The five highest-priced home sales reported in Southern Maryland for the week ending November 1, 2026, came to a combined $4.827 million. Two were in Charles County, two in Calvert County and one in Saint Marys County, and every one of the five sits on at least two acres.
The group runs from a brick Cape Cod on the water to a Colonial in a planned community, with stops at a pair of rural properties built around barns, pastures and workshops.
No. 1 — $1,400,000 · 1100 Cataway Pl, Bryans Road, Maryland
The home at 1100 Cataway Place in the River Watch community of Bryans Road sits directly across the Potomac from George Washington’s Mount Vernon, and the river is the point of the whole property. The 12.74 acres include woods, a pond and open fields, along with private river access suited to a canoe or kayak, a private dock site and a riparian grant.
The brick Cape Cod dates to 1948, the oldest home in this week’s group. It sold for $1,400,000. The property has seven bedrooms and five baths, with 4,983 square feet of living area, and both residences on it have been renovated. In the main residence there are four bedrooms and three full baths, with hardwood floors and windows turned toward the river. A short walk away, the guest house has three bedrooms and two full baths and a Trex deck facing the water. Outside there is also a patio, a deck and an above-ground pool, and the three-car garage faces the rear. The listing puts Washington, D.C., about 40 minutes away. The property last sold for $875,000 in 2020.
Rocky Bowers of Compass was the listing agent. Casey A Sutherland of Rosemont Real Estate, LLC represented the buyer.
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No. 2 — $930,000 · 1008 Horse Pen Run, Huntingtown, Maryland
Built in 2011, the Colonial at 1008 Horse Pen Run in the Farms At Hunting Creek community of Huntingtown is the newest home in this Top 5, and at 5,480 square feet it is also the largest. It sold for $930,000 and stands on 2 acres that back to trees.
Inside, a two-story foyer opens to tall ceilings and a catwalk above the family room. The main level has a gourmet kitchen with granite counters, double wall ovens and an island, along with a breakfast area, a formal living room, a formal dining room and a private office. The home has four bedrooms, four full baths and a half bath across three stories. The primary suite includes a walk-in closet and a bath with two vanities, a jetted tub and a separate walk-in shower. The finished lower level walks out to the yard and has a full bath, a recreation area wired for surround sound and an unfinished room that could become a fifth bedroom, a gym or a theater.
Behind the home is a heated, saltwater in-ground pool with a waterfall and a sun shelf, set off by a patio and a wooded backdrop. The community has walking and jogging trails, a lake, a playground, a picnic area, a basketball court and a soccer field, and Chesapeake Beach and North Beach are minutes away. The property last sold for $584,373 in 2011.
Pelin Basiliko of JPAR Real Estate Professionals was the listing agent. Heather Heath of Deep Roots Real Estate represented the buyer.
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No. 3 — $850,000 · 2020 Wash Hance Rd, Port Republic, Maryland
At 2020 Wash Hance Road in Port Republic, much of the story is outdoors. The 6.09-acre property has fenced pastures and a two-stall horse barn, and a wraparound driveway leads in from a road with no through traffic. A detached steel building measuring 44 by 44 feet has three bays for vehicles and equipment. A separate 32-by-40-foot mechanics workshop has two bays, high ceilings, a vehicle lift, its own half bath and 400-amp electric service. The record lists garage space for 10 vehicles.
The all-brick split-level home was built in 1983 and has 2,467 square feet, four bedrooms, two full baths and a half bath. Recent work includes new vinyl plank flooring in the den and new carpet in the bedrooms. An in-ground pool sits on the grounds, and the land backs to trees.
The home went under contract one day after it was listed and sold at its full asking price of $850,000. Randy Utz of EXP Realty, LLC was the listing agent with Vicky Rawlings, also of EXP Realty, LLC. Jo Hernandez of Atlas One Realty represented the buyer.
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No. 4 — $847,000 · 42000 Pleasant Valley Ct, Hollywood, Maryland
Once part of a historic farmette, the 15.85 acres at 42000 Pleasant Valley Court in the Pleasant Valley Farmstd community of Hollywood are the largest piece of land in this week’s group. The wooded property has its own ATV trails and reaches nearly to McIntosh Run, and deer and wild turkey are regular visitors. Closer to the home, river birch, Japanese maples, azaleas and boxwoods line the entrance, and a paved circular driveway has room for boats and trailers.
The 2007 home combines Craftsman and ranch styling across two levels, with four bedrooms, three full baths, a half bath and 3,196 square feet. The main level has a living room with a gas fireplace, an office and the primary suite, which has a walk-in closet with custom built-ins and a bath with two vanities and a walk-in shower. The gourmet kitchen has granite counters, a five-burner propane cooktop and a center island that seats six. Downstairs, the finished lower level has its own outside entrance, three more bedrooms, two full baths, a family room and a second office. Lighting, climate, cameras and garage doors run on an Apple HomeKit smart-home system.
An Amish-built pole barn, 40 by 36 feet and finished in 2022, has two oversized bays, a workbench and a ceiling lift for removing and storing a Jeep or Bronco hardtop. There is also dedicated RV parking with 50-amp service and a storage shed. The property last sold for $60,000 in 1994, before the current home was built.
The home went under contract one day after it was listed and sold for $847,000, $17,000 above its asking price of $830,000. Kathy Dean of RE/MAX One was the listing agent, and Karen Simmons of RE/MAX Realty Group represented the buyer.
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No. 5 — $800,000 · 4570 Hawthorne Rd, Indian Head, Maryland
The brick raised ranch at 4570 Hawthorne Road in Indian Head sold for $800,000. Built in 2007 on 2.08 level acres that back to woods, the custom home has 4,752 square feet, four bedrooms, three full baths and a half bath. Its garage space is the main attraction for a car collector or contractor: a 43-by-30-foot bay area with three 10-foot-wide bays, 12-foot doors and a hydraulic lift rated for 10,000 pounds.
Indoors, cherry plank floors, crown molding and tall windows run through an open plan where the kitchen meets the family room, which has a brick wood-burning fireplace. The kitchen has double ovens, a large island, a pantry and a built-in china cabinet. Three bedrooms are on the main level, among them the primary suite, which has a large walk-in closet, a soaking tub, a walk-in shower and its own door to a screened porch that looks over the backyard. The fourth bedroom is in the partially finished walk-out basement, which also has a full bath and storage.
Jenna Bare-Anderkovitch of CENTURY 21 New Millennium was the listing agent with Cheryl A Bare, also of CENTURY 21 New Millennium. Seti Tabatabai of Long & Foster Real Estate, Inc. represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 1, 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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