We had one criterion when renting on the Vineyard in the mid-nineties: the house had to be informal and indestructible. With two families consisting of four energetic children, the last thing any of us wanted to worry about was damaging an overly precious rental. But on first approach, the house the realtor wanted to show us in Chappaquonsett – the stretch of barrier beach that separates Lake Tashmoo from Vineyard Sound on the up-Island side – looked anything but easy. It was neoclassical in composition, with a distinctive two-story central structure and two symmetrical appendage wings. Painted in clean rosy pink and white hues, it looked almost regal against a backdrop of lush green woods and surrounded by conservation land. We were looking for an easy beach getaway and it looked almost Jeffersonian. The only aspect of the building that belied its feigned grandiosity was a faint patterning of ordinary off-the-shelf masonry blocks peeking through layers of pink paint.

Upon entering its formal front door our eyes were drawn directly across the room, through floor-to-ceiling windows, to a magnificent 180-degree view of Vineyard Sound. The vista was even more impressive from the massive semicircular screened-in back porch, and only when we got past ogling the view and returned to check out the interiors did I begin to notice that the inside of the house did not follow the classical symmetry of its exterior. The floor plan was open, flowing, and functional. So functional, in fact, that at various locations within the house the windows, which had been arranged to facilitate the strict façade of the exterior, abutted walls, closets, and cabinets at odd and seemingly unplanned junctures.

The concrete blocks were also much more pronounced on the inside. The rest of the finishes consisted of linoleum and wood flooring, tile and Formica baths and kitchen, and pickled wood on the fireplace and cabinets. A summer rental with well-worn furnishings, void of any fussy finishes, a wonderful yard and close to the water; despite its formal exterior the Pink House did, in fact, fit our families’ vacation needs. We loved it so much that when it became available for sale in 2002, we bought it.

As an architectural historian specializing in mid-century modern architecture, I knew that the house functioned in a distinctly modern way in spite of its neoclassical exterior. But it wasn’t until I decided to winterize the building four years ago that I really began to study its design eccentricities in detail. Having long since come to appreciate the modern elements – the open floor plan, the extensive floor-to-ceiling windows, the intentional use of functional materials such as concrete block – the first and easiest decision I made was to preserve its mid-century aesthetic as much as possible, and to make sure that any changes respected its historic character. Perhaps not surprisingly, the more I thought about what made the building work and what must absolutely be preserved and what could change, the more I wanted to know about the architect and clients who were responsible for creating this very quirky and very much loved house.

When we bought the Pink House it was one of four houses on thirty-five acres owned by the descendants of Helen Pratt Emmet Philbin, whose grandfather, Charles Pratt, was an early partner in the Standard Oil trust and founder of the Pratt Institute in Brooklyn, New York. Fondly called “Moo” by her offspring, she purchased her original Chappaquonsett property in 1946, the same year she lost both her father and her eldest son, William, a World War II fighter pilot shot down over Germany. More happily, in November of that year she married her second husband, J. Holladay Philbin, who had been secretary of the Federal Reserve Bank of New York in the 1920s. Generous benefactors both on-Island and off, in the late 1960s the couple donated to the town of Aquinnah the waterfront property that is now Philbin Beach.

Helen Philbin built the Pink House in 1949 next door to her own home on the property to accommodate the rapidly growing families of her three children from her first marriage, William, Richard, and Jane. For help with the design, she turned to her architect son-in-law, Lawrence Drake, and to her old friend John Dwight Winston Churchill. (His father, Winston Churchill, was a celebrated American novelist but they were not related to the British statesman.) A seasoned architect, by all accounts Churchill was the quintessential bon vivant, a ladies’ man and a man’s man, who traveled in the same well-heeled, stylish, and socially progressive New York circles as Helen and her first husband. He hunted, fished, sailed, smoked cigarettes, drank martinis, and charmed just about everyone he met. He was a frequent guest at Helen’s various estates – the 10,000-acre hunting lodge in South Carolina as well as her home on Long Island. And in the 1940s, after both he and Helen had divorced their first spouses and remarried new partners, their friendship continued on the Vineyard.

