St Leonard MD Real Estate & Homes for Sale

Wake up each morning with a cup of coffee in hand as the sun rises over the Chesapeake Bay - this is the lifestyle you've been waiting for. This beautifully remodeled four-bedroom, two-bath Cape Cod in Saint Leonard offers stunning water views and modern upgrades throughout. The open-concept kitchen is as functional as it is stylish, featuring all-wood cabinetry, sleek quartz countertops, and the perfect space to cook while taking in views of the Bay. Luxury vinyl plank flooring flows throughout the main living areas, blending durability with modern appeal, while the bedrooms offer plush wall-to-wall carpeting for added comfort. Comfort meets efficiency with a brand-new high-efficiency heat pump, complemented by a cozy gas fireplace for those chilly winter evenings. A tankless water heater provides hot water on demand, adding everyday convenience. The home also features a new architectural shingle roof for long-term peace of mind, while the exterior stands out with vertical siding, black gutters, and matching shutters that create striking curb appeal. A brand-new paved driveway will be installed soon, adding even more value and ease. With every detail thoughtfully updated, this home is truly move-in ready. Don't miss your opportunity - homes like this don't last long.

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 scenic vista's natural beauty! Inside, Anderson windows and doors bring in natural light and frame beautiful views of the water and surrounding trees. The main level is designed for both comfort and entertaining, with spacious gathering areas, warm wood details, and seamless flow from room to room. Upon entry you are greeted by expansive creek/nature views. The oversized main floor half bath is located just to the left. The large sunken living room boasts floor to ceiling windows and a cozy gas fireplace. Adjacent to the living room, the formal dining room features a built-in buffet area with a wine fridge and a glass door with access to the large rear deck. The chef's kitchen is well appointed with luxury appliances including a double wall oven, side by side refrigerator, built-in microwave, glass induction cooktop, bosch dishwasher and a warming drawer. The solid wood cabinets, quartz countertops, and custom tile backsplash add to the elegance of the space. Just off the kitchen, the family room features a wood stove insert with a 2-story brick facade, creating a cozy and inviting space to relax. The main level primary suite offers the ease of first-floor living along with a spacious bath featuring heated travertine tile floors and a jetted soaking tub, creating a true retreat. Upstairs, the home's spacious feel continues with two generously sized bedrooms, including a private upper-level primary-style suite with its own sitting area which overlooks the family room. The upper level primary bedrooms features include a walk-in closet, a private balcony and an en-suite bath which boasts a double sink vanity, ceramic tile flooring, a soaking tub, and a separate tiled shower. The hall bath, which serves the additional oversized bedroom on this floor, includes granite countertops and a skylight, bringing in soft natural light and adding to the airy feel of the upper level. The lower level expands the home's flexibility even further with a large recreation room or possible 4th bedroom/in-law suite, outdoor access to a wonderful patio area, a wood stove insert, a full bath, and a laundry area with storage space - ideal for entertaining, guests, hobbies, or everyday convenience. Outside, the property truly shines. A large Trex deck, accessible from both the kitchen and dining room, overlooks the private backyard and the gorgeous natural setting of St. Leonard Creek , creating the perfect place for outdoor dining, morning coffee, or evenings by the water. The detached two-car garage with an unfinished space above adds even more versatility. With water views, generous indoor and outdoor living areas, and a peaceful setting on St. Leonard Creek, this is a rare opportunity to enjoy the kind of waterfront lifestyle that feels like a getaway every day. Set up a showing ASAP so you don't miss this opportunity!

Where Privacy Meets Presence | Some homes make you pause at the door. | This is one of them. | Set on over five acres of mature woodland in Saint Leonard, 4200 Henry Court is a renovated dramatic estate that commands attention from the moment you arrive. The bold double entry doors, brick exterior, and Juliet balcony above the portico signal something exceptional before you ever step inside. | And then you do... | A soaring two story foyer opens into one of the most dramatic living spaces in Calvert County. Hardwood floors stretch beneath cathedral ceilings, a statement staircase rises to the upper level, and natural light pours in from every direction. The great room anchors the main level with generous proportions designed for both everyday ease & effortless entertaining. A dedicated home office (flex room) with wooded views brings calm focus to the day. The layout offers a very rare flexibility across 4 bedrooms and 3.5 baths. A main level in law suite with full bath, multiple formal and casual living areas, and 3 fireplaces create warmth & character throughout. The kitchen sits nicely between the great room and the formal dining for seamless flow that today's buyers expect. Upstairs, the owner's retreat delivers!! A private fireplace, spa bath with soaking tub, and generous proportions make this a true exceptional escape. A Juliet balcony along the upper hallway frames elevated views of the surrounding tree line, quiet, and quite cinematic. The finished walkout basement extends the home further still, featuring a built in sauna, direct patio access, and the kind of flexible space that becomes whatever you want or need it to be. Outside, over 5+ wooded acres create the privacy that most buyers only dream about. A rear deck and lower patio offer multiple settings for gathering or just sheer privacy. No neighbors pressing in. No noise. Just trees, sky, and the kind of peace that has real value. Renovated in late 2025 this home has thoughtful updates throughout. |Welcome to 4200 Henry Court | | KEY HIGHLIGHTS | 4 bedrooms | 3.5 baths | Over 6,000 sq ft on 5+ wooded acres | Renovated late 2025 | Soaring two story family room | Dramatic entry staircase | Three fireplaces | Owner's suite with fireplace and spa bath | Main level in law suite | Home office with wooded views | Finished walkout basement with sauna | Rear deck and lower patio | Two car garage | 25 miles to NAS Patuxent River via MD-4 | Close to entertainment, shopping, restaurants, hospital, and more. Come Tour Today!

No HOA. Total square footage of 3520, which includes the 1120 sq ft apartment. The house's total sq ft is 2400. 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, and just across the water sits Vera's Restaurant, a local favorite you can reach by boat for dinner, drinks, or a relaxed afternoon on the dock. 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 Calvert County Forestry Program, has many tall pines, poplar, and other trees , making this property secluded and private. A large three-car garage includes a half bath and is topped by a spacious apartment with a bedroom and a full kitchen. In the garage there's built-in shelving, 3 massive bays, making it functional for hobbies, storage, or extended stays. 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. 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 by the original contractor, Stevenson Pools. Aquapro Pools is installing a new automatic pool cover, bringing a polished finish to the backyard setting. 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.

Beautiful and meticulously maintained home on over 2 private acres. The house boasts approx 3300 sq ft of finished space...perfect for entertaining! The main level boasts a well-appointed kitchen and breakfast area overlooking a step down family room. You'll also find a formal dining room great for holidays or special occasions and a formal living room. The upper level offers a generous primary suite with a large walk in closet & a luxurious en-suite bath, along with three additional well-sized bedrooms, a full bath, and the laundry. The finished basement includes a versatile bonus room with a closet, perfect for guests, a home office, or additional living space. Enjoy a private backyard that backs to woods, providing a peaceful and secluded setting. Attached garage is big enough for 2 small cars, or 1 large car. No HOA! Enjoy country living with the benefits of shopping, dining, theaters, and more just a short drive away!

Perched atop a scenic hill in the sought-after community of Oriole Landing, this beautiful home at 6115 Canary Lane in St. Leonard offers the perfect blend of comfort, space, and charm. This spacious residence features 4 generously sized bedrooms and 3.5 bathrooms, providing plenty of room for both everyday living and entertaining. A welcoming front porch sets the tone, offering a peaceful spot to relax and take in the views, while the large back porch, deck, and pool create an ideal space for outdoor gatherings, summer cookouts, or simply enjoying the surrounding nature. Inside, the home is thoughtfully designed for convenience and functionality, boasting two separate laundry areas - one conveniently located just off the garage for easy everyday use, and another in the basement for added flexibility. The layout supports both busy lifestyles and comfortable living, with ample room to spread out. With its prime location, desirable neighborhood, and well-appointed features, this home combines privacy, practicality, and inviting spaces - making it a standout opportunity in Oriole Landing.

