33 High Street, the John and Sarah Dillingham Caldwell house (1660/1709)

The Caldwell House at 33 High St. is listed by the Ipswich Historical Commission as having been built in 1660, but Abbot Lowell Cummings gave a more likely date of “after 1709” when John Caldwell’s widow conveyed the property to their son, Dillingham Caldwell.

Unlike many First Period homes that began as half-houses, the present house was built in full as a two-over-two-room, central chimney plan house with massive summer beams, a huge fireplace, and heavy chamfered frame. A lean-to was added at a later date, and has since been replaced. Early 18th century details include fine paneling in the chambers and the front stairway. The attic stairway is also of considerable age, and is fastened with rose headed handwrought nails.

Abbott Lowell Cummings recorded the following history of this house at a conference of the Colonial Society in 1974:

“Deeds mention a house on this site as early as August 31, 1654, when it was conveyed to John Caldwell for £26. At Caldwell’s death in 1692 the “house & lands at home” were appraised at £109, implying a major improvement, probably a new structure altogether. The present house, however, of two-room, central-chimney plan with added leanto, appears on structural and stylistic analysis to be later still. Caldwell’s widow conveyed the property to their son, Dillingham Caldwell, on January 19, 1709, reserving one end for her own use, and the present house may possibly have been erected by the son following this transfer, or, more likely, after the widow’s death on January 26, 1722, the key being the early and probably original interior finish trim which cannot be much earlier than the latter date. The house was acquired August 17, 1956, by Charles Woolley and restored, at which time the later lean-to was entirely reconstructed. Privately owned.”

Earlier history of the lot

Simon Bradstreet, who became Governor of Massachusetts, and his wife Anne Bradstreet, America’s first published poet, lived in the first home on or near this site from 1635 to 1644 before moving to Andover. The next known owner of the old Bradstreet property was Richard Betts, who was in Ipswich by 1648. He sold the house in 1652 to Cornelius Waldo, and moved to Newtown, Long Island, New York, where he developed a large plantation at the “English Kills” and became a prominent citizen, dying at the age of 100.

On Aug. 31, 1654, Cornelius Waldo sold to John Caldwell for £26 “the house I bought of Richard Betts, the land of Edward Brown southeast, the street southwest, house and land of Robert Collings, northwest.” (Ipswich Deeds 2: 128). Caldwell removed the old house and built a new one.

Waldo-Caldwell house, circa 1900.
Waldo-Caldwell house, circa 1900

This house was restored in 1956 to its original form, exposing a huge walk-in fireplace, massive chamfered summer beams.

Waldo-Caldwell House, 33 High St. Preservation Agreement

The house is protected by a preservation agreement between the owners and the Ipswich Historical Commission. Protected elements include:

  • Front facade and framing of the original 1660/90 dwelling.
  • All front and side exterior features
  • Wooden architectural elements (stairs, paneling, moldings, mantelpieces, doors in the two front second story bedrooms
  • Central chimney
First floor summer beam, Waldo-Caldwell house
Well-worn attic stairs in the Waldo-Caldwell house. There is a half-way landing in front of the chimney. The steps continue on the left at a 90 degree angle, but the steps on the left are winders, for no apparent reason.

History of the Waldo-Caldwell house

From John Caldwell and Sarah Dillingham Caldwell, his wife, Ipswich, Mass., 1654 : genealogical records of their descendants, eight generations, 1654-1900 (1904)

Cornelius Waldo

Cornelius Waldo, the ancestor of all the Waldos now in America so far as has been learned was born about 1624 probably in England where we know his family was living in 1653. He was here as early as 1647, for at a Court held at Salem ye 6th of 5th mo 1647 by adjournment,

“Cornelius Waldo hath left a fowling piece for further security of the 40 sh for which he stands ingaged for his brother Thomas for a fine unto ye coutree & thereupon The Court is pleased to forbear Leviing ye sd fine from him before Ipswich Court next.”

Cornelius probably first settled at Ipswich where he became John Cogswell’s farmer, and he married Hannah daughter of John and Elizabeth Thompson Cogswell of Ipswich who was born 1624 at Westbury Leigh Co Wilts England before Jan 2 1651, for on that date John Cogswell Sr. conveyed to his son-in-law Cornelius Waldo a house and 49 acres of land at Chebacco Falls. This estate was sold by Cornelius Waldo of Chelmsford and Hannah, his wife, February 15, 1668 and it was there that he probably lived during his residence at Ipswich, although in September 14 1652 he bought the house on High Street in Ipswich, known as the old Waldo house, but which he sold August 31, 1654. (from Four Generations of the Waldo Family in America)

Richard Betts’ Deed of Sale

“This present writing witnesseth that Richard Betts of Ypsvvich (Ipswich) and Joana his wife of Ipswich for and in consideration of thirty pounds by bill and otherwise in hand paid before the sealing hereof, Have Granted, Bargayned. & Sould, and by these presents doe fully Grant, Bargayne, & Sell, unto Cornelius Waldo of the same Towne and County, Marchent, all that his dwelling house situate and being in Ipswich, aforesayd, with all the yards, fences, and lands about it, haveing the house and land of Edward Browne toward the south east, the house and land of the late (Daniel Rolfe?) toward the northwest, abutting on the street toward the southwest, and on the land of Thomas Lovell toward the Northeast, To have & to hould and peaceably enjoy all the sayd house & land, yards & fences, and all other aptenances and privileges thereunto belonging, vnto the sayd Cornelius Waldo, his heirs and assigns forever. In witness whereof the said Richard Betts and Joanna his wife have hereunto sett their hands and seales this 14th of September, 1652. Richard Betts. Joana Betts. (E) Signed, sealed & delivered in presence of Robert Lord, William Inglish.”

John and Sarah Dillingham Caldwell house

Col. Luther Caldwell, while he was Mayor of Elmira, N. Y., 1873, wrote of this ancient home of his ancestor:

“The house on High street is one of the oldest in Ipswich; and, unless changed very much from what it was when I roamed in boyhood through its rooms and peered into its closets, will well repay a visit. It has descended from sire to son or daughter by the settlement of the Probate, and not for filthy lucre.” John 2 and Sarah ( Foster) his wife, willingly sold “the right of redemption” to the brother Dillingham. (Their house most beautifully located on the Town Hill top, corner of Brook (Spring) and East streets, with a view of miles away to the south and west, and at the east reaching even to the Bay, attractive and most wholesome to the eye and thought. One could hardly surrender such an outlook for a home on the rim of the street below.) At the death of Dillingham Caldwell 2, in 1745, his son, Daniel 3 and Elisabeth (Burley) his wife, occupied it.

John Caldwell’s timeline

  • Lord’s Day. April 12, 1674. John Caldwell and Sarah (Dillingham,) his wife, were admitted to full communion with the First Church.
  • 1677. May 23. He was made freeman.
  • 1679. He built a barn and shed; mention is made of his cattle and sheep.
  • In the list of old commoners who drew their thatch lots and marsh lots, John Caldwell is designated as having Lot 62, “six rods wide, and running to the Cove.”
  • 1691. John Caldwell, sen’r “appointed Searcher and Sealer and Viewer of Leather; he refusing yt office as not being capable threw business & otherwise.” The “otherwise” was his failing strength, probably; for the next record is of his final effort and the departure.
  • 1692, June 20: John Caldwell signed his will in the presence of William Stewart and Simon Stacey.
  • July 7, 1692, he departed this life, aged sixty-eight years. John Caldwell’s entire estate was valued at £221, 16s. 4d.

John Caldwell’s Will

In the name of God, Amen. I John Caldwell, Senior, of Ipswich, of Essex, being Sicke and weake of body, and having my perfect memory and understanding, doe make this as my last will and Teastament, as followith:

Imprimis, I give my soul into the hands of my blessed Redeemer, my body to decent burial in the assured hope of a blessed resurrection.

As for my outward Estate that God of his goodness hath given me, I dispose as follows:

  • Item, I give to my beloved Wife, Sarah Caldwell, the use and improvement of all my Estate during her widowhood, and also to dispose of it, or any part of it, for her necessity : if she marry, then to have a third part as the law directs in that case, and this to be understood after my debts and funeral expenses are satisfied.
  • Then my will is that after my wife’s decease or widowhood, that my son, John Caldwell, shall have a double part of my estate that remaineth, that is two parts out of eight; and that he shall have my dwelling house with all the appurtenances and privileges thereto belonging, if he desire it, paying to his brothers and sisters what may belong to them out of it as portions besides his eight part.
  • Then my will is that my daughter, Anna Caldwell, after John hath had out his parts, that she shall have a double part of what remaineth, that is, two parts out of six.
  • Then my will is that my sons Dillingham Caldwell, William Caldwell, Nathaniel Caldwell, and my Daughters Sarah Ayres, Mary Caldwell, Elisabeth Caldwell, shall have an equal share of what remaineth : that is, all a like part, after all those parts are taken out that are made mention of before.
  • And I doe appoint and constitute my beloved Wife and my son John Caldwell to be my Executrix and executor to this my last Will ; desiring them firstly to take care that all my lawful debts may be paid in the first place :
  • And as a Confirmation of this my last Will, I here set my hand and Seale, this twentieth day of June, one thousand six hundred and ninety-two, being the fourth, year of the Rains of our Sovorains, William and Mary, King and Queen of England, Scotland, and Ireland,
The Caldwell house

John Caldwell. Signed and sealed in presence of us : William Stewart, Simon Stacy.

