Saint Leonard MD Homes For Sale

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:

$560,000

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

$599,000

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

$299,900

5 Beds ⋅ 4 Baths

BEACH COMMUNITY INVESTMENT PROPERTY. Discover the unbeatable Long Beach location and extraordinary upside potential with this St. Leonard property located at 5705 Oakcrest Drive. This home has Over 4,000 SF total space, with 3788 SF finished space!! The property is located in a highly desirable, water-focused community with easy access to nearby beach and Flag Harbor marina within walking distance. It is ideal for coastal lifestyle enthusiasts who want a sprawling home with main level living plus income potential, multi-generational living, or even future caretaker accompaniment. The 65 x 32 rambler on basement with a 24 x 24 garage and massive rear outdoor living spaces has incredible renewal potential to customize, modernize, and create your dream home or investment property. Sold AS-IS at an attractive price point, this property represents an exceptional equity-building opportunity for savvy homeowners and real estate investors alike looking for maximum return in a prime Southern Maryland community. Property and home are in need of some attention and updating, and some safety issues exist with the decking along the entire rear of the house and it is a hazard. DO NOT ENTER DECK AREA-BUYER BEWARE!! ** Septic must be replaced and perc just completed-see MLS docs. ---J. Calvin Wood did the perc and has the system details** *** OFFER DEADLINE TUESDAY JULY 28, 5:00PM***

5705 Oak Crest Dr, Saint Leonard

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

$434,900

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

$619,900

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:

$739,900

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:

$330,000

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:

$825,000

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

$119,000

Lush 3.34 acre lot in a small subdivision adjacent to Jefferson Patterson Park. Take a walk and breathe it in, let your shoulders relax - you are home! Nature abounds with mature trees and a small creek running through the property. If you can imagine building your new home with all the benefits of living in the country, but keeping your commute to Solomons, Prince Frederick, or even into St. Mary's for Pax River NAS all under 20 miles! There is a previous satisfactory perc that would need to be renewed.

2745 Vivians Way, Saint Leonard

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$899,900

3 Beds ⋅ 5 Baths

**ST. LEONARD CREEK WATERFRONT RETREAT** **Where Every Day Feels Like a Vacation.** Nestled on 2.21 private waterfront acres along the tranquil shores of St. Leonard Creek, this extraordinary retreat offers far more than an exceptional home—it offers a lifestyle centered around nature, comfort, and unforgettable waterfront living. With **4,468 square feet, 3 bedrooms, 4.5 bathrooms, a beautifully finished lower-level recreation room with a full bath that could serve as a 4th bedroom, guest suite, home office, hobby room, or fitness space,** and a detached two-car garage, every space has been thoughtfully designed for relaxing, entertaining, and enjoying the beauty just beyond your windows. Wake each morning to the sound of songbirds, sip coffee as bald eagles glide overhead, and spend your afternoons kayaking peaceful waters right from your backyard. Watch great blue herons stalk the shoreline, turtles bask in the sunshine, deer quietly wander through the trees, and experience the changing seasons from one of the most peaceful settings Southern Maryland has to offer. Inside, expansive Anderson windows and doors blur the line between indoors and out, filling the home with natural light while showcasing breathtaking water views throughout. The chef's kitchen, warm wood accents, multiple fireplaces, and two spacious primary suites create an inviting atmosphere perfect for everyday living or hosting family and friends for long weekends by the water. Whether you're entering a new chapter of life looking for a peaceful waterfront escape or searching for a property that lets you fully embrace kayaking, wildlife photography, fishing, birdwatching, or simply reconnecting with nature, this home delivers an experience that's increasingly difficult to find. As evening settles in, gather around the fire pit beneath a canopy of stars, listen to the gentle sounds of the creek, and end the day exactly as it should be—surrounded by nature, waterfront serenity, and the people you love. This isn't simply waterfront living. It's the lifestyle you've been waiting for.

