The five highest-priced home sales reported in Upper & Mid-Shore, Maryland for the week ending October 25, 2026, totaled $6.04 million. The sales were spread across Talbot, Caroline and Queen Annes counties, from Oxford and Saint Michaels to Preston and Chester, where two homes in the same new community both made the list.
The group runs from a farmhouse built in 1890, the oldest of the five, to two homes built in 2026. Four are single-family homes and one is a condominium.
No. 1 — $2,210,000 · 206 S Morris St, Oxford, Maryland
The week’s top sale is a Traditional home in Oxford, built in 1936, that sold for $2.21 million. The home is on the river and has river views from its 0.52-acre lot. Its 3,200 square feet are spread over two stories, with all three bedrooms on the main level and four bathrooms, two full and two half.
Inside, the home has hardwood floors and a fireplace, and the exterior is finished in HardiPlank-type siding. The basement has a connecting stairway and a drainage system, and a driveway provides off-street parking. The property last sold for $850,000 in 2020.
Debra Crouch of Benson & Mangold, LLC was the listing agent, and Chuck Mangold JR., also of Benson & Mangold, LLC, represented the buyer.
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No. 2 — $1,400,000 · 7347 Harmony Rd, Preston, Maryland
In Preston, in Caroline County, a 38.17-acre poultry farm sold for $1.4 million. Its farmhouse dates to 1890, making it the oldest home of the five, and it is also the largest, with 3,958 square feet on two stories. The farmhouse was extensively updated in 2024 and has three bedrooms, one of them on the main level, and four bathrooms, three full and one half.
The working side of the farm centers on four tunnel poultry houses, each 40 by 500 feet, built in 1993. They run on computerized controls with alarm systems and recirculating cooling pads, and a 175-kilowatt diesel generator with an automatic transfer switch stands behind them. The poultry houses have updated metal siding, and a new manure shed was added. The property also includes farmland, a grain bin, a hay shed, a renovated mobile home and several other outbuildings.
The farm lies in the agricultural country of Maryland’s Eastern Shore, with major routes leading toward Easton, Denton, Annapolis and the Delaware beaches. The property last sold for $625,000 in 2019.
The farm went under contract 28 days after it was listed. Damon Brockenberry of Keller Williams Preferred Properties was the listing agent, and Mrs. Deborah Figgs of Long & Foster Real Estate, Inc. represented the buyer.
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No. 3 — $840,000 · 7964 Pond Haven Ct, Saint Michaels, Maryland
A Coastal-style home in Saint Michaels, built in 2004, sold for $840,000. Its 0.39-acre lot backs to open common area and adjoins open space and public land, with a pond among its features, and the home has water access.
The home has four bedrooms and four bathrooms, three full and one half, in 2,955 square feet on two stories. There is a fireplace and a breakfast area, one bath with a walk-in shower and another with a tub and shower, and carpet and ceramic tile floors. An attached, front-entry garage has additional storage space.
The home went under contract six days after it was listed and sold for $45,000 above its $795,000 asking price. Cornelia C Heckenbach of Long & Foster Real Estate, Inc. was the listing agent.
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No. 4 — $830,000 · 110 Boatswain Way #3031, Chester, Maryland
A new condominium in Four Seasons At Kent Island in Chester sold for $830,000. Built in 2026 in the Severn floor plan, the Coastal-style home is on one level, with three bedrooms, three bathrooms, two full and one half, and 2,602 square feet. It has water views, the community is on the river, and an attached one-car garage comes with it.
The owner’s suite includes its own sitting room and large walk-in closets, and its bath has double sinks, quartz counters and a walk-in shower with a seat and a handheld wand. Elsewhere, an electric fireplace and a built-in dry bar set up the living space for entertaining. The kitchen pairs quartz counters and a tile backsplash with a gas cooktop and pendant lights, and laminate floors run through the home, with tile in the two full baths.
Residents share a clubhouse and both indoor and outdoor pools. The community also has a fitness center, a library, tennis courts and a pier.
Mary Anne Kowalewski of KOVO Realty was the listing agent, and Dave Luptak of Long & Foster Real Estate, Inc. represented the buyer.
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No. 5 — $764,990 · 715 Warbler Way, Chester, Maryland
A second new home in Four Seasons At Kent Island in Chester, a Traditional-style single-family home built in 2026, sold for $765,000. Four Seasons At Kent Island is an active adult community for residents 55 and older on the Chesapeake Bay, built around a 24,000-square-foot clubhouse with indoor and outdoor pools and a fitness center, along with tennis and pickleball courts. A full-time lifestyle director runs a calendar that includes kayaking, yoga and a mahjong club.
The home, the Simone floor plan, has four bedrooms, two of them on the main level, three full bathrooms and 2,791 square feet on two stories, on a 7,000-square-foot lot with a three-car attached garage. The main living area is built around a fireplace, and a home office and a screened patio add space for work and for time outdoors. Upstairs, a loft opens the second floor.
The kitchen has quartz counters, a gas cooktop with a range hood and a French-door refrigerator. In the owner’s bath, a double-sink vanity sits alongside a walk-in shower with a seat and handheld wand. Luxury vinyl plank covers most of the floors, with tile in the baths and the laundry room.
David Willman of Berkshire Hathaway HomeServices PenFed Realty – OP was the listing agent.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 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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