Refine Search
Sort by
$450,000
2 Beds 1 Baths
Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing, fishing, kayaking, or canoeing, this location is an outdoor enthusiast’s paradise. Enjoy the sights and sounds of ospreys, fish, and abundant wildlife right from your doorstep. Key features include: ✔ Approximate water depth: 2.5 ft at low tide, 4.5 ft at high tide ✔ Seawall refurbished in 2020 for added shoreline protection ✔ Private pier with an electric boat lift—perfect for boating adventures Don’t miss this rare chance to own a piece of paradise with endless potential. Whether you’re looking for an investment, vacation retreat, or future dream home, this waterfront gem is a must-see! Currently listed on Air B&B and VRBO.

20798 Waterside Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4105356291

$780,000
5 Beds 4 Baths
Updated photos coming soon! Wake to the soft glow of sunrise spilling across the Chesapeake Bay and end your evenings watching the sky melt into watercolor reflections over the water. Nestled in the heart of Scotland, this exceptional Bayfront retreat captures sweeping, unobstructed views and the quiet serenity only true waterfront living can provide — all secured by a brand-new seawall for lasting peace of mind. Walls of windows invite the outside in, filling the home with natural light and endless horizon views from multiple vantage points. The living spaces feel open, airy, and effortlessly connected — designed for both intimate mornings and memorable gatherings by the water. Step onto the expansive Trex and vinyl balcony and breathe in the salt air as boats drift by in the distance. Slip into the hot tub on the enclosed porch and let the day melt away beneath a painted evening sky. With direct beachfront access, spontaneous sunset strolls and days spent out on the Bay become part of everyday life. A spacious two-car garage adds comfort and convenience to this peaceful coastal escape. 15370 Holly Drive is more than a home — it’s a private waterfront sanctuary where time slows, views stretch endlessly, and every day feels like a getaway. Chesapeake Bay living at its most magical.

15370 Holly Dr, Scotland

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$999,999
4 Beds 5 Baths
PRICE IMPROVED, READY FOR SETTLEMENT! SHOP AND RESIDENCE on 18+ ACRES. All brick rambler on 18.64 acres of wooded, private land offering exceptional craftsmanship and versatility. Geothermal heat pumps and Andersen windows, extensive power supply specs are just a couple of the steps taken by the owner to make this a long-lasting home. Three-bay garage and shop space in the lower level of the home AND a large shop building, separately located on the acreage for home privacy. The 4-bedroom, 4.5 bath brick residence features a massive central great room with vaulted ceilings and a striking masonry fireplace with custom wood elevator. The adjacent gourmet kitchen is designed for both function and style, featuring stainless steel appliances, custom backsplash, and a huge center island. The large main level owner's suite is large in scale with huge closet and bath. Owner's shower has body sprays, corner tub is jetted! This suite also enjoys access to the rear patio. Two more large bedrooms share a second full bath, and the laundry room is on this main level as well. The entire floor plan is perfect for large gatherings, making lasting memories, holiday events. The finished basement includes a small in-law apartment, mechanical room and storage, room for a large recreation room. Outdoor living areas are equally impressive, with two levels of poured concrete patios, including a built-in grill station off of the kitchen. Car enthusiasts and hobbyists will appreciate the two garages within the home, totaling 5 bays!! Lower level shop-garage has another full bath, room for multiple vehicles and shop area, perfect for collectors and mechanics. SHOP BUILDING- a 55 x 60 shop with 14 x 40 lean-to, half bath and other outbuildings for storage. Various tools and equipment conveyances, offering endless possibilities. Multiple uses with motor lifts, plasma table, air hoist on steel beam from front to back of the main space. The property is conveniently accessible to Route 5 and Route 235, offering easy access to shopping, dining, and commuter routes. SOLD AS IS.

27320 Harpers Ct, Mechanicsville

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

$776,220
3 Beds 4 Baths
The PARKER Model, Elevation One ** Please excuse our mess while construction is underway ** Wonderful Front Porch ** One Acre Plus WOODED Level Lot **FABULOUS KITCHEN w/Super Island & Granite Counters *** Huge PANTRY *** Upgraded STAINLESS Appliances *** First Floor Primary Bedroom complete with Custom Box Ceiling *** Master Bath with CUSTOM Walk in SHOWER w/Custom Seat ** Two Additional Main Floor Bedrooms with private Bath *** OPEN Floor Plan ***Full BASEMENT w/ FINISHED REC ROOM, DEN with closet & Full BATH with TUB *** Two Car Garage ** LUXURY VINLY FLOORING throughout Main Level ** Internet Available *** Street Lights ** Builders Warranty *** One of St. Mary’s county’s best locations. The community is over 300 acres. Porto Bello offers a rare opportunity to live in a quiet oasis of 1+ plus acre wooded lots. Just minutes away from Rt. 2/4 located just south of Leonardtown, Maryland. Drayden, Maryland is a beautiful town that is bordered by water and close to the PAX base, shopping and entertainment.

