The 9 Most Expensive Homes For Sale In Southern Maryland, From $20 Million Estates To Private Islands

SOUTHERN MARYLAND — Ever wondered what a $20 million home in our region looks like? From a historic Potomac River manor and sprawling Chesapeake Bay estates to private islands, working farms and resort-style retreats, some of the most extraordinary properties on the market are far beyond the typical Southern Maryland home.

The BayNet searched Zillow listings across Calvert, Charles and St. Mary’s counties—and included one standout estate just outside the region in Brandywine, Prince George’s County—to round up the most spectacular luxury homes currently for sale. Here’s a look inside the multimillion-dollar properties turning heads across the area.

Here are some of Southern Maryland’s most notable luxury homes currently on the market as of Thursday, July 2, 2026.

1. Mulberry Fields In Leonardtown — $20 Million

Topping the list by a wide margin is Mulberry Fields, located at 19700 Mulberry Fields Road.

Built in 1755, the Georgian manor sits on nearly 500 acres overlooking the Potomac River and includes six bedrooms, five bathrooms and more than 13,400 square feet of living space. The property also features roughly a mile of private white sand shoreline, historic tobacco barns, a carriage house, seven fireplaces and several original outbuildings.

The estate was first listed for $30 million before dropping to its current $20 million asking price.

Mulberry Fields is also one of Southern Maryland’s most historically significant homes. It was added to the National Register of Historic Places in 1973 and is protected by multiple preservation and conservation easements. Any future owner must preserve the historic character of the property, which includes the manor and its original dependencies.

Photos: Long & Foster Real Estate/Bright MLS via Zillow

2. 50645 Holly Point Road In Dameron — $7.5 Million

Coming to the market July 16 is a Chesapeake Bay estate unlike anything else in Southern Maryland. Priced at $7.5 million, the waterfront property at 50645 Holly Point Road includes a four-bedroom, three-bathroom home on approximately 280 acres with more than 6,100 feet of Chesapeake Bay frontage. The sale also includes 91 lots in St. Jeromes Shores and 71 lots in Bay Harbor, making it one of the largest land offerings currently available in the region.

The home features hardwood floors, a wood-burning fireplace, an open kitchen and a bayfront primary suite, while outside, the property offers a private beach, roof deck, multiple patios, a pond and a tennis court ready for restoration.

Photos: Century 21 New Millennium/Bright MLS via Zillow

3. 24730 Half Pone Point Road In Hollywood — $4.595 Million

The largest home on this list is the waterfront estate at 24730 Half Pone Point Road, listed as coming soon with a July 15 market date. With more than 13,600 square feet of living space, the home includes four bedrooms and seven bathrooms overlooking the water. At $4.595 million, it’s one of Southern Maryland’s premier luxury listings and offers the most interior living space of any property featured here.

Photo: Bright MLS via Zillow

4. P.A. Bowen Farmstead In Brandywine — $3.9 Million

One of Southern Maryland’s most unique listings isn’t just a luxury home—it’s an operating farm with more than 350 years of history. Most recently listed at $3.9 million and offered through a no-reserve luxury auction, P.A. Bowen Farmstead spans nearly 95 acres and includes a restored Italianate manor house built in the 1870s on land first patented in 1665.

The six-bedroom, seven-bathroom home offers more than 6,000 square feet of living space, seven fireplaces and views of rolling pastures and woodlands. Beyond the historic home, the estate includes a second residence, cottage, three working barns, a greenhouse, an event barn, an in-ground pool, a pond with a dock and numerous outbuildings. The property is also home to the nationally recognized P.A. Bowen Farmstead, an award-winning regenerative farm known for its artisan cheeses, pasture-raised livestock and farm store.

Photos: Keller Williams Lucido Agency/Bright MLS via Zillow

5. 6675 Marshall Road In St. Leonard — $2.8 Million

The most expensive home currently for sale in Calvert County sits behind a gated entrance on more than 103 acres of woods, trails and open countryside. Listed for $2.8 million, the contemporary lodge-style estate at 6675 Marshall Road offers more than 8,100 square feet of living space with five bedrooms, five bathrooms and soaring 23-foot ceilings in the main living area.

