Refine Search
Map
Sort by
$449,000
3 Beds ⋅ 2 Baths
Waterfront on Smith Creek! Just in time for summer fun, this waterfront rambler, with private pier, will have you fishing and crabbing from morning until night. Hardwood flooring greets you upon entering and flows throughout most of the main level. Tilt-out windows and a screened porch ideal for relaxing and enjoying all the sights and sounds of living on the water. New paint and ceiling fans throughout add a fresh new look. All the electric upstairs has been replaced. Roof is 2 years old. Septic is newer to include drain-fields and distribution box. Washer and dryer and well pump are 2-3 years old. The basement is unfinished and a blank canvas to make your own. Situated on a shaded lot with approximately 100 feet of waterfront, the property also features a paved driveway, generous parking, and a handicap-accessible ramp. Tucked away on a quiet dead-end street, yet conveniently located near Webster Field, this all-electric home offers privacy, comfort, and plenty of potential. Come see everything this waterfront property has to offer! Additionally, this home is not in the flood plain.

17248 Gum Landing Rd, Saint Inigoes

Listing courtesy of CENTURY 21 New Millennium. Contact:

$420,000
4 Beds ⋅ 3 Baths
***Just 10 minutes away from Pax River Naval Base*** This property offers an effortless commute for military, contractors, and buyers looking for an easy commute. This almost new, built in 2025, townhouse comes packed with modern upgrades. Designed for premium comfort, the main level features built-in, in-ceiling speakers for seamless whole-house audio, a gorgeous designer kitchen complete with stainless steel appliances, and an EV charger in the garage. Walk right out to your private, screened deck; the perfect, insect-free spot to unwind or host a weekend gathering.Peace of mind comes standard with a fully integrated security system already in place. Tucked away in a quiet Great Mills pocket, this hidden gem keeps you close to local schools, neighborhood dining, and daily conveniences. Upgrade your lifestyle and your daily commute with this turn-key, like-new home. Schedule your tour today.

22503 E Maxine Way, Great Mills

Listing courtesy of The Southside Group Real Estate. Contact:

$465,000
4 Beds ⋅ 4 Baths
NEW PRICE! If you've been looking for space, privacy, and acreage in Mechanicsville, this property is worth another look. Situated at the end of a quiet cul-de-sac on 3.39 acres with NO HOA, this spacious 4-bedroom, 3.5-bath home offers over 2,800 square feet and a flexible floor plan that's difficult to find. One of the home's standout features is its two primary suites, including a main-level primary suite and a second upstairs, providing flexibility for a variety of living arrangements. The home also features a spacious living room, dining area, kitchen, dedicated laundry room, and a large recreation room with a unique built-in aquarium. Outside, surrounding trees create a private setting, and the property backs to hundreds of acres of largely undeveloped land with no homes directly behind it. The large, level side yard provides plenty of usable outdoor space for recreation, equipment, additional storage, or future improvements. A storage shed provides additional space for tools and equipment. Recent improvements include a replaced well pump, upgraded water-pressure system, freshly painted shutters and exterior doors, rear railings, and exterior power washing. Enjoy the privacy and space of country living while remaining convenient to Charlotte Hall, Mechanicsville, shopping, dining, schools, and major commuter routes. Now offered at $465,000 — schedule your showing and come experience the setting and space this property has to offer.

38002 W Edinview Ct, Mechanicsville

Listing courtesy of Baldus Real Estate, Inc.. Contact:

$486,000
Mixed-use investment or Owner-user opportunity offering 3,845 SF commercial building on a 29,620 SF parcel with prime visibility just off Point Lookout Road. Zoned VMX, this versatile property accommodates a wide range of commercial uses and can be demised into three separate retail bays, creating excellent flexibility for owner-users or investors seeking multiple income streams. The property also includes an income-producing rental home located at the rear of the site, providing immediate cash flow. For investors, the current owner is willing to lease back approximately one-third of the commercial building, offering built-in rental income after closing. Alternatively, the property can be delivered for an owner-user seeking to occupy the entire commercial space. For buyers looking to expand an existing operation or step into an established business, the current business may also be included in the sale, if desired.

