All listing photos by Samuel Rodriguez & Steve Rossi for Sotheby’s International Realty

Fashion mogul Tommy Hilfiger has unloaded the last of his Greenwich, Connecticut properties for $45 million, Sotheby’s International Realty tells 6sqft. The 22-acre estate was built in 1939 and resembles a French chateau from the outside, with an eclectic, European flair inside. It’s located on the summit of Round Hill, the highest point in Greenwich, providing views of the Long Island Sound and Manhattan skyline. Other lavish amenities include a baronial Elizabethan-style spiral staircase, six fireplaces, a pool house, tennis court, and parterre gardens. According to the Post, he and his wife Dee Ocleppo bought the home for $31.37 million in 2010, after which they spent millions more on renovations.

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All photos by Borgatta Photography

A $2.6 million estate that “transports you to the pastoral English countryside” is for sale in Weston, Connecticut. The historic eight-acre property at 5 Norfield Road was once home to Alice DeLamar, an heiress and patron of the arts who was once considered America’s richest woman. DeLamar built the home, later named Stonebrook, in 1930. The estate includes a 10-room main residence, a guest cottage, a horse barn, and a 50-foot-long swim tunnel that leads from the basement to the oversized outdoor pool.

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Downtown Rhinebeck, NY. Photo by Juliancolton via Wikimedia Commons

It’s not news at this point that throughout 2020 the suburbs of New York City were flooded with new home buyers, pushing up prices and leading to unbelievable bidding wars. But what is news is just how much certain upstate areas saw a rise. According to Houlihan Lawrence’s Q4 2020 Market Report, Putnam and Dutchess counties saw a 269-percent increase in home sales $1 million and over. And in Westchester county, sales $2M and higher grew by approximately 53 percent.

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All photos courtesy of Borgatta Photography

In Fairfield County, a 13-acre compound with a grand six-bedroom main residence, guest cottage, greenhouse, and a barn-style detached garage is now on the market for $5.195 million. Known as Byebrook, the sprawling property at 232 Newtown Turnpike was once home to late New York City real estate mogul Lawrence Wien, who used the property as a hunting lodge, as Westport News first reported. Surrounded by nature, the estate sits along the Saugatuck River and is near the Devil’s Den Nature Preserve, while still being just a 75-minute drive to Midtown Manhattan.

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The Connecticut estate of Grammy Award-winning musician Paul Simon has returned to the market for $11.9 million, roughly $2 million less than when the property first listed last year. The 1938-built brick home at 82 Brookwood Lane sits on 32 private acres in New Canaan, about an hour’s ride from Manhattan on Metro-North. Simon and his wife, singer-songwriter Edie Brickell, bought the home in 2002 and raised their three children there.

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All photos courtesy of Sean Fowler, Planomatic

A five-acre estate in Connecticut that once belonged to a New York City heiress and patron of the arts is now asking $1.995 million. The property at 453-455 Newtown Turnpike was once owned by Alice DeLamar, the daughter of Joseph Raphael DeLamar, a mining mogul who made a fortune in the industry during the late 19th century. Throughout her life, Alice financially supported the careers of many artists and writers, even allowing many of them to stay at her multiple properties. The unique compound includes a four-bedroom main house, two guest cottages, an 1800’s blacksmith forge, and a three-room “dollhouse.”

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All photos courtesy of Houlihan Lawrence

With its vaulted ceilings, wood paneling, pink details, and retro rec room, this 1960-built home in Greenwich, Connecticut is the textbook definition of mid-century modern design. In addition to the attractive interiors, the home features a patio and is also set back from the road, which provides privacy and additional outdoor space. Located at 261 Cognewaugh Road in Cos Cob, the three-bedroom, two-bath home is now on the market for $1.125 million.

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All photos by Caryn B. Davis Photography

Legendary 60 Minutes news correspondent Morley Safer was on the show for more than four decades, and during most of that time, he split his time between NYC and this gorgeous, seven-acre estate in Chester, Connecticut. The property includes the main stone house built in 1908, a cozy writer’s studio, a heated pool and gazebo, and a 19th-century barn. Safer passed away in 2016, and his wife Jane Fearer is now selling the estate for the first time in 30 years. It’s asking $1,450,000.

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Photo by Ravi Capeles

This unusual home in Stamford, Connecticut is thought to be the only private residence in the Tri-State area with its own private indoor hockey rink. It even comes with a Zamboni, heated team benches, lighted scoreboard, and locker rooms–and it’s hosted players from the Rangers. Listed for $7,690,000, the 18,000 square feet home sits on 13 acres and also comes with two guest houses, a pool, and a small lake.

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All photos courtesy of Houlihan Lawrence

This sprawling English Manor-style estate in Greenwich, Connecticut was built in 1928 by Paul Starrett, one of the main developers behind the Empire State Building and the Plaza. Set on nearly three acres, the seven-bedroom home has grand interiors, romantic landscaping, and a gorgeous pool. It’s just hit the market for $8,295,000.

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