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Some properties come along once in a generation. This is one of them. Tucked within the coveted Holland Point community of North Beach, Maryland, this rare and expansive waterfront compound offers something the Chesapeake Bay area simply does not produce anymore — significant water frontage, a grandfathered private dock that is the longest in North Beach, and the kind of breathing room and flexibility that coastal dreamers spend a lifetime searching for. From sunrise to sunset, the views across the bay are nothing short of extraordinary. Whether you’re casting a line off the dock, pulling in with your boat after a day on the water, or simply sitting on the porch watching the last light melt into the Chesapeake, this property delivers the full Bay experience in a way few others can. The main waterfront residence has been thoughtfully updated where it counts — featuring a refreshed kitchen, dining area, and bath — and opens into a generously scaled living area designed for effortless entertaining. Multiple bedrooms, each with its own in-room sink, offer a charming nod to a bygone era of gracious hosting, while a spacious family room positioned closest to the water keeps you connected to the views at every turn. Step outside to a lovely enclosed wraparound patio that flows naturally to the oversized dock — the perfect perch for avid boaters and sunset watchers alike. What truly sets this compound apart is what’s included beyond the main house. A second improved waterfront property, directly adjacent, comes with the sale — featuring a substantial garage base suitable for boats and vehicles, and an upper level that opens into a bright, airy great room with a full bath and flexible space ideal for guests, a studio, or a private home office. Completely self-contained, it functions as its own retreat while remaining part of your larger compound. Together, these two properties create something genuinely rare on the Chesapeake — a compound with room to spread out, house your toys, welcome your people, and savor coastal living exactly on your own terms. Whether your vision is multigenerational living, a boater’s paradise, a creative haven, or simply an extraordinary primary or vacation retreat, this Holland Point compound has the bones, the footprint, and the waterfront to make it all possible. Opportunities like this do not come twice.
#MDAA2134056

NORTH BEACH

852 BAY FRONT AVENUE

4 Beds

2 Baths

N/A

$2,000,000

MLS#: MDAA2134056

Exceptional opportunity to own three acres in the heart of the Prince Frederick Town Center. Ideally positioned at the highly visible intersection of Main Street and Church Street, this prime commercial property is located in the center of "downtown" Prince Frederick. Within walking distance of the Calvert County Courthouse, State and County government offices, professional businesses, retail shops, restaurants, and other community amenities, this location offers outstanding convenience and accessibility. The property's walkable setting, excellent public transportation access, and exceptional visibility make it an ideal site for a wide variety of permitted public or private commercial uses. Listing is for 125 Main Street and 91 Church St. They are adjoining properties with separate tax id numbers. The two properties are only being sold together! Please do not ask-They are NOT being sold separately. Existing house on 125 Main St parcel is being sold as is. Value is in the land! Whether you're planning professional offices, retail, mixed-use development, or another business venture, this is a rare opportunity to invest in one of Calvert County's most desirable commercial locations. Don't miss the chance to bring your vision to life in the center of Prince Frederick. Please reach out with any questions. Listing agent is a member of the selling entity. Boundary survey is in Documents
#MDCA2027892

PRINCE FREDERICK

125 MAIN AND 91 CHURCH STREET

None Beds

None Baths

3.02 acres

$2,000,000

MLS#: MDCA2027892

The clients and workers of the boarding business all would like to stay if given the opportunity. The facility consists of 50 stalls on 58.77 acres. The "lower barn" is a 32 stall center aisle barn with an adjoining building that has a heated tack room with lockers, a bathroom for clients and a wash stall. Above this barn is a 4 bedroom apartment and a one bedroom apartment both of which are currently occupied by farm employees. The "upper barn" is a center aisle barn with 18 stalls, a heated tack room and wash stall. There is a 160 x 80 indoor ring with lights and a watering system. There are 2 outdoor rings! The larger of the two outdoor rings is 225 x 120. The smaller outdoor is 80 x 60. The lights on the farm have been replaced with high efficiency LEDs. There is direct access to trails from the farm! In addition to the two apartments there are 2 detached homes on the property. One home is a traditional farmhouse style with a large welcoming front porch, eat-in kitchen, living room, dining room, 2 bedrooms on the main level and 3 bedrooms upstairs. The second home is a brick cape cod. This home has a living room, dining room, country kitchen, 2 bedrooms on the main level and 2 bedrooms upstairs. The huge loft above the "lower barn" would be an amazing venue and the multiple homes/apartments could be used as B&Bs. The farm is centrally located for many equestrian disciplines with access to Rtes 270 and 70. The total acreage is a combination of 3 parcels totaling 58.77 acres. In the documents section is an aerial picture that shows the outline of each pasture, the fence line and all the buildings. This property is listed as MDMC2088400 and MDMC2088394. The property is also known as 11415 Bethesda Church Road.
#MDMC2088400

DAMASCUS

11437 BETHESDA CHURCH ROAD

9 Beds

6 Baths

3,140 Sq.Ft.

