The five highest-priced home sales reported in the Baltimore metro area for the week ending October 4, 2026, came to a combined $14.54 million. Annapolis accounted for three of them, and the other two were in Woodbine and in Chester, across the water in Queen Annes County.
The group spans nearly two centuries of building, from a landmark farm estate to a newly built home, with a log-walled retreat, a brick Cape Cod and a Mediterranean-style home in between. The top two sales were both listed by agents of the same brokerage.
No. 1 — $3,900,000 · 16449 Ed Warfield Rd, Woodbine, Maryland
The week’s top sale was Oakdale, a 180-acre estate in Woodbine that sold for $3,900,000. The property is listed on the National Register of Historic Places and was the ancestral home of Edwin Warfield, who served as governor of Maryland. Its story begins well before the home itself, with a land grant surveyed in 1766.
The brick Federal-style home was built in 1838, and substantial additions came in 1898. It rises three stories and has 16,270 square feet, with 16 bedrooms and 12 bathrooms, ten full and two half. There are 12 fireplaces, finished in marble and brick with mantels. Inside are a double staircase, two-story ceilings, wood floors, wainscoting, crown molding and chair rails. A formal dining room and a butler’s pantry serve entertaining, and the home also has an eat-in kitchen and a second kitchen.
The land is a working landscape of pasture and woods, with a pond and a creek. The grounds include a private in-ground pool, along with outbuildings, sheds and grain storage. Oakdale is about 20 miles from both the Washington and Baltimore beltways.
The estate sold at its full asking price. Richard Watson of Long & Foster Real Estate, Inc. was the listing agent, and Dan Swisher of Keller Williams Flagship represented the buyer. With this sale and the No. 2 sale in Annapolis, Long & Foster Real Estate, Inc. agents listed the two highest-priced homes of the week.
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No. 2 — $3,500,000 · 1715 Porters Hill Rd, Annapolis, Maryland
At 1715 Porters Hill Road in Annapolis, a Craftsman-style home on Luce Creek sold for $3,500,000. The 1.70-acre property has 265 feet of waterfront and looks down the Severn River. Down at the shoreline are a large boathouse and a private pier with more than seven feet of water depth, room for a big boat and several smaller ones. A tram runs down to the water.
The listing says the log walls at the center of the home came from a log structure first built in the 1880s, one of three identical hunting lodges, and that those logs were reused in a later renovation. The record dates the home to 1945. Local lore adds color: the peninsula is thought to take its name from Admiral David Porter, a Naval Academy superintendent, and in the 1920s the Whitehead brothers, bootleggers who ran liquor to Baltimore and Washington, entertained there before the state confiscated the land in the 1940s.
Those log walls frame the great room, which has a quarried stone fireplace, a vaulted ceiling and tall windows facing the water. The kitchen sits under its own vaulted, beamed ceiling, with custom cabinetry, GE Monogram appliances and a large island, and it opens to a dining area that looks out to the creek. The primary suite is on the main level. Its bedroom has a vaulted ceiling and a screened porch over the water, and its bath has a freestanding soaking tub, heated floors and a walk-in shower. An office with a gas fireplace is part of the suite.
The home has four bedrooms and six bathrooms, four full and two half, in 6,594 square feet. Upstairs are two more bedrooms, one with a balcony on the water side, and a guest suite with its own living area and bath sits above the garage. The property last sold in 1997 for $187,500.
Reid Buckley of Long & Foster Real Estate, Inc. was the listing agent, and Meagan Buckley, also of Long & Foster Real Estate, Inc., represented the buyer.
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No. 3 — $2,535,320 · 703 A Glendon Ave, Annapolis, Maryland
The newest home of the five, completed in 2025, sold for $2,535,320 on Glendon Avenue in the Parkwood neighborhood of Annapolis. It stands on a corner lot of 0.26 acres on Back Creek, in the Eastport area, and was sold as new construction.
The Coastal-style design calls for walls of glass facing the creek, wide plank floors and a kitchen with custom built-in cabinetry, quartz countertops, a full-height backsplash and an oversized island. An elevator was offered as an option. The home has four bedrooms and five bathrooms, four full and one half, in about 4,300 square feet over three stories, along with a gas fireplace, HardiPlank-type siding and a partially finished basement.
Eastport’s marinas, coffee shops and waterfront restaurants are close by. Parkwood has a voluntary civic association that helps maintain local green spaces, among them Hoffman Park and the community docks, and membership is required to apply for a dock slip.
The home sold for $160,320 above its asking price of $2.375 million. Colleen Smith of EXP Realty, LLC was the listing agent.
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No. 4 — $2,300,000 · 3260 Harness Creek Rd, Annapolis, Maryland
Two homes tied at $2,300,000. The first, at 3260 Harness Creek Road in the Harness Creek neighborhood of Annapolis, is a brick Cape Cod built in 1945 on 1.63 acres with river views. It is the smallest home of the five, with 2,500 square feet on one level, three bedrooms, two of them on the main floor, and two bathrooms. Inside are wood floors, a fireplace, an eat-in kitchen with an island and a family room off the kitchen. Outside are a patio and a private dock site on a rip-rapped shoreline, with the water open to powerboats, kayaks and fishing. The property last sold in 2012 for $1.325 million. Brad Kappel of TTR Sotheby’s International Realty was the listing agent, and Alex Clark, also of TTR Sotheby’s International Realty, represented the buyer.
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No. 5 — $2,300,000 · 2882 Cox Neck Rd, Chester, Maryland
The other $2,300,000 sale was a Mediterranean-style home on Cox Creek in the Southwind community of Chester, on Maryland’s Eastern Shore. Built in 2001 and finished in stucco, it has four bedrooms, three of them on the main level, and four bathrooms, three full and one half, in 4,331 square feet on 1.20 acres.
The main living room has soaring ceilings and a wet bar, and it leads to a sunroom with heated tile floors. A three-season room at the back opens to the yard through a wall of sliding doors. A double-sided fireplace is one of two in the home, and the kitchen has stainless steel appliances, including a wall oven and a cooktop.
Outdoors, the property has a private concrete pool and a covered built-in Lynx grill with bar seating. The rear yard runs to a rip-rapped shoreline and a private dock, with direct access to Cox Creek for boating, kayaking and fishing. Southwind offers residents a beach, a community center, tennis and basketball courts, a playground, a fishing pier and a boat launch. The property last sold in 1999 for $299,000, before the current home was built.
The home went under contract 20 days after it was listed. Tricia Z Wilson of Wilson Realty & Staging LLC was the listing agent, and Ashton Kelley of Gunther-McClary Real Estate represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 4, 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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