28420 Point Lookout Rd, Loveville

Listing courtesy of Hyatt Commercial. Contact:

$325,000
3 Beds ⋅ 1 Baths
Nestled on a serene 2.17-acre lot, this charming ranch-style home offers a perfect blend of comfort and nature. Surrounded by lush trees and partly wooded areas, the property provides a tranquil retreat, ideal for those seeking peace and privacy. Imagine sipping your morning coffee while enjoying views of the garden and woods from your rear yard, where you can create your own outdoor oasis. Inside, the home features three cozy bedrooms and a full bathroom, making it a delightful space for relaxation. The detached garage and gravel driveway offer ample parking and storage options. Focus on enjoying the expansive outdoor space, perfect for gardening or simply unwinding in the fresh air. This property is a rare find, making it an inviting place to call home. Embrace the opportunity to create lasting memories in this peaceful setting, where nature and comfort come together.

44911 Buck Redman Rd, Callaway

Listing courtesy of Coldwell Banker Premier. Contact:

$257,900
2 Beds ⋅ 3 Baths
Price Improvement -Welcome to 21076 Jenna Court—a beautifully maintained 2-bedroom, 2.5-bath townhouse offering the perfect blend of comfort, style, and convenience. This inviting home features two spacious primary suites, each with its own private full bath, making it ideal for guests, roommates, or anyone seeking flexible living space. The bright and functional eat-in kitchen offers ample cabinet storage and pantry space, while the open living area provides the perfect setting for relaxing or entertaining. Step outside to enjoy the private, fenced backyard—ideal for outdoor gatherings, pets, or simply unwinding after a long day. Additional highlights include a convenient main-level powder room, dedicated laundry area, assigned parking, central heating and air conditioning, and low-maintenance living. Located close to shopping, restaurants, schools, PAX River Naval Air Station, and commuter routes, this home offers exceptional value in a desirable neighborhood. Whether you're a first-time homebuyer, downsizing, or looking for an investment opportunity, 21076 Jenna Court is move-in ready and waiting for you to call it home. Schedule your private tour today!

21076 Jenna Ct, Lexington Park

Listing courtesy of Keller Williams Preferred Properties. Contact:

$1,450,000
1 Beds ⋅ 1 Baths
A rare opportunity to own an extraordinary 11.83-acre wooded property in the prestigious Half Pone Point community. Located directly across from the spectacular waterfront estate at 24730 Half Pone Point Rd, this versatile property offers endless possibilities for a private family compound, car collector, hobbyist, business owner, or recreational enthusiast. The property is improved with five buildings, including two stick-built structures, one featuring a second-floor one-bedroom, one-bath apartment with beautiful water views. Two metal buildings and an impressive airplane hangar-style garage with two oversized roll-up doors provide exceptional space for vehicle collections, RVs, boats, equipment, workshops, or storage. An additional A-frame building adds even more flexibility. Designed for convenience and functionality, the property features multiple 60-amp RV hookups, along with plumbing and electric throughout the buildings, making it ideal for a variety of residential, recreational, or commercial-style uses. This property is exceptional on its own, but when assembled with the waterfront estate across the street, it creates one of Southern Maryland's most remarkable legacy properties. Whether you're seeking privacy, expansive acreage, unmatched storage, or the opportunity to create a one-of-a-kind estate, this offering is truly unlike any other.

24715 Half Pone Point Rd, Hollywood

Listing courtesy of HomeZu by Simple Choice. Contact:

$1,590,000
5 Beds ⋅ 4 Baths
Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare opportunity to own a private waterfront oasis with an expansive shoreline along both Breton Bay and Combs Creek, extending all the way to the point of its sandy beach peninsula. Enhanced riprap protection, extensive landscaping, and mature surroundings create a truly unforgettable setting. Enjoy 1,545 feet of bay-front water life. Kayakers, yachters, dolphin enthusiasts, fishers, crabbers, and star-gazers are just a few who may find interest in this exemplary waterfront gem. The centerpiece of the outdoor living experience is the spectacular saltwater pool, thoughtfully designed for both relaxation and entertaining. The saltwater pool is finished with premium Wet Edge Premier Stone and Artistic Paver tiles, (featuring embedded seashells sourced from Miami). The tanning ledge measures approximately 8x16' providing the perfect place to lounge and enjoy waterfront views, while a diving board adds to the fun. A dedicated pool pump house and separate dual pool storage unit with its own half bath supports the pool operation. Water enthusiasts will appreciate the exceptional marine amenities. Walking down the hill from the residence leads to a private boathouse and pier system designed with serious boaters in mind. The pier features new stringers, updated power and water service, two slips including the boathouse, and one open slip, a fish cleaning station, and kayak launch area. Low water depth at the end of the pier averages approximately eight feet, making this deep-water location highly desirable for larger vessels and year-round boating. The boathouse, along with the pier, pool house, and detached garage, are all serviced through a dedicated electrical panel system. Water is also available on the pier. Inside, the home has undergone substantial improvements over the years, including a complete transformation of the kitchen and dining areas, creating a stunning gourmet gathering space that serves as the heart of the home. Updated Andersen windows, updated flooring, fresh interior paint, and a beautifully finished laundry and utility room further enhance the home’s appeal. The impressive enclosed sunroom, encompassing approximately 440 square feet, offers year-round enjoyment and flexible living space while showcasing the property’s incredible waterfront views in all seasons. Additional improvements include HardiePlank fiber cement siding, a whole-house generator capable of operating the kitchen and well systems during outages, and a detached 2.5-car garage with a raised floor to improve site grading. The garage offers exceptional storage and future potential for additional finished space should a buyer desire to build up. The well is approximately eight years old. When drilled, the well and pump were upgraded to provide for the additional water needs of the pool, pier and future lawn irrigation. The laundry and utility area features a Navien boiler installed in 2016, providing domestic hot water as well as support for the home’s heating systems. For added value and future convenience, the sellers are in the process of connecting the property to public sewer, which is available within the property. We cannot wait for you to come see the lifestyle that Combs Creek Way has to offer you.

40115 Combs Creek Way, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact:

$799,000
4 Beds ⋅ 3 Baths
Two Homes, One price! Imagine waking up each morning to breathtaking, unobstructed views of the Chesapeake Bay. Here, the water isn’t just something you see—it’s part of your everyday life. Relax on your private pier, launch your kayak, cast a fishing line, or simply watch the sun dance across the Bay. A sandy beach has been thoughtfully created, allowing you to enjoy carefree days by the water regardless of the tide. Nature lovers will appreciate watching the resident ospreys return each year to build their nests, hatch their young, and soar above the shoreline—a front-row seat to one of the Chesapeake’s greatest treasures. The charming waterfront A-frame has been enhanced with a beautifully enclosed porch, creating the perfect space to gather with family and friends for steamed crabs, oysters, and unforgettable waterfront dinners in every season. Expansive decking on the front, rear, and second level provides multiple outdoor living spaces where panoramic bay views become the backdrop to everyday life. Inside, you’ll find a warm and inviting atmosphere highlighted by a cozy fireplace for crisp winter evenings. Recent improvements include updated bathrooms, a renovated kitchen, new kitchen appliances, fresh interior and exterior paint, new pier boards, and updated fencing, making this home move-in ready. A detached carport with an attached storage shed offers covered parking and plenty of room for all your beach gear, boating equipment, and tools. Just across the driveway sits an equally charming one-bedroom, one-bath guest cottage. Whether you use it for visiting family and friends, a private home office, or continue its success as a short-term vacation rental, it offers exceptional flexibility and income potential. Rarely does an opportunity like this come along. Own not one, but two highly sought-after vacation rental homes in the picturesque waterfront community of Scotland, Maryland. Whether you’re looking for a personal waterfront retreat, a family compound, or an income-producing investment, this exceptional Chesapeake Bay property delivers the best of coastal living.

14940 Chesapeake Bay Dr, Scotland

Listing courtesy of CENTURY 21 New Millennium. Contact:

$399,900
7 Beds ⋅ 3 Baths
Spacious and versatile home offering 7 bedrooms and 3 full baths in a convenient Lexington Park location. With 4 bedrooms upstairs and 3 on the lower level, this home provides plenty of room for multi-generational living, guests, or flexible work-from-home space. Enjoy an oversized attached two-car garage and a huge, flat backyard perfect for outdoor entertaining, recreation, or future possibilities. Ideally located near Historic St. Mary’s City, PAX River Naval Air Station, and local favorites like St. James Deli, this property offers space, comfort, and convenience all in one.