Experience breathtaking, panoramic views of the Chesapeake Bay in this beautifully updated coastal retreat. Wake each morning to stunning sunrises, spend your days strolling the shoreline in search of shark's teeth, and unwind in the evenings as cruise ships drift by on the horizon. The main level and exterior have been thoughtfully renovated within the past six years, featuring new windows, updated plumbing and electrical systems, Hardie board siding, and a new architectural shingle roof. A welcoming foyer opens to a gourmet Kitchen designed for both function and style, complete with a spacious center island, wet bar, abundant cabinetry, and generous workspace - all perfectly positioned to capture sweeping water views. The expansive bayfront Great Room seamlessly blends Living and Dining areas, highlighted by oversized windows and a marble-surround gas fireplace for cozy evenings. Hardwood floors run throughout, adding warmth and elegance. A stunning sunroom with two walls of glass fills the space with natural light and features built-in bookcases and French doors - an ideal setting for relaxation or showcasing your indoor garden. You and your plants will flourish in this space! The main level offers two generously sized bedrooms with cedar-lined closets, along with a beautifully appointed full bath featuring a whirlpool tub, custom walk-in shower, and thoughtfully designed storage. A third bedroom - currently used as an office - boasts spectacular views and its own private entrance via a charming garden walkway. A spacious half bath completes the main level. Highlights include solid wood doors, ceiling fans, and Hunter Douglas blinds throughout the bayfront windows, creating a refined yet comfortable living environment - all on one level. Annual service contracts on furnace and HVAC. The lower level adds flexibility with a finished office space featuring water views and a full bath with shower.. The remaining area offers endless potential to customize, with the existing plumbing, from a former wet bar, still in place. A brand-new sliding door opens to the backyard, providing another peaceful spot to take in the bay views. Outdoors, the property continues to impress with beautifully landscaped grounds, gardens, and a unique private labyrinth - circuitous path for walking, meditation and relaxation. A storage shed is also included. Enjoy a short stroll to the beach for swimming, crabbing, or fossil hunting. Boating enthusiasts will appreciate nearby Flag Harbor Marina within the Long Beach community, offering deep-water slips for purchase and quick access to the Bay. Flag Ponds Nature Park, known for its scenic cliffs, beach access, and fossil hunting, is also within walking distance. Road fees of $75/yr Civic Association fee of $125/yr giving you Beach access. Whether you're seeking a full-time residence or the perfect weekend escape, this move-in-ready home offers the ideal blend of comfort, style, and coastal living. Summer is calling - don't miss this exceptional opportunity. Better yet, NO Bay Bridge to cross!!!

OPEN HOUSE Saturday, April 18th | 10am-12pm! Opportunity awaits in this well-maintained 3-bedroom, 1-bathroom home in Saint Leonard, MD! Offering just over 1,200 square feet of comfortable one-level living, this property sits on a spacious corner double lot, a rare find in the area. Enjoy outdoor living with a lovely side deck that wraps around the back of the home to a covered rear deck, complemented by newly installed siding and ceiling. A new septic was installed 3 years ago! Located just a short walk to the beach, this home offers the perfect blend of location and potential. This home presents a fantastic opportunity for buyers looking to make a home their own or investors looking to add to their portfolio. This would make a great rental, as well! Carpets have been professionally cleaned. The whole house is currently being painted.

