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$764,987

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.

3 Beds ⋅ 3 Baths

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.

43816 Raspberry Ln, Hollywood

Listing courtesy of O'Brien Realty ERA Powered. Contact: 3018632400

$999,900

This exceptional custom home on a double waterfront lot offers nice privacy and premium boating access just minutes from the Patuxent River, Chesapeake Bay, and Solomons Island. The exterior features a 149-foot pier with three slips, a jet ski lift, and accommodation for a large sailboat(6-foot draft), alongside beautifully landscaped grounds, waterview porches and a plumbing-ready waterside shed. An impressive 8-foot stained-glass front door opens to a dramatic two-story foyer and open floor plan featuring 10-foot ceilings and radiant-heated beautifully refinished oak floors. The gourmet kitchen boasts custom cabinetry, granite countertops, premium Wolf and Bosch appliances, new refrigerator, stylish backsplash and an expansive breakfast bar. It flows seamlessly into a dining room with loads of natural light and breathtaking water views . Also a cozy family room equipped with a gas fireplace and custom built-ins. A main-level guest bedroom, full bath, and mudroom complete the first floor. Upstairs features luxury vinyl flooring throughout and an extra-large primary suite featuring cathedral ceilings with exposed barn beams, a gas fireplace, a large private waterfront balcony, and a spa-inspired bath complete with a unique heating stove, whirlpool tub, and custom walk-in shower. A second spacious bedroom and laundry room complete this level. A stunning spiral staircase leads to the unique tower solarium, offering panoramic creek views perfect for a meditation space or home office. High-end mechanicals include an efficient Buderus furnace (powering domestic hot water and the radiant floors across the main level and the oversized, heated 2-car garage/workshop), a 13kW Generac whole-house generator and central vacuum!

3 Beds ⋅ 2 Baths

This exceptional custom home on a double waterfront lot offers nice privacy and premium boating access just minutes from the Patuxent River, Chesapeake Bay, and Solomons Island. The exterior features a 149-foot pier with three slips, a jet ski lift, and accommodation for a large sailboat(6-foot draft), alongside beautifully landscaped grounds, waterview porches and a plumbing-ready waterside shed. An impressive 8-foot stained-glass front door opens to a dramatic two-story foyer and open floor plan featuring 10-foot ceilings and radiant-heated beautifully refinished oak floors. The gourmet kitchen boasts custom cabinetry, granite countertops, premium Wolf and Bosch appliances, new refrigerator, stylish backsplash and an expansive breakfast bar. It flows seamlessly into a dining room with loads of natural light and breathtaking water views . Also a cozy family room equipped with a gas fireplace and custom built-ins. A main-level guest bedroom, full bath, and mudroom complete the first floor. Upstairs features luxury vinyl flooring throughout and an extra-large primary suite featuring cathedral ceilings with exposed barn beams, a gas fireplace, a large private waterfront balcony, and a spa-inspired bath complete with a unique heating stove, whirlpool tub, and custom walk-in shower. A second spacious bedroom and laundry room complete this level. A stunning spiral staircase leads to the unique tower solarium, offering panoramic creek views perfect for a meditation space or home office. High-end mechanicals include an efficient Buderus furnace (powering domestic hot water and the radiant floors across the main level and the oversized, heated 2-car garage/workshop), a 13kW Generac whole-house generator and central vacuum!

23719 Bill Dixon Rd, California

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$1,167,000

4 Beds ⋅ 3 Baths

21485 Canoe Neck Way, Abell

Listing courtesy of ExecuHome Realty. Contact: 4436323000

$875,000

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.

4 Beds ⋅ 4 Baths

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.

17597 Whitestone Dr, Tall Timbers

Listing courtesy of O'Brien Realty ERA Powered. Contact: 3018632400

$775,000

Enjoy effortless waterfront living in Southern Maryland from this premier end-unit condominium on Oakwood Lodge Lane in Piney Point, offering expansive views across the Potomac River to Virginia and a white sandy beach just steps from your door. Nestled within an exclusive 6-unit condominium community, this maintenance-free waterfront retreat offers over 3,500 square feet of beautifully designed living space with 3 bedrooms, 2 full baths, and a convenient main-level half bath. The main-level primary suite provides comfort and convenience, while hardwood floors, a chef’s kitchen, gas fireplace, and panoramic river views create the perfect setting for everyday living and entertaining. Upstairs, you'll find an additional primary suite featuring a private balcony overlooking the Potomac River and sandy beach—an ideal spot to enjoy morning coffee, watch boats pass by, or take in spectacular sunsets. The upper level also includes a a third bedroom, a spacious bunk room, and an additional full bath, providing plenty of room for family and guests. Step outside and sink your toes into the sandy beach, launch your boat from your deeded slip equipped with a 12,500-pound boat lift, or relax on the expansive deck overlooking the river, beach, and community pier. An attached 2-car garage provides ample storage for vehicles and beach gear. For boating enthusiasts, the property is located just minutes from the mouth of the Potomac River and approximately 15 minutes by boat from the Chesapeake Bay, providing easy access to some of the region's best fishing, cruising, and waterfront destinations. Located within walking distance of the Piney Point Lighthouse Museum, this exceptional waterfront residence offers a rare opportunity to enjoy one of the finest waterfront lifestyles in Southern Maryland, where boating, fishing, beach days, and unforgettable sunsets become part of everyday life.

3 Beds ⋅ 3 Baths

Enjoy effortless waterfront living in Southern Maryland from this premier end-unit condominium on Oakwood Lodge Lane in Piney Point, offering expansive views across the Potomac River to Virginia and a white sandy beach just steps from your door. Nestled within an exclusive 6-unit condominium community, this maintenance-free waterfront retreat offers over 3,500 square feet of beautifully designed living space with 3 bedrooms, 2 full baths, and a convenient main-level half bath. The main-level primary suite provides comfort and convenience, while hardwood floors, a chef’s kitchen, gas fireplace, and panoramic river views create the perfect setting for everyday living and entertaining. Upstairs, you'll find an additional primary suite featuring a private balcony overlooking the Potomac River and sandy beach—an ideal spot to enjoy morning coffee, watch boats pass by, or take in spectacular sunsets. The upper level also includes a a third bedroom, a spacious bunk room, and an additional full bath, providing plenty of room for family and guests. Step outside and sink your toes into the sandy beach, launch your boat from your deeded slip equipped with a 12,500-pound boat lift, or relax on the expansive deck overlooking the river, beach, and community pier. An attached 2-car garage provides ample storage for vehicles and beach gear. For boating enthusiasts, the property is located just minutes from the mouth of the Potomac River and approximately 15 minutes by boat from the Chesapeake Bay, providing easy access to some of the region's best fishing, cruising, and waterfront destinations. Located within walking distance of the Piney Point Lighthouse Museum, this exceptional waterfront residence offers a rare opportunity to enjoy one of the finest waterfront lifestyles in Southern Maryland, where boating, fishing, beach days, and unforgettable sunsets become part of everyday life.

17295 Oakwood Lodge Ln Unit #6, Piney Point

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$7,500,000

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.

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: 3018622169

$780,000

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.

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

$1,099,900

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.

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