Over the Hill

“Itought not to change people, but people do love to think of something as the oldest—it’s one of our human frailties,” says Abbott Lowell Cummings, one of the nation’s premier experts in historic Colonial houses. “And it is always a little unsettling for people to realize something isn’t the oldest in town.” But there are other people who are surprised to find out that their home might be the oldest. When Debby and Tony Angotti bought the Georgian-style house across the street from theirs on Old Hill Road in Westport, they had no idea it would turn out to be one of the few “medieval” homes in New England and that they had unwittingly joined the informal competition for the title of “oldest house in town.”

The couple bought during the hot real estate market of the late 1990s. At that time, 6 Old Hill was sagging, leaning, and dilapidated —the poster child for the perfect Westport teardown. Situated on the highest point between the Norwalk and Saugatuck rivers, the location is ideal for a new construction. And while certainly historic, the 1707 house had not yet been embraced within the protective arms of the Kings Highway North Historic District.

The home sits atop a road that was once a narrow country lane; even today it ambles past houses that have been rooted there for more than three centuries. The Angottis live at 1 Old Hill, a 1711 house, and had always wondered what 6 Old Hill had looked like in its original splendor. Once they bought the house, they wasted no time having it designated historic. They also hired Colonial home historians Christopher Wuerth and Richard Hershner to lead the renovation project. All were committed to a true and lasting restoration, thus giving a historical gift to Westport. Two years later, they were honored by the Westport Historical Society for their efforts. The unexpected bonus? The architectural and historical secrets they uncovered.

Today, the house belongs to Brad Lamensdorf and Julia Gross, who also revere its long history. “I was a history major and now a social studies teacher,” says Gross. “We enjoy living in an historical home.”


For starters, the relatively modern siding was hiding “Elizabethan” shingles, which themselves were hiding original beaded clapboards. These were nailed to twenty-inch-wide oak planks that ran from the sills to the rafter plates. The shingles were rare and unusual: three feet long with sixteen-inch exposure and made of 300-year-old white pine and oak from “first growth” trees as tall as 150 feet. This confirmed the date of the structure to a very early period. The Angottis had discovered a house within a house within a house: an historical gem hidden for three centuries inside layer upon layer upon layer of ancient wrapping.

Then there were the massive sixteen-inch summer beams in the open parlor, which were “chamfered” (beveled as decoration). This is a medieval detail seen only in the oldest of Colonial houses, before beams were encased in beaded pine or poplar planking late in the eighteenth century. And then a seeming contradiction: the 300- year-old beams at 6 Old Hill weren’t ax-hewn but sawn. Research revealed that they had probably been cut at one of the first sawmills in Fairfield County, most likely the one on the Saugatuck, which opened for business in the 1680s. “Modern” technology had been used to build a house with medieval features, one of the rare examples of “transitional” architecture to be found in New England. “It is almost impossible to determine the exact age of house foundations,” says Wuerth, who managed the project. While early homes were regularly destroyed by fire, replacement homes were usually rebuilt on earlier foundations. The foundation here could have been on that site before the 1707 house was built—perhaps as early as the 1600s, before beams were sawn by mills.


The home is not the only “oldest house” still standing in Westport. The current official designation is held by the Mills-Osborne House, a low, red saltbox at 187 Long Lots Road. Prior to an investigation by Bob Weingarten, a local Realtor and the official historian for the Westport Historical Society, Dutch and Susan Wynkoop’s historical home had been dated to the Revolution, and the swaybacked structure had been proudly “plaqued” at 1775 for years.

The Wynkoops believed their house had been built in an earlier era because of the usual summer beams, low ceilings, and wide pine flooring common to houses of pre-Revolutionary vintage. Their house also sported a collapsible door that protected a narrow staircase—presumably a hiding spot for early settlers living in hostile surroundings. Acting on “some facts, some intuition, and some guessing,” Weingarten dated the original construction to between 1683 and 1687, and the Wynkoops successfully applied for landmark status.

There are others. The John Platt House, at 46 Kings Highway South, is “plaqued” at 1700 but has been dated to 1695. The house incorporates hand-hewn timbers, gun-stock posts on its second floor, wide chestnut flooring, and, like 6 Old Hill, chamfered summer beams. It also showcases a rare and early form of construction to support the overhung steep-roofed attic: a double-framed-out girt, typical of medieval overhangs (cantilevers): a “vestigial” style once employed in crowded medieval European cities.

There are also smaller historical houses. The cozy John Green House on Compo Road North was built around the turn of the eighteenth century; it was already more than fifty years old when the British marched by on their way to burn Danbury. Another “cottage,” now called the Goodsell–Grumman House, contains early corncob wall insulation and served as a tollhouse on Easton Road after being a family residence for half a century.