19166 N Porto Bello Dr, Drayden

Listing courtesy of RE/MAX One. Contact: 4437718009

$559,900
3 Beds 2 Baths
Priced Reduced $15,000 WATERVIEW From Every Room. Completely repainted inside. Wake to a beautiful sun rise and doze to a beautiful sunset. Beautiful 3BR/2BA one-level waterfront home with boathouse, 6’x40’ pier w/ boat lift, and newer bulkhead with 6’ MLW. Enjoy an all-season sunroom with water views, brand new roof, newer windows, and updated systems including a 6-yr HVAC, new washer/dryer, and microwave. Two sheds provide extra storage. Primary bedroom has private entrance—ideal as an accessory apartment or guest suite. Home has a transferable gutter leaf guard and a generator hook up. This home is move-in ready with modern updates and direct access to boating, fishing, and crabbing—your waterfront lifestyle awaits! Peace of mind also knowing you'll have a home warranty. Get home and want to fish? Do it. Get home and want to crab? Do it. Get home and want to relax by the water? Do it. Get home and don’t want to cook? Walk a few steps to Morris Point Restaurant. This is real waterfront easy living.

38819 Morris Point Rd, Abell

Listing courtesy of RE/MAX One. Contact: 4437718009

$397,500
3 Beds 2 Baths
An extraordinary opportunity awaits—where home and land come together in perfect harmony. Nestled on 1.04 acres, this property includes an incredible bonus of 6.56 additional acres behind the home, creating a rare total of 7.60 acres to explore, enjoy, and make your own. This charming three-bedroom, two-full-bath home offers the ease of highly sought-after one-level living, paired with thoughtful updates and timeless character. A new heating system installed in March 2025 and a new roof completed in June 2024 provide peace of mind, while the rear porch (2011) invites you to slow down and savor the outdoors. Beneath the carpet, beautiful hardwood floors are waiting to be revealed, and the retro tile bathroom has been lovingly maintained, blending vintage charm with enduring quality. Additional updates include new insulation and a dehumidifier installed under the home in November 2025. The enclosed sunroom off the kitchen is pure magic—a cozy spot to sip your morning coffee, watch the birds, and soak in the serenity of the surrounding land. Outside, the detached two-car-plus insulated garage (to include insulation in the attic) with workshop, is a dream come true, complete with its own oil furnace and window air-conditioning unit to keep you comfortable year-round, whether you’re working on projects or pursuing your passions. Even better, the seller is leaving the porch furniture, so you can start enjoying the space from day one. This home checks so many boxes—land, updates, charm, functionality, and possibility. Be sure to put it at the very top of your list and schedule your showing as soon as possible. Opportunities like this don’t come along often. 🌿✨

49078 Wynne Rd, Ridge

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$1,099,900
3 Beds 3 Baths
PRICE IMPROVEMENT! Experience an exceptional waterfront lifestyle in this newly constructed custom home, thoughtfully designed with luxury, comfort, and breathtaking water views in mind. Situated on over 2 private acres with approximately 340 feet of waterfront, this one-of-a-kind residence offers a rare opportunity to own a truly distinctive property in Southern Maryland. Inside, you’ll find high-end finishes, an open-concept floor plan, a gourmet chef’s kitchen, an elevator serving multiple levels, two gas fireplaces, spacious balconies, skylights, dual-zone HVAC, and two laundry areas for ultimate convenience. Wake up to spectacular sunrises, enjoy boating, fishing, kayaking, or simply relax while taking in the peaceful waterfront setting from your own backyard. Unlike older waterfront homes, this newly built residence offers the peace of mind that comes with modern construction, energy efficiency, and premium craftsmanship. The adjacent 3.36-acre waterfront lot is also available for purchase, creating an extraordinary opportunity for additional privacy, a future guest home (subject to approvals), or a multi-generational waterfront estate. Conveniently located within driving distance of Washington, DC, Northern Virginia, and Annapolis, this home is ideal as a primary residence, luxury weekend retreat, or vacation getaway. Significant price improvement. Schedule your private tour today and discover one of Southern Maryland’s most exceptional waterfront opportunities.

