuring year-round comfort, this immaculately maintained home blends elegance with practicality. There are also 2 separate Energy Recovery Systems to maintain air quality and humidity. Discover the limitless potential of this extraordinary property-your dream lifestyle awaits!

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$2,800,000
761
5bedrooms
4bathrooms

By Annonceur International

10 listings near St. Leonard

Nearby
42

Apartment with terrace Solomons (United States)

The open design of the Tred Avon floor plan of this top floor end unit is a stunning Solomons Landing offering creating a waterfront lifestyle facing the Back Creek shoreline that can be enjoyed at your doorstep. A waterside trail surrounds the community where there are piers and kayak racks, as well as a community marina that offers a variety of slip possibilities, providing numerous opportunities to enjoy the water. The living room features Palladian windows with views to the water, beautiful maple flooring, and dramatic ceilings. Enjoy a fabulous kitchen with extensive cabinetry, expansive granite food prep surfaces, gas cooking, recently replaced stainless appliances, a large pantry, and a breakfast nook - it will be loved by those who appreciate the culinary experience, the kitchen opening to a large dining area that is a perfect entertainment space. Relax in the spacious primary suite featuring transom windows creating architectural interest and a bright and welcoming area, with an ensuite bath featuring separate vanities, walk-in shower and soak tub, The large corner deck can be accessed from the main living area as well as the primary bedroom, providing extended outdoor living. A number of attractive appointments have been added by the sellers making this unit a very special option for full time or second home living. Waterfront living and resort style amenities await - and yes, there is pickleball, with newly refurbished courts - convenient to charming Solomons where the Chesapeake Bay lifestyle is incomparable.

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$549,000
3bedrooms
2bathrooms

By Monument Sotheby's International Realty

Nearby
Contract pending
46

Apartment with terrace Solomons (United States)

Enjoy incomparable waterfront living with this top floor condominium in the Harbor View point location building in Solomons Landing. This unit features an elegant entry to an open floor plan with wood floors and water views from the main living area and primary suite which both access the deck with retractable awning overlooking the water and marina. Your boat slip is visible from the unit and easily accessible for boating enjoyment. The kitchen is nicely appointed with attractive on trend white cabinetry, granite prep surfaces, pantry, and breakfast area, opening to a dining room and living room area, a perfect entertaining space. The Solomons Landing amenities complete the perfect waterfront lifestyle convenient to charming Solomons.

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$585,000
3bedrooms
2bathrooms

By Monument Sotheby's International Realty

Nearby
Contract pending
31

Apartment with terrace Solomons (United States)

Excellent water views from this thoughtfully upgraded condominium in the Harbor View point location building in Solomons Landing create the perfect island lifestyle in charming Solomons. The unit offers an open floor plan featuring beautiful marble and wood floors and water views from the main living area and primary suite. The screened deck is accessible from the main living area as well as the primary suite and office, and overlooks the water and marina. Your boat slip is visible from the unit and convenient to the unit for boating enjoyment. A nicely appointed kitchen provides a great space for food preparation with attractive cabinetry, granite prep surfaces, pantry, and breakfast area. The kitchen opens to a dining room and living room area, perfect for entertaining. Solomons Landing offers resort style amenities where residents enjoy the best in waterfront living.

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$575,000
3bedrooms
2bathrooms

By Monument Sotheby's International Realty

Nearby
50

House with pool and garden Huntingtown (United States)

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.

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$1,375,000
7bedrooms
4bathrooms

By Ttr Sotheby's International Realty

Nearby
44

Property Cambridge (United States)

Escape to this rare waterfront retreat on Brooks Creek in Cambridge, offering Two Thousand ft of water frontage with sandy beaches, Private pier and Pond. The property features a Four Bedroom, Two and One half Bath Colonial-style main home plus a Three Bedroom, Two Bath guest house with great potential. Enjoy a large barn, pond, and multiple outbuildings, ideal for hobbies, storage, or fishing. With serene views, abundant space, and endless opportunities, this property blends waterfront living with country charm.

