Photo credit: James Gagliardi / Brown Harris Stevens

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.

Find out more, take the tour

Photo courtesy of Douglas Elliman

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.

Step inside this historic hilltop estate

Photo credit: Houlihan Lawrence

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.

Waterfront estate tour, this way

Photo credit: Home Tour Vision

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.

Tour the house and barn

Listing photos by Michael Bowman

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.

See the whole place

Photographs by Bleacher Everard Photography

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.

See inside

Listing photos by CT Plans

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.

Take the tour

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.

Have a look around

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.

Go inside

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.

Get the details