Saint Leonard Real Estate

Saint Leonard Real Estate

Welcome to Saint Leonard, Maryland – a hidden gem nestled in the heart of Calvert County! This charming community offers a perfect blend of serene waterfront living and vibrant local culture, making it an ideal place to call home.

Saint Leonard is situated along the picturesque shores of the Chesapeake Bay, providing residents with breathtaking views and a wealth of recreational opportunities. From boating and fishing to kayaking and paddleboarding, the area's natural beauty invites outdoor enthusiasts to explore its many waterways and lush landscapes. The nearby Calvert Cliffs State Park is a must-visit, where you can hike scenic trails and hunt for fossils along the stunning cliffs.

The community is rich in history, with roots dating back to the 17th century. Visitors and residents alike can enjoy the quaint charm of local shops, eateries, and historical landmarks that reflect the town's heritage. Saint Leonard's welcoming atmosphere fosters a strong sense of community, making it easy to meet neighbors and forge lifelong friendships.

Families will appreciate the area’s highly-rated schools and safe neighborhoods, while retirees can relish the peaceful lifestyle that Saint Leonard offers. With its proximity to larger cities like Annapolis and Washington, D.C., residents can enjoy the tranquility of small-town living without sacrificing access to urban amenities.

Whether you're looking for a cozy waterfront home or a spacious family residence, Saint Leonard has something for everyone. Come experience the charm and warmth of this delightful Maryland community, where every day feels like a vacation!

Newest Listings in Saint Leonard

5 Beds ⋅ 5 Baths

MOTIVATED SELLER- Offering buyer credit of $20,000 with acceptable offer. Nestled in the serene community of St. Leonard Shores, this charming Colonial home offers a perfect blend of comfort and peace. Built in 1988, this residence boasts a generous 3,979 square feet of living space. Step inside to discover beautiful wood oak floors, an open floor plan connecting the kitchen, with upgraded granite countertops, to the family room, making it an ideal space for gatherings. Enjoy cozy evenings by one of the two brick fireplaces. The home also features a formal dining room, perfect for hosting dinner parties, and a spacious living area that invites relaxation. The primary suite offers an en suite bathroom while the additional 4 bedrooms provide ample space for guests. The partially finished walkout basement includes a bar and presents endless possibilities for customization, whether you envision a recreation room, additional bedrooms, or a personal gym. Outside, the property spans 2.39 acres, providing a private, partially fenced, and secluded oasis surrounded by trees. Enjoy the outdoors on the expansive deck, perfect for summer barbecues or quiet evenings under the stars. A large newly renovated shed provides excellent outdoor storage. In addition this home comes with several improvements including a new fiberglass shingle roof (2024), a new septic system (2023), new hot water heater and oil tank, and a whole house back up generator powered by an underground propane tank. Seller is also including a 1 year 2-10 home warranty. The community amenities include a boat ramp, picnic area, and pier/dock, making it easy to embrace the waterfront lifestyle along the Patuxent River and Saint Leonard Creek. This property is more than just a house; it's a place to create lasting memories.