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$1,200,000
7bedrooms
5bathrooms
land 5.9ha

By Monument Sotheby's International Realty

Nearby
Contract pending
36

House with garden Tilghman (United States)

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 thoughtfully designed with a large center island, wet bar, and French door access to a beautiful screened porch overlooking the cove - perfect for morning coffee, quiet afternoons, or casual evening entertaining. The primary suite is a peaceful retreat, featuring an ensuite bath, walk-in closet, and convenient laundry cubby. An adjoining second bedroom offers flexibility as a private office, sitting room, or additional sleeping space. A third bedroom and full hall bath provide comfortable accommodation for guests. Additional highlights include a garden shed and a fully conditioned “she shed” with heat and AC, currently used as an art studio – a versatile space for hobbies or creative pursuits. Numerous improvements include a new roof, Pella architectural windows, encapsulated crawlspace, 3-zone Mitsubishi mini-split system, reverse-osmosis water filtration, and more. This thoughtfully updated cottage offers the best of Eastern Shore living with a relaxed, waterside feel.

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$580,000
2bedrooms
2bathrooms

By Ttr Sotheby's International Realty

Nearby
38

House Woolford (United States)

Improved Pricing! Was $875,000 now $849,500. Major Interior Renovations completed in 2022 (see attachment for full list). This beautifully updated and meticulously maintained, 3-bedroom, 2-bath home offers over 2,300 square feet of bright living space designed to capture the beauty of waterfront living. Panoramic water views greet you from nearly every room, with the living room highlighting breathtaking vistas of Fishing Creek. Two spacious living areas, each with a cozy fireplace, make relaxing or entertaining effortless year-round. The open gourmet kitchen features custom finishes, modern updates, and a built-in wine cooler—perfect for gathering with family and friends. The primary suite includes a private bath, while the open floor plan provides both functionality and seamless flow. Major systems have already been taken care of for you—roof replaced in 2018, HVAC replaced in 2022, and new thermostats installed in 2024—so you can move in with confidence. A new sprinkler system, plus all French gutter drains installed in 2025 and an improved Dry-Zone encapsulated crawl space further enhance efficiency and long-term protection. For added reassurance, the home includes transferable flood insurance and annual Dry-Zone, HVAC and pest control inspection contracts. Home is connected to public sewer, helping to simplify ownership from day one. Ideally located just a short distance from historic Cambridge, the Hyatt Regency Chesapeake Bay Golf Resort, and within easy reach of Easton, Oxford, and St. Michaels, you’ll also enjoy close proximity to Blackwater Wildlife Refuge—perfect for exploring nature, spotting eagles’ nests, or enjoying canoeing, biking, and hiking trails.

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$849,500
3bedrooms
2bathrooms

By Ttr Sotheby's International Realty

Nearby
Contract pending
50
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Property Park Hall (United States)

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.

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$1,495,000
3bedrooms
2bathrooms
land 1.2ha

By Ttr Sotheby's International Realty

Nearby
50
Video

House with pool Tilghman (United States)

PRICE IMPROVEMENT*** 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 living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! NEW ROOF & FIREPLACE 2024, NEW APPLIANCES 2019

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$1,150,000
4bedrooms
3bathrooms

By Ttr Sotheby's International Realty

Nearby
33

House Fishing Creek (United States)

Perfect Starter, Retirement Home, or Vacation Getaway! This charming 2-bedroom, 1.5-bath home features a spacious kitchen with breakfast bar, formal dining room, and a large living room with beautiful hardwood floors. A versatile flex space on the first floor could easily serve as a home office or cozy den. Additional highlights include a first-floor laundry room, ductless mini-split system, and enclosed front porch for year-round enjoyment. The 0.50-acre lot offers room to roam, plus a detached garage for extra storage or hobby space. Just minutes from Old Salty’s Restaurant, the General Store, and PL Jones Marina. Bring your finishing touches and make it your own!

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$184,000
2bedrooms
2bathrooms

By Ttr Sotheby's International Realty

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