The original home and property have always been admired—even revered, by those familiar with its history. They comprehend the wealth and privilege responsible for building such a glorious monument to success during the “Roaring-Twenties,” but also acknowledge its legacy of invention, exploration, and the sharing of good fortune with the community by its inhabitants.

The vast tract of land known as Round Hill has been considered one of the most desirable properties along the SouthCoast—dating back to 1652—when settlers of Plymouth split off and purchased prime acreage from Native American Chief, Massasoit. The sale included what is now known as New Bedford, Fairhaven, Acushnet, and Westport.

People and technology associated with Round Hill include: Hetty Green, the infamous “Witch of Wall Street;” Colonel Edward Howland Robinson Green (Ned), a man years ahead of his time, Bert and Pricilla Hill, who managed the Colonel’s airport; WMAF Radio; the Mayflower Blimp; the Charles W. Morgan; even Massachusetts Institute of Technology (MIT).

In the late ‘80s, real estate developer Robert M. Desmond began the initial conversion of the property into a luxury condominium complex that was to include “Mansion Units,” off-site homes, a nine-hole golf course, sandy beach, pool, and tennis courts.

As a weekend vacation home, primary residence, or a summer-long retreat, each property has its own personality.

Initially, the new project hobbled, locals knew about the exciting opportunity, but sales suffered; it wasn’t the level of living the market had an interest in purchasing.

Looking for a fresh start, real estate broker, Marianne MacDonald, who represented Round Hill, brought on an ad agency, Turner & Company, who recently opened an office on Smith Neck Road—directly across from the project. While enjoying distant views of the Mansion from a second-story office window, the agency’s creative director developed an advertising campaign that went right to the heart of marketing to an affluent demographic audience. Within weeks, “Round Hill” was being advertised in the New York Times and the Wall Street Journal, resulting in hundreds upon hundreds of leads, all with the intension of owning a fabulous piece of history.

Today, Round Hill continues on a journey. It boasts improved amenities, many more luxury free-standing homes, and exclusivity only found in an iconic landmark.

The Mansion Units and Oceanside Homes, represented by Milbury & Company of South Dartmouth, Westport, and Cape Cod, offer a stunning level of elegance combined with comfort and versatility. Shingled, Nantucket Style residences nestled along the historic setting possess charm and grace.

Private, with unmatched common areas offering acres of natural growth in combination with manicured landscapes and a host of amenities, create masterful living spaces and a luxury lifestyle.

Residents come from around the country to share eclectic pursuits and are pleased to find their expectations exceeded when it comes to personal choices and in common interests.

As a weekend vacation home, primary residence, or a summer-long retreat, each property has its own personality.

Round Hill is considered by many to be the most exclusive residential properties in New England. With its private beaches, tennis, and golf, easy access to Padanaram Harbor, and extraordinary views of boat traffic and the Elizabeth Islands, time spent at the estate is unforgettable.

The expansive green lawn leading down to the shore where peace, quiet, and an ocean breeze is a gift of life; the single pleasure of reading a book will become a ritual that only
a few will experience, but cherish.

The gated community feels secure and contained, but not so separated from the outside world that you feel isolated. When desired, Round Hill can be socially active and exciting.

Milbury & Company have five homes for your review and invite you to contact them for a private showing of the property you find most enchanting.

The representative agency and their brokers are sensitive to health precautions requested by officials and mandates ordered by the state. Rest assured, your health and safety are a priority to all associates. They will keep you safe by every means possible.

For detailed information or to schedule a visit go to or contact the Brokerage Team or agent listed.