$2,000,000

MLS#: MDMC2088400

Incredible investment opportunity in the heart of Fells Point! This 9-unit multi-family property at 1516 Lancaster Street offers everything a savvy investor could want—high ROI potential, prime location, and rare amenities. Each unit features 1.5 or 2 bedrooms, and the building includes 9 dedicated parking spots, 9 storage units, and a detached garage—a true luxury in this area. With close proximity to the waterfront, restaurants, and nightlife, this turnkey property is perfectly positioned for strong rental income and long-term appreciation. Don’t miss your chance to own a premier asset in one of Baltimore’s most desirable neighborhoods.
#MDBA2161694

BALTIMORE

1516 LANCASTER STREET

13 Beds

None Baths

7,520 Sq.Ft.

$2,000,000

MLS#: MDBA2161694

New Subdivision of Five (5) Residential Building Lots Ranging From 1.5 - 7 Acres. Private Driveway Is In. Buyer to Replace Seller on $85,000 Storm-Water Management Bond. All Wells are in, Perk Tests are Current, Electric and Comcast are In. Private Driveway is Not Paved. Beautiful Elevated Building Lots, Backs to Several Large Farms in Preservation. Five Minutes to Glyndon and 795. Nothing Like This in Baltimore County, Large Lots, Ready to Start Building, Beautiful Setting...
#MDBC2160042

REISTERSTOWN

13943 OLD HANOVER ROAD

None Beds

None Baths

18.75 acres

$2,000,000

MLS#: MDBC2160042

A Rare Offering! Exquisite Craftsmans style estate on 1 acre with sweeping pastoral views. This exceptional four-year-old Toll Brothers built home offers a rare combination of refined design, thoughtful functionality, and elevated indoor-outdoor living—all overlooking breathtaking pastoral scenery. A dramatic two-story great room serves as the heart of the home, highlighted by a floor-to-ceiling stone gas fireplace and expansive windows that frame the serene landscape beyond. The space flows effortlessly into a designer gourmet kitchen featuring granite countertops, an oversized center island, premium Wolf appliances, and a well-appointed prep kitchen complete with its own refrigerator, sink, dishwasher, and stove. A generous walk-in pantry adds both convenience and storage. The main level is thoughtfully designed to accommodate multigenerational living, offering a private suite with a spacious bedroom, sitting room with wet bar, luxury bath, walk-in closet, and its own dedicated laundry. Elegant details are found throughout, including custom millwork in the formal dining room and private study, along with hardwood flooring spanning throughout most of the home. Upstairs, the primary suite is a sophisticated retreat, showcasing a tray ceiling, private wet bar, and a spa-inspired bath with soaking tub, expansive walk-in shower, and ample closet space. Three additional bedrooms each feature en suite bath, complemented by a conveniently located second-floor laundry room. The fully finished lower level extends the home’s versatility with a sixth bedroom or fitness space and an upgraded wet bar with wine storage, designer tile backsplash, and custom lighting. Outdoor living is truly exceptional. A covered patio, accessed through French sliding doors from the great room, features a second fireplace—perfect for year-round enjoyment. In addition, a separate outdoor kitchen and living area includes a built-in grill, dedicated prep space, and ample room for dining with table and chairs, all perfectly positioned to take in the sweeping pastoral views. Extensive hardscaping, including a paver patio and fire pit, creates an ideal setting for both intimate gatherings and large-scale entertaining. Additional features include a whole-house generator, irrigation system for both front and rear grounds, upgraded lighting throughout, and a six-zone in-ceiling sound system. This is a rare opportunity to own a meticulously upgraded, turnkey residence offering luxury, privacy, and exceptional outdoor living in a truly scenic setting.
#MDHW2066124

WOODBINE

15625 LINDEN GROVE LANE

6 Beds

6 Baths

7,348 Sq.Ft.

$2,000,000

MLS#: MDHW2066124

SERIOUS SELLERS!!!! Stunning Craftsman home built by Churchill Classics in 2013 boasts 5 Bedrooms & 5.5 Baths. This fabulous residence is a beautiful blend of sophisticated features including a sensational kitchen, grand family room and enormous master suite. Lower level includes 5th bedroom, full bath and spacious den. Custom pool and landscaping are an inviting oasis. The screen porch has a stone fireplace and outdoor kitchen. Located within walking distance of Bannockburn ES. This happy home is truly wonderful - AT THIS NEW PRICE, HOUSE CONVEYS "AS IS"
#MDMC670216

BETHESDA

6609 PYLE ROAD

6 Beds

5 Baths

6,300 Sq.Ft.

