DARIEN — Back in the earliest days of the American colonies the town of Darien did not exist. In the 17th century the land that now comprises Darien was part of a much larger community. “Originally part of Stamford, the area we know as Darien became Middlesex Parish in 1737,” the Darien town website says.

It was around that time that the Zachariah Dibble House was built at 258 Hollow Tree Ridge Road. The Darien Historical Society plaque that hangs at the front entrance indicates it was built circa 1735.

Decades earlier Zachariah Dibble Sr. was engaged in what must have been scandalous news of that time period. “In 1672, only thirty odd years after the colonists had first settled a Puritan colony in Stamford wilderness, his wife Sarah Waterbury Dibble divorced him, a rare proceeding for the time,” according to a document from the Darien Historical Society. The house was built by Zachariah Dibble Jr. on what was then a 10-acre property, which he inherited from his father’s estate, according to the historical society document.

This rustically charming historic home has enjoyed much familial happiness and tranquility since that time. The current family has lived there harmoniously since 1981. The house and 1.53-acre largely level property combine to create a magically peaceful setting, even though the property sits along the well-traveled Hollow Tree Ridge Road. It is a private paradise hidden behind a scrim of shrubbery and fencing that seems worlds away from everything when it is really quite convenient to everything. This location puts the house within walking distance of the Metro North Noroton train station as well as the middle and high schools, and it is close to shops and restaurants along Post Road (Route 1).

The grounds are exquisitely decorated with red brick and slate walkways, boxwood hedges, specimen plantings, mature trees, open lawn, and perennial gardens brimming with colorful blossoms; all of which can be enjoyed from what the current owners call their “summer living room.” That outdoor “room” is a covered patio off the guest cottage, which can also serve as a cabana for the in-ground swimming pool at the back of the property.

The pre-Revolutionary War brown shingle house with pale coral shutters and white trim comprises 2,930 square feet of living space. It beautifully blends past and present with the promise of even more rustic elegance should the next owner decide to update rooms with trending neutral interior colors.

Entrance to the property is through two separate driveways on opposite sides of the main house. One driveway opens to a large parking, where there is an ivy-covered wood and fieldstone structure over a water pump. This driveway also accesses the front entrance to the main house and the guest cottage. The other longer driveway leads to a gate that accesses the backyard and the rear attached two-car garage topped by a cupola and a weathervane. A fieldstone wall borders the front of the property.

More Information


STYLE: Antique Colonial

ADDRESS: 258 Hollow Tree Ridge Road

PRICE: $2,195,000


FEATURES: 1.53-acre largely level property, fenced backyard, guest cottage, in-ground swimming pool, terraced gardens, covered patio, two driveways, close to town amenities, walking distance to the Metro North Noroton train station, walking distance to the middle and high schools, one fireplace, stone wall, wood shingle roof, hardwood flooring, breezeway, full partially finished basement, attached two-car garage, pull-down attic stairs, four bedrooms, three full baths

SCHOOLS: Ox Ridge Elementary, Middlesex Middle, Darien High School

ASSESSMENT: $ 988,820

MILL RATE: 16.08 mills (new tax rate)

TAXES: $15,900

Inside the main house, the family room features a huge stone fireplace with a beehive oven and swiveling metal arm to hang pots and a tea kettle. One wall contains built-in bookshelves around one of the six-over-six double-hung windows. Throughout the original part of the house there are very wide-planked hardwood floors. A later addition has standard width boards.

The formal dining room has a built-in corner china cabinet and a door to the open breezeway that connects to the cottage. In the kitchen there are natural-colored pine cabinets and butcher block counters on two walls. Included in the listing agent’s photos are virtually staged images that show what the dining room and kitchen would look like if they were updated. Off the kitchen there is a breakfast room with cabinetry and counter space. This room provides access to the laundry room and the garage, and it has a door to a brick courtyard.

The master bedroom suite is on the first floor and enjoys a private sitting room. There are two more bedrooms on the second floor that share a Jack-and-Jill-style bath.

In the cottage the spacious living room has a ceramic tile floor and sliding doors to the covered patio. There is also a bedroom, full bath, and plenty of storage space.

For more information or to make an appointment to see the house contact Eileen B. Hanford of Halstead Property at 203-253-0995 or eileen@eileenhanford.com.