Local historians weren’t sure when the one-and-a-half-story cottage had been built but put their best guess at between 1830 and 1850, when the village of Sag Harbor, a port at Long Island’s east end, was flooded with whale money. Now here it was, wind whistling through and a little the worse for wear, as if it had taken the town’s name a little too literally. It was also under the care of a new owner, Paul Rogers, who had summered in the town as a child and returned to buy his “dream” house in a restless burst of nostalgia. He was acutely aware of the precious nature of his find, which sits in a district on the National Register of Historic Places. But he also realized that to save it he’d have to do more than just paint. Shown: To enhance his circa 1840s home, owner Paul Rogers (on wheels), focused on architectural details, from the fit of the clapboards to the addition’s 19th-century gable and six-over-six windows. Vintage window panes: Fairview Glass

Old Charmer

Before poking its ribs and thumping its core, “I really lived in the house,” Paul says, cohabiting for five years with its creaky beams, leaky windows, and quirky layout. Over the decades a kitchen and screened porch had been tacked on in back, and a one-story addition with a den, bedroom, and bath stuck on one side. Another bath had been inserted upstairs. To get to it from the master bedroom, you had two choices: Leap over the stairwell or go around it and bang your head on the sloped ceiling. When Thompson finally opened up the cottage, he found not only bowed posts and tired joists (“precariously separate from the frame,” in Paul’s words), but a roof saddled by a heavy patchwork of cedar and asphalt shingles. A chimney was deteriorating, the basement was diminutive, and the floors were as off-kilter as the walls. Shown: Outside of the cottage, before the renovation.

Refining the Rustic

Paul was eager to bring the amenities up to snuff, too: Homes lacking central air, a pro-style range, and Wi-Fi are now, after all, as rare in Sag Harbor as sperm whales. “I loved this old house,” he says. “But it wasn’t quite livable for the 21st century.” Working fireplaces, cozy bedrooms, and sight lines to the garden also sprang to his mind. But first came the question of how to straighten the place and brighten its warren of dark, stooped rooms. Shown: Clean-lined furnishings and polished crown molding contrast with a weathered mantel, exposed beams, and salvaged wood trim. Vintage window panes: Fairview Glass; Curtains: Spruce Design+Decor; Floor lamps, mirror, and armchairs: Mecox Gardens; Console table and lamp: Comerford Hennessy; Sofa: Crate & Barrel

Added Outdoor-Living Space

The crew began work in back, tearing off the old kitchen and porch. With the help of architect Gregory Zack, Paul mapped out a step-down addition with a basement large enough for a workroom, a kitchen open to a sitting area on the first floor, and a real master suite overhead. The sitting area would in turn open onto a small deck, which would step down to the lawn, then to a stone patio, in effect lengthening the house while capitalizing on its deep, narrow lot—and incidentally giving the cook a great view.

Straightening Up

Thompson was soon joined by another seasoned builder, Dwight Stephan, and as the work unfolded, other old-house saviors joined in. The result was an every-man-on-deck group venture led by a homeowner with a curator’s eye. Framed with hand-hewn timbers, the cottage sat on locust posts and a stone foundation. To improve its posture, Thompson used a come-along winch like a whalebone corset. To make it more true, his crew jacked up the house to level the floors—or almost level them. “We did some shimmying and bolstering,” he says, “but we still wanted it to feel old. We didn’t want a four-inch dip, so we made it an inch and a half.” Shown: The back of the cottage before the renovation.

Open Living Space

Upstairs, the plan was to remove the worn rafters, raise the roof, and drop in a dormer, yielding a more livable second floor. But not so fast. The preservation-minded building inspector objected to demolition of the roof and an exterior wall where Paul had found dozens of painted boards holding the shingle siding in place. “That’s how they built in those days; they threw up whatever they had and shingled over it,” he says. Eventually a deal was struck that allowed him to put up plywood walls and beefier rafters while giving the historic flotsam more visibility inside. Ceilings tumbled, along with a crumbling chimney and a brick flue that had vented the old gas furnace. A replacement chimney went up to serve the dining room fireplace and a new one in the kitchen. Walls were stuffed with insulation and ductwork and covered with wood over drywall. “That meant thicker windowsills and jambs, which give the house a strong old-world feel,” says Paul. Shown: A rustic table, made with a salvaged bar top, keeps the connection between kitchen and sitting room open and airy.

New Uses

Ceramic tiles fill notches originally cut in the joists for lath. “They were the perfect size,” says homeowner Paul Rogers, “and better than filling in with wood putty.” Tile: Emu Tile

Attention to Details

The amount of handwork was pretty 19th century, too. “We back-primed each piece,” Thompson says of the new clapboards, “then let it dry, installed it, and had it sit for a year so the oils could leach out before painting.” To further enhance the facade’s historic-street cred, Paul replaced broken panes with old glass and had the crew fabricate gutters and flashing out of copper coated with lead for a soft, antiqued finish. Shown: The small deck in back of the cottage after the renovation.

Opened Up and Airy

It was almost a year before the team turned its attention inside, reworking the layout to bring in better light, height, and sight lines. “By allowing a clear shot through the house on both floors,” says Paul, “we made the house feel much larger.” The existing staircase was rather steep and narrow, so carpenters reversed its direction, sending it down to the new basement, and crafted a new one to the second floor with a banister and newel post left over from a neighbor’s remodel. And those old siding boards? They found a new home as flooring and shelves. The warped rafters are now decorative ceiling beams. Shown: Exposing the ceiling added height and airiness to the once-cramped dining and living rooms.

Modernized Kitchen

“Every single ounce of space was put to use, whether for closets, plumbing, or heating and cooling,” says Paul. “Because plots in the historic district are generally small, and you can only build on a percentage of your land, there is this constant utilitarian ethos running through both the house and the entire town.” Shown: Ceiling-hung cabinets hold the vent hood and frame an opening that allows the cook to keep an eye on guests. Paint: Benjamin Moore’s In the Midnight Hour (cabinets), Concord Ivory (walls); Range and range hood: Wolf; Sink, door casing, base molding, and seeded glass for cabinet fronts: Van Dyke’s Restorers; Faucet: Blackman; Dishwasher: Bosch; Pendants: Suffolk Designer Lighting; Backsplash tile: Alan Court & Associates; 631-324-7497

Harmonizing Colors

Rather than replaster, Stephan lined rooms with old fir, oak, and pine boards painted on all sides to discourage warping. “You get a wall surface that has such character, texture, depth, and detail,” he says. Not historically accurate, maybe, “but it looks really cool.” Paul finished the interior with rich shades of red, blue, and gold tied together by trim painted a uniform pale gray. “You think the contrast is going to make a small house claustrophobic,” he says, “but if the colors work together it can make it feel bigger—and warmer.” Shown: The Master Suite bedroom is lined with pine boards that hide ductwork while showcasing brass fixtures and an ornate register grate. Paint: Benjamin Moore’s Buckland Blue (walls); Bed: Crate & Barrel; Sconces: Visual Comfort; Vintage fan: ebay; Register grate: Reggio Register; Sisal rug: The Carpet Man

Light-Filled Window Seat

All told, the redo took about 18 months. “And it’s not huge,” says Paul, “2,200 square feet on a good day.” Even now, each team member seems to regard the house as a personal trophy. “People adore this house,” Paul says. Stephan, who has worked on his share of old houses, thinks of it another way. “If you can work well together, it’s fun—and everything comes out great.” Shown: The master suite includes a reading nook. Armchairs: Ralph Lauren Home; Bench: Mecox Gardens

Floor Plans

The whole-house redo raised ceilings, opened sight lines, and enlarged the three-bedroom cottage to 2,200 square feet with an addition that replaced the old kitchen and screened-in porch.

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