These are the highest-priced home sales reported in Upper & Mid-Shore, Maryland for the week ending November 8, 2026, and together they came to $8.555 million. Four of the five homes are in Talbot County, two of them in Easton, with the others in Tilghman and Trappe; the fifth is in Stevensville in Queen Annes County.
Every one of the five is a two-story single-family home, and they range from a 1954 Colonial to a Victorian built in 2006. Benson & Mangold, LLC was the listing brokerage on three of them, including the top two.
No. 1 — $3,000,000 · 27625 Parkway Rd, Easton, Maryland
The week’s top sale sits on 3.18 acres on the Miles River, where a private dock with two boat lifts and about five feet of water at mean low tide gives a straight run to the Chesapeake Bay. The shoreline is protected with riprap, and a barn and several sheds on the grounds provide room to store a boat and gear. The home sold for $3,000,000.
Built in 1965 and faced in stone, the Traditional-style home was renovated in 2017, the same year the property last sold, for $1.25 million. Its 2,785 square feet, the smallest living area among this week’s five, include three bedrooms, three full baths and two half baths, with one bedroom on the main level. The kitchen is built around a large island with custom cabinets and stainless steel appliances, and it opens to a dining area and a river room lined with big windows facing the water. Wood floors, crown molding and two fireplaces run through the rooms, and most of them look out on the river.
Outside are an infinity-edge pool with fire features, a patio and extensive stonework. A circular driveway leads to an attached, side-facing garage for three cars.
The home went under contract three days after it was listed and sold just above its asking price of $2.995 million. Chuck Mangold JR. of Benson & Mangold, LLC was the listing agent, and Cornelia C Heckenbach of Long & Foster Real Estate, Inc. represented the buyer. Mangold was also the listing agent on the No. 4 sale this week, a country property in Trappe.
See this property in Google Street View →
No. 2 — $1,790,000 · 5698 Leeward Ln, Tilghman, Maryland
On Tilghman Island, in the Paw Paw Cove neighborhood, this Contemporary home faces west across the Chesapeake Bay,. It sold for $1,790,000.
The home was built in 1996 and redesigned and updated in 2023. Its center is a great room with a vaulted ceiling, a gas fireplace and windows that run from floor to ceiling. The renovation added a screened porch with its own vaulted ceiling and fireplace. The primary suite is on the first floor, with views of the bay, a large bath and walk-in closets.
There are five bedrooms in all, three of them on the main level, along with three full baths and a half bath in 3,906 square feet. The 1.48-acre lot has composite decking, several seating areas along the water and a heated gunite pool. A private dock with a boat lift and a jet ski lift sits off a riprap shoreline, and the attached garage holds two cars. The property last sold in 2017 for $810,000.
Brian Gearhart of Benson & Mangold, LLC was the listing agent, and Rochelle Rubin of Stuart & Maury, Inc. represented the buyer.
See this property in Google Street View →
No. 3 — $1,555,000 · 28706 Hope Cir, Easton, Maryland
The newest home in this week’s group, built in 2006, is a Victorian in Cooke’s Hope, a community near downtown Easton with its own dock, a canoe launch and storage, walking and exercise trails, tennis and pickleball courts and a fitness center. The home sold for $1,555,000.
A wraparound porch frames the front. Inside, the first floor has the primary suite, a family room with a gas fireplace, a formal dining room and a separate sitting room meant for a piano, along with a large laundry room. The kitchen was recently refreshed with new appliances and countertops and has its own dining area, plus a coffee and bar station with extra storage. Upstairs are two more bedrooms, two bathrooms, an office area and a second family room. In all, the home has three bedrooms and four bathrooms in 4,172 square feet.
The 0.30-acre lot is the smallest of the five, but the backyard has a heated pool, professional landscaping and an irrigation system. The detached two-car garage is heated and cooled, with doors nine feet wide and a finished storage space on its upper floor. The property last sold in 2023 for $1.1 million.
The home went under contract 16 days after it was listed. Robert Lacaze of TTR Sotheby’s International Realty was the listing agent, and Debbie Mangold Lipscomb of Benson & Mangold, LLC represented the buyer.
See this property in Google Street View →
No. 4 — $1,495,000 · 4401 Grove Rd, Trappe, Maryland
In Trappe, a 6.50-acre country property is the largest of the week, and at 4,518 square feet its home is the largest as well. It sold for $1,495,000.
The Traditional-style home was built in 1999 and has five bedrooms and the most bathrooms of the group, five full and one half. The kitchen is equipped with a Viking range and a wine refrigerator, and a large center island with seating anchors it before the room opens to the living and dining areas. There is also a formal dining room and a pantry. The primary suite is on the main level. A covered front porch and a screened porch both look out on the surrounding land.
Outside, an in-ground pool has a pool house beside it, along with a covered outdoor kitchen and sitting area. A detached guest apartment has one bedroom, a kitchenette and a wood-burning stove. A large pole barn adds room for equipment, hobbies or a workshop, and the detached garage has space for three cars. The property last sold in 2013 for $687,500.
The home went under contract two days after it was listed and sold at its full asking price of $1.495 million. Chuck Mangold JR. of Benson & Mangold, LLC was the listing agent, as on the week’s top sale in Easton, and Henry Gibbons-Neff of Meredith Fine Properties represented the buyer.
See this property in Google Street View →
No. 5 — $715,000 · 135 Vestfield Rd, Stevensville, Maryland
The oldest home of the five, a Colonial built in 1954, stands on 2.75 acres in Stevensville on Kent Island, and it has the most bedrooms of the group, with six. It sold for $715,000.
The grounds are the draw. There is a full barn, a chicken coop, garden beds, trails, a pond and mature trees, with woods along the back of the lot. The sale includes a waterfront easement: a private wooded path, about a five-minute walk from the home, leads to the water, with a view of the Chesapeake Bay and the Bay Bridge.
Inside, a large living room with a fireplace opens to a big dining room set around a whitewashed decorative fireplace, with a country kitchen on one side and a sunroom on the other. Behind the fireplace is a main-level playroom. The home has three bathrooms in 3,184 square feet, solar panels, and a fenced backyard with a patio and pergola. The detached two-car garage includes finished space. The property last sold in 2023 for $685,000.
Jessica DuLaney of Next Step Realty was the listing agent, and Vera Spilker of Douglas Realty, LLC represented the buyer.
See this property in Google Street View →
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.
Were you involved in one of these transactions? Contact RealtyWire to verify or correct your professional credit or submit information for a future edition.