48448 Mattapany Rd, Lexington Park

Listing courtesy of The Southside Group Real Estate. Contact:

$4,595,000
4 Beds ⋅ 7 Baths
A legacy waterfront estate at the tip of coveted Half Pone Point. Commanding one of the most prestigious waterfront settings in Southern Maryland, this extraordinary residence offers more than 14,000 square feet of meticulously crafted living space designed to capture breathtaking panoramic views of the Patuxent River from nearly every room. Architectural excellence and exceptional craftsmanship are evident throughout, blending timeless elegance with modern luxury. Designed for both grand-scale entertaining and comfortable everyday living, the estate features a private elevator, state-of-the-art theater room, wine room, game room, custom entertaining bar, and resort-style amenities including a spectacular infinity-edge pool and expansive outdoor living spaces. The property is further enhanced by advanced whole-home automation, integrated smart-home technology, comprehensive high-definition surveillance systems, a secure safe room, and numerous additional proprietary security features. For sport and recreation, the residence also includes a private indoor commercial-grade shooting range—a rare amenity seldom found in residential properties. Just minutes by boat from Solomons Island and the Chesapeake Bay, this remarkable property delivers an unparalleled waterfront lifestyle where privacy, sophistication, and natural beauty converge. Created for those who value discretion as much as luxury, certain features and specifications of the estate are intentionally withheld from public marketing materials. Qualified purchasers only. Private showings are available by appointment for financially qualified buyers. Proof of funds or lender pre-approval may be required prior to touring the property. Due to the nature of certain security, technology, and infrastructure systems, prospective purchasers may be asked to execute a confidentiality agreement before receiving access to selected property information and features.

24730 Half Pone Point Rd, Hollywood

Listing courtesy of HomeZu by Simple Choice. Contact:

$288,900
Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or creating the family compound you've all been dreaming of. This beautiful land is conveniently positioned just off Rt. 5, in a prime location between St. Mary's State Park and the charming St. Mary's County seat, Leonardtown. Note that the location is not actually ON Whirlwind Rd; it is best accessed at the end of Redgate Ln. Future potential to create access from both Rt. 5 and Redgate Ln. Call for more details!

Whirlwind Road, Leonardtown

Listing courtesy of RE/MAX One. Contact:

$624,900
4 Beds ⋅ 4 Baths
Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside. The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant cabinetry, a spacious walk-in pantry, and a convenient mudroom just off the rear-entry garage. Adding to the home’s incredible value are solar panels, allowing the current owners to enjoy a minimal electric bill—an exceptional benefit that provides long-term energy savings. Step outside to your fully fenced backyard, where you’ll find an expansive paver patio designed for relaxing and entertaining. Gather around the built-in fire pit, host summer cookouts, or simply unwind in your own private outdoor retreat. Located in one of Leonardtown’s most desirable neighborhoods, Leonard’s Grant offers outstanding community amenities, including a pool, clubhouse, playgrounds, walking trails, tennis and basketball courts, all just minutes from downtown Leonardtown, restaurants, shopping, and not far from NAS Patuxent River. Move-in ready, energy-efficient, and perfectly located, this home offers the ideal combination of comfort

41462 Culpepper Way, Leonardtown

Listing courtesy of RE/MAX One. Contact:

$250,000
2 Beds ⋅ 2 Baths
Opportunity awaits on this beautiful 3.05-acre parcel tucked away on a quiet paved road in the heart of Callaway. Whether you're looking for a renovation project, a homesite to build your dream home or an investment property, this property offers incredible potential with existing infrastructure already in place. The current mobile home is in need of significant renovation or removal, making way for a fresh start on a spacious and private lot surrounded by mature trees. Existing improvements include a detached 16' x 18' garage with 100-amp electric service, an existing well and septic system, and a circular driveway for easy access and ample parking. Enjoy the convenience of a prime location just minutes from shopping, restaurants, schools, and Patuxent River Naval Air Station, while still enjoying the peace and privacy of country living.