7440 Sedwick Ct, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$1,250,000

Experience exceptional waterfront living on the beautiful Patuxent River! This stunning ranch-style home offers over 3,300 square feet of thoughtfully designed living space with 4 bedrooms, 4 full bathrooms, and 50 feet of private river frontage complete with a private pier and charming crab shack. Designed for both everyday living and entertaining, the gourmet kitchen features stainless steel appliances, a six-burner commercial-grade range, a butler's pantry, and an open-concept layout that flows seamlessly into the dining area and spacious family room. Elegant shiplap accents, exposed beams, crown molding, and expansive windows frame breathtaking views of the Patuxent River, creating a warm and inviting atmosphere. The main level also features a private in-law suite offering two bedrooms, a full bathroom, a walk-in closet, and laundry room—an ideal setup for multigenerational living, extended family, guests, or a private home office. The luxurious waterfront primary suite, located on the lower level, is a private retreat offering panoramic river views, an oversized walk-in closet, and a cozy gas fireplace. The spa-inspired primary bath features heated floors, a relaxing jetted soaking tub, and luxurious finishes designed for ultimate comfort. Step outside and embrace the waterfront lifestyle. Spend your days boating, fishing, crabbing, or kayaking from your private pier, then unwind in the hot tub or entertain family and friends on the expansive deck while taking in spectacular sunsets. The authentic crab shack adds the perfect touch for enjoying fresh catches and making unforgettable waterfront memories. This exceptional property offers the perfect blend of luxury, comfort, and the unmatched beauty of Chesapeake Bay waterfront living. A rare opportunity to own a private riverfront retreat where every day feels like a vacation.

7737 Patuxent Dr, Saint Leonard

Listing courtesy of Taylor Properties. Contact:

$639,900

Enjoy the ease of one level living in this beautifully situated home on a secluded 2.25- acre lot in a sought-after community with top rated schools. Featuring an open floor plan, the main living areas flow seamlessly, creating an inviting space for both everyday living and entertaining. The main level features 3 spacious bedrooms and 2 full baths. The primary suite is a true retreat, featuring a spa-like feel with a walk-in shower and pedestal soaking tub- perfect for unwinding at the end of the day. The heart of the home is the kitchen, showcasing a large center island - perfect for meal prep, casual dining, and gathering with family and friends. Relax year- round in the bright and inviting sunroom. Enhanced by a mini split system for heating and cooling, and offering a peaceful, treehouse -like feel in the summer surrounded by lush greenery. Step outside to enjoy the rear deck, positioned for relaxing with a direct walk-down access to a beautiful paver walkway. This home delivers the perfect blend of privacy, space and versatility in a desirable location. A standout feature is the private basement apartment. It is complete with its own separate entrance, full kitchen and fully equipped laundry area. It is perfect for guests, extended family or rental income. The basement provides even more flexible space with a recreation room, and an additional half bath, along with a dedicated storage room, with shelving. With the apartment's additional bedroom and full bath, the home offers a total of 4 bedrooms and 3.5 baths. Car enthusiasts and hobbyists a-like, will appreciate the generous 2 car side load garage complete with attached shelving for added organization and convenience. So much to appreciate throughout this home - offering space, privacy, and a peaceful wooded 2.25- acre lot in a wonderful community.

