Listing photos by Michael Bowman

This 19-acre estate in West Cornwall, Connecticut is called “The Barn.” It was designed in 1920 by architect Henry Olko and has been “beautifully and cleverly redesigned for modern living,” according to the listing. The main house has a cool glass entry vestibule, as well as rustic details like beamed ceilings and a massive cut fieldstone fireplace. There’s also a four-car garage, pond, stone walls, and extensive gardens, all surrounded by views of the Catskills, Taconic Range, and the Housatonic River. It’s on the market for $2,200,000.

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Listing photos by Dennis Carbo

It’s hard to believe this home is just two hours from New York City, as its unusual location above a saltmarsh feels more like a moody northwest setting. Located on 1.7 acres in Branford Connecticut, the contemporary house was designed and built just this year by renowned architect Peter Kurt Woerner to take advantage of its site high on a granite promontory. Woerner titled the property “Osprey House & Studio” as a nod to the surrounding marsh wildlife sanctuary that’s home to osprey, geese, ducks, seagulls, hawks, and falcon. Comprised of a 4,800-square-foot main house and a 746-square-foot studio/guesthouse, it’s asking $2,800,000.

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All photos courtesy of Rise Visual Media

The sprawling countryside estate of celebrity wedding planner David Tutera is on the market for $1,450,000. Located at 176 Tater Hill Road in the Connecticut town of East Haddam, the property contains four separate buildings, including a renovated main residence originally constructed in the 19th century. With a guest home, three-car garage with a loft, and a one-room schoolhouse surrounded by nine acres of land, the next owner has plenty of opportunities to turn the grounds into a dream residence.

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Photos by Bernadette Queenan for William Pitt Sotheby’s International Realty, unless otherwise noted

The Connecticut mansion once owned by the author Samuel Clemens, aka Mark Twain, is on the market for $4,200,000. Located in the Fairfield County town of Redding, the yellow home, built in the style of a Tuscan villa, sits on nearly 29 private acres and contains four bedrooms. Twain, who lived at the property from 1908 until his death in 1910, called the home “Stormfield” after his own short story titled “Captain Stormfield’s Visit to Heaven.”

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Listing photos by Alan Barry Photography

Sixty years ago, carpenter and contractor Ed Cady founded East Coast Barn Builders, which not only constructs new homes made to look like 18th- and 19th-century barns, but actually preserves and relocates historic English- and Dutch-style barns. This Cady masterpiece in Roxbury, Connecticut incorporates both. The 17.5-acre Rockridge estate includes a 10,346-square-foot mansion that is a Colonial reproduction flanked by two pristine Civil War-era barns from upstate New York, which were dismantled and reassembled onsite. The incredible interiors include hand-built cabinetry, locally forged hardware, and soaring beamed ceilings. The property is on the market for $4,250,000.

You’ve gotta see the whole place

Listing photos courtesy of Brown Harris Stevens

An equestrian estate in Connecticut found about 90 minutes from Manhattan is now on the market for $1.25 million. Located in the town of Sherman within the Housatonic Valley, the 10-acre Blue Bell Farm contains a nine-stall barn, riding ring, and a log cabin that serves as the cozy main residence. The quiet property is surrounded by 200 acres of protected land, adding to its peacefulness.

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In Weston, Connecticut, about an hour-and-a-half drive from NYC, you can buy this amazingly converted church for $865,000, the price of a very tiny one-bedroom apartment in Manhattan. Built in 1890, the former Swedish church has been transformed into a quirky yet beautiful single-family home, complete with stained-glass windows, cathedral ceilings, and wooden ceilings beams. At 2,382 square feet, it has three bedrooms, plus a lovely rear patio.

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All photos by Randy O’Rourke

A sprawling property in Connecticut that has a five-bedroom main residence, a 50-seat Greek-style amphitheater, tennis courts, and an indoor-outdoor pool, all spread across 100 acres, is on the market for $11,950,000. Designed by Gray and Organschi Architecture, the modern gem at 46 Senff Road was actually built into the hillside, constructed with a mix of granite, limestone, and Alaskan cedar to fit more seamlessly with the surrounding landscape.

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Listing photos courtesy of Houlihan Lawrence

For the price of a not-huge Manhattan apartment, you can own this entire 17.5-acre farm in New Canaan, Connecticut, just one hour from NYC. The Extown Farmhouse was originally constructed circa 1776 in the Georgian vernacular style, and it retains much of its original character including structural timber framing, woodwork, floorboards, and fireplace mantels. Also on the property are a main barn with a silo, a three-bay garage, a restored farmhouse cottage, a wood shed, hobby house, chicken coop, turnkey shed, smoke house, large raised-bed vegetable garden, and a fruit orchard.

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All photos courtesy of Brown Harris Stevens

A charming 18th-century farmstead in Connecticut’s Fairfield County is on the market for $1,150,000. Located on two private acres at 289 Nod Hill Road in Wilton, the property includes a four-bedroom main house, a barn, four additional detached structures, and a chicken coop. Built in 1790, the cozy home boasts some original details, including the historic hearth in the “keeping” room.

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