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This Old House

Brief histories of the older places and those who lived there


The James Benjamin Homestead (1182 Flanders Rd.) was built circa 1782 and is considered to be the oldest surviving house in Flanders.  Listed in both the National and State registers of historic places it at one time also served as the Flanders post office. James was born in Southold, which at the time included all of today's Riverhead, in 1753. During the Revolution he first served in the 1st Reg. of the Suffolk County Minutemen under Col. Josiah Smith. Afterwards, during the British occupation, he removed to Guilford, Conn. and served  in Col. Chester's Connecticut Regiment . James returned to L.I. after his service and purchased his homesite from Josiah Goodale in 1782.                   G.Cobb photo

James_Benjamin_s.jpgSeveral additions to the original "center chimney" homestead are shown in this view taken from the Reeves Bay side of the property.       G.Cobb photo

Benjamin_House_-inside2.jpgThe original framework can be seen in this circa 1980 view of the interior.                                                       photo courtesy of Mary VanDeusen

Benjamins_and_the_landing_002.JPGJames' son Zachariah is most likely to have been the Benjamin family member responsible for building this house (38 Pleasure Drive) at the turn of the 19th century and his son Capt. Zachariah also lived here. Zachariah's brother Alanson was the owner/proprieter of, the "Benjamin Villa", a hotel/boardinghouse that stood on the hillside near the location of today's firehouse.         G.Cobb photo


Benjamins_and_the_landing_004.JPGBenjamins_and_the_landing_006.JPGAlthough it has undergone many renovations over the years Zachariah's wide plank pine flooring has survived (on the first and second floors and in the attic) along with many other details of the period including the fireplace surround and various doors and hardware. The parking area 's retaining wall utilizes "ballast stone" ( a common feature in many area houses) that was salvaged from the original foundation when it was upgraded. The house today provides an excellent example of a thoughtful renovation of a historically significant structure.      G.Cobb photos

Benjamin_s_Boarding_House.jpgAnother hotel/boardinghouse that was owned by a Benjamin family member was located just around the corner at 1181 Flanders Rd.         G.Cobb photo

_1194_Berti.jpg Located at 1194 Flanders Rd., adjacent to the James Benjamin homestead and opposite the United Methodist Church, is the former home of Oscar and Millie (Squires) Goodale and their son Oscar "Dwight" Goodale. Oscar was the great-great-grandson of Josiah Goodale who had built his home on some portion of this property prior to 1761. Josiah was the first of a long line of Flanders Goodales and he has been credited with clearing the majority of the woodland that surrounded the early settlement. The members of the Goodale family who founded and currently own Riverhead Building Supply are 5th and 6th generation direct descendents of Josiah. This property and the penninsula that is attached (known as Goodales or Fifteen Mile Island) represented the demarcation line that separated the Southold and Southampton settlers in their 1667 dispute over ownership of the southern section of the "Akkobauk" lands       G.Cobb photo_1212_Kessler.jpgJosiah Hallock Goodale, Oscar's father, had also built his home on a portion of the original Goodale parcel (1212 Flanders Rd.) It too was operated as a summer hotel/boardinghouse that was known as "Willow Cottage". During the War of 1812 J. H. Goodale's grandfather, Josiah Goodale Jr., served, in Capt. David Haines' Co., in the defense of Sag Harbor alongside his uncle David Goodale and his neighbor John Fanning Jr.                    G.Cobb photo

Flanders5.jpgAlthough barely recognizable today the center section of this house, located at 2043 Flanders Rd., was very likely the home of Josiah Goodale's son Joseph which had been left to him in his father's will dated January 15, 1786. Joseph was listed in the "1st Co.of Minutemen of Southampton" of August 10, 1776 and it is likely that he built his home here after his marriage to Mary Mapes of Southold in 1775. Joseph's daughter Elizabeth and her husband David Brown Sr. built their home on the north side of Flanders Rd. opposite her father. During the War of 1812 David Sr. and his wife's brother, Joseph Goodale Jr., (who were both cousins of Josiah Jr. mentioned earlier) also served in the defense of Sag Harbor but under the command of Capt. John R. Satterly. David and Elizabeth's son, Capt. David Brown Jr., a mariner, would eventually make his grandfather's property his home along with his wife Martha (Webb) and their sons George and Cornelius.            G.Cobb photo

George W. Brown, David Jr's son, purchased this property, which is located at 1553 Flanders Rd,  from Charles Sanford whose wife, Nancy (Goodale), was George's cousin. George and his wife Rozella (Smith) expanded the original modest homestead in 1883 and in later years their son Elbert added on further.   G.Cobb photo

G.W.Brown_s_Outbuildings.jpgGWBrown_s_barn.jpgA few of the Brown family's surviving outbuildings.                       G.Cobb photos

Elbert_Brown_s_Service_Station.jpgGeorge Brown's son Elbert became a renowned local carpenter who is credited with the construction of many local structures. Among those that survive are this former filling station which he built on his property at 1551 Flanders Rd.    G.Cobb photo

Oppenhiem_s.jpgGeorge's daughter Denise (Brown) Oppenheim lived just east of her father on a parcel that had originally belonged to him. This circa 1900 house is located at 1885 Flanders Rd. This is one of several structures, including the schoolhouse, that were not relocated, as others had been, when Flanders Rd. was widened and straightened in 1931.     G.Cobb photo