1947 Oriole Way, Saint Leonard

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

$565,000

Enjoy peace of mind from the start with a new roof (2021) and HVAC system (2022), recently serviced and ready for its new owners. Located in the sought-after Mutual Elementary School district, this beautifully maintained 4-bedroom, 3.5-bath home offers the perfect blend of comfort, space, and privacy. Nestled on a private 1-acre lot surrounded by mature trees, you’ll enjoy a peaceful setting while remaining just minutes from shopping, dining, parks, and everyday conveniences, and only 20 minutes from beautiful Solomons Island. The main level features plank flooring and a welcoming family room with a wood stove, creating the perfect spot to gather on cooler evenings. Sliding glass doors lead to the backyard, seamlessly connecting indoor and outdoor living. The kitchen offers table space and a bay window overlooking the scenic rear yard. An additional room provides flexibility and can serve as a formal dining room, home office, playroom, or additional living space. The mostly finished lower level adds valuable living space and includes a full bathroom, making it ideal for entertaining, guests, a home gym, or recreation area. Additional unfinished basement space and a floored attic provide excellent storage options, while a French drain system offers added peace of mind. Upstairs, the spacious owner’s suite features a walk-in closet and dual vanities. Three additional bedrooms and another full bath provide plenty of room for family and guests. Outside, enjoy the privacy of the tree-lined backyard from the large patio, perfect for entertaining, grilling, or simply relaxing. An oversized side-entry two-car garage with abundant shelving and a large storage shed offer plenty of room for vehicles, tools, and hobbies. The outdoor patio set, featuring an oblong table and six chairs, conveys with the property, along with the children’s play equipment, making it easy to start enjoying the outdoor space from day one.

1155 Scenic Way, Saint Leonard

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636

$580,000

Beautiful Brick Rambler on 3 Acres. Spacious Living Room, Country Kitchen, Dining Room, Family Room with 3 Bedrooms. Lower Level boasts Rec. Room with Brick Fire Place, pool table conveys , sitting room, storage area. Enjoy eating hard crabs on the screened in porch. Enjoy swimming in Inground pool (20x 40) . Also a sheds for storing equipment.

5330 Cove View Dr, Saint Leonard

Listing courtesy of RE/MAX One. Contact: 4105356291

$629,900

3 Beds ⋅ 4 Baths

Welcome to 548 Windmill Drive, in the desirable community of Parran's Grant. Located in beautiful St. Leonard, this is a place to call home for many years to come! If you're looking for that special, move-in-ready home, well-maintained by the original owners, search no more! The immaculate interior blends seamlessly into the verdant surroundings on this private 1.1 acre flag lot. Tucked just off the main drive, it enjoys a quiet and peaceful setting while remaining part of an established neighborhood. The main floor is arranged for easy entertaining and good flow between spaces, featuring durable hardwood and tile floors, custom window treatments, and fresh, neutral walls throughout. The kitchen is a retreat in itself, complete with granite counters, quality custom cabinets, and views from the sink and breakfast area that will draw you outside to the elevated deck and screened gazebo. Hardwood stairs lead to a charming upper level, tastefully appointed, with a ceiling fan in each bedroom. The finished basement offers a recreation room/FR, ample storage, a bonus room, and a full bath, with walkout to the tranquil fully-fenced backyard, shed, stacked stone firepit, and attractive landscaping. The paved driveway includes an additional pad for storing an RV/boat. This Calvert County location affords a healthy, wholesome lifestyle, in a rural setting surrounded by farmland and bordered by the Chesapeake Bay. Nearby Chesapeake Bounty offers a trove of locally grown farm-to-table foods and seafood from local watermen. Flag Ponds Nature Park is a short drive, offering plenty of hiking trails and a sandy bayfront beach. Also nearby: Jefferson Patterson Park, Perigeaux Winery, Running Hare Vineyard. If a boat slip/boat launch is needed, Flag Harbor Marina and Boatyard is just 4 mi. away. Shopping, restaurants, and amenities are easily accessed via a 10-minute drive to Prince Frederick and a 20-minute drive to Solomons, and over the Patuxent River to St. Mary's County. Although you won't want to leave your lovely new home, you may need to commute to work. This location makes commuting easy: NAS Patuxent River is 20 miles away, and Joint Base Andrews, DC, and Annapolis are also within commuting distance.