16242 Thomas Rd, Piney Point

Listing courtesy of Realty ONE Group Capital. Contact: (202) 932-5100

$714,900
4 Beds 3 Baths
YOUR DREAM HOME, YOUR WAY – TO BE BUILT on 1 acre, please note the tax record is wrong. Why spend your weekends touring older homes that need "just a little work" when you can build exactly what you want? Avoid the bidding wars and move into a masterpiece designed specifically for you. This 4-bedroom, 2.5-bathroom "Ariana" floor plan by Litz Custom Homes is the perfect blend of luxury and functionality on a beautiful Mechanicsville lot. The Custom Experience: Unlike most builders, we don't limit you to a few "packages." Bring your Pinterest boards! From the tile and flooring to the hardware and light fixtures, you are the designer. Want to move a wall, vault the ceilings, or add a sunroom? This is a full-service custom build where your ideas actually matter. Home Highlights: Stunning Curb Appeal: A stone facade and a charming wrap-around front porch made for rocking chairs and relaxation. Gourmet Heart of the Home: An open-concept kitchen featuring 42-inch cabinets, a center island with bar-top seating, and a walk-in pantry, all overlooking a living room anchored by a cozy stone fireplace. Primary Retreat: A massive second-floor owner's wing featuring a private sitting room, a huge walk-in closet, and a spa-style ensuite with a freestanding tub and custom-tiled shower. Space for Everything: Three additional spacious bedrooms share a large hall bath, plus a versatile loft space for a home office or playroom and a convenient second-story laundry room. Room to Grow: Includes a 2-car garage and a full unfinished basement with a bathroom rough-in already in place. Build Where You Want: We can build the Ariana on this lot, or if you already have land (or need help finding some), we can build there too! This is your chance to get a tailored lifestyle that simply isn't available in the current resale inventory. Call now to start designing and building your dream home! Please note: Images are for illustrative purposes and represent similar quality; final finishes and specifications are subject to change based on your custom selections.

28590 Old Village Rd, Mechanicsville

Listing courtesy of RE/MAX Realty Group. Contact:

$320,000
4 Beds 2 Baths
Recent Price Adjustment…Submit an offer today! Nestled in the charming Patuxent Park neighborhood, this beautifully renovated, move-in ready Colonial home is set to impress with its thoughtful updates and inviting atmosphere. With a major renovation completed in 2025, this residence seamlessly blends classic charm with modern conveniences, making it the perfect sanctuary for those seeking comfort. Major updates include a new roof, new siding, new windows and doors, all-new electric, recessed lighting throughout, new drywall, and fresh paint inside and out. Plus, there is brand-new flooring, stainless steel appliances, granite countertops, and a washer and dryer included. As you step inside, you'll be greeted by a spacious and airy layout that invites natural light to flow throughout. The fully finished basement offers additional living space, ideal for a cozy family room, home office, or play area, complete with windows that brighten the space and a full bathroom. Upper level features well appointed bedrooms and a full bathroom, this home provides ample room for relaxation and privacy. The heart of the home is undoubtedly the kitchen, where you can envision preparing meals and dining in the adjacent dining room. The design allows for easy interaction with guests, ensuring connectivity. The warm tones and modern finishes create an inviting ambiance that makes every meal feel special. Outside, the property boasts a manageable lot size that backs to woods, providing the right amount of outdoor space for gardening, barbecues, or simply enjoying the fresh air. The driveway offers convenient parking, making it easy for you and your guests to come and go. Located in a neighborhood that is in close proximity to shopping and dining venues.The Colonial architectural style adds a timeless elegance to the property, while the aluminum siding ensures durability and low maintenance. This property is not just a house, it's a place where memories are sure to be made. Whether you're hosting a summer barbecue in the backyard or enjoying a quiet evening in the cozy living room, this home is designed to cater to your lifestyle. With its blend of modern updates and classic charm, it's ready to welcome you home. Don't miss this rare turnkey opportunity to make this inviting space your own! If you are ready to move, this is the one—don’t miss out!!