1151 Thompson Ct, Saint Leonard

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990

4 Beds ⋅ 4 Baths

Professional photos coming Aug 8th. VA assumable mortgage at 2.625%! Welcome to 1054 Kings Creek Dr., Saint Leonard, MD 20685 — a beautifully maintained Colonial in the sought-after Kings Creek Estates community, offering nearly 3,200 finished square feet, major recent capital improvements, and a private, wooded setting on more than one-half acre. Thoughtfully maintained, this home offers the ideal combination of generous living space, modern mechanical upgrades, and the privacy today's buyers are seeking. The inviting main level features hardwood floors; a spacious family room with a gas fireplace; formal dining room; dedicated home office, and an updated kitchen with granite countertops, stainless steel appliances, pantry, breakfast area, and recessed lighting. Upstairs, the spacious primary suite offers a walk-in closet, double vanity, soaking tub, and separate shower. The three additional bedrooms provide comfortable accommodations for family and guests. The finished walkout basement significantly expands the home's versatility with a large recreation room, media room, fifth bedroom or flexible bonus space, full bathroom, and abundant storage — ideal for multigenerational living, long-term guests, a home gym, hobby space, or remote work. Major capital improvements provide exceptional value and peace of mind, including a new roof (2018), dual HVAC systems replaced in 2024 and 2025, basement flooring (2022), kitchen sliding glass door (2022), washer and dryer (2023), and a newer refrigerator, helping reduce future maintenance costs while making this home truly move-in ready. The outdoor living is equally impressive with a covered front porch, spacious rear deck, fenced back yard, mature trees, oversized two-car garage, and a storage shed. Situated on a private lot backing to trees, the property offers the perfect balance of peaceful surroundings and everyday convenience. Enjoy easy access to many of Southern Maryland's premier attractions, including: Solomons Island, Calvert Cliffs State Park, Flag Ponds Nature Park, Jefferson Patterson Park & Museum, Chesapeake Bay beaches, local marinas, shopping, restaurants, wineries, breweries, and public boat ramps. Enjoy endless opportunities for boating, fishing, hiking, waterfront dining, and year-round outdoor recreation. Commuters will appreciate the convenient location, approximately 20 miles to NAS Patuxent River, 37 miles to Joint Base Andrews, 42 miles to Annapolis, and 48 miles to Washington, DC, making this an exceptional choice for military personnel, government employees, and anyone seeking more space while remaining connected to major employment centers. Offering nearly 3,200 finished square feet, including a walkout basement, dedicated home office, oversized two-car garage, major capital improvements, and a private wooded setting in one of Calvert County's most desirable neighborhoods, 1054 Kings Creek Dr. presents a rare opportunity to own a move-in-ready home that perfectly combines space, comfort, quality, and location.

1054 Kings Creek, Saint Leonard

Listing courtesy of RE/MAX One. Contact: 4105356291

4 Beds ⋅ 5 Baths

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 of riprapped shoreline, and over 6 private acres set the stage for a true waterfront lifestyle. The creek opens easily to the Patuxent River. Many people say the Best Crabs in Maryland are found in St. Leonard Creek, and this pier is a place to find them! The pier is built for serious water use. New Trex decking gives it a clean, low-maintenance finish. A covered boathouse, multiple slips, floating dock, dock shed, and room to move make this ideal for boaters who want everything in one place. Whether it’s fishing at sunrise or heading out for a cruise, this setup is ready. The 6.24 acres, five of which are in a Maryland Forestry Program, has many tall pines, poplar, and other trees , making this property secluded and private. A large three-car garage built in 2017 topped by a spacious apartment with a bedroom and a full kitchen. On the main level of the garage there's a half-bath, built-in shelving, 3 massive bays, making it functional for hobbies and storage. This opens up options. Live in the apartment while building your dream home, or use it as a private guest space. The main home has been well cared for over the years and offers a solid foundation for someone ready to make it their own and was renovated in ‘97. You can move in now and update at your own pace without pressure. The large gunite swimming pool was redone in the summer of 2024 . Recently installed was a new automatic pool cover. Additional outbuildings include a machine shed and a smaller shed, giving you room for equipment, projects, or expansion of how you use the land. Location matters here, too. You are minutes to Broomes Island, Solomons Island, and local marinas. Easy access to Route 4 keeps commuting to Prince Frederick, Annapolis, DC, or Pax River within reach while still feeling completely removed once you are home. This is not just a house on the water. It is space, shoreline, and flexibility. Use it as it stands, reimagine it over time, or build something entirely new. Properties like this do not come along often, especially with this kind of frontage and deep water access.

2237 Garrity Rd, Saint Leonard

Listing courtesy of Deep Roots Real Estate. Contact: 4439676687

4 Beds ⋅ 3 Baths

Welcome home to this spacious 4-bedroom, 2.5-bath home, situated on over an acre, offering a traditional floor plan designed for comfortable living and effortless entertaining. The main level features a formal living room, dining room, and a welcoming family room, providing plenty of space for gatherings both large and small. The kitchen flows seamlessly into the living areas, creating a functional layout for everyday living. Step outside to the deck, perfect for relaxing, grilling, or enjoying the private backyard setting. The unfinished basement offers a blank canvas with endless potential for additional living space, a home gym, workshop, or storage. Combining classic charm, generous living areas, and privacy, this home is ready for its next owner to make it their own.