548 Windmill Dr, Saint Leonard

Listing courtesy of RE/MAX One. Contact: 4437718009

$1,200,000

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 Calvert County Forestry Program, has many tall pines, poplar, and other trees , making this property secluded and private. A large three-car garage built in 2017 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 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

$425,000

2 Beds ⋅ 2 Baths

Beautifully refreshed and full of potential, this charming rambler on basement sits on approximately 1 private acre in the peaceful rural setting of St. Leonard. This property features no HOA, a fully unfinished basement with rough-in for an additional bathroom, and an impressive approximately 75’ x 40’ pole barn ideal for contractors, hobbyists, car enthusiasts, equipment storage, workshop space, or additional storage needs. Inside, the home has been recently freshened up with updates made to the kitchen and baths, in addition to fresh paint throughout, updated flooring, and new carpet installation, creating a clean and move-in ready feel. The living room offers cathedral ceilings, ceiling fan, sliding glass doors, The laundry is conveniently located on the main level. Located just minutes from the Chesapeake Bay, Solomons Island, local marinas, waterfront dining, parks, and beaches, this home offers easy access to boating, fishing, and all that Southern Maryland coastal living has to offer while still remaining within commuting distance to Joint Base Andrews, Pax River Naval Air Station, Washington DC, Annapolis, and surrounding areas.

2020 Woods Rd, Saint Leonard

Listing courtesy of Redfin Corp. Contact: 3016586186

$509,900

5 Beds ⋅ 4 Baths

As a special surprise the sellers have ordered new vinyl, single hung, thermal pane windows and screens from Thompson Creek! Installation to follow soon, so come out and see all the quality features this wonderful colonial has for the next lucky buyer. New windows help maximize energy efficiency along with the secure gas fired back-up power generator. This will ensure you never loose power. This well established beachfront community with annual events for family and friends awaits you soon! Enjoy visiting this beautiful home as you pull into the expansive driveway after a hard days work! The new steel 2 car garage door with remote will keep you out of the weather too! Enjoy relaxing on your concrete front porch or sun-filled rear deck with stairs. As you enter the home after a hard days work, enjoy gleaming hardwood flooring throughout the entry foyer, living, dining and family room. The expansive kitchen has a brand new range/oven as well as stainless steel appliances and generous center island for fun and gatherings to come! The second floor boasts 4 bedrooms with generous room sizes. An owners suite offers a large walk-in closet and ensuite with separate corner soaking tub & shower. The three additional bedrooms enjoy large sun filled windows. Heading to the lower level has wonderful flex space, perfect for home gym, office, recreation room or even as separate living area with a 5th bedroom & kitchenette. A covered rear entry includes a double French door. The well maintained yard and exterior is perfect for fun times to come. The paved drive was expanded for recreation vehicles, boat or extra cars for family & guests. No formal HOA lets you enjoy the flexibility with a non-mandatory civic association with a voluntary small annual fee. Come and enjoy the beach and all recreational fun to come. Never worry about power outages with the Generac 24kw whole house generator supported by two new 120 gallon propane tanks. Four exterior mounted cameras and security system will convey.

5817 Magnolia Cir, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$280,000

3 Beds ⋅ 1 Baths

Welcome home to this inviting rambler nestled in the Long Beach community of St. Leonard. Perfectly situated in a peaceful, established neighborhood, this 3-bedroom, 1-bath home offers comfortable living with modern convenience. Step inside to hardwood floors that flow throughout the main living areas. The living room is anchored by a cozy pellet stove, ideal for relaxing evenings or entertaining friends and family. The heart of the home is the generously sized eat-in kitchen with tile floors and flooded with natural light. It provides ample cabinetry and counter space, making meal preparation a breeze while offering a bright, welcoming spot for casual dining. Outside, enjoy your private fenced-in backyard perfect for summer barbecues, or creating your own garden oasis. Located in the heart of Calvert County, you’ll love the proximity to the Chesapeake Bay, local marinas, fishing, boating opportunities, and scenic walking trails. Don’t miss your opportunity to make it yours!

1440 Plateau, Saint Leonard

Listing courtesy of O'Brien Realty ERA Powered. Contact: 4103263133

$869,900

5 Beds ⋅ 4 Baths

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. Underground sprinkler system for yard. 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.