46600 Midway Dr, Lexington Park

Listing courtesy of AIP Realty, LLC. Contact: 3012647215

$599,900
4 Beds 3 Baths
*** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE ARUNDEL Model, Elevation II*** 2 CAR GARAGE ****FABULOUS KITCHEN w/Super Island & GRANITE Counters *** Pantry *** STAINLESS appliances *** Open Concept ** 1st Floor FAMILY ROOM open to the Kitchen *** full BASEMENT w/Rough in for a FULL BATH ** Optional REC ROOM and DEN *** INTERNET Available *** Street LIGHTS ** WARRANTY *** Pick this ARUNDEL Model or ANY one of our offered floor plans *** Builder will CUSTOMIZE *** This is One of St. Mary’s county’s best locations. The community is over 300 ACRES *** Porto Bello offers a rare opportunity to live in a quiet OASIS of 1+ plus acre WOODED lots. Just minutes away from Rt. 2/4 located just south of Leonardtown, Maryland. Drayden, Maryland is a beautiful town that is bordered by water and CLOSE to the PAX base, shopping and entertainment ** PICTURES are for illustrative purposes and may contain upgrades not included in the base price ***

19163 Porto Bello, Drayden

Listing courtesy of RE/MAX One. Contact: 4437718009

$499,900
2 Beds 2 Baths
Enjoy waterfront living with this cottage style home offering breathtaking views of the Patuxent River and St. Thomas Creek. The open main-level floor plan of this 2BR 2FB home captures water views from most areas of the home, as does the rear of the fully finished walkout-level basement. The spacious walk-up attic could potentially offer future expansion into a third floor, perhaps maybe with dormers, to further expand living space with even more stunning panoramic views. Enjoy the outdoors from the large rear deck or take advantage of direct water access with a private pier, jet ski ramp, boat lift, pier-side storage shed, and small beach area at the water’s edge. The pier provides easy access to navigable waters, perfect for boating, fishing, and exploring the Patuxent River, the Solomons Island area and the many Chesapeake waterways. A detached screened patio with a wood burning stove invites outdoor dining or peaceful relaxation with picturesque water views. Set in a peaceful, private country setting, this property invites you to entertain or just simply relax and unwind while enjoying unforgettable sunrises and sunsets over the water, all from the comfort of your own backyard. Don't miss this rare opportunity to enjoy your own piece of waterfront paradise. The horse shoe style driveway with parking area offers plenty of off street parking. The home is being sold in as-is condition. Current septic system has failed and seller is in current contact with the St. Marys County Health Department determining what septic options will be available for buyer installation upon purchase. The cost of the system replacement could potentially be offset through the The Maryland Bay Restoration Fund. Interested purchasers may want to contact the St. Mary’s County Health Department’s Clear Water Program, which administers the Bay Restoration Fund (BRF) in St. Mary’s County, for further information.

43979 Drum Cliff Rd, Hollywood

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

$395,000
3 Beds 3 Baths
This home offers an opportunity, a level of finish, and details that stand out. Featuring 3 bedrooms and 2.5 baths on one level, the layout feels open, spacious, and welcoming. Located in a USDA eligible area with no HOA, 100% financing may be available for qualified buyers. Major systems have been replaced, including electrical, plumbing, HVAC, and roof, providing added confidence. The kitchen features granite counters, soft-close cabinetry, island seating, a walk-in pantry, and upgraded stainless steel appliances, including a craft ice refrigerator. The owner’s suite includes a tiled shower, double vanity, and walk-in closet. Waterproof luxury vinyl plank flooring, fresh paint, wide baseboards, and recessed lighting create a clean, modern feel throughout. Additional features include a dedicated laundry room with cabinetry, ceiling fans in each bedroom, and attic storage with pull-down access. The well has passed water quality testing, and major well components have been replaced. A recent septic evaluation included a hydraulic load test with satisfactory observations, with some root intrusion noted in portions of the system. Schedule your showing to see everything this home has to offer.

41010 New Market Turner Rd, Mechanicsville

Listing courtesy of Samson Properties. Contact: 7033788810

$679,900
4 Beds 3 Baths
*** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE CANTERBURY II Model *** GARAGE ****FABULOUS KITCHEN w/Super Island & GRANITE Counters *** Pantry *** STAINLESS appliances *** Open Concept ** 1st Floor FAMILY ROOM open to the Kitchen *** full BASEMENT w/Rough in for a FULL BATH ** Optional REC ROOM and DEN *** INTERNET Available *** Street LIGHTS ** WARRANTY *** Pick this CANTERBURY II Model or ANY one of our offered floor plans *** Builder will CUSTOMIZE *** This is One of St. Mary’s county’s best locations. The community is over 300 ACRES *** Porto Bello offers a rare opportunity to live in a quiet OASIS of 1+ plus acre WOODED lots. Just minutes away from Rt. 2/4 located just south of Leonardtown, Maryland. Drayden, Maryland is a beautiful town that is bordered by water and CLOSE to the PAX base, shopping and entertainment ** PICTURES are for illustrative purposes and may contain upgrades not included in the base price ***