5335 Majesty Ln, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

4 Beds ⋅ 4 Baths

Some homes make you pause at the door. This is one of them. || Renovated in 2025, this custom built home is Set on 5+ wooded acres offering privacy, presence, and over 6,000 sq ft of beautifully updated living space. 4 bedroom, 3.5 bath estate features a soaring two story foyer, dramatic staircase, cathedral ceilings, hardwood floors, and a light filled great room designed for everyday comfort and entertaining. || The flexible layout includes a main level in law suite with full bath, a dedicated home office with wooded views, multiple living areas, and three fireplaces throughout. Upstairs, the owner’s suite feels like a private retreat with its own fireplace, spa bath, generous proportions, and elevated views of the surrounding tree line. || The finished walkout basement adds even more room to live, gather, and unwind with flexible space, a built in sauna!!!, and direct access to the lower patio. Outside, the rear deck, patio, and mature woods create the kind of quiet privacy buyers hope to find but rarely do. || Close to shopping, dining, entertainment, hospital access, and approximately 25 miles to NAS Patuxent River via MD 4, this home delivers space, privacy, and convenience in one unforgettable setting.

4200 Henry Ct, Saint Leonard

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

3 Beds ⋅ 3 Baths

Discover the charm of this split level, nestled on a generous 1.0128- acre lot in mid Calvert County. With 1,977 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ensuring ample room for relaxation and privacy. The home layout is perfect for both entertaining and everyday living with a seamless flow between rooms. The updated Kitchen (20 x 19) has beautiful cabinetry, porcelain tile flooring, updated GE Appliances, convection double oven/microwave, recessed lighting, fresh paint. Upgraded living room and upper hallway to hardwood flooring (Bloodwood). The Family room upgraded to laminate flooring. All bathrooms have been updated. Outside, the expansive rear yard offers so many options. Host many outdoor activities or peaceful retreats. Large composite deck with sunshade canopy system over part of deck, large hardscape patio with hot tub with electric and outdoor lighting with 5 foot tall metal ornamental fencing around back yard, two sheds (12x 14) (12x16), paved driveway with plenty of parking. Leaf Guard gutter installed, insulated Vinyl Siding, 30 year architectural shingles, encapsulated crawl space, blown in insulation upstairs attic R 49, fully insulated garage, upgraded Insulated Vinyl Siding. Geothermal heating/ac.

5031 Timber View, Saint Leonard

Listing courtesy of RE/MAX One. Contact: 4105356291

3 Beds ⋅ 3 Baths

Coming soon! So many things to fall in love with here at this two level rambler located on 3 acres in a quiet community with NO HOA. Head through the one of a kind front door with custom stained glass that carries through to the kitchen with matching windows to the kitchen area. Family room opens to the dining room and the renovated kitchen with spacious breakfast bar, stainless steel appliances including a fridge with a built in I pad on the door where you can watch tv, use it to keep track of all your household needs etc. Spacious pantry with gorgeous doors give so much character. Updated counters, back splash, new floors and light fixtures throughout. Just off of the dining area is a covered side porch where you will spend evening relaxing and enjoying being surrounded by nature. Head down the hallway to find three bedrooms and two full baths including a private primary suite with full bath. Sellers have added a pull down ladder for easy access leading to attic space. The lower level includes a spacious rec room, bonus room currently used for storage, laundry room and workshop. Walk out to your back yard oasis with ground level deck w/shaded cover and lights, lily pond, gazebo, fire pit and more! Detached and oversized two car garage has automatic door openers and plenty of storage. Find even more storage with the garden shed and the metal storage container. Whole house generator, wired for rv hookup , covered grilling deck, mature apple and pear trees, strawberries, mint, lavender and more. Plenty of space to enjoy a vegetable garden, store boats and campers or just enjoy being outdoors. Water softener, new water heater, newer hvac, and more. Truly nothing to do but move in and enjoy your home.