1000 Solomon Frazier, Saint Leonard

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

$896,000

Nestled amongst the trees with a breathtaking view of the waterfront, this stunning contemporary split-level home offers the perfect escape from the city in under an hour or if you're lucky enough you can call Saint Leonard home year round! The only way to describe the feeling of walking the property is a serene, luxury retreat. Take a deep breath and exhale, this is really your new home! Featuring outdoor amenities like the brand new 50' pier, a firepit along the water's edge, the beautiful gazebo built around a mature tree overlooking Rock Creek, a majestic stone staircase or one of the gently winding gravel paths to the meditation garden, there is something for everyone and room to share with many friends and family. While still outside, be sure to enjoy time on the porch swing, in the hot tub, or simply relaxing on the new stone patio or wrap around deck! When it's time to come inside, you will not be disappointed with the expansive layout and room for large gatherings. The main level centers around the stone fireplace soaring up to gorgeous vaulted wood ceiling, then wraps seamlessly into an open kitchen, dining room, and family room. The home boasts four bedrooms, all with water views, and three and a half bathrooms, including a completely renovated primary bath that allows you to enjoy the waterfront from a jacuzzi bath! The property features direct access to Rock Creek, offering 200 feet of waterfront, ideal for fishing, kayaking, or simply enjoying the tranquil water views. With an attached oversized garage and ample parking, convenience is at your fingertips. The peaceful location, away from busy streets, enhances the sense of privacy while still being close to nature's beauty. This home is a rare gem. Don't miss the opportunity to make this exquisite property your own!

4721 Rock Creek Cir, Saint Leonard

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$399,900

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!

5860 Lilac Cir, Saint Leonard

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

$450,000

Dramatic price drop!!! 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.

1815 Highland Dr, Saint Leonard

Listing courtesy of Hyatt & Company Real Estate LLC. Contact: 4107056296

$280,000

3 Beds ⋅ 2 Baths

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?

6070 Hill Rd, Saint Leonard

Listing courtesy of O'Brien Realty ERA Powered. Contact: 4103263133

$25,000

Located in the desirable Long Beach community of Saint Leonard, 6055 Poplar offers a peaceful Chesapeake Bay–area lifestyle in Calvert County. The neighborhood is quiet and residential, known for its coastal charm, friendly community feel, and proximity to the water—ideal for a primary residence or weekend retreat. Just a short drive away are local restaurants, seafood spots, and everyday conveniences in Saint Leonard, Lusby, and Prince Frederick. Residents enjoy easy access to some of Southern Maryland’s most loved waterfront destinations, including Flag Ponds Nature Park, Breezy Point Beach, Calvert Cliffs State Park, and the boardwalk and beach in North Beach. This location combines privacy, nature, and bay access with convenient driving distance to dining, shopping, and recreation—perfect for buyers seeking relaxed coastal living without the crowds.

6055 Poplar Rd, Saint Leonard

Listing courtesy of Samson Properties. Contact: 7033788810

$359,900

3 Beds ⋅ 2 Baths

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.

6045 Bayview Rd, Saint Leonard

Listing courtesy of Five Star Real Estate. Contact:

$549,900

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!

6041 Hill Rd, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$2,800,000

5 Beds ⋅ 5 Baths

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!

6675 Marshall Rd, Saint Leonard

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$910,000

2 Beds ⋅ 1 Baths

"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.

4870 Calvert Dr, Saint Leonard

Listing courtesy of RE/MAX One. Contact: 4105356291

$825,000

Located in downtown St. Leonard with two commercial buildings. Great light, lots of parking & town center. Discount when packaged for two commercial buildings with 4821 St. Leonard Rd. MLS#2017926. If purchased together sales price $1,590,000. Rare investment opportunity to purchase 2 homes and a lot, along with two commercial buildings. Potential to develop into commercial for all the properties because they are within the town limits & adjacent to each other. All five properties can be sold together at a discount. Also seller is willing to hold some financing. Current Occupancy is 80%. End unit cleaning company just moved out. Discount when packaged for two commercial buildings with 4821 St. Leonard Rd. MLS#2017926. If purchased together sales price $1,590,000.

4865 Saint Leonard Rd, Saint Leonard

Listing courtesy of RE/MAX One. Contact: 4105356291

$633,900