46234 Stasha, Drayden

Listing courtesy of RE/MAX One. Contact: 4437718009

$649,500
3 Beds 2 Baths
Your dream home on nearly 4 acres is waiting for your personal touch! Currently framed and securely enclosed with a solid roof, this exciting property is at a stage where your imagination can run wild. With the structure already in place, you have the unique opportunity to customize every detail to suit your taste. Now is the perfect time to choose your favorite finishes, whether it's selecting elegant flooring, beautiful cabinetry, or stunning countertops. You can also pick the perfect colors to adorn the walls, creating a warm and inviting atmosphere throughout your new living space. Imagine how satisfying it will be to create a home that reflects your style and meets the needs of everday living. Don’t let this chance slip away to transform this house into the perfect haven just for you! Call your agent today for more details!

17881 Three Notch Rd, Dameron

Listing courtesy of Topside Realty. Contact:

$635,900
3 Beds 3 Baths
** ONE ACRE Plus Wooded Level LOT *** The Stella Model or Select from one of our other Plans ** To Be Built ** Still time to Customize Selections and upgrades *** FABULOUS KITCHEN w/Super Island & Granite Counters *** Huge Pantry *** STAINLESS Appliances *** First Floor Primary Bedroom complete with walk in Closet *** Master Bath with Soak Tub and Walk in Shower *** Tow Additional Main Floor Bedrooms with a Jack & Jill Bath *** OPEN Floor Plan ***Full BASEMENT w/ Rough in Plumbing for a full bath *** Two Car Garage ** Internet Available *** Street Lights ** Warranty *** PICTURES are for illustrative purposes and may contain upgrades not included in this purchase **CUSTOMIZED" *** One of St. Mary’s county’s best locations. The community is over 300 acres. Porto Bello offers a rare opportunity to live in a quiet oasis of 1+ plus acre wooded lots. Just minutes away from Rt. 2/4 located just south of Leonardtown, Maryland. Drayden, Maryland is a beautiful town that is bordered by water and close to the PAX base, shopping and entertainment.

19103 Windsor, Drayden

Listing courtesy of RE/MAX One. Contact: 4437718009

$15,000,000
6 Beds 5 Baths
LUXURY PROPERTY AUCTION: 13 August - 27 August. Accepting starting bids through 27 August. Listed for $20M. Earn an incentive by 13 August. OPEN HOUSES EVERY WEEKEND SATURDAY AND SUNDAY 1-3 PM. PLEASE COME AND TAKE A LOOK AT THIS MAGNIFICENT 500 ACRE ESTATE WHERE THE FOUNDING FATHER'S ONCE MINGLED! Mulberry Fields is one of those rare places where the land itself tells the story. The mile-long cedar avenue announces the approach, its rows planted at an ever-widening angle to draw the eye toward the Potomac below, a feat of 18th-century landscape design so precise it has appeared in gardening textbooks for centuries. At the end of that drive stands the last surviving Georgian manor house in St. Mary’s County, a ca. 1755 brick estate where the center hall, great room, and dining room are paneled in raised wood from floor to ceiling, the original moldings, doors, and mantels intact after nearly 270 years. Beyond the manor, two Georgian brick dependencies anchor a formal north courtyard, and the grounds unfold across just under 500 acres of fertile land before meeting 1,700 feet of white sand Potomac riverfront. There is simply no other property like this on the Eastern Seaboard.

19700 Mulberry Fields Rd, Leonardtown

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

$1,750,000
4 Beds 2 Baths
Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The house is well-kept with 4 Bedrooms and 2 Baths; a place-to-relax front porch; the master bedroom and the laundry room (washer and dryer included) are on the entry level. Also, a foundation for a 3,000+ square-foot house has been started near the water and has the electric meter installed. A pier on the farm is on the protected Cecil Creek where boaters and non-boaters can enjoy the tranquility and hours of fishing, crabbing, and just enjoying life. If it's hunting you want, many deer, turkeys, ducks and other waterfowls have been sighted on this sportsman's paradise. A 24-Hour Appointment Notice is necessary for all showings. To show/view the house, call the Listing Agent who will schedule an appointment for/with you.

Bayside Rd, Leonardtown

Listing courtesy of Haley Family Realty. Contact: