The stories behind some of New Canaan, Connecticut’s treasure trove of modernist homes have been less than uplifting. In addition to Philip Johnson’s famous Glass House, the wealthy enclave boasts dozens of homes by Johnson and his colleagues known as the Harvard Five. An ongoing battle simmers between some of the town’s wealthy residents who favor sprawling McMansions and a passionate contingent of modern architecture fans. At least 20 of the homes, built in the 1940s, ’50s and ’60s–have been torn down, usually to build larger houses on the property. One embattled example is a lesser-known Johnson house known as the Alice Ball House. The 1,700-square-foot home, built in 1953, has been referred to as a “livable version of the Glass House.” And it’s now for sale for $7.7 million–along with approved plans by the current owner, an architect who has envisioned a companion property on a much grander scale, including an indoor pool and a massive skylit underground garage.

Find out more about this storied modernist gem

A private island in Long Island Sound known as Rogers Island just got a new owner, who paid $21.5 million for the seven-acre property off the Connecticut coast. The sellers, a couple of “island collectors” by the name of Christine and Edmund Stoecklein, are bound for the West Coast, according to Mansion Global, unloading their gorgeously landscaped land mass and even lovelier Tudor mansion for less than the $22.3 million they paid for it in 2003, to an anonymous buyer.

Take the cross-island tour

This incredible Greenwich, Connecticut mansion looks like something out of a television show, and, in fact, it has made many an appearance in the reality tv world. Owned by Tommy Hilfiger until 2006, it was the setting for his CBS design show “The Cut” and his kids’ MTV show “Rich Girls.” Built in 1999 on nearly five acres, the residence, known as “Appleyard Estate,” boasts stone walls and a cobblestone courtyard, a professional grade theater and music studio, a massive pool and hot tub, and tennis courts. And it’s just hit the market for $6.75 million.

Get a full look around

Not only is Great Island in Darien, CT, the largest private island to be offered for sale on the East Coast, but before it was listed in 2016 for $175 million, this iconic property hadn’t been offered for sale or changed hands for more than a century. Purchased in the early 1900s by baking powder tycoon William Ziegler, the estate that lies just 50 miles north of New York City has remained in the family ever since.  It’s asking $120 million this time around.

Have a look at this unusual island property

Own your very own private island that feels like it’s a million miles away, or at least off the coast of Maine, but is actually off the shore of Connecticut for only $4.9 million (h/t Mansion Global). With the not-at-all charming name of Potato Island, named for a group of potato-looking boulders near the shore (you say potato, we say po-tentially change that name!), this private island is part of the Thimble Islands, an archipelago of small islands, 23 of which are inhabitable, in the Long Island Sound in and around the harbor of Stony Creek in the southeast corner of Branford, Connecticut.

Get a look at island life

Originally built in 1904, “Orient Lodge” is a restored Arts and Crafts compound on Saw Mill Pond that looks like it belongs on an Adirondack lake. The original 40-acre lot housed a saw and grist mill, dating from 1825. Legend has it that the owner cut down chestnut trees on the site to build the house. The lot has since been reduced to just over two acres but it still has an estate feel and is now up for sale asking $1,950,000 (h/t CIRCA). Not only will that get you the three-story main house–which has been fittingly outfitted with historic Asian features–but a detached two-car garage with deck, a separate cottage, and the original landscaping.

Tour the whole property

From May 15-18, the Iconic Houses Network will hold its bi-annual international conference in New Canaan, Connecticut and the surrounding area. This year’s conference, titled “Modernism on the East Coast – Philip Johnson and the Harvard Five,” will highlight the work of the famous five Harvard architects–Philip Johnson, John M. Johansen, Marcel Breuer, Landis Gores, and Eliot Noyes–who “stirred up an experimental modernist movement in the sleepy New England town.” There will be a number of different events, but perhaps most exciting is the slew of tours of modernist icons such as Johnson’s Glass House, Frank Lloyd Wright‘s Usonia community,

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