Available Listings

$2,500,000 (USD)
Pending

Leonardtown Area Residential Home

Pending

40111 Army Way Leonardtown, MD 20650

4 Bed
7 Baths
7679 sqft
MLS# MDSM2032468
Virtual Tour
Beautiful Southern Maryland Coastal Retreat. Gracious and sophisticated. Elegant details throughout this incredibly, well-appointed home. Custom barrel ceiling and stained glass make a beautiful statement in the grand entry foyer. Inviting Family Room with serene water views. Newly renovated gourmet chef's kitchen is a coastal lovers dream. Enjoy sub-zero Wolf and Cove stainless appliances throughout. Custom white Cabinets and a blueberry hued Island grace this light and bright kitchen. Creamy quartz counter-tops and backsplash w/ Kohler ceramic and cast-iron sinks. Custom lighting and hardware. So very pretty with island seating and prep sink, all with water views. Kitchen and casual dining access to the large waterside screened porch for that morning coffee or evening dinner. Enjoy the walk-in pantry and open sight lines from the kitchen through the casual dining spaces and into the expansive Family Room. Warm Brazilian Cherry hardwood flooring flows through most of this spectacular home. Stunning water and garden views abound. Formal Dining Room with Cherry Built-Ins and pretty French pocket doors. A newly remodeled cozy mud room w/ fireplace makes a fabulous drop-zone for family and friends. Enjoy your Office library with cherry Built-Ins. Main Floor Primary Suite Wing has dual renovated bathrooms complete with heated floors and steam shower. Dual walk-in closets. Relax in the Great Room with cherry built-ins, a gas fireplace and custom windows to optimize all the pretty water-views. Front and Back Deep Covered porches to enjoy Alfresco Dining, Entertaining and Peaceful Tranquility. Take the Elevator or stairs up to the 2nd floor for the additional 3 bedroom suites. Lovely bonus Room upstairs for additional guests or a tucked away water view retreat. Custom arched doorways and rounded corners throughout. Niches and storage make this home so very special. Basement has multiple rooms and of course, MORE storage; a walk-in safe, a severe weather safety room, exercise and hobby space, a half bath and more.4+ Car Garage is attached to the home via covered Breezeway. The entire space above the Garages is available for storage or expansion with upper access from the house via a gallery w/skylights or a wide staircase inside the garage. Pier is Large and has been expanded to include two lifts (20,000lb and 7,500lb) to meet all your boating and kayaking needs. Over 300' of shoreline on scenic Combs Creek (6-8' deep at end of pier) and 5 minute boat ride to Breton Bay and the Potomac. This home blends one-of-a-kind customized luxury with Southern Living Charm. Located 5 minutes from the heart of Leonardtown you'll have all the privacy you could desire in your waterfront home yet still be close to area shopping and events. So much to love and see in this stunning custom home. Over 5900 finished sf above grade alone! Another 1720 sf is partially finished in the basement. The unfinished space above the garages is sub-floored and ready for your next expansion project. You will have room for everything and more. The perfect Retreat. 30 Minutes to NAS Patuxent River and 90 minutes to DC and VA. Appointment ONLY listing with prior notice required.
Listing Courtesy of BRIGHT IDX / Listed By: Maryanne "MaryAnne" Crewse, O'Brien Realty ERA Powered
$875,000 (USD)
Active

Tall Timbers Area Residential Home

Active

17597 Whitestone Drive Tall Timbers, MD 20690

4 Bed
4 Baths
3106 sqft
MLS# MDSM2031074
Virtual Tour
The Landings at Piney Point is a highly sought-after waterfront community offering exceptional amenities and a true coastal lifestyle. Residents enjoy one of the most beautiful private beaches in Southern Maryland, along with a community pool, tennis court, playground, harbor with boat slips, boat trailer storage, and more.Whether you enjoy boating, fishing, kayaking, or simply relaxing by the water, this community offers something for everyone. Conveniently located just a short commute from Naval Air Station Patuxent River, The Landings provides the perfect balance of peaceful waterfront living and everyday convenience.This home offers numerous upgrades and exceptional features, including new shingles, siding, gutters, a stone-front garage, and beautiful hardscaping in both the front and back yards. On the waterfront side, a fire pit creates the perfect setting for relaxing evenings by the water and space for grilling.The home is filled with natural light, thanks to dramatic wall-to-wall windows topped with transom windows that showcase the stunning water views. There are two spacious primary suites, one on the main level and one on the upper level—both with soaking tubs, dual sinks, and separate showers. The upper level has a balcony for enjoying lovely sunsets.Situated on one of the largest lots in The Landings, this beautiful, level 0.409-acre property overlooks the harbor and includes a deeded boat slip # 69 with a lift is located directly in front of the home. The slip size is 25 ' x 10'. Water source available. Seller is unsure of the capacity of the boat lift; it appears to be 8,000-10,000 LBS. The wooden platform that is on top of the lift is for launching kayaks. Additional features include an in-ground electric fence for pets and recent landscaping with beautiful trees and shrubs that enhance the property’s charm and privacy.The main level features a wide-open floor plan with wall-to-wall windows to enhance the view. The spacious bedrooms offer comfort and character, each with its own special features, making this waterfront home truly one of a kind.
Listing Courtesy of BRIGHT IDX / Listed By: Dawn Wood, O'Brien Realty ERA Powered
$764,987 (USD)
Active

Hollywood Area Residential Home

Active

43816 Raspberry Lane Hollywood, MD 20636

3 Bed
3 Baths
2551 sqft
MLS# MDSM2032448
Experience timeless English Tudor character paired with sweeping, unobstructed views of the Patuxent River. From the moment you step inside, the home’s expansive windows frame miles of serene waterfront, filling each room with natural light and a sense of calm that only riverside living can offer. With three bedrooms plus a dedicated office, the layout balances comfort and functionality—ideal for a full‑time residence or a peaceful weekend retreat. The original portion of the home features a classic kitchen, while the thoughtfully renovated section adds a second kitchen, offering flexibility for entertaining, multigenerational living, or reimagining the space to suit your vision. A two‑car garage and an unfinished basement currently used as a workshop provide abundant storage and room for hobbies, projects, or future expansion. Whether you dream of crafting the perfect waterfront getaway or designing a year‑round sanctuary, this property is ready to become your canvas. Beyond the walls of the home, the property invites you to fully embrace the natural beauty and recreation the Patuxent River is known for. Hunt for age‑old shark teeth along the shoreline, harvest oysters straight from the water, and enjoy crabbing during warm Maryland seasons. Whether you’re an outdoor enthusiast or simply love the idea of stepping into a slower, more peaceful rhythm, this location offers experiences you won’t find anywhere else. Waterfront living is within reach. Come experience the view, feel the tranquility, and imagine the possibilities waiting for you here.
Listing Courtesy of BRIGHT IDX / Listed By: Patrick Dugan, O'Brien Realty ERA Powered
$749,999 (USD)
Pending

Callaway Area Residential Home

Pending

44481 Boxwood Drive Callaway, MD 20620

5 Bed
4 Baths
4764 sqft
MLS# MDSM2031968
Property will go LIVE on July 15th. Schedule your showings now!Welcome to your own private retreat! Nestled on 2.2 beautifully landscaped acres, this stunning 5-bedroom, 4-bathroom brick-front home offers the perfect combination of space, comfort, and outdoor living.From the moment you arrive, you'll appreciate the home's impressive curb appeal, complete with a side-load 2-car attached garage and a setting that provides exceptional privacy. Inside, you'll find spacious living areas designed for both everyday living and entertaining. The recently added home theater in the finished basement creates the ultimate movie-night experience and provides additional space for gathering with family and friends.Step outside and discover a true backyard oasis. Enjoy summer days relaxing by the sparkling in-ground pool featuring a diving board and safety fencing, or unwind on the large screened-in porch overlooking the peaceful, private backyard. Whether you're hosting pool parties, enjoying morning coffee, or taking in the tranquil surroundings, this property offers the lifestyle you've been dreaming of.Major updates provide peace of mind, including a new upper-level HVAC system installed in May 2024 and a new lower-level HVAC system installed in May 2026.Offering 5 bedrooms, 4 full bathrooms, abundant indoor and outdoor living space, and a highly desirable private setting, this exceptional property is priced to sell and won't last long. Schedule your private showing today and experience everything this remarkable home has to offer!***Professional Photos are COMING SOON!
Listing Courtesy of BRIGHT IDX / Listed By: Mariah Riedell, O'Brien Realty ERA Powered
$729,900 (USD)
Active

Mechanicsville Area Residential Home

Active

27962 Cathedral Drive Mechanicsville, MD 20659

6 Bed
3 Baths
5366 sqft
MLS# MDSM2029922
Virtual Tour
This private 2.58-acre property is surrounded by mature trees, offering a peaceful and secluded setting. The impressive colonial home features an open floor plan with spacious rooms across all three levels, designed for both comfortable living and entertaining.The main level welcomes you with a dramatic two-story foyer and features a wide-open layout, including a formal dining room and a living/music room, both accented with tray ceilings, crown molding, and wainscoting. The generously sized family room, enhanced by a 4-foot bump-out, flows seamlessly into the kitchen and eat-in area​. A main-level primary suite provides the perfect space for an in-law or au pair.​The upper level ​overlooks the 2-​ story foyer, and b​oasts the luxurious primary suite, ​with vaulted ceilings, a dressing room, soaking tub, dual sinks, a​ separate shower, and expansive owner’s closets​. The two other spacious bedrooms share a hallway bathroom.The walkout lower level is filled with natural light and offers incredible versatility, featuring a spacious family room, a large bonus room perfect for a bedroom or office, a full bathroom, a kitchenette, and additional space for a game room or recreation area.Additional highlights include custom drywall with rounded corners, granite countertops, ​a large kitchen island with seating area, stainless steel appliances, a gas stove, a large walk-in pantry, vaulted ceilings, hardwood floors, a beautiful stone front, and a covered front porch.Step outside to the expansive Trex deck—ideal for entertaining, grilling, or simply relaxing while enjoying the serene surroundings.
Listing Courtesy of BRIGHT IDX / Listed By: Dawn Wood, O'Brien Realty ERA Powered
$615,000 (USD)
Pending

Prince Frederick Area Residential Home

Pending

2037 Baythorne Road Prince Frederick, MD 20678

4 Bed
4 Baths
3117 sqft
MLS# MDCA2027368
Price Improvement! Welcome to 2037 Baythorne RD located in the desirable neighborhood of College Station! This home has been well maintained and is ready for its next owner. Sitting on a 1.5-acre lot that backs to the trees, this home offers privacy even in a neighborhood setting. Enjoy cooking in a modern kitchen that features recessed lighting, granite counter tops and stainless-steel appliances. After a long day, come home and relax in your primary bath jacuzzi tub! Enjoy the endless entertainment opportunities with the large back deck perfect for birthdays, cookouts, get-together's and so much more. The property also has a maze of dirt bike trails ready to ride! Some highlighted features are the finished basement, hard wood floors, ceramic tile, updated appliances including newer dishwasher and fridge (2021), tankless hot water heater (2023), 100gal propane tank (2023), UV cleaning system and HVAC (2022) and a detached shed with electric. Let's not forget about location convenience! Shopping, dining and entertainment is a stone's throw away to Prince Frederick and PAX River Naval Base, Andrews Air Force Base and Washington DC are under an hour away. Sellers are offering $5,000 towards buyer closing costs! This is not an opportunity you want to miss!
Listing Courtesy of BRIGHT IDX / Listed By: Dezi Collins, O'Brien Realty ERA Powered
$600,000 (USD)
Pending

Lusby Area Residential Home

Pending

1002 Secret Court Lusby, MD 20657

6 Bed
4 Baths
3948 sqft
MLS# MDCA2027994
✨ Spacious, Updated, and Ready for Your Next ChapterWelcome to a home that truly has it all — space, style, and the kind of features that make everyday living feel effortless. Set on a level 1.65‑acre lot with no HOA, this property gives you freedom, privacy, and room to live the way you want. Inside, you’ll find 6 bedrooms, 3 full baths, and 1 half bath, all beautifully updated. This home has about 2344 finished above grade square footage and 1604 below grade finished square footage thus you will have plenty of room! The kitchen shines with granite counters, tile backsplash and floors, and a layout perfect for cooking, gathering, and entertaining. The main‑level primary bedroom offers comfort and convenience, paired with a main‑level full laundry room that keeps daily life simple. A formal dining room with wood floors sets the stage for holidays and celebrations, while the two‑story great roomalso with wood floors adds drama, light, and an open, airy feel. The finished basement is a true bonus — complete with a bar area and a theater room, giving you the perfect setup for movie nights, game days, and hosting friends. Step outside to enjoy a large deck, an above‑ground pool, and even a hen house for those who love a touch of homestead living. A 2‑car garage and plenty of open space make parking and storage easy. This is the kind of property that offers flexibility, comfort, and room to grow — all in one beautifully maintained package.
Listing Courtesy of BRIGHT IDX / Listed By: Jan Kleponis, O'Brien Realty ERA Powered