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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.

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