Completely turnkey and ready for you to move right in! This charming 2 bedroom, 1 bath log cabin has been refreshed with brand-new, easy-to-maintain flooring and fresh paint throughout, creating a clean and inviting feel from the moment you step inside. The kitchen cabinets have been beautifully updated with a fresh coat of paint, adding to the home's overall appeal.Offering the perfect blend of rustic charm and coastal living, this home feels like a peaceful mountain retreat - yet the beach is just a short five-minute walk away. Spend your evenings unwinding by the fire or start your mornings with coffee surrounded by nature. The thoughtfully landscaped yard comes alive with beautiful flowers and plants that bloom throughout the seasons, making every day feel like a getaway. Additional parcel conveys with hom.

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 room with soaring ceilings and abundant natural light. Upper-level primary suite retreat with gas fireplace, sitting area, dual walk-in closets, and spacious bath. Convenient upper-level laundry with direct primary suite access. Finished walk-out lower level includes theater room, custom bar crafted from on-site wood, secondary kitchenette, and fitness or hobby room. Outdoor living features a heated 9-ft deep gunite pool with diving rock and fountain. Community marina and boat ramp on Saint Leonard Creek off the Patuxent River for boating, fishing, and waterfront recreation. Private acreage. Luxury features. Southern Maryland lifestyle.

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 has been designed to give buyers the open concept they have been looking for along with good sized bedrooms to boot. Oversized 1.5 Car Garage is perfect for storing your car and having a workshop! Engineering is already under way shortening the wait time! Call to discuss standard features/upgrades! It's hard to find new construction w/ Water Access and Bay Views under $600k!!! Reach out now to be in your new home by the second half of 2025! Inquire ASAP Before this opportunity is GONE!

Come and see this beautifully renovated property! As you step inside, you're welcomed by a stunning, updated kitchen featuring modern cabinets and newer appliances. Enjoy the seamless flow into the open-concept living and dining areas - perfect for entertaining or relaxing. Step outside onto the spacious deck and take in the serene backyard, ideal for outdoor gatherings. Upstairs, you'll find three comfortable bedrooms and two full bathrooms. Downstairs offers even more living space, including a full bathroom, a cozy family room, a utility room, and a dedicated laundry room. The basement features a walkout level that leads directly to the beautifully landscaped backyard - perfect for enjoying both comfort and convenience. Enjoy the renovated outdoor pool and fishing along the beautiful Patuxent River

Welcome to a well crafted custom-built Colonial home nestled on a serene .5790-acre cul-de-sac lot with Chesapeake Bay Access. Built in 1997, this SMECO-certified energy-efficient property offers approximately 3,800 square feet of living space, modern updates, and access to two private beaches on the Chesapeake Bay. Key Features: Elegant Design: Two-story Colonial style with vinyl siding, vaulted ceilings, skylights, and arched windows for abundant natural light. First Floor: Tile and hardwood floors, a spacious living room with a stone propane fireplace, formal dining room with crown molding, a den with French doors, two vaulted decks, a custom sunroom, and an updated kitchen with granite countertops, stainless steel appliances, and a breakfast nook. Second Floor: Luxurious master suite with vaulted ceilings, a walk-in closet, and a spa-like tiled bathroom featuring a soaking tub and glass shower. Two additional bedrooms, a second full bathroom, and versatile spaces for an office or study. Newly recarpeted in 2023. ?Finished Basement: Includes two bedrooms, a large living area, kitchen, walk-in closets, and a decked patio. This area could be an in-law or other family member living area. OR....Maybe a rental and income potential. There is a set up even if desired to have a home business of a beauty or barber shop. Just so much flexibility for you. Lowest level also features a humidity-controlled safe room for secure storage. ?Outdoor Living: Covered front porch, landscaped grounds with rhododendrons, hollies, azaleas, and camellias, and a detached electrified storage shed. ?Garage: Finished double garage with A/C, workbenches, and built-in cabinets. ?This home offers the perfect blend of comfort, style, and functionality, with modern updates like newly installed 6" gutters and downspouts. Enjoy the tranquility of wooded surroundings while being just steps away from the Chesapeake Bay. Schedule today to plan your Holiday Season in your own home!

