BOB Weinstein was happy in Sag Harbor, in the little gray house on Suffolk Street he had owned for a decade. It was a quiet second home on a lot thick with old-growth trees, away from the busiest parts of the roughly 260-year-old former whaling village on the South Fork of Long Island, but a short walk from a downtown lined with restaurants and small shops.
He was so happy, in fact, that he and his longtime partner, Eric Hensley, got used to making the two-hour drive out to Sag Harbor every weekend, all year long, and sometimes when they only had one night — though they already lived in a 5,600-square-foot loft in the Chelsea neighborhood of Manhattan, where Mr. Weinstein also runs a brand positioning and graphic design company.
Both dwellings were furnished in the same style: sleekly modern, full of mid-20th-century modernist furniture picked up over the years at auctions, antique stores, the 26th Street flea market in Manhattan and yard sales in Sag Harbor.
There were tables and settees from names like Florence Knoll and George Nelson in the Sag Harbor house, a basement studio where Mr. Weinstein produced monoprint artwork and a sun-drenched room off the back for weekend relaxing.
“I think we really live here,” Mr. Hensley, 40, a former fashion stylist who now works as a flight attendant, said on a mild recent Saturday in the village. “It could be snowing, it could be raining — we’re always here.”
Friends who knew the home the couple had made for themselves amid the house’s clean, quiet lines, were surprised by what Mr. Weinstein — who is not the film producer of the same name — did next. He bought another house down the block, spending more than $2 million on a rambling old homestead on a nearly one-acre lot with low ceilings and a picket fence that had been in the same family for four generations.
Built in the mid-1700s with a series of additions that began about a century later, the house, on the corner of Suffolk and Jefferson Streets, came on the market when the previous owner, a 100-year-old woman who was born there, died. Mr. Weinstein and Mr. Hensley, it turned out, had been curious about the place for years, eyeing it on their way toward Main Street, or on walks with their grayish-black terrier, Spencer.
“We’d walk along that long white fence and sort of slow down, peer into the property through the overgrown boxwoods,” Mr. Weinstein recalled, “and we’d catch a glimpse of the old chicken coop, the old carriage house, walk by the old hitching post, and we’d just sort of wonder about its history, all the things that may have happened during the centuries of people living in that house.”
So, ever the antiques collector, Mr. Weinstein pounced. “I just knew it would be very hard for me to have never done this project, and to have been on Suffolk Street, and walking by all the time,” he said, wincing a bit at the thought.
Mr. Weinstein, whose wry smile and athletic frame make him look younger than his 49 years, said this while perched on a stool under a newly vaulted ceiling and near a hanging 1960s Swedish light fixture made of spun aluminum.
But amid these and other modern touches, like the new saltwater Gunite pool, other details are meant to keep the house grounded in the past: there are still 150-year-old boxwoods outside, most of the original windows and moldings remain, and a rosewood Saarinen table rests on 150-year-old floorboards, some as wide as 20 inches, that were bleached and refinished to a pale white.
A massive wooden cabinet that once held a previous owner’s law files — “It had little index cards with thumbtacks hanging: ‘Foreclosures, A to B,’ ” Mr. Weinstein said — is now a dresser in the hall outside the main bedroom. In the mud room downstairs, a coat rack was salvaged from the carriage house, where Mr. Weinstein believes it may have once held saddles.
While the house retains a sense of its history, though, it has also been transformed into something loftlike — not what it was, but not quite what Mr. Weinstein’s other places are either. It is bright inside, even on a cloudy afternoon, and open: Mr. Weinstein likes to position visitors at a few strategic locations and tell them to look right and left, where they can see all the way from one end of the house to the other.
“I think 10 years of sharp minimalism made me feel that maybe it’s time to let loose a little bit,” he said, adding that, as always, part of the appeal was the challenge. “I wanted to see if I could take my eye and blend my midcentury furniture into a setting that is midcentury — but mid-18th century.”
Mr. Weinstein started planning the renovation, in fact, in the spring of 2005, long before the sale was complete, using a methodology called “Image Architecture” that his company, Concrete Brand Imaging Group, developed to help clients define their brand identities. In a briefing for his architect, Mr. Weinstein highlighted the emotional and cultural factors involved in his purchase and transformation of the property.