If you go
1. Dragonfly, 21669 Pebble Beach Court, Leonardtown Owners: Ron and Kathy Glockner Situated on Cherry Cove, the gardens at Dragonfly turn 25 years old in 2018.The entrance garden features American boxwood, Sky Pencil hollies, topiary holly trees, hydrangea, magnolia, and Japanese maples.
This garden area yields to more casual plantings throughout the property. Dragonfly features extensive use of evergreens, along with perennial and annual plantings.
2. Taylor house, 21651 Rose Bank Road, Leonardtown Owners: Frank and Susan Taylor Situated on three acres along Combs Creek, this home was built in 2004. The current home replaced a dated Cape Cod style house and was limited in size to the square footage of the previous dwelling.
The natural woodsy setting opens up to a sunny lawn and patio, providing the perfect peaceful place to enjoy elevated views of Combs Creek.
3. Redbud Thicket, 21745 Newtowne Neck Road, Leonardtown Owner: Christine Sterling Senese This scenic six-acre property overlooking St. Clement’s Bay became the family home of Billy and Marion Sterling in 1952. After a fire destroyed the original house in the early 1970s, the couple engaged local custom builder William Dean to rebuild the home in the same Cape Cod style.
Sterling, who named the property Redbud Thicket, lovingly designed and tended the landscaping, propagating English boxwoods from existing shrubs and collecting seedlings and cuttings from family and friends. There are multiple groupings of large boxwood, towering Southern magnolias, dogwoods, crape myrtles and redbuds lining the driveway.
4. St. Francis Xavier Church and Newtowne Manor House, 21370 Newtowne Neck Road, Leonardtown
Mass will be celebrated at 4 p.m. the day of the tour. William Bretton received a patent from Cecilius Calvert
in 1640 for the 750 acres that comprised Newtowne Neck.
Tour participants are welcome to explore the 776-acre Netwowne Neck State Park on the peninsula adjacent to the church and manor house. park rangers will be available to answer questions.
5. Minipany, 21652 Joe Hazel Road, Leonardtown
Owners: Tim and Cherie Heely
Cherie and Tim Heely purchased this home in 2008 when Tim retired from the U. S. Navy. Built in 2001, the house sat on two acres of grass field overlooking Combs Creek and Breton Bay with minimal landscaping other than the Callery pear trees lining the drive.
Cherie designed, planted and maintains numerous gardens on the property, including an English garden, Japanese garden, shade garden, kitchen garden, French garden and landscaping surrounding the waterside deck with a pergola that the couple built.
6. Pennysworth, 40075 Army Way, Compton
Owner: Patricia King Jackson
Judge Penfield Jackson bought this property in 1969 from the estate of Betty Buck Williams, widow of Chink Williams who was a waterman and ran a boat charter on Combs Creek.
The house is situated on 2.5 acres bordered by water on two sides. Built in the 1930s, the original house was 900 square feet with porches on three sides and an attic with drop-down stairs. The main house was renovated and expanded in 1995. The gardens were landscaped bit by bit over the past 25 years, with the recent shoreline restoration also providing a home for ospreys.
7. Port of Leonardtown Winery, 23190 Newtowne Neck Road, Leonardtown
Winery opens at noon, and tours start at 12:30 p.m. The Port of Leonardtown Winery is the production element of the Southern Maryland Wine Growers Cooperative.
The Southern Maryland co-op was incorporated in 2007 with 17 owner/growers. The winery commenced operations in 2009 and had its first sales in May 2010. The winery building is the old state highway department building located in the McIntosh Run town park.