$2,000,000

MLS#: MDMC670216

Welcome to this glorious garden-view residence with an expansive wraparound terrace to take in the tulips, walkways, and wisteria while enjoying your morning coffee! Tennis or pickleball enthusiast? Watch a game on a sunny afternoon! This gracious 2,547 sq ft home boasts two bedrooms (the primary bedroom has two baths & walk-in closets, the second bedroom has an ensuite bath) and a den, generously sized living and dining rooms, a cozy den/family room, office/work areas, and ample closets! Two parking spaces and a storage unit convey. Enjoy the marvelous amenities that this 17+acre luxury high-rise community has to offer: 24-hr security & gatehouse, 24-hr concierge & valet, community rooms with terraces, beautiful gardens, and walking paths, a 3-story clubhouse with a huge party/events room and board meeting room, catering kitchen, state-of-the-art exercise facilities, racquetball court, billiards & ping pong, art projects/hobby room, an aerobics room, plus indoor and outdoor pools with lifeguards, and tennis courts. Friendship Heights Metro Station, shops, restaurants, Whole Foods, and more are only a few blocks away!
#MDMC2119732

CHEVY CHASE

5610 WISCONSIN AVENUE 208

2 Beds

3 Baths

2,547 Sq.Ft.

$2,000,000

MLS#: MDMC2119732

Embrace authentic luxury waterfront living in this exceptional three-level, 3,100 plus SF fully finished residence, showcasing a private beach, a pier with multiple boat slips and two lifts, and a fully renovated interior designed to capture sweeping water views from every level. The sun-drenched open floor plan welcomes you with living spaces and immediate water views framed by picture windows and skylights streaming abundant natural light. Hardwood floors and a gas fireplace add comfort and refinement. Architectural details such as wood beams and a shiplap ceiling lend warmth and character to the designer kitchen and breakfast area, beautifully appointed with recycled Italian glass pearl tile backsplash and Kashmir dual-finish granite countertops. The upgraded gourmet kitchen is ideal for the culinary enthusiast, featuring an impressive, oversized island with gas cooktop, premium stainless-steel appliances, a walk-in pantry, and custom soft-close cabinetry with roll-out spice racks for optimal organization. A spacious three-season sunroom extends from the kitchen, offering access to one of three expansive decks offering an ideal setting for entertaining or enjoying tranquil waterfront views year-round. Main level living includes a powder room to service the open floor plan, and recent upgrades include an additional service kitchenette outfitted with custom cabinetry and a private In-law/Guest bedroom suite with skylights, a new full bath, and a private secondary entrance. Upstairs, the primary bedroom suite takes full advantage of panoramic waterside views offering a private screened porch, and gas fireplace with stone surround. The water views extend into a spacious and fully upgraded luxury bath enhanced with heated tile flooring, makeup and dual quartz vanities, and a frameless shower with seating and three shower heads. Two additional bedrooms, a full bath, and a new waterside deck, complete the upper level. Downstairs, the walk-out lower level invites outdoor waterside living with an architectural folding glass wall system that stacks open to one side offering a seamless indoor-outdoor transition with a large recreation area, another full bath, and an expansive unobstructed view of the Severn River. Simply open the folding glass wall and enjoy endless waterside fun including an 18 ft. crab table, Tiki bar with sink and water service, and an enclosed outdoor shower. A multi-level stair offers scenic landings as it cascades from the main house down to a private sandy beach and newly decked pier with two boat lifts, (10k and 24k) and multiple slips. Experience premier waterfront living with deep, navigable water that provides effortless boat access to the vibrant heart of downtown Annapolis within minutes. The Herald Harbor community has a neighborhood feel and amenities that include a community center, boat ramp, Bonaparte Beach, and walking trails. Gather with friends for book clubs, pickleball, local dining options and endless water-oriented activities. Enjoy easy access to downtown Annapolis, or commuter routes to Baltimore, DC, and BWI airport.
#MDAA2130812

CROWNSVILLE

330 S RIVERSIDE DRIVE

4 Beds

4 Baths

2,600 Sq.Ft.

$2,000,000

MLS#: MDAA2130812

Exceptional home on quiet street in English Village, close to downtown Bethesda! Gorgeous details & craftsmanship throughout this 6BR, 6.5 BA home. 4 finished levels offering 7600 square feet of fantastic living space. Beautiful gourmet eat-in kitchen & large family room opens to stunning backyard w/ saltwater pool & flagstone terrace. 2-car garage, mudroom w/ shower, gym in large basement & more!
#MDMC707648

BETHESDA

7707 RADNOR ROAD

6 Beds

6 Baths

7,685 Sq.Ft.