20275 Jackson Rd, Callaway

Listing courtesy of EXP Realty, LLC. Contact:

$175,000
Tucked along the peaceful, navigable waters of Cuckold Creek, this waterfront lot ready to build offers the perfect blend of privacy and possibility! With a recent perc approval (April 2025), it’s ready for your dream home plans! Community pier borders the lot and a perfect spot for fishing, kayaking, or just enjoying the views. Neighboring homes feature piers—buyer to verify any desired water access or improvements with the county.

Ewell Lane, Hollywood

Listing courtesy of CENTURY 21 New Millennium. Contact:

$15,000
Prime Beach Community Lot for Sale – Waterfront Access & Private Dock Discover the perfect opportunity to build your dream coastal retreat in this exclusive beachside community. This spacious, flat lot is ideally situated near the entrance of the neighborhood, offering both convenience and tranquility. With direct water access just steps away and ownership including access to a private dock, you can enjoy boating, fishing, and breathtaking waterfront views with ease. Nestled in a serene yet vibrant coastal setting, this lot provides the ideal foundation for a custom home designed to embrace the beauty of the beach lifestyle. Whether you’re looking for a peaceful getaway or a full-time residence, this property offers the best of both worlds—privacy, natural beauty, and the convenience of a well-established community. Don’t miss this rare chance to secure your piece of paradise! Contact us today for more details. Due Diligence is the responsibility of the buyer.

Longview Boulevard, Bushwood

Listing courtesy of KW Metro Center. Contact:

$450,000
4 Beds ⋅ 3 Baths
One of the best locations in the community, this brick home with two car garage overlooks the community park. If you are are looking for space, this home has it! A grand double-door entrance welcomes you into the foyer then head up to main level featuring hardwood floors, a spacious living room, a formal dining room perfect for gatherings, and kitchen with ample cabinet space, and room to expand. The main level also includes primary suite with a private bath alongside two additional bedrooms and a hall bath. The expansive lower level features a recreation room anchored by a cozy wood-burning insert fireplace, a huge fourth bedroom, a third full bath, dedicated laundry, storage, and an ideal workspace. Entertain effortlessly on the massive deck spanning the entire width of the home, or relax below on the full-width covered patio providing perfect shade. Additional Amenities: Attached two-car garage plus plenty of driveway parking. Detached outbuilding equipped with electricity, perfect for a workshop or extra storage. Exceptional storage solutions with two separate attics. This home is not part of the association so you are not tied to any rules or regulations.

37580 Asher Rd, Mechanicsville

Listing courtesy of Home Towne Real Estate. Contact:

$299,900
3 Beds ⋅ 3 Baths
Welcome to 45611 Longfields Village Dr, Great Mills, MD 20634 Welcome home to this beautifully updated 3-bedroom, 2.5-bath residence in the desirable Greenview West community. Built in 1990, this well-maintained home offers a perfect blend of comfort, functionality, and modern updates. Step inside to a bright and inviting foyer featuring soaring ceilings, large glass windows, and skylights that fill the home with abundant natural light. The spacious main living areas showcase luxury vinyl plank flooring, while brand-new carpet by the steps adds warmth and comfort to the upper level. The thoughtfully designed kitchen is equipped with a brand-new Samsung refrigerator, Whirlpool dishwasher, and GE electric range, making meal preparation both stylish and convenient. Upstairs, you'll find three generously sized bedrooms, including a comfortable primary suite with a private en-suite bath. An additional full bathroom and convenient main-level powder room provide ample space for family and guests. The walk-up unfinished basement offers endless possibilities for future expansion. Whether you envision an additional bedroom, recreation room, home gym, office, or entertainment space, this area provides plenty of storage today and room to grow tomorrow. Outside, enjoy the privacy of the fully fenced backyard—perfect for entertaining, pets, gardening, or relaxing after a long day. A front-entry one-car garage and driveway provide convenient parking and additional storage. Ideally located just minutes from Naval Air Station Patuxent River (PAX River), shopping, restaurants, parks, schools, and everyday conveniences, this home offers an easy commute while being nestled in an established neighborhood. Don't miss this exceptional opportunity to own a move-in ready home in the heart of Great Mills. Schedule your private showing today!

