Connecticut

Modernist architectural gems turn up everywhere, often priced to reflect an unflagging interest in the modern design and clean lines pioneered in the middle of the 20th century. This circa 1969 home at 35 Dibble Hill Road in Cornwall, Connecticut, was designed by Sherwood Smith, a Gordon Bunshaft protege with the well-known Skidmore, Owings & Merrill architecture firm. The house sits on 25 remote acres, where you'll also find an in-ground pool and an antique barn. The home, asking $1,300,000, is being sold, according to the listing, as a "diamond in the rough" stripped down to the studs, awaiting a complete restoration after an electrical fire.
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Distinctive Homes

Stephen Sondheim’s Connecticut country home sells for $3.25M

Photos courtesy of Klemm Real Estate & Michael Bowman Photography

April 18, 2024

Stephen Sondheim’s Connecticut country home sells for $3.25M

The longtime Connecticut home of late Broadway legend Stephen Sondheim sold for the full asking price of $3,250,000. After hitting the market last November, the Roxbury property, which includes a main house, one-bedroom pool house, and a detached garage, found a buyer in just 12 days, according to Klemm Real Estate, the firm with the listing.
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Frank Lloyd Wright’s horseshoe-shaped home in Connecticut sells for $6M

Photos by Udor Photography

January 29, 2024

Frank Lloyd Wright’s horseshoe-shaped home in Connecticut sells for $6M

A 1950s Connecticut home designed by Frank Lloyd Wright has sold for $6 million. Known as "Tirranna," an Australian Aboriginal word meaning "running waters," the home at 432 Frogtown Road in New Canaan measures over 7,000 square feet and sits on 14 acres, making it one of the largest private residences ever completed by the famous architect. The horseshoe-shaped home, which cantilevers over a pond and waterfall, has had only four owners in the last 70 years, according to Mansion Global. The property was listed in May by Coldwell Banker Realty's Marsha Charles and Albert Safdie for $8 million and closed last week.
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Real Estate Trends

Stephen Sondheim’s Connecticut country retreat lists for $3.25M

All photos courtesy of Klemm Real Estate & Michael Bowman Photography

November 13, 2023

Stephen Sondheim’s Connecticut country retreat lists for $3.25M

The Roxbury, Connecticut home of late Broadway icon Stephen Sondheim is now on the market, asking $3,250,000. The celebrated composer and lyricist's retreat is for sale for the first time in nearly 40 years. Situated on nine secluded country acres, the historic 1792 property features a three-bedroom main house, a pool, a one-bedroom pool house, and a detached garage. Within, the home boasts a 21st-century renovation, with more than a passing nod to its former owner's remarkable creativity.
elegance and country charm, this way

Treat your guests to a 5,000-square foot-wellness center at this $14.9M New Canaan estate

All photos courtesy of SERHANT. Studios

April 24, 2023

Treat your guests to a 5,000-square foot-wellness center at this $14.9M New Canaan estate

Built in 1929, designed by noted New York architect William Tubby, the undeniably grand estate at 544 Oenoke Ridge in New Canaan, CT, is an icon of the state's Great Estate era. With 18,000 interior square feet, a guest house, tennis court, and pool, and a newly-added 10,000-square-foot extension that includes a wellness center, this grand home is a country retreat for the ages. Asking $14,900,000–a record-breaking sum for the town–the limestone home, known as Orchard's End, received a multi-million-dollar renovation in 2014, helmed by architect Dinyar Wadia.
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Distinctive Homes

Donald Trump’s former Connecticut estate tries again for $29.9M, nearly half its highest listing price

Photo credit: James Gagliardi / Brown Harris Stevens

August 23, 2022

Donald Trump’s former Connecticut estate tries again for $29.9M, nearly half its highest listing price