$2,000,000

MLS#: MDMC707648

Gorgeous waterfront home in Prospect Bay. Lovely floor plan. First floor Primary.
#MDQA2009150

GRASONVILLE

203 PROSPECT BAY DRIVE W

4 Beds

3 Baths

3,304 Sq.Ft.

$2,000,000

MLS#: MDQA2009150

Live authentically. Solitude. One of a kind offering with two building sites perched above Belfast Valley. Endless possibilities. Privacy and peace. An extensive trail network on your own park like 130.94 acres. Cultivate your existence. The art of uniting human and home.
#MDBC2110138

SPARKS GLENCOE

15651 DUNCAN HILL ROAD

None Beds

None Baths

130.94 acres

$2,000,000

MLS#: MDBC2110138

Attention builders and developers....Nearly 12 acres in desirable Glenn Dale...... Beautiful wooded parcel owned by the same family since the 1970's...... zoned for 1/2 acre lots.... churches also permitted.... near area shopping and employment... close to NASA Goddard.....very few opportunities to build SINGLE FAMILY homes in area. ... public water and sewer available.....owner lives in house... please DO NOT disturb her!!!!
#MDPG2002322

GLENN DALE

8215 SPRINGFIELD ROAD

None Beds

None Baths

11.94 acres

$2,000,000

MLS#: MDPG2002322

Situated just half a mile from the acclaimed Bretton Woods Golf Course and Country Club, with a prestigious River Road address, this secluded estate backs to a 630 acre Potomac riverside preserve. Including the pool house, the home delivers 7 bedrooms, 7 full baths, and 3 half baths, plus a jacuzzi room, 5 garage spaces -- and 3 kitchens. A peak of the river teases the imagination through the Wintertime trees. Immerse yourself in the absolute privacy of this serene estate, with lush green surroundings punctuated by bursts of color in the spring. Enter through the gates down a long private driveway, leading to the grand entrance with dazzling granite staircases, and into this Embassy-sized home for entertaining in extravagant style. Whether you crave peace and privacy for your family, or to entertain , this stately home provides that, enveloped in the sights and sounds of nature’s splendor. This custom beauty has just been upgraded with a gorgeous new kitchen and primary bathroom suite, featuring waterfall quartz counters and stunning finishes. An exquisite Schonbek crystal chandelier (motorized) is sure to be noticed by all your guests upon entering the foyer, which ushers into a stunning family room with 2 story ceilings, wood burning fireplace, and floor to ceiling French doors providing verdant views across the expansive deck that frames the rear of the home. From there, the expansive pool with heated spa and the independent 2-story guest cottage/pool house with kitchen are visible. So many living spaces on the main level: banquet sized dining room, butlers’ pantry, breakfast area off the open kitchen, formal living room with fireplace, and an elegant library/home office with custom millwork. 10 foot ceilings throughout. Upstairs, a magnificent primary bedroom suite with a propane fireplace, stunning new ensuite bath with sculpted tub and spa-sized shower, with tree top views and privacy. Two expansive walk in closets. All of the other 4 spacious bedroom suites on the upper level feature ensuite baths, with marble or granite vanities, and walk in closets. The laundry is on the upper level as everyone desires. In the walk out lower level, natural light is brought in by 2 sets of French doors leading to a patio and the expansive yard. The space features wood-burning fireplace, wet bar with mini-fridge, 400 bottle wine cellar, a guest room with ensuite full bath, billiards area, 2nd kitchen for catering, large ballet studio or home theater, exercise room, a half bath and a jacuzzi party tub room. Crown moldings throughout, extensive ceiling medallions, a total of 3 Schonbeck chandeliers and so much more attest to the quality workmanship in this once in a lifetime estate. Contract previously fell apart due to buyer financing. Come see it again now that we're active as of July 4th weekend.
#MDMC2048528

DARNESTOWN

15330 RIVER ROAD

6 Beds

7 Baths

10,777 Sq.Ft.

$2,000,000

MLS#: MDMC2048528

Prime waterfront and panoramic views of the Chesapeake Bay, the Severn River and the mouth of Back Creek located on arguably one of the best streets in the City of Annapolis! Southeastern exposure on Back Creek, this diamond in the rough is nestled between multi million dollar homes waiting for a renovation. This property has two structures on it. Located on the Horn Point Shoal with MLW of 2-3 Feet. Value is in the land, location and views. Rip wrap added five years ago. Property sold "As Is".
#MDAA2032568

ANNAPOLIS

23 EASTERN AVENUE

2 Beds

1 Baths

1,984 Sq.Ft.

$2,000,000

MLS#: MDAA2032568

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