45611 Longfields Village Dr, Great Mills

Listing courtesy of JPAR Real Estate Professionals. Contact:

$459,900
3 Beds ⋅ 2 Baths
Motivated seller! One owner for almost 60 years! Home recently had new roof, new windows, new doors, and appliances. If you desire no subdivision, 1+ acres, detached garage/workshop, extra outside storage, secluded area, centrally located, and ONE level, this may be what you're looking for. Unfinished walk up/out basement with french drains, centrally located in Hollywood less than 1500 feet from Dorsey Park. Close proximity to downtown walkable Leonardtown, hospital, shopping, and schools.

24301 Old Hollywood Rd, Hollywood

Listing courtesy of RE/MAX One. Contact:

$395,000
5 Beds ⋅ 3 Baths
This move-in-ready 5-bedroom, 3-bath split-foyer home offers modern comfort and timeless appeal. Enjoy all-new windows, HVAC, water heater, kitchen cabinetry, stainless-steel appliances, and updated baths—every detail has been refreshed with quality in mind. The spacious layout features spacious bedrooms with ceiling fans in every room for year-round comfort. A covered deck off the dining room overlooks the large in-ground pool, creating the perfect setting for relaxing or entertaining. Located just minutes from PAX River, shopping, and dining, this home offers convenience for work and leisure. Nearby parks, Solomons Island, and ongoing area growth make this a vibrant place to live. Move in with No Money Down 100% USDA Financing if qualified.

21491 Lynn Dr, Lexington Park

Listing courtesy of Green Home Realty, LLC. Contact:

$229,900
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained townhouse nestled in the highly sought-after Westbury community. Offering the perfect blend of comfort, style, and convenience, this home is completely move-in ready and designed for effortless living. Step inside to a bright, inviting main level featuring a seamless layout perfect for both daily living and entertaining. The heart of the home is the kitchen fully equipped with sleek stainless-steel appliances. Upstairs, you’ll find three spacious, sunlit bedrooms. This property offers a fenced in backyard with low-maintenance, giving you more time to enjoy your home! Cool off this summer with access to the community pool! Minutes away from NAS Pax River, restaurants, and stores!

46097 Lucca Way, Lexington Park

Listing courtesy of Home Towne Real Estate. Contact:

$250,000
1,582 SF ± office condominium available in the prestigious Keystone Building, conveniently located just minutes from Patuxent River Naval Air Station. This premier medical and professional office building offers excellent access to Three Notch Road (MD Route 235) and outstanding visibility along one of Southern Maryland's busiest commercial corridors. The versatile open floor plan provides endless possibilities for medical, professional, or service-oriented users and features a coffee service bar, abundant natural light, and an ADA-compliant restroom. The property benefits from exceptional exposure to over 65,000 vehicles per day along Route 235. This Class A office building features an attractive all-brick exterior, elegant tiled lobby entrance, elevator access, and ample on-site parking for tenants and visitors.

22888 Three Notch Rd Unit 301, Lexington Park

Listing courtesy of Hooper & Associates. Contact:

$290,000
Discover a prime 15-acre parcel of land, offering a unique investment opportunity with significant potential returns. This property features a serene backdrop of trees and wooded areas, providing a tranquil setting while ensuring privacy. The sloping terrain enhances the natural beauty and could be ideal for various development projects, from residential homes to recreational retreats. The wooded landscape adds aesthetic value. The natural surroundings and potential for development make it a compelling choice for those looking to maximize their investment in real estate. Don't miss out on this opportunity to secure a piece of land with both beauty and potential. 15 Acres in Leonardtown. This could be a great property for the right buyer. Lots of potential, could possibly be sub-divided. Has an old house on property, with failed septic system. (Please do not enter home for your safety)

42700 Moll Dyer Rd, Leonardtown

Listing courtesy of Coldwell Banker Premier. Contact:

$7,500,000
4 Beds ⋅ 3 Baths
Nestled within the prestigious St. Jeromes subdivision, this exquisite Bayfront residence offers an unparalleled lifestyle defined by luxury and tranquility. Spanning over 175 acres just with the main house, this coastal architectural masterpiece seamlessly blends sophisticated design with nature's beauty, providing a serene retreat for discerning homeowners. Step inside to discover a harmonious open floor plan adorned with rich hardwood. The expansive family room, complete with a cozy wood-burning fireplace and elegant mantel, invites relaxation and gatherings. The kitchen is a culinary enthusiast's dream, featuring an island, ample pantry space, and an inviting eat-in area. The primary suite is a sanctuary of comfort, boasting a Bayfront view, and a luxurious primary bath equipped with a walk-in shower. Additional highlights include built-ins, recessed lighting, and a dedicated entry-level bedroom, ensuring convenience and style throughout. The exterior of this residence is equally impressive, showcasing extensive hardscaping that enhances the property's aesthetic appeal. Enjoy the ultimate outdoor lifestyle with a private beach, perfect for sunbathing or leisurely strolls along the sandy shore. The roof deck offers panoramic views of the Chesapeake Bay, while the tennis court (should you choose to restore it) provides an active lifestyle option right at your doorstep. Multiple patios and decks create inviting spaces for al fresco dining and entertaining, all set against a backdrop of lush greenery and serene Chesapeake Bay views. This premium lot is a true gem, bordered by trees and offering a secluded atmosphere that feels worlds away from the hustle and bustle. With direct access to the Bay, indulge in fishing, boating, or simply soaking in the natural beauty that surrounds you. Ample parking with an attached garage and expansive driveway. Breathtaking views of the Bay, pond, and wooded areas create a picturesque setting that changes with the seasons. Located just steps from the water's edge, this home offers a unique opportunity to embrace a lifestyle centered around nature and luxury. With over 6,136 feet of water-frontage, this property provides direct access to the Chesapeake Bay, where swimming, kayaking, and water skiing await. This exceptional residence is not just a home; it's a lifestyle choice that embodies luxury, comfort, and the beauty of nature. Experience the ultimate in coastal living, where every day feels like a vacation. Sale includes 91 lots in St. Jeromes shores and 71 lots in Bay Harbor totaling approximately 280 acres. There is nothing else like this in Southern Maryland. Your legacy awaits.

50645 Holly Point Rd, Dameron

Listing courtesy of CENTURY 21 New Millennium. Contact:

$724,900
8 Beds ⋅ 3 Baths
Welcome to this truly one-of-a-kind Mechanicsville property offering an incredible combination of space, style, and functionality! Situated on a beautiful 1.6-acre lot, this impressive home features 8 bedrooms and has been thoughtfully updated to create the perfect blend of modern luxury and comfortable living. The heart of the home is the stunning, fully renovation, highlighted by an expansive open-concept design that's perfect for entertaining. The gourmet kitchen is a showstopper, featuring a massive center island, custom cabinetry, stylish finishes, abundant counter space, huge walk in pantry and an effortless flow into the living and dining areas. Whether you're hosting holiday gatherings or everyday family meals, this space was designed to bring people together. The spacious primary suite offers a private retreat with a luxurious spa-inspired bathroom, complete with a freestanding soaking tub, oversized custom tile shower, elegant finishes, and a large walk-in closet. Throughout the home you'll find generous rooms, updated flooring, abundant natural light, and flexible living spaces ideal for multi-generational living, large families, home offices, guest accommodations, or hobby rooms. Outside, enjoy the privacy and possibilities of 1.6 acres, offering plenty of room for outdoor entertaining, The Custom Brick Patio and fireplace with grill and Firepit are perfect for enjoying the peaceful Southern Maryland setting. With eight bedrooms, extensive renovations, a magazine-worthy kitchen, spa-like owner's suite, and room to spread out both inside and out, opportunities like this rarely come along. This is the home you've been waiting for!