Fireplace at 33 High St,

Sarah Dillingham Caldwell

“In 1645, when John Caldwell was nineteen years of age, his name occurs in the records cf the General Court of Massachusetts: “Oct. 1643, Richard Collecot, Edward Fuller, John Cauldwell and Richard Smith, were appointed to fetch the Cattle from Providence.” John Caldwell made Ipswich his home. He is styled husbandman in legal papers; he was also familiar with weaving, as were two of his sons, Dillingham and Nathaniel, and several later descendants. He married Sarah Dillingham, of Ipswich, an orphan, who was ten years younger than himself, and a woman of qualities that caused her to be graciously remembered by her descendants to the third generation. Her name has never been forgotten.

The story of Sarah Dillingham Caldwell, wife of John Caldwell is of tender interest. As we review it, we shall not wonder that traditionary memories give her the gracious record of a loving and most thoughtful life. She was one of the earliest born babes of the earliest settlers of Ipswich. Her birth month was April, 1634, five months before the town was incorporated. She was the daughter of John and Sarah (Caly) Dillingham, who immigrated to American in 1630 from Leicestershire, England in 1630. In 1634 they were in Ipswich, where Sarah Dillingham was born. Her father died in his early manhood, less than a year after her birth. The mother died two years later, 1636, leaving the babe in the care of two names, most worthy, Mr. Saltonstall and Mr. Appleton. Her last expressed wish was the entreaty, “in the bonds of Christian love,” that the tiny girl should be “religiously educated, if God gave her life.”

John and Sarah Caldwell are buried within a few feet of Stephen Caldwell's gravestone at the Old North Burying Ground.
John and Sarah Caldwell are buried within a few feet of Stephen Caldwell’s gravestone at the Old North Burying Ground.

Sarah Dillingham grew from cradle to early womanhood in Ipswich town, and at nineteen years of age she became the wife of John Caldwell, who was ten years her senior. She was homeless no more forever. She may not have inherited the accumulations of her father, but as the years multiplied she was entrusted with treasures better than gold, with eight children gathered at her fireside and records and traditions picture them all as worthy people. When old age crept nearer, and the children had secured homes of their own; when the husband had departed to the realm unseen, then her son Dillingham and his wife Mary (Hart) cared for every need. She acknowledged their filial goodness, and gave them her interest in the High street homestead, that was, when all the years were counted, earth’s choicest spot to her for sixty-seven years.

The last resting places of John and Sarah Caldwell

“In the ancient High street burying-ground, at Ipswich, at its northeast corner, near the tombs and the wall, may be seen a cluster of grave stones bearing the name of Caldwell. In the midst of these marbles of recent dates, is a slate stone inscribed, “Stephen Caldwell, died January 14th, 1754, aged 31.” This ancient memorial is on a line with and only a few feet from the graves of our ancestors, John and Sarah. No memorial stone was ever erected above their dust, but the graves are yet pointed out.”

The last Will and Testament of Sarah Dillingham of Ipswich, Widow, mother of Sarah Dillingham Caldwell

For my Soul, I commend it into the hands of God, in the mediation of Jesus Christ. For my temporal estate, I give to my only child, Sarah Dillingham, my whole estate inlands and goods, (except such particular legacies as hereafter are named,) and if my child die before it shall be married, or attain the age of one and twenty years, then my will is that the same shall be divided equally between my mother Thomasine Caly, my brothers Abraham Caly and Jacob Caly, my sister Bull and my sister Base, the wives of John Bull and John Base, and my sisters Rebecca Caley and Anne Caley, or such of them as shall be living at the time of the decease of said child all which, my mother, brethren, and sisters, are now living in England.

Also,I give to Mr. Ward, Pastor of the Church at Ipswich five pounds; and to Richard Saltonstall, Esq., ten pounds; and to Mrs. Saltonstall his wife, a silver bowl; to Mr. Samuel Appleton, five pounds; and to his wife a silver porringer; and of this my will I make executors, the said Mr. Saltonstall and Mr. Appleton; committing the education and government of my said child, and the estate I leave her, unto their faithful ordering ; entreating them, in the bonds of Christian love, to see this my will fulfilled, my due debts paid, my body decently buried, and my child religiously educated, if God give it life; and that they will order the estate as they would do their own.

In witness that this is my true will, made in my perfect memory, though my body be weak and sick,I publish it,after it hath been read unto me, in the presence of those whose names are underwritten, this tenth day of July, 1636. Thomas Dudley, Sarah Dillingham. Robert Lord. Phillip X Fowler’s mark. (source: Memorial of Samuel Appleton.)

The Caldwell women, lace-makers of Ipswich

Melissa Berry wrote about Sarah Caldwell and the lacemakers of Ipswich in AnceSTORY Archives:

“Sarah Dillingham Caldwell was a woman “of quality so graciously remembered by many generations of descendants” that they visited her resting place for years after her passing. The Caldwell women were not just proper society ladies, handing out alms to the less fortunate and attending sewing circles — they were inventive, industrious, highly skilled crafters. The Ipswich Historical Society asserted that lace-making was the first women’s industry in America, and members of the Caldwell family were among the forerunners.”


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