The property is designed for entertaining, featuring a resort-style pool, outdoor kitchen, pavilion, fire pit, multiple decks and a finished walkout basement complete with a large wet bar. A separate guest house, workshop and heated pole barn add even more flexibility, while miles of wooded trails make the estate ideal for hiking, horseback riding or outdoor recreation.

Photos: Coldwell Banker Realty via Bright MLS/Zillow

6. 820 Bay Front Avenue In North Beach — $2.2 Million

If waking up to panoramic Chesapeake Bay sunrises is on your dream-home checklist, this waterfront property delivers. Listed for $2.2 million, the custom home at 820 Bay Front Avenue offers 4,400 square feet of living space with four bedrooms and four bathrooms, plus sweeping bay views from nearly every room.

The centerpiece is a 1,000-square-foot great room with vaulted ceilings, while the chef’s kitchen features granite countertops, stainless steel appliances and three oversized dining islands built for entertaining. Outside, the property boasts 105 feet of private waterfront, complete with a pier, boat lifts and sun decks for easy days on the water. Sold fully furnished, the home also sits on three lots, with one additional lot offering the potential to build another home or expand the property.

Photos: Keller Williams Realty/Bright MLS via Zillow

7. 15188 Lake Drive In Scotland — $1.8 Million

Perched high above the Chesapeake Bay, this custom waterfront retreat at 15188 Lake Drive was designed to make the view the star of the show. Listed for $1.8 million, the four-story home offers five bedrooms, six bathrooms and nearly two acres with more than 2,100 feet of Chesapeake Bay and Hollis Lake frontage. Walls of glass, expansive decks and a private elevator connect every level, while the chef’s kitchen features professional-grade stainless steel appliances, sleek metal countertops and double pantries built for entertaining.

The entire top floor is dedicated to a luxurious primary suite with a spa-inspired bathroom and wraparound deck overlooking the Bay. The property also includes a private sandy beach and a separate one-bedroom guest house, making it an ideal waterfront getaway just 90 minutes from Washington, D.C.

Photos: Century 21 New Millennium via Bright MLS/Zillow

8. 1970 Old Anchor Road In Huntingtown — $1.75 Million

Rounding out the waterfront estates is a newly built farmhouse-style home at 1970 Old Anchor Road. Built in 2022, the five-bedroom, four-bathroom home sits on 33.2 acres with 1,636 feet of frontage along Hunting Creek.

The 4,388-square-foot home features a wraparound porch, gourmet kitchen with a butler’s pantry and a main-level owner’s suite. Outside, the property truly stands out with a newly installed private pier, room for a pool and pickleball court, and two private islands surrounded by protected marshland that’s home to deer, wild turkeys and migratory waterfowl. At $1.75 million, it offers a rare combination of waterfront living, privacy and natural beauty.

Photos: Berkshire Hathaway HomeServices PenFed Realty/Bright MLS via Zillow

9. 4100 Hidden Creek Road In Port Republic — $1.469 Million

This custom-built estate proves you don’t need hundreds of acres to live large. Listed for $1.469 million, the five-bedroom, seven-bathroom home at 4100 Hidden Creek Road offers more than 8,600 square feet of living space on two private acres in the heart of Calvert County.

Designed for entertaining, the home features a gourmet kitchen, executive office, private guest wing and a finished lower level complete with a second kitchen, media room, billiards area and four fireplaces. Outside, the backyard feels like a private resort, with a heated 20-by-40-foot pool, stone waterfall, diving board, oversized pavilions and plenty of patio space for summer gatherings.

Photos: Bright MLS via Zillow

Prices and listing information are based on Zillow listings viewed Thursday, July 2, 2026, and are subject to change as homes are listed, sold or repriced.

This monthly feature is sponsored by The Mark Frisco Team of CENTURY 21 New Millennium.

Each month, look forward to The BayNet’s roundup of some of Southern Maryland’s most interesting homes for sale—from historic estates and waterfront retreats to one-of-a-kind properties with incredible views, unique history and standout features.

Interested in sponsoring an upcoming edition? Contact Vicky at vicky@thebaynet.com.

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