These were the five highest-priced home sales reported in Upper & Mid-Shore, Maryland for the week ending November 1, 2026, and together they came to $5.4 million. Chester accounted for three of them, all in Queen Annes County, while Easton and Preston had one each. Two of the five were new construction, and the list runs from homes on lots of 7,000 square feet to a property of more than 20 acres.
No. 1 — $1,200,000 · 2513 Cecil Dr, Chester, Maryland
The top sale of the week was a home with a nickname. In the 1940s, a Dr. Keister put up a cinder block barn above Cox Creek on Kent Island, planning to raise Black Angus cattle. The land proved too small for a herd, and locals took to calling the barn Keister’s Folly. In the early 1960s, the developer of the Harbor View community turned it into a residence. The record dates the home to 1948.
The property covers 1.65 acres and has 205 feet of shoreline on Cox Creek, reinforced with rip-rap. A private pier runs 75 feet out into tidal water, with two boat slips and about 3.5 feet of depth at mean low tide. The water is open to swimming, fishing, kayaks and powerboats. From the upper level, the home looks out over the river.
Inside, the converted barn has five bedrooms, three of them on the main level, two bathrooms and 2,700 square feet of finished space across two levels, with roughly 700 more square feet of unfinished room for expansion on the second and third levels. Ceilings rise past nine feet throughout, the floor plan is open, and there is a wood-burning stove for heat. The kitchen has been updated with granite countertops and upgraded cabinetry. Upstairs, the primary suite has hardwood floors, a walk-in closet, its own bath, a coffee bar with a refrigerator and a deck that looks out over the creek. A circular driveway leads to the home. The property last sold for $215,000 in 1994.
The home went under contract 19 days after it was listed. Mr. David J Moore of Real Broker, LLC was the listing agent, and Debbie McQuaid of TTR Sotheby’s International Realty represented the buyer.
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No. 2 — $1,150,000 · 6674 Schoolhouse Ln, Easton, Maryland
In Royal Oak, outside Easton, a Colonial built in 2017 sold for $1,150,000. The two-story home sits on 6.02 acres and has four bedrooms, one of them on the main level, along with three full baths and a half bath in 3,375 square feet. It has a fireplace and an attached two-car garage that faces the side. The property last sold for $739,000 in 2022.
The home went under contract seven days after it was listed. Corbin Griffith of Compass was the listing agent, and Tim Miller of Benson & Mangold, LLC represented the buyer.
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No. 3 — $1,100,000 · 111 Flycatcher Way, Chester, Maryland
Two of the week’s top sales were new model homes on the same street in Four Seasons At Kent Island, an active adult community for residents 55 and older on the Chesapeake Bay in Chester. The larger of them, the Tuscaloosa model, sold for $1,100,000 and came with all of its model furniture.
The two-story home has five bedrooms, two of them on the main level, four full baths and a half bath, and 3,225 square feet on a 7,000-square-foot lot. Its design leans on texture: exposed ceiling beams, sliding barn doors and a feature wall. Hardwood covers the main level, which also includes a home office and a fireplace, and a screened patio opens the living space to the outdoors. The kitchen has quartz countertops, a Profile range, pendant lights and a tile backsplash, and quartz continues into the owner’s bath, where the shower has a built-in seat beside double sinks. There is also a loft and an attached three-car garage.
Residents share a 24,000-square-foot clubhouse with indoor and outdoor pools, a fitness center, a billiard room and a game room, plus tennis and pickleball courts. A full-time lifestyle director runs a calendar that includes yoga, mahjong, a walking club and kayaking.
David Willman of Berkshire Hathaway HomeServices PenFed Realty – OP was the listing agent.
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No. 4 — $995,990 · 117 Flycatcher Way, Chester, Maryland
Also on Flycatcher Way, the Franklin model sold for $995,990, its full asking price. Like the Tuscaloosa, it is new construction and was sold with its model furniture included.
The Franklin has three bedrooms, all on the main level, three full baths and a half bath in 2,930 square feet on a 7,000-square-foot lot. Crown molding, barn doors and a custom feature wall give the rooms their character, and luxury vinyl plank runs across the main floor. A home office, a fireplace and a screened patio round out the living space. The kitchen has quartz countertops, pendant lighting and a tile backsplash, and the owner’s bath has double sinks and a shower with a built-in seat. The home has an attached two-car garage.
David Willman of Berkshire Hathaway HomeServices PenFed Realty – OP was the listing agent here as well, which gave the agent two of the week’s top five sales. Mariya Oldfather of Compass represented the buyer.
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No. 5 — $950,000 · 6354 Statum Rd, Preston, Maryland
The largest property on the list, at 20.17 acres, was a horse farm in the countryside northeast of Preston that sold for $950,000. The equestrian setup is the heart of it. An indoor riding arena measures 75 by 225 feet, and an outdoor dressage arena measures 66 by 195 feet. The concrete center-aisle barn has eight stalls, a heated tack room, a grooming stall, a wash stall with hot water and a loft. There are numerous paddocks and two run-ins, and a large stretch of woods gives the property privacy.
The one-story ranch home, built in 1995, has 4,368 square feet, the most of any of the five. The great room has heated tile floors and a brick fireplace with a raised hearth, along with a small kitchenette and a full bath. The kitchen has granite countertops and a stainless steel backsplash. Outside, a terrace surrounds the pool, a screened porch looks over it, and there is a putting green and a deck. The home also has a large basement and a backup generator. The property last sold for $580,000 in 2015.
A John Price of Patterson-Schwartz-Middletown was the listing agent, and Erin Anderson of Chesapeake Real Estate Associates, LLC 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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