wellfleet vacationHistory of Hidden Hollow


wellfleet vacation house, rentalBuilt in 1847 by Squire Cole’s son, William, it was first referred to as the Paine house. Frank Paine lived in the Main House while his brother, Harold, was stationmaster for the South Wellfleet Railroad Station. Harold, it is believed, lived next door in what we now fondly call, Lost Oak.

In the mid 1900’s the property was purchased by the Maguires. The Maguires were regarded with such respect that at one time the Town voted to rename LeCount Hollow Beach to Maguire’s Landing, a name that is still heard today, but not commonly used. James Maguire, Jerry, was very active in the Wellfleet Historical Society, serving as chairperson to many worthwhile committees. It is written in the Massachusetts Historical Commission in Boston that he chose to use his retirement in the kindest of ways. When a woman in the neighborhood was widowed, he always went to her to urge her to call him when she needed help with pumps, furnaces, plumbing, or any other jobs that needed to be taken care of.

The property was owned by Jerry and his wife “Scottie” until their passing in the 1990’s. After that the property was held in probate and occasionally rented, but over the next several years it was not maintained and fell into disrepair.

In 2006 the homestead was purchased by Bill and Joy O’Connor.

We have been in the process of restoring the houses and the property ever since.