27656 Cannon Ln, Mechanicsville

Listing courtesy of CENTURY 21 New Millennium. Contact:

$624,900
5 Beds ⋅ 4 Baths
Beautifully maintained and thoughtfully updated, this spacious home offers over 3,800 finished square feet of versatile living space on a picturesque 1-acre lot. Built in 2013, this impressive residence features 5 bedrooms, 3.5 baths, and a 2-car garage, providing ample room for today's evolving lifestyles. Enjoy the space and privacy of Mechanicsville living while remaining well positioned for access to NAS Patuxent River, NAVAIR/NAWCAD and Southern Maryland's surrounding defense and technology employment corridor. The heart of the home is the inviting kitchen, featuring granite countertops, a center island, and an open layout designed for both everyday living and effortless entertaining. Beautiful hardwood floors grace the main level, while fresh paint, updated lighting, and brand-new wall-to-wall carpeting enhance the home's warm and welcoming atmosphere. The fully finished lower level offers exceptional flexibility with its own living area, kitchen, bedroom, full bath, laundry area with dedicated washer and dryer, and private French-door entrance—ideal for multigenerational living, extended guests, or a private retreat. Recent improvements provide peace of mind and make this home truly move-in ready, including upgraded dual HVAC systems, a new well pump, fresh paint, updated lighting, brand-new carpeting, and a freshly seal-coated driveway. Offering over 3,800 finished square feet of thoughtfully designed living space and numerous recent upgrades, this exceptional property combines comfort, functionality, and modern convenience in a beautiful setting. Don't miss the opportunity to experience all that this wonderful home has to offer.

26185 T Wood Dr, Mechanicsville

Listing courtesy of Real Broker, LLC. Contact:

$220,000
3 Beds ⋅ 2 Baths
*** Price Improvement *** Welcome to your new home! This charming, well cared for townhouse, located in the Westbury neighborhood, is ready for its new owner. With summer right around the corner, enjoy your days staying cool at the community pool! The property comes with two assigned parking spots directly in front of the unit. Have peace of mind with a new A/C condenser installed in 2023. This home couldn't be in a more convenient location with PAX River Naval base less than 10 minutes away and all the shopping, food and entertainment you need right down the street. Thank you for your interest and good luck!

46104 Lucca Way, Lexington Park

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

$9,950
Enjoy the natural beauty and privacy of Southern Maryland while benefiting from the community's water access and nearby outdoor recreational opportunities. No perc test information is currently available, and buyers are encouraged to perform their own due diligence regarding building suitability and utility availability. Conveniently located within commuting distance of Lexington Park, Waldorf, and the surrounding areas, this property presents a rare chance to own land in the established waterfront community of Mill Point Shores.

36070 Carver Rd, Chaptico

Listing courtesy of RE/MAX One. Contact:

$300,000
3 Beds ⋅ 2 Baths

23955 Hollywood Rd, Hollywood

Listing courtesy of Real Broker, LLC. Contact:

$575,000
3 Beds ⋅ 3 Baths
REDUCED OVER 30K - SELLER MOTIVATED! - AMISH BUILT! New Construction in Chaptico! Adorable Cape Cod situation on over one acre, surrounded by mature trees, creek, gorgeous pastoral views and beautiful Chaptico Sunsets! This Cape Cod welcomes you home from your hectic day to a serene surrounding with a convenient location to all amenities. You are only minutes away from Leonardtown shopping /entertainment and Pax River /Dalgren and less than two miles from the breathtaking Chaptico Warf! The main level boasts a large open kitchen, dining area, and huge open den. The main level also offers an office that could be utilized as a 4th bedroom. Upstairs there are 3 large bedrooms, 2 full baths, and a sitting/flex area with stunning views! Luxury vinyl plank flooring flows through every room in this bright home. The back deck is off the heart of the home, kitchen, and is tucked in between mature woods with creek. The front porch is the place to be for "cocktail hour" to catch stunning Chaptico sunsets! You will have peace of mind living in this NEW home and all it offers, including: completely conditioned & sealed crawl space; new septic; and new well pump just installed! This is a must see, one of kind home located in the best hidden gem of St. Mary's County; a rare opportunity to own new construction in Chaptico. All certifications and permits in hand and ready for you to move right on in. Yards have just been graded, seeded and hayed. Do NOT miss this one!

23690 Maddox Rd, Chaptico

Listing courtesy of RE/MAX Realty Group. Contact: