athaniel Ayer did not actu-ally build this house, he bought it in 1860 from the Denton brothers; and he's not the best known of its residents, since he was certainly outranked by Henrietta Joanna Wagener Monell, who owned and occupied it for pretty much the whole last quarter of the 19th century. But Ayer perhaps had the most interesting use for it: he ran what was called in those days a "Female Seminary", or girls' residential secondary school, in it.
The house was built about 1854 by Henry Wood (of Wood and Bruen) and sold shortly by him to the brothers Lewis and Samuel Denton, who are shown as owners on the 1857 map of the village.
Mrs. Monell was Abraham's youngest and longest-surviving child, who died here in 1909 and left a great deal of money to beautify Lake View Cemetery as a memorial to her family.
Most people nowadays would remember the house as the home of two generations of the Sheppard family, George S. and Oliver Sheppard, descended from Morris Fletcher Sheppard who came to Penn Yan at the dawn of the 19th century. The Sheppards were related to the Wageners (through marriage) and perhaps had a greater effect on the village's development than their nowadays better-known cousins.
This was the first lot from the corner that was not burned over by the 1867 fire; this house already stood here, so although the fire companies were much criticized, they obviously must have worked hard to save it. Reform of the companies took place only after the much more destructive fire of 1872.
Miles Benham sold the lot in 1840 to Roscius Morse, who in partnership with Leander Reddy (who lived across the street), had a "Pill Factory" here. They were also partners in a drugstore down the street, so this use was probably not unrelated. Reddy bought the matching lot adjacent on the south, on the same day. Both lots were 50 feet across, front and rear, and 17 rods (280 feet 6 inches) deep.
Lewis and Sylvester Denton acquired the property from Henry Wood, who built this house a few years before as a residence. The lot was part of the Wood & Bruen carriage factory lot, and just this small piece at the southwest corner was sold.
Henry Wood's widow Persis sold the rest of the Wood & Bruen lot for good in 1867 (after the fire) to Andrew F. Chapman of Benton, who already owned #167 on the south. The deed acknowledged the foreclosure of the mortgage on Wood's remaining property, pointing out that Isaac W. Hartshorn had forced the sale of all property owned by Henry Wood and John C. Bruen.
Nathaniel Ayer bought this house and lot from the Denton brothers and opened his Female Seminary. The school couldn't have been all that successful, as Henrietta Monell owned it by 1876, and held on to it until her death.
The Sheppards inherited the property from her, first George S. (who held it in his wife Lillian's name) and then Oliver, who kept it into the 1960s. From this vantage point the two men collected for decades evidence on local happenings; these "Sheppard Scrapbooks" are now in the collection of the Oliver House Museum across the street.