Good architecture often takes its lead from its clients and patrons, which was true for all three of the houses Churchill ultimately designed on the Vineyard. As an architect practicing at this particular time in history, however, he brought an interesting perspective to his work, one that had to balance traditional and modern ideas. Graduating from Harvard in 1926 and studying architecture at MIT, he entered the field nearly a decade before European Bauhaus émigrés “modernized” Harvard’s architecture program. His first job was with Pennington, Lewis & Miller in New York, a firm with a coterie of wealthy clients. The firm’s principal, Pleasants Pennington, was the favorite architect of Dorothy Draper, who was without a doubt the most influential interior designer to the rich and famous of her time. Churchill may well have learned how to use color and finishes from exposure to Draper and Pennington’s work for wealthy clients, but the project that seemed to have most strongly influenced his later Vineyard work was Piping Rock, a country house development intended to appeal to middle class urban dwellers seeking to emulate the Great Gatsby estate experience in a more affordable way.

Pennington and Draper designed Piping Rock in 1927 for a thirty-seven-acre Long Island plot they jointly owned. There were four different models of homes ranging in size from small to grand, and prototypes and floor plans were prominently featured in splashy illustrated spreads in both The New York Times and New York Post. Each house was to have a private garden and share vast outdoor spaces, which would allow residents to experience the feel of grand estate living without expensive upkeep. As with the Pink House and the other homes Churchill would later design for the Vineyard, exterior designs were based on picturesque vernacular prototypes while the interiors revealed a new functional sensibility indicative of changes in middle-class living, including the reduction of separate service spaces and more open and flexible floor plans. Draper’s unique touch could be seen in her clean, uncluttered modern interiors, which she rendered with simple finishes and bold colors.

The stock market crash of 1929 ended the plans for Piping Rock and curtailed the building of many ostentatious homes in New York. There were lingering opportunities in luxury design, particularly in the south where Churchill ran an office for Pennington and Miller into the early thirties. Then, notably for Churchill, in 1941 he created The Locusts for Helen Huntington Astor Hull. The Locusts, now a luxury resort, was a formidable home on the Hudson River. It was, however, decidedly smaller and less assuming than the turreted palace it replaced, which Hull’s grandfather had built in the mid-nineteenth century. Churchill’s design was for a stripped-down version of the French Regency style, with a gently curving floor plan that opened onto a formal landscape. The interiors were clean and uncluttered, with nearly floor-to-ceiling triple-hung sash windows that flooded rooms with light. This indoor/outdoor connectivity was a hallmark of burgeoning modern architectural thinking, which clearly influenced his later designs for the Pink House.

Despite occasional plum assignments, there was no way around the fact that luxury commissions were few and far between during the Great Depression, so Churchill began to seek work funded by grants from the Works Progress Administration. These were usually large-scale infrastructure projects with advanced technological components, and by the late thirties Churchill and his partner created a niche for themselves designing modern food processing facilities in and around New York.

Of their works during the period, the New Market Building for the Fulton Fish Market was the most celebrated for its technological achievements, fiscal practicality, and aesthetic flair. It was quintessential WPA Moderne; an architectural blend of Art Deco, Streamline Moderne, and the Beaux Arts styles. Built using prefabricated construction methods and newly engineered materials, its functionality, thrift, and design restraint reflected the values of the New Deal that also informed modern architects moving forward. Through the fish market and other projects like it, Churchill developed an easy way of applying formal aesthetics to modern building programs and became comfortable using new industrial materials to replace many of the natural materials he had used in the past.

The Great Depression ended with the war, but by then Churchill had lost interest in seeking luxury architectural commissions. He and his second wife, Katherine Emmet Canfield, also known as Katsie, had left New York to live year round on the Vineyard, where he had a position supervising the maintenance of the fleet at the Woods Hole Oceanographic Institution (WHOI). An avid sailor all of his life, Churchill moored his Q-class sloop Taygeta in Vineyard Haven harbor and occasionally set off on long sailing voyages for days at a time, much to the consternation of his wife. He also began working with Lincoln Laboratories, an MIT think tank formed in 1951 to research aeronautical defense systems, and after the war moved permanently to Cambridge to continue his work in the defense industry.