5401 Cove View Dr, Saint Leonard

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

3 Beds ⋅ 3 Baths

Nestled in the charming Long Beach Heights community, this delightful split foyer home offers a perfect blend of comfort and functionality. This residence boasts a spacious layout with three inviting bedrooms and two and a half bathrooms, making it an ideal retreat for those seeking a warm and welcoming atmosphere. The heart of the home is the country-style kitchen, complete with modern appliances including a built-in microwave, dishwasher, and electric oven/range, ensuring meal preparation is a breeze. The adjoining breakfast area is perfect for casual dining, while the formal dining area sets the stage for memorable gatherings. Natural light floods the home through double-pane, low-E windows, providing energy efficiency and a serene ambiance. The primary suite features a walk-in closet and a private bath, offering a personal sanctuary to retreat to at the end of the day. The fully finished basement, accessible via a connecting stairway, adds valuable living space and includes a laundry area for convenience. With an attached oversized 2 car garage and additional storage options, this home is designed for practicality and ease. Outside, the property sits on a generous 0.44-acre lot, providing ample space for outdoor activities or gardening. Enjoy the fresh air on the deck or porch, perfect for morning coffee or evening relaxation. Long Beach is not just a place to live; it's a community that thrives on connection and convenience. Residents enjoy access to nearby parks, perfect for leisurely strolls or picnics, and a variety of local amenities that enhance daily living. The neighborhood is known for its friendly atmosphere and well-maintained surroundings, making it a wonderful place to call home. Pay the minimum civic association membership fee and enjoy the 2 private beaches. Looking to have an event and need more space pay the small fee and rent the community center. For an added convenience Flag Harbor Boatyard is close by. This home is more than just a property; it's a place where memories are made and cherished. Experience the warmth and comfort of Long Beach-your new beginning awaits!

5760 Eucalyptus Dr, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

4 Beds ⋅ 4 Baths

Welcome home to 4585 Mattapany Road, where peaceful country living meets everyday convenience. Nestled on nearly 1.5 private acres in the desirable Woodhaven community, this beautifully maintained Colonial offers approximately 3,300+ finished square feet of thoughtfully designed living space across three finished levels. The main level features formal living and dining rooms, a welcoming family room with a cozy fireplace, and a generously sized eat-in kitchen with upgraded stainless steel appliances. Whether you’re entertaining friends or enjoying a quiet evening at home, the thoughtfully designed floor plan offers comfortable spaces for every occasion. The inviting covered front porch is the perfect place to enjoy your morning coffee while taking in the peaceful surroundings, while the expansive rear deck overlooks the private backyard—a wonderful setting for entertaining and making lasting memories. Upstairs, you’ll find four generously sized, light-filled bright bedrooms, all featuring beautiful hardwood flooring. The spacious primary suite offers a walk-in closet and an en-suite bath with a double vanity, soaking tub, and separate shower. A full hall bath and a conveniently located upper-level laundry room complete the second floor. The fully finished walk-out lower level offers exceptional flexibility with a spacious recreation room featuring high quality surround sound, a full bath, a wet bar with cabinetry and countertop space, and an oversized bonus room. Whether you need additional space for extended family, visitors, a home office, media room, fitness area, or hobbies, this versatile level adapts beautifully to your lifestyle. Let your imagination run wild! Recent improvements include a new roof (2020), upgraded stainless steel kitchen appliances, a newer washer and dryer, and additional mechanical updates, providing added peace of mind for years to come. Surrounded by mature trees, the property offers exceptional privacy and a peaceful setting to enjoy nature. The attached two-car garage and expansive driveway provide parking for at least 8 or more vehicles, making it ideal for entertaining, multiple drivers, boats, trailers, or recreational vehicles. Conveniently located just minutes from shopping, dining, schools, Solomons Island, and Patuxent River Naval Air Station, with an easy commute to Joint Base Andrews, Washington, D.C. and Annapolis this move-in-ready home offers the perfect balance of privacy and convenience. Discover the space, flexibility, and tranquility that make 4585 Mattapany Road a wonderful place to call home.

