An age old preoccupation of the English landed gentry, foxhunting arrived on American shores in 1650, when one such wealthy landowner, Robert Brooke, brought the first hounds to Maryland. The practice became popular on the sprawling estates of Green Spring Valley, north of Baltimore, and competition between hunt clubs generated a series of steeplechase races that survive to this day—as, thankfully, do many of the historic estates where the hounds and horses were kept. Dating to the late 1700s and expanded several times since, the Oakdene estate (above) was for two decades the home of Thomas Deford, Jr., the longtime master of hounds for the Green Spring Valley Hunt Club. Today listed for $2.9M, the Oakdene property includes nearly 25 acres, a 10,000-square-foot main house, and two noted historical outbuildings.
? This Saturday, the 104th running of the My Lady's Manor Point-to-Point race will be held in Monkton, Md., very close to where this stately brick mansion has been holding court since 1815. Known alternately as Lindenhope or Talley Ho, the 189-acre property is presently listed for $4.5M. That price includes the six-bedroom, six-bath main house, three cottages, a sizable barn, and a fully fenced equestrian facility, including five riding rings. The land originally belonged to Lord Baltimore Benedict Calvert, 4th Baron Baltimore, who gifted 10,000 acres to his daughter, Charlotte, in 1731.
? Located in a prime position—adjacent to the Green Spring polo field and the Green Spring Valley Hunt Club, Willowbrook might not be as architecturally impressive as some others on this list, but has plenty of history. Originally the site of the Maryland Polo Club, the house was expanded four times in the past 200 years, with the last addition in the 1950s. The historic sections of the house offer towering ceilings and classic detailing, while the midcentury addition provides the opportunity to update the kitchen without disturbing the historic integrity of the house. Listed on the National Register of Historic Places, Willowbrook is currently asking $1.599M.
? When the Maryland Hunt Cup race was first run in 1897, the course took the racers across the front lawn of this valley manor, known as Green Spring Punch. In the same family since the 1920s, the 98-acre estate had been listed for as much as $5M, but has since seen that price slashed to $3M. Built in 1885, the seven-bedroom, eight-bath mansion—with nine fireplaces and a grand, three-story staircase—is joined on the property by extensive gardens, a swimming pool, a four-stall barn, a three-bed "tenant house," and a caretaker's residence.
? Located in the northwestern corner of what is properly considered Maryland hunt country, Cold Saturday Farm today lies a bit far afield from the annual races, but does not suffer from a lack of history. Built around 1800, the fieldstone manor, according to the National Register, "embodies the characteristics of the Anglo-American gentry farm" in its Federal architecture and woodwork. Used for centuries as a working farm—until man-made Liberty Reservoir claimed some of the acreage—Cold Saturday is today a charming country retreat, listed for $2.89M.