The Annan clan came south from the Scotch Irish Presbyterian area of Adams County prior to 1798. That year Robert Annan was assesses on a new house, 9.5 acres and five slaves. The family arrival probably was sometime in the early 1790s. They choose a grove of large pine trees surrounding a never failing spring near the western edge of Emmitsburg. This spring is the headwaters of Willow Rill a pretty much intermittent stream that runs down past Emmit’s Gardens and empties into Flat Run.

The Annan family, not yet having a house to live in, had the women sleeping in the wagons while men slept under tarps attached to the wagons. [On March the 1st 1806 Robert L. Annan put himself forward as a canadate for sheriff. On Feb 21st 1807 and again in June 21st he was involved in real estate dealings in Emmitsburg.] Soon a rustic log house was completed which stood for a number of years. A new barn was built in 1876 replacing the old barn that was blown down by a heavy wind storm years earlier. A new house was built about 1797. Perhaps it was log house built from squared up logs or a wooden frame house [perhaps known as Graystone Manor] followed the log house and was in use until 1897.

In 1897 I. S. Annan had the frame house torn down. He had a three story (actually a 2½ story) stone house he called Craggystone built. It was the finest house in northern Frederick County.

1920

Excerpts from the Emmitsburg Chronicle:

January 19, 1889. -‘A Big Blaze at the West End’

...the barn of Messer I. S. Annan & Bro. at the old Annan homestead [Craggystone], was ablaze The firemen responded promptly to the alarm, but the distance and heavy condition of the roadway made their progress somewhat slower than usual. Notwithstanding these drawbacks, it was but a few minutes until they had two streams of water playing on the fire and the surrounding building… The barn was a new one, having been built in 1876, to replace the old barn which was blown down by a heavy wind storm during the month of May in that year….

July 29, 1898. –‘A Fine House’

The house is built of mountain stone on the rustic plan. The stones were not dressed or polished, but were laid in the walls by the masons, just as nature formed them. The outside walls are exceedingly rough, to which many so called critics find objections. But Mr. Annan had the house built to suit his self. The material in the building is first class in every respect. Only the best lumber being used and the workmanship is of a high order. The entire house is lighted with gas and heated by steam, and all the other modern household improvements have been placed within its walls. Taken as a whole, the building is a fine piece of architectural work, and Mr. Annan has every reason to feel proud of his home. The trimmings on the outside of the house are painted white, creating very pretty effect, while the inside of the building is finished with in hard wood. The door locks, hinges, chandeliers, etc, are beautifully bronzed. The painting is of a very high order, exhibiting a high degree expert workmanship. The painting was done by Mr. John F. Adelsberger, who says he has been painting for about twenty-five years, and that it is the finest painted house he ever worked on. The mason work was done by Mr. S. B. Florence; carpenter work by Messrs. Tyson and Lansinger, and the plastering by Mr. John D. Sebold.

February 3, 1899.

Several weeks ago Dr. R. L. Annan purchased Messrs. J. T. Hays & Son’s Sunlight Automatic Gas Machines, and his new house is now lighted by acetylene gas. The machine has been subjected to a thorough test and has proved satisfactory in very way.

Twenty five years later (25 Jan 1922) fire did $25,000 damage to the house. In that the exterior walls were little damaged the Annan’s rebuilt it as a 1½ story house. Electricity was installed through the farm. After being rebuilt it was still one of the finest houses in town. In 1925 the Annan’s sold the house and two farms to David and Dorothy O’Donoghue.

 
1925

The O’Donoghue family lived here until 1935. No other occupants have been known to live here since that date except maybe some tenants who may have lived in the two story wash house or persons who slept in the tack room at the back of the wagon shed. The Frailey family operated this as a horse farm but lived across the road in their own house. For the past fifty years or so this magnificent manor house has been vacant and now locally known as the Spooky House.

Frederick-Post 26 Jan 1922

Emmitsburg Fires Yesterday Morning

Cause an Estimated Loss Of $35,000 I. M. Annan Home Burns; Kershner Barns Destroyed Earlier.

Two fires cause a loss estimated at between $30,000 and $35,000 broke out in Emmitsburg and vicinity yesterday. The large modern barn on the farm of Nathan Kershner tenant by the Dorsey brothers, located one mile from Emmitsburg, was destroyed at 6 o'clock yesterday morning and the large stone house of Isaac Motter Annan, in the western section of Emmitsburg, caught fire five hours later, and was totally destroyed.

The fire in the Annan house started in the third story and is supposed to have been caused by defective wiring. As soon as it was discovered an alarm was turned in and the Volunteer Fire Company of Emmitsburg responded, and with the assistance of a large force of volunteers from Emmitsburg and vicinity, fought the flames, but were unable to save the building.

The furniture on the first floor and part of that on the second was removed but the rest of the contents was destroyed with the building. The fire continued to blaze until 4 o'clock in the evening.

Since no wind was blowing, and the roof of the different buildings were still covered with snow and ice the fire-fighters were able to keep the flames from spreading to any of the outhouses.

The Annan home, which was erected 25 years ago, was supposed to be the largest and most attractive building in Emmitsburg. The loss of the building and contents is estimated to be between $20,000 and $25,000, which is only partly covered by insurance.

Lantern Caused Blaze

The explosion of a lantern caused the fire in the barn on the Kershner farm. The tenants were feeding the cattle about 6 o'clock in the morning and the lantern exploded in the hay mow. The flames spread so rapidly that it was not possible to get anything out of the barn except the livestock. A large quantity of grain, straw, hay, farming implements, etc, was destroyed with the barn. The total loss is placed at about $10,000. It is not known whether any part of this is covered by insurance. The Dorsey’s had advertised for a public sale to be held in March and had intended offering the farm implements for sale then. By a remarkable coincidence the original barn was destroyed by fire just 15 years ago yesterday.