Welcome to your dream home in the heart of St. Leonard! This stunning 4-bedroom, 3.5-bathroom residence offers the perfect blend of comfort, style, and functionality - nestled in a quaint and calming neighborhood just minutes from beautiful Chesapeake Bay beaches and a nearby primary school. On the main level, you'll find a thoughtfully designed layout featuring a kitchen with ample counter space, modern appliances, and room for gathering - ideal for both everyday living and entertaining. The spacious family room and formal dining area are filled with natural light, creating a warm and inviting atmosphere throughout. Upstairs, retreat to find the grand primary suite, featuring a spa-like ensuite bathroom with plenty of room to unwind. The fully finished basement expands your living space even further with a dedicated theatre room, home office, and a convenient kitchenette - ideal for entertaining guests or multigenerational living. Enjoy peace of mind with a brand-new roof installed in 2025, and relish the outdoors in the massive, fully fenced backyard, offering privacy, space, and plenty of room to relax, garden, or play. This home combines modern amenities with a warm, community-oriented setting - making it a rare find in St. Leonard. Don't miss your chance to call this exceptional property your own!

"DO NOT KNOCK ON DOOR" Tenant occupied Investment opportunity to purchase 2 homes and a lot, along with two commercial buildings. All five properties are being sold together at a discount. Also seller is willing to hold some financing. This listing is for the three residential units. The two commercial are listed together.

Charming Home in Calvert Beach Estates Welcome to 5440 Bayview Ave, a 3-bedroom, 1-bath home on a corner lot in the peaceful Calvert Beach Estates. This bright, move-in-ready gem is filled with natural light and set amidst beautifully landscaped gardens. Outside, enjoy a spacious deck, cozy fire pit area, and pergola, perfect for entertaining or relaxing. The side yard is ready for evenings by the fire, and the community beach and pier are just a short walk away. This home boasts major recent upgrades for your peace of mind, including a new high efficiency HVAC (2023), hot water tank (2023), 50-year roof (2022), room thermostats (2023), newer stove and dishwasher (2024), septic pumped (2025), and fresh paint throughout. Enjoy coastal living in this serene move-in ready home! Schedule a visit today!

Just a short walk to the Beach! This Great Contemporary Home offers 5 Beds/2.5 Baths, an Open Floor plan, Stainless Steel Appliances, Granite Kitchen counters, Hardwood Floors throughout, Spiral Stairs lead up to the Owners Suite and down to the Basement! The Roof was replaced in 2017 w/ 45 yr Architectural shingles, Hot Water heater was replaced 2018, Sewage ejector pump was replaced 2018, and New Master bath Shower 2018!

TO BE BUILT NEW CONSTRUCTION. Beautiful lot Co- Marketed with Caruso Homes. This Model is the -----DEERFIELD--- The Deerfield is a four-bedroom floor plan with the option to add an In-Law suite downstairs. Enjoy gathering with family and friends in this open concept home which features a large great room that flows right into the kitchen. A 9-foot island and plenty of counter space will please the chef and a formal dining room is perfect for serving up family meals. Upstairs, the large owner's suite offers an ensuite bath with his and her walk-in closets. Three additional bedrooms, a hall bath and a convenient laundry room complete the second floor. An optional third floor provides a loft and full bath for additional living space. Plenty of options and upgrades are available to personalize this home and make it your own! --- Buyer may choose any of Caruso's models that will fit on the lot, prices will vary. Photos are provided by the Builder. Photos and tours may display optional features and upgrades that are not included in the price. Final sq footage are approx. and will be finalized with final options. Upgrade options and custom changes are at an additional cost. Pictures shown are of proposed models and do not reflect the final appearance of the house and yard settings. All prices are subject to change without notice. Purchase price varies by chosen elevations and options. The price shown includes the Base House Price, The Lot and the Estimated Lot Finishing Cost Only. Builder tie-in is non-exclusive. Associated Land listing #MDCA2013614.

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!