Hollins, a native New Yorker educated in private schools, was married to socialite Evelina Meserole Knapp on January 25, 1877.

The couple had four sons, Harry B. Jr., McKim (Kim), John K. (Jack), Gerald Vanderbilt,[3] and a daughter, Marion.

After the news of the firm failure had spread through the financial district, Hollins's attorneys, Beekman, Menken & Griscom, released a press statement downplaying the collapse: A large portion of the securities was understood on the Street to represent a number of companies in Mexico that were adversely impacted by political turmoil south of the border at the time.

Jerome told Brown that Hollins continued to work as a broker in the city and managed to pay back the entire debt, less what was forgiven by Vanderbilt and the Morgan estate, by 1928.

[9][10] After Hollins's bankruptcy, Meadow Farm, the country manor, was sold to Charles L. Lawrence along with 116 acres (0.47 km2) bordering the Great South Bay and Champlin Creek.

After the death of Mrs. H. B. Hollins, a month after her husband, her daughter Marion as the administrator of the estate sold most of the property not utilized by the family.

This project was completion of The Moorings, a wealthy gated community by the subdividing Meadow Farm's remaining 16 acres (65,000 m2) into 11 lots.

The purchaser of the 5.88-acre (23,800 m2) parcel (now 150 Meadowfarm Road) containing Meadow Farm learned the cost of refurbishing the mansion would have well exceeded $1 million and opted to replace it with a newer estate.

According to a New York Times article written in 1999, the new estate's owner planned to salvage marble fireplaces, paneling and other appurtenances from the mansion.

A company, Yarmouth Estates of Bay Shore, New York, has purchased the house at 42 Blackmore and is requesting a subdivision.

This land had been purchased from the Nichol estate by HB Hollins Jr. in 1906 and was the site of one of the earliest settlements in Islip Town.

Replete with a small damn and ice pond, the area had been a self-sufficient working farm until the last Nichol passed away at the turn of the 20th century.

by the 1990s the land and remaining buildings were part of Hecksher State Park and will not suffer the development of the Hollins's other holdings.

house, Crick Holly, was one of the earliest roads in the area and connected the first Nichol settlement located on the shore of the bay in Hecksher Park with Gibbs Patent, and a grist mill which Nichol and Gibbs operated on the west side of Chaplain's Creek and on to the village of islip.

In 2016, amateur East Islip historian Steven Cymbalski had been reviewing a late 19th century photograph of the Hollins family as seated in the dining room of their East Islip mansion and noticed a painting hanging on the wall in the background; further inspection revealed it was Waldo and Jewett's The Knapp Children.

Legend tells that the island was a hideaway for pirates' gold, most notably Captain Kidd's buried treasure of the Spanish Main.