These are the highest-priced home sales reported in Southern Maryland for the week ending November 8, 2026, and together the five sold for $4.81 million. Prices ran from $780,000 in Bryantown to $1.52 million in Lusby, with the other three sales in Drayden, Hollywood and Waldorf.
The list reaches across Calvert, Charles and Saint Marys counties, and it covers a wide range of homes: a 1960 rambler on the water, a pair of homes finished within the past two years, and a 1992 contemporary on more than six acres at the top.
No. 1 — $1,520,000 · 7335 Perry Ln, Lusby, Maryland
The week’s top sale is a deep-water property on St. Leonard Creek in Lusby, a 6.45-acre setting the listing calls Perry Point. It is the largest lot among the five. The water along this stretch of the creek is calm and protected, and bald eagles, osprey and herons are common sights. A private pier with two 12,500-pound boat lifts serves the property, and a flat, bulkheaded lawn runs right down to the shoreline, with room for crab feasts and tent parties.
The contemporary coastal home was built in 1992 and has 3,618 square feet over three stories, with an exterior of natural stone and copper gutters and downspouts. Inside, a two-story wall of glass takes in the water views. Wide-plank white oak and slate cover most of the floors, a stone fireplace burns wood, and the kitchen is part of an open plan, with custom cabinets and views of the water. The primary suite is on the upper level, behind mahogany doors, with a spa bath that has heated floors. The home has four bedrooms and four bathrooms, three full and one half.
The lower level has a bar known as the Perry Point Ale House, outfitted with a four-tap kegerator, an ice machine and a retractable cinema screen. The property last sold for $1.275 million in 2005, and this time it sold for $1.52 million.
The home went under contract two days after it was listed. Christine McNelis of Berkshire Hathaway HomeServices PenFed Realty was the listing agent, and Jen Holden of Compass represented the buyer.
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No. 2 — $874,482 · 19115 Windsor Ct, Drayden, Maryland
The newest home on the list was built in 2026 in Portobello Estates in Drayden, on a lot of 1.15 acres. It is a Craftsman-style home, the builder’s River model, with five bedrooms, four of them on the main level, and four bathrooms in 2,336 square feet.
The kitchen was upgraded with better cabinets, a custom vent hood and stainless appliances, and luxury vinyl floors run through the first floor and the lower level. Custom shelving fits out both the pantry and the primary bedroom. The full basement is partly finished and has ceilings of nine feet. Outside are a screened porch of 12 by 16 feet and an oversized side-load garage, 30 feet square, with room for two cars.
Lisa Riggleman of RE/MAX One was the listing agent, and Jennifer Lesesne, also of RE/MAX One, represented the buyer.
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No. 3 — $825,000 · 44015 Drum Cliff Rd, Hollywood, Maryland
From its hilltop in the Drum Cliffs community of Hollywood, the property known as Turtle Watch looks out over the Patuxent River, and water shows through nearly every window. The 1.91-acre lot has more than 350 feet of frontage on St. Thomas Creek, close to where it meets the river. A living shoreline protects the water’s edge and gives young oysters and other marine life a place to grow. The private pier has an upper sun deck built over covered boat storage, along with a covered boat lift, a storage locker, kayak racks, electricity and water.
Built in 1960, the single-story rambler is the oldest home in this group and, at 1,783 square feet, the smallest. It is clad in cedar. Knotty pine walls and hardwood floors give the open living, dining and kitchen space a rustic feel, Andersen windows and sliding doors take in the view, and a propane fireplace on a tiled hearth warms the living room. The galley kitchen has antique white wood cabinets and Corian counters. Out the sliders, a deck of Ipe, a Brazilian hardwood, sits in the shade of a large oak, with a retractable awning for late afternoons.
The home has two bedrooms and two bathrooms. The primary bedroom and a full bath are in the main living space, and a breezeway leads to a guest house with a main room and the second bedroom. A three-season studio with good natural light sits across the patio, and the garage has space for four cars. Steps with level landings and a cleared trail for ATVs and wagons both lead down to the water.
The property last sold for $500,000 in 2003. Listed by Andy Shemeta of CENTURY 21 New Millennium, it went under contract six days after it came on the market and sold at its full asking price of $825,000. Kara Shaffer of Engel & Volkers Annapolis represented the buyer.
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No. 4 — $808,635 · 10407 Halmstad Dr, Waldorf, Maryland
The largest home of the five, at 4,637 square feet, also sits on the smallest lot, 7,080 square feet in the Sunstone Preserve community in Waldorf. It is the Sienna, a contemporary model built in 2025, with a brick and stone front, three stories, five bedrooms and five bathrooms.
A grand foyer opens to a family room with a fireplace, next to a gourmet kitchen with premium appliances and generous storage. There is a dining area as well as a covered porch extension for entertaining. On the upper floor, the primary bedroom has its own spa-style bath, and three more bedrooms share a hall bath. The basement adds a flex space, a home office and another full bathroom. Sunstone Preserve has a community pool, a playground, a picnic area and common grounds.
The home sold for $808,635, which was $15,000 above its asking price of $793,635. Martin K. Alloy of SM Brokerage, LLC was the listing agent, and Terry Champagne of RLAH @properties represented the buyer.
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No. 5 — $780,000 · 14305 Flowing Creek Ct, Bryantown, Maryland
In Bryantown, an all-brick contemporary rambler on three acres was custom built in 2016 as the Poindexter model. With six bedrooms, five of them on the main level, it has the most bedrooms on this list, along with five bathrooms and 3,633 square feet on two stories.
The plan is laid out in two wings off a spacious foyer, a family room with a fireplace and a formal living room. Two bedrooms share a Jack and Jill bath in the right wing. The left wing has two more bedrooms with a full bath and the primary suite, which includes a sitting area, walk-in closets, a soaking tub and a walk-through shower. The kitchen has skylights, a breakfast nook and a dining area, and it opens onto a deck of 20 by 20 feet. A library, a half bath and the laundry room connect to the three-car garage. The finished basement adds a theater room, another bedroom and a full bath.
The property last sold for $675,000 in 2023. It went under contract 19 days after it was listed, with Daniel Ungar of FAB Realty LLC as the listing agent and Anitra Allen of Samson Properties representing the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 8, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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