Some old homes were constructed earlier than the recognized date would have them. One house on Cross Highway was assumed to have been built in 1850 but recently was found to have been built on an older foundation, circa 1762. And the Goodsell–Grumman House was moved to Easton Road from its original site on Catamount. Building new houses on old foundations, moving parts of or entire houses to new locations for new and different purposes, and employing vestigial urban European architecture in the vastness of rural North America were not uncommon. In the “good old days,” house fires were common and moving an existing house was not impossible, given a strong team of oxen and hardy friends. And those vestigial cantilevers and medieval chamfered summer beams? New Englanders have always revered tradition, even if purely decorative.


Old homes are full of evidence that has yet to be deciphered. Hoping to rely on written records to date early houses might be a disappointment waiting to happen. For example, the books for North Kings Highway, which the Angottis researched at the Norwalk Town Hall, were incomplete and hard to read because some of the writing has been obscured by three centuries of moisture, mildew, and perspiration. This underscores the importance of knowing local history.

Between 1692 and 1707, John Buttler of Stratford, a self-described “docter of phisick,” accumulated more than 120 acres of land in the Old Hill area. Before he died in 1707, he had built the current structure, 6 Old Hill, and reported already “having enjoyed fifteen years on said land.” This places the date of the earliest occupation to at least 1692, the first year of the Salem Witch Trials. Norwalk, however, was founded in 1650, and scattered settlers were reported in the area as early as 1638, just a year after the Pequot War came to its bloody conclusion in Fairfield’s Southport section. Therefore, it’s possible that Old Hill was settled even earlier than when Dr. Buttler found it.

The doctor left his estate to his “successors,” who eventually sold it to John Taylor of Norwalk for 40 pounds and 12 shillings. This is the first mention of money changing hands in almost twenty years of property exchanges (in the early history of New England, economies operated largely on the barter system). The property stayed in the Taylor family for 180 years. So many Taylors were living on the Hill by the time of the Revolution that the area was referred to as “Taylor Town,” a name that is still emblazoned on the sign of the bridge down the hill that spans the Saugatuck.

Chris Wuerth and his restorers, after stripping away the home’s impossible-to-preserve exterior, were left with just the basics: a medieval post-and-beam frame leaning fifteen inches out of plumb, massive chamfered oak beams measuring sixteen inches in depth, an original foundation of uncertain date, three fireplaces, and one beehive oven—all of various vintage—one fireplace surround, and lots of floor planking, one inch in thickness and eighteen inches in width.

The restorers concluded that the classical, symmetrical Georgian Colonial house had been converted much earlier from a “two-over-two” one-and-a-half-story asymmetrical structure with variously sized windows and constructed with mortise and tenon and pegs but secured to the exterior vertical planking using hand-wrought iron nails (Wuerth hired blacksmiths to hand-forge new ones.)

Allen Raymond, executive vice president of the Westport Historical Society, has been leading excursions around Westport landmarks for years. The eighty-eight-year-old town native notes an increased interest in both historic houses and events. “North Kings Highway has lots of history,” he says. “The first school building still stands, lots of sea captains lived in the area, and Benedict Arnold, who came by here with his militia, is best remembered for being upset when he shouted, ‘Charge!’ as he planned an attack on the British and no one followed him.”


Current owners of 6 Old Hill, Brad Lamensdorf and Julia Gross, went through the renovation process with a previous Westport home, a 1900s cottage. Gross says they got lucky with the Old Hill house. “We found this property, which had already been restored by the Angottis.” The new owners made it their own. “The existing décor and color palette were authentic and very ‘of the period’…we selected more contemporary pieces that are mixed with many Asian things—I grew up in Taiwan and Japan,” says Gross. They turned to interior designer Lynne Scalo for help. “Lynne has assisted us in blending these various styles in a coherent way,” Gross says. For lighting, they went to Devon Allen Lighting Design. “The home is now brightly and tastefully illuminated,”  Gross adds.

Lamensdorf and Gross also turned their attention to the outdoors. They engaged Sheri Forster, a graduate of the New York Botanical Garden School of Horticulture, to design their colonial garden. Calling the project “an interpretation of the past, not a duplication of it,” Forster planted more than 2,500 spring-blooming bulbs, saved an ancient Norway Maple, and installed sixty trees and shrubs. She mixed flowers, vegetables and fruit, and mature hemlocks, viburnum and inkberry holly. “The color palette is white/yellow/purple with red accents,” says Forster. “Heirloom perennials include rose of Sharon, magnolia, hardy geraniums, anemones and grasses. Evergreen foundation plants provide the year-round ‘bones’ for the foundation beds, and include American holly, inkberry holly, pieris, sweetbox, iberis, and liriope.” The plants have been arranged to maximize the view of the property from inside the home and for year-round enjoyment.

Appreciating the discoveries of the past through a historic home is one thing, living in one, is quite another. Gross says, “Purchasing such a property comes with a responsibility, but it does not mean that the home can’t be resolved in ways that make it suitable for a modern family.”