4585 Mattapany Rd, Saint Leonard

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

4 Beds ⋅ 3 Baths

The original owner / contractor incorporated upgrades in the construction valued at $250,000 over lesser choices for his forever home. Custom built colonial with Water Access, Brand New Roof with a transferable 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. With 4 bedrooms and 2.5 baths, situated on a corner lot with 3.5 acres, this beautiful property offers an incredible blend of privacy and nature. Complete with access to the St. Leonard creek, this home is nestled in a close-knit community with frequent neighborhood parties and wine tasting events. Enjoy the convenient access to the community boat ramp (right across the street!), boat slips, pier, and picnic area are also just steps away. The perfect home for water enthusiasts, nature lovers, and those who appreciate the builders commitment to quality. A double wide foundation is one of the many material upgrades to ensure lasting stability for generations to come! The geothermal HVAC system provides incredible efficient heating and cooling, combined with Anderson windows, solid wood 6 panel doors, and the show stopping oak spiral staircase to highlight the craftsmanship and attention to detail. Attached two car garage and the detached garage give you, the new owners, plenty of parking and storage options, or the potential for a separate home office or workshop. The main level showcases beautiful hardwood floors, elegant crown molding, a formal living room, dining room, home office, and a sunlit family room leading to the patio area and and backyard. Enjoy entertaining family and friends on the back patio and deck, in the park-like setting, with the beautiful flowering trees, serene nature and privacy this home offers. The gourmet kitchen impresses with plenty of space, stainless steel appliances, granite countertops, ample cabinetry, and eat-in kitchen. On the upper level, you'll find the expansive primary suite, with a sitting room (perfect for a secondary office, nursery, or dressing room!), and not one, but two walk-in closets. Three more generously sized bedrooms and a full bath complete the upper level. The finished basement provides a versatile space for a recreation room or guest suite area, with a rough-in for a future bathroom and tons of storage.

7421 Stone Ct, Saint Leonard

Listing courtesy of Keller Williams Flagship. Contact:

3 Beds ⋅ 2 Baths

Welcome to 1430 Plateau Road in Saint Leonard, Maryland—a charming property that offers the perfect blend of comfort, privacy, and the beauty of Southern Maryland living. This well-maintained 3-bedroom, 2-bathroom home features a functional floor plan designed for everyday living and entertaining. The spacious living areas provide plenty of natural light, while the thoughtfully designed kitchen offers ample cabinetry and workspace for preparing meals. The primary suite includes a private full bath, creating a comfortable retreat at the end of the day. Enjoy the peaceful outdoor setting with room to relax, garden, entertain, or simply take in the surrounding scenery. Whether you're enjoying your morning coffee on the porch or hosting a backyard gathering, this property offers the flexibility to make the outdoor space your own. Conveniently located near local parks, marinas, shopping, dining, and commuter routes, you'll appreciate the balance of tranquility and accessibility this location provides. Don't miss the opportunity to make this beautiful Saint Leonard property your next home. Schedule your private showing today!

1430 Plateau, Saint Leonard

Listing courtesy of IGOLDENONE REALTY AND CONCIERGE LLC. Contact:

5 Beds ⋅ 3 Baths

Vacation year-round at this charming Chesapeake Bay waterfront retreat, offering breathtaking panoramic views, walkable private/community-only beach access, and access to the community boat ramp for enjoying life on the water. From the moment you arrive, the curb appeal and landscaping set the tone. Inside, beautiful hardwood flooring flows throughout the home, leading into an open and inviting layout. The living area features a cozy wood-burning fireplace with built-in shelving and opens seamlessly to the dining space, where large windows capture stunning water views. A sliding glass door leads to the expansive rear deck, creating an effortless indoor-outdoor flow for relaxing or entertaining. Just off the family room, the kitchen offers ample cabinet space and recessed lighting. Designed with flexibility in mind, the home offers a spacious primary suite with two closets, a private attached bathroom, and direct access to the rear deck overlooking the Chesapeake Bay. The perfect spot for morning coffee, evening sunsets, or simply taking in the view! An additional spacious bedroom is located nearby with access to a full bathroom, while two more rooms provide options for bedrooms, game rooms, office space, or whatever best suits your needs. One of these rooms, currently used as an entertainment space with a built-in murphy bed, opens to a screened-in porch with composite decking, adding even more room to relax and enjoy the setting. A convenient laundry area completes this level. Upstairs, a private loft or second primary-style retreat offers an additional bedroom, spacious walk-in closet, and full bathroom. Step out onto the attached upper-level sun deck for another incredible vantage point overlooking the Chesapeake Bay. With the community beach just a two-minute walk from the front door, this home offers the waterfront lifestyle you have been looking for with space, views, and access to the best of Chesapeake Bay living.

5424 Beach Dr, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

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