The six-acre estate on the Greenwich, Connecticut, waterfront that was owned by former president Donald Trump and his late ex-wife Ivana in the 1980s is back on the market for $29.9 million, the Wall Street Journal reports. The home's present owners, investment banker Robert Steinberg and his wife Suzanne, bought it for $15 million in 1998. The Georgian mansion at 21 Vista Drive, with sweeping views of Long Island Sound, has been on and off the market since 2009 when the Steinbergs listed it for $50 million; it was relisted for $54 million in 2014. As 6sqft previously reported, it has seen several price cuts since then, but no takers.
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$5.2M Stanford White-designed hilltop estate in New Canaan has a history of Gilded Age glamour

Photo courtesy of Douglas Elliman

July 27, 2022

$5.2M Stanford White-designed hilltop estate in New Canaan has a history of Gilded Age glamour

Known as Stoneleigh Manor, this landmarked estate at 255 Brushy Ridge Road in New Canaan, Connecticut, designed by renowned American architect Stanford White, was built in 1903 for Charles E. Diefenthaler and his wife Antonia F. Fischer as a summer getaway. Asking $5,199,000, the home has been restored by its current owners with care taken to honor its 118-year history while adding modern infrastructure and sensibility.
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Distinctive Homes

This $35M Old Greenwich custom waterfront estate has a boathouse and a deep-water pier

Photo credit: Houlihan Lawrence

July 15, 2022

This $35M Old Greenwich custom waterfront estate has a boathouse and a deep-water pier

For $35 million, you can own 13,428 square feet of lavish waterfront living, with open water views of Long Island Sound from nearly every room. In addition to over 200 feet of water frontage, this custom-built eight-bedroom home at 45 Binney Lane in the Old Greenwich, Connecticut community comes with a boathouse and deep-water pier, along with standard mansion amenities like a pool, guest house, spa, terraces, and a wine room. Winner of the 2021 HOBI award, the bespoke contemporary home is LEED-certified, boasting a geothermal heating/cooling system and loaded with smart home technology.
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Distinctive Homes

For $899K, this Connecticut country house has a heated barn, a pool, and a winery

Photo credit: Home Tour Vision

November 2, 2021

For $899K, this Connecticut country house has a heated barn, a pool, and a winery

In a verdant spot that's seriously away from it all in Redding, CT, this 3,484-square-foot contemporary home–and 3,000-square-foot heated barn–on two acres is asking just $899,000. A veritable country estate for less than $1M, the property also features an Olympic-sized pool, a solarium, and a winery. The main house has been renovated with new flooring throughout.
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Distinctive Homes

A converted dairy farm in Connecticut is now a cool, rustic residence asking $1M

Listing photos by Michael Bowman

October 1, 2021

A converted dairy farm in Connecticut is now a cool, rustic residence asking $1M

Just 90 minutes from Manhattan, this dairy farm in Kent, Connecticut was built in 1900 and converted to a residence by its previous owners. In addition to retaining the beautiful silo (which now holds an office and home gym), they preserved the original hand-hewn posts and beams and cathedral ceilings with skylights and invested in antique furniture and art to highlight the history of the space. The kitchen and bathrooms were modernized, and a wonderful pool deck was added. The property sits on 14 acres along the Housatonic River, and the grounds include hiking trails. All of this is asking just $1 million.
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Distinctive Homes

For $829K, this Connecticut ‘Deck House’ is an intact gem from the 1960s prefab boom

Photographs by Bleacher Everard Photography

September 30, 2021

For $829K, this Connecticut ‘Deck House’ is an intact gem from the 1960s prefab boom

We all love a good mid-century-modern time capsule, but this property in Woodbury, Connecticut has the added retro perk of being an original "deck house." In the 1960s, the Deck House Co. built more than 20,000 prefabricated mid-century homes, mainly in the northeast. This specific deck house was built in 1966 and features the signature open floorplan, glass walls, and high ceilings. It sits on seven acres and has three bedrooms, two-and-half bathrooms, and 2,000 square feet of space. It's on the market for just $829,000.
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Asking $1.7M, this Tuscan-style Connecticut villa has a 500-bottle wine grotto and a ‘Western lodge’

Listing photos by CT Plans

September 21, 2021

Asking $1.7M, this Tuscan-style Connecticut villa has a 500-bottle wine grotto and a ‘Western lodge’

Located in Easton, Connecticut, just 60 miles from NYC, this incredible Tuscan-style villa was built in 1990 by the late Arnie D’Angelo, credited with inventing the idea of the "tea chest" for Bigelow Tea. He created a true entertainer's paradise, complete with a 500-bottle wine grotto, "Jackson Hole"-themed game room, a "car club" garage complete with a bar and pit crew lounge, and a Mediterranean-style backyard and pool deck. The home, which is nearly 9,000 square feet and sits on three acres, is on the market for $1,725,000.
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Distinctive Homes

Contemporary Connecticut barn sits on 19 acres with views of the Catskills for $2.2M

Listing photos by Michael Bowman

July 30, 2021

Contemporary Connecticut barn sits on 19 acres with views of the Catskills for $2.2M

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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$2.8M contemporary Connecticut home sits on a granite outcropping overlooking the saltmarsh below

Listing photos by Dennis Carbo

July 22, 2021

$2.8M contemporary Connecticut home sits on a granite outcropping overlooking the saltmarsh below

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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Celebrity wedding planner David Tutera lists Connecticut estate for $1.45M

All photos courtesy of Rise Visual Media

July 21, 2021

Celebrity wedding planner David Tutera lists Connecticut estate for $1.45M

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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Mark Twain’s former Tuscan-inspired mansion in Connecticut asks $4.2M

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

July 12, 2021

Mark Twain’s former Tuscan-inspired mansion in Connecticut asks $4.2M

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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Asking $4.25M, this 17-acre Connecticut estate includes two transported Civil War-era barns

Listing photos by Alan Barry Photography

June 28, 2021

Asking $4.25M, this 17-acre Connecticut estate includes two transported Civil War-era barns

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.
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For the price of a Manhattan apartment, get a 10-acre horse ranch and cabin in Connecticut for $1.25M

Listing photos courtesy of Brown Harris Stevens

May 27, 2021

For the price of a Manhattan apartment, get a 10-acre horse ranch and cabin in Connecticut for $1.25M

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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Distinctive Homes

May 7, 2021

For just $865K, you can live in this beautiful converted church in Connecticut

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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$12M modern home in Connecticut has a Greek temple-inspired amphitheater

All photos by Randy O’Rourke

April 30, 2021

$12M modern home in Connecticut has a Greek temple-inspired amphitheater

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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Distinctive Homes

For $3.5M, you can own this entire 18th-century farm set on 17 acres in New Canaan

Listing photos courtesy of Houlihan Lawrence

April 22, 2021

For $3.5M, you can own this entire 18th-century farm set on 17 acres in New Canaan

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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230-year-old Connecticut farmstead with original 18th-century details asks $1.2M

All photos courtesy of Brown Harris Stevens

March 5, 2021

230-year-old Connecticut farmstead with original 18th-century details asks $1.2M

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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Tommy Hilfiger sells lavish, chateau-style Connecticut estate for $45M

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

January 19, 2021

Tommy Hilfiger sells lavish, chateau-style Connecticut estate for $45M

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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$2.6M English-style estate in Connecticut has a 50-foot underground swim tunnel leading to the pool

All photos by Borgatta Photography

January 12, 2021

$2.6M English-style estate in Connecticut has a 50-foot underground swim tunnel leading to the pool

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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Distinctive Homes

2020 luxury home sales rose 270% in some upstate New York counties

Downtown Rhinebeck, NY. Photo by Juliancolton via Wikimedia Commons

January 8, 2021

2020 luxury home sales rose 270% in some upstate New York counties