Saint Leonard MD Real Estate & Homes for Sale

This private cedar cottage is situated on a quiet cul-de-sac within view of boats docked at Flag Harbor Yacht Haven. The cottage has two levels with bedrooms and bathrooms on both levels. The kitchen has an open floor plan to the dining area and living room. It has been completely painted inside as well as new luxury vinyl planking (LVP) in place. Use it as your primary residence or your weekend retreat. Wouldn't it be wonderful to have your boat docked a block away with the Chesapeake Bay right outside of the marina? Don't let this opportunity slip away!

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 inside to discover a warm and inviting interior, highlighted by a cozy gas fireplace that serves as the heart of the living area. The galley kitchen is equipped with a wall oven, cooktop, and a refrigerator/freezer, making meal preparation a delight. A charming breakfast area and a formal dining room provide versatile spaces for gatherings, while a second kitchen in the basement adds convenience for separate living. The finished basement, accessible via a side entrance and interior entrance, offers additional living space and a workshop, catering to various lifestyle needs. Outside, the property boasts a generous 0.63-acre lot with no thru street, ensuring privacy and tranquility. Enjoy breathtaking water and bay views from your own private beach, perfect for relaxing, fishing or launching your watercraft from the private community beach and ramp. The sandy beach invites leisurely strolls and fishing adventures, while the expansive outdoor space is ideal for gatherings or quiet evenings under the stars. With a detached garage accommodating two vehicles and driveway parking, this home combines functionality with coastal charm. Experience the ultimate bayfront lifestyle in this remarkable property. Within a short commute to shopping and entertainment. Close Proximity to Washington DC, Joint Base Andrews, Pax River and Annapolis.

CALLING ALL CASH BUYERS, INVESTORS AND BUILDERS! This 3 Bedroom, 1.5 Bath 1975 Gibraltar manufactured home with an oversized 1-car detached Garage on .26 acres is located on a quiet street in Long Beach on the Bay (a Chesapeake Bay beach community). Although this well-cared-for home has been Seller's primary residence for 40 years, tradition government-backed financing is not an option since it was built pre-1976 HUD requirements. Home is on a fixed foundation, has a working septic and is connected to public water. 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 Room - Great for enjoying outdoor dining and activities! A Patio Enclosure with sliding doors and screens is off the Primary Bedroom - a great spot for a hot tub! This home is just a few blocks to walk or drive to the community beaches on the Chesapeake Bay. By joining the voluntary Long Beach Civic Association ($100/yr) and paying the mandatory road fees ($56/year), one can enjoy access to the Long Beach private community beaches - kayaking, fishing, swimming, collecting shark teeth and shells... Flag Harbor Private Marina is adjacent to Long Beach on the Bay, so if you're a boater, rent or buy a slip! BOUNDARY SURVEY and recent APPRAISAL are available upon request. An immediate vacation rental? A great lot for a future rebuild?

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 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.

*****BACK ON THE MARKET **** Youre second chance is here. Don't miss your opportunity to make this exceptional home yours before it's gone again. Some homes make you pause at the door. This is one of them. Set on 5+ wooded acres in Saint Leonard, 4200 Henry Court offers privacy, presence, and over 6,000 sq ft of beautifully updated living space. Renovated in late 2025, this 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.

The beach is calling! Step into this charming 3-bedroom, 1-bath home at 5457 Bayview Ave, St. Leonard, MD, completely renovated in a boho-organic modern style. This beachside sanctuary features new LVP floors, a fresh kitchen with butcher block counters, gold hardware/fixtures & new appliances, a luxurious retreat-style bath with sage green custom tile, large vanity & gold accents, new architectural shingle roof, and new hot water heater. Enjoy the refreshed gravel driveway and fully fenced backyard - perfect for furry friends. Store the kayaks and bikes in the large back shed (as-is). New septic in 2016. Just steps to the Chesapeake Bay community beach for sand-beneath-your-toes vibes, plus a nearby marina/boat ramp for easy water adventures. Low $70 annual civic association fee + a one-time $17 key fee for secure beach and boat ramp parking access (fees subject to change; details at community site). May qualify for USDA loan with no money down for qualified buyers! Seller offering $5,000 closing cost credit if preferred lender is used. Broker/owner

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 areas. The spacious living room with heavy duty luxury vinyl tile flooring and recessed lighting, creates a warm ambiance perfect for both relaxation and entertaining. The gourmet kitchen is a chef's dream, featuring upgraded quartz countertops, an island for casual dining, and high-end stainless steel appliances, including a built-in microwave, dishwasher, and electric range. This home boasts three generously sized bedrooms, including a primary suite with an en-suite bath, ensuring privacy and comfort. An attic offers extra storage space, while the main floor laundry hookups add to the home's practicality. Outside, the property is equally enchanting. The 0.12-acre lot features a cleared front and rear yard, perfect for outdoor activities or simply enjoying the tranquility of your surroundings. Lush trees and manicured lawns provide a picturesque backdrop, while the bay views invite you to unwind and appreciate nature's beauty. Just two blocks away, the Chesapeake Bay offers private access for fishing enthusiasts and water lovers, enhancing your outdoor lifestyle. Located in a desirable area, this home combines the charm of a peaceful neighborhood with the allure of waterfront living. Enjoy leisurely strolls along the bay, or take advantage of the navigable waters for boating and exploration. On-street parking ensures convenience for you and your guests. This property is not just a home; it's a lifestyle. Experience the perfect blend of luxury, comfort, and nature in this stunning residence, where every detail has been curated for your enjoyment. Embrace the exclusive lifestyle that awaits you in this remarkable bayblock retreat.

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 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 complete shortening the wait time! Call to discuss standard features/upgrades! It's hard to find new construction w/ Water Access, a Deeded Boat Slip and Bay Views under $600k!!! Reach out now to be in your new home by Early 2027! Inquire ASAP Before this opportunity is GONE!

Almost 1.5 acres surrounded by farmland in mid Calvert location. Bring your vision and bring this old farmhouse back to life. Home is being sold as is. Call for more details.

New 25K Roof with a Lifetime Shingle Warranty! Water access right across the street! Extremely efficient Geothermal HVAC system! Crafted with precision by the original owner, a skilled custom homebuilder, this stately colonial reflects uncompromising quality with no 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. Schedule your tour today and don't miss this opportunity to claim this home with acreage, water access, and incredible bones, as 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.

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.

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!

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!