The post-war Vineyard years were a delightful time for the Philbins, Churchills, and their extended families. Summers revolved around days on Quansoo Beach, martinis at cocktail hour, and a variety of entertainments with their growing collection of children, grandchildren, and friends. When he wasn’t taking friends on Taygeta, Churchill fished and hunted with his dogs. He liked working with his hands, whether building a duck blind or fixing a sill, and baked his own bread, raising the dough on the radiators in his home. He forced bulbs to add to his ever-evolving classical gardens. He loved telling stories and holding court with friends. His social life was in a steady whirl thanks to Katsie, who kept a phone nook the children referred to as “command central” from which every morning she scheduled the day and evening activities.

During that period Churchill designed and contributed to several houses for family and friends on the Vineyard. Besides the Pink House and key additions and gardens he added to Philbin’s main house, he also designed two more homes in Lambert’s Cove, including one for his own family. His home was called the Ice House, named for the utilitarian building he had moved from Oak Bluffs to be the centerpiece of the design. The house was passed on eventually to Churchill’s only son, Jonathan, and is still being enjoyed very much in its original state by his surviving wife, Judith. The second Lambert’s Cove house, the Blue House, was designed for a colleague from WHOI and today belongs to Friederike Biggs, whose gardens were featured in this magazine in the spring of 2014.

All of Churchill’s Vineyard houses shared similar design characteristics, most notably open floor plans, a preponderance of large windows, an easy flow of indoor to outside space, and the use of off-the-shelf, man-made materials. He used exposed concrete block on all three and employed bold monolithic colors – pink, yellow, and blue – that contrasted beautifully with the muted colors of nature. He liked to re-imagine familiar items: at the Ice House he transformed ordinary metal rain gutters into decorative moldings. And he liked to recycle: as with the Ice House, one of the wings of the Pink House was a tiny wooden cottage he found elsewhere on the Island.

Relative to the grand country houses of bygone eras, or the looming palaces of the recent crop of the well-jetted class, Churchill’s 1940s Vineyard houses were modest in scale and nestled humbly into their natural settings. Their floor plans were all open and functional, a hallmark of modern design. The interiors flowed with airy circulation spaces and had interesting tucked-away nooks and built-ins to provide for a variety of everyday functions.

In the Pink House, for example, Churchill fit a tiny crib room in the small hallway that connected the cottage to the main house. In the Ice House he created a sleeping nook off of the main living area with built-in bunk beds to accommodate his and Katsie’s three boys – an unusual open sleeping area he must have seen in the modest houses of the Piping Rock project. On the crescent plan of the Blue House, he created an enfilade, an open hallway that allowed each room to connect to the garden outside. In addition, the Blue House master bedroom could only be reached by a breezeway outside of the house, a circulation concept more common to the West Coast than the East that fit with the modern concept of indoor/outdoor living.

Of all of Churchill’s Vineyard houses, the Blue House was the most characteristically mid-century modern aesthetically, most likely because unlike the other two it was conceived as a whole. Originally it was a single-story structure with a flat roof and long horizontal curving eves that sat streamlined and low slung on the landscape. The Blue House was also the most significantly modified in later years, with a second story addition and an applied classical cladding. Interestingly, though no longer overtly modern, the Blue House now is somewhat reminiscent of The Locusts, which was a two-story house with a similar crescent-shaped plan.

As it turned out, the Blue House was Churchill’s last on the Vineyard. In 1961 he was commissioned to design a new facility for WHOI. It was a dream job that would marry his architectural skill set with his interests in the ocean and the defense industry, and his past experience designing large industrial facilities. But the day the commission was announced he died of a heart attack while mooring his beloved Taygeta in Vineyard Haven harbor after a day sailing with friends.

Helen Philbin lived another decade. In 1971, the year before she died, she divided her land at Chappaquonsett into three parcels to leave to her children. Richard Emmet received the main house, where his widow, Alan, and their children and grandchildren continue to summer. Richard had the foresight to place a conservation restriction on sixteen acres of the original estate, thereby ensuring the house’s privacy and long-term connection to nature. Jane Emmet Drake inherited the Pond House, which now belongs to her daughter Erin Drake Gray. The Pink House went to William’s widow, Eleanor Lee, who shared it with her four daughters. One of these daughters, Linsey Lee, who is the oral history curator at the Martha’s Vineyard Museum and the author of several well-known collections of Island remembrances, was living at and caring for the Pink House at the time my family bought it.

Like the Emmets, Lees, Drakes, and numerous vacationers over the years, our family fell in love with the Pink House. We spent a decade of summers there with family and friends creating wonderful memories and watching our children grow into young adults. Over the years we found ourselves stretching the official closing-of-the-summer-house until Thanksgiving, and were disappointed from time to time when frost curtailed fall visits.

Winterizing seemed unthinkable, however, considering how much we loved the house exactly as it was, and understanding that heating or cooling a house made of concrete block might require considerable visible changes. I could not imagine how we might insulate walls or run ducting without losing the beauty of the exposed concrete block. I decided to hire preservation architect Alex Adkins from DiMella Shaffer Architects in Boston because he had stayed several times at the house and understood my thinking about preserving modern buildings. I also hired Colin Whyte of Martha’s Vineyard Construction Co. because he was known to be meticulous, had an appreciation for maintaining the historic nature of the house even though it was atypical of most Island construction and materials, and he seemed patient enough to cope with me.

The solution we finally arrived at to solve heating and cooling was rather creative. First, I had to get comfortable with the idea that we had to frame out and stucco one side or the other of the concrete block wall to create space to blow in insulation. I decided to save the concrete block on the interior because its tactile and visual qualities can be best appreciated close up. So we built out the exterior, which then in turn required reworking window and doorway fittings. The new shell wasn’t thick enough to leave space for ducting for a central HVAC system, so the architect cleverly tucked individualized units in closets to service various quadrants around the house and ran what few stretches of ducting we did need in built-in cabinets and existing closets.

Glass was the next issue as it is key in harnessing heat. On the upper floor where we had smaller cranking casement windows that had failed over time, we were able to match the quality and look of the historic windows with new insulated windows. I decided, however, that the large sash windows on the first floor had to stay, as it was impossible to find or make windows that were quite as large with mullions quite as thin. These windows were a hallmark of Churchill’s modern design. But because the old windows did not retain heat, we had to create old-fashioned storm windows to be placed on the exterior of the building in winter.

While winterizing we did a variety of upgrades, particularly on the kitchen and bathrooms, areas that needed considerable freshening. My overriding goal, however, was to make the changes in a way that they would go unnoticed. To this end we reused any historic detail or finish that still functioned, including assorted doors, windows, door knobs, toilets, sinks, medicine cabinets, hardware, etc. With the same mandate we expanded the kitchen by opening up a part of the room that had once been a screened-in entryway later closed in to create a laundry room. Since the house has no dining room, this expansion allows for ample kitchen dining in winter months.

Although we used new appliances, our replacement finishes were all items available in the late forties, including linoleum and Formica, metal-edged counters, and painted plywood cabinets. In the bathrooms we added showers and replaced failed finishes with simple white subway tile and hexagonal tile flooring. We also added a single-car garage, connecting it to the existing house via the basement in compliance with conservation considerations and local codes that do not allow more than one out-building on this property. We already had a delightful historic shack on the property fondly known as the Turkey House, named for its original use, and had no intention of parting with it for a garage.

Throughout the construction process, we took great measures to preserve the natural grade of the land and original plantings, especially those abutting vulnerable conservation land. All of our new landscaping uses only native and non-invasive plants. While the house has an abundance of lawn at this juncture, our next phase is to return much of the lawn to a natural meadow condition. We are also installing a solar field to supplement energy use.

The Pink House project was completed for the summer of 2014. I was relieved to find, when welcoming returning family members and house guests, that most could not immediately tell the old construction from the new. Importantly, all agreed that the Pink House was still the Pink House in spite of our interventions. Now family and friends are busy making plans to enjoy its newfound year-round potential.

I’m thinking…New Year’s Eve 2016 at the Pink House…anyone?