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Whether for sale or for rent, Connecticut is no stranger to expensive properties. This fall, Litchfield County’s most expensive listing clocked in at $16 million, while a Greenwich estate for sale with a 30-car garage had a price tag of $33.8 million.
As a pricey 2022 real estate year comes to a close, the current top 10 most expensive listings have a price range from $25.5 million to over $80 million. Here are the 10 most expensive in the state going into 2023.

The more than 51-acre property on Long Neck Point Road in Darien, Conn. is for sale for $85 million.
Known as Ziegler Farm, the 51.28-acre property on Darien’s Long Neck Point Road is part of the “Great Island Property Owners Association,” according to the listing. It's a “sub-division with 14 remaining oversized building lots totaling 34.51 acres, two private paved roads (2.85 acres) with electric, sewer and water lines in place and preserved open space of 13.92 acres.”
The Ziegler Farm property is located next to Great Island, which was recently purchased by the town of Darien. The town has not yet decided how it will use the property, which has nine buildings, including a 13,000-square-foot mansion. Ziegler Farm and Great Island were initially offered as one listing comprised of 110 acres, but the Ziegler family that owned the land split them in two.
The Long Neck Point Road property is listed by Sotheby’s International Realty – Greenwich Brokerage and is presented by Leslie McElwreath and Joseph Barbieri.

The castle on 580 Brickyard Road in Woodstock, Conn. is listed for $50 million.
In November 2021, the castle on Brickyard Road in Woodstock was listed for $35 million, but by January 2022, the price of the property known as Chris Mark Castle jumped to $60 million. Now it's priced at $50 million. The castle is named after its owner Christopher Mark, a philanthropist and descendent of steel industrialist Clayton Mark, according to the castle’s website. As a teenager, Christopher Mark created Mark Miniatures, the website notes, a collection of hand-painted figurines that were sold by retailers like Bergdorf Goodman. According to listing agent John Pizzi, Mark began construction on the castle in 2003 and oversaw the build from start to finish before it was completed in 2010.
The castle sits on 75 acres of land, the listing notes, and its next residents can view the pond from all year round from the radiant-heated decks and patios that can melt snow in the winter. And in case privacy was a concern, the castle also includes one distinct fairy tale feature: a moat.
In its time on the market, the castle was featured twice on the viral Instagram and TikTok account Zillow Gone Wild.
The Brickyard Road castle is listed by Compass and is presented by John Pizzi of Randall Realtors.
Available “for the first time in over a generation,” the listing for 7 John St. in Greenwich notes that the property is known as Robin Hill Farm. Designed in 1937 by the designer behind The Whitney Museum of American Art, Auguste L. Noel, several additions were added to the property over the years to create a fully restored “family compound,” according to the listing.
Landscape architect Jacqueline Osty, who received the National Prize of Landscape in 2005 for the Park Saint-Pierre in Amiens, France and worked on several projects in France, designed the grounds of the compound. On its 22-acre lot, the listing notes that the property includes three separate, deeded lots with stables, paddocks and a riding ring, as well as two cottages with a pool and a 7-acre grazing field.
The John Street property is listed by Compass and presented by Shelley S. Tretter.
This custom waterfront home in Old Greenwich is descried as a waterfront "oasis" in the listing. It was also a 2021 Home Building Industry (HOBI) Award winner, which recognizes "excellence in design and construction in homes."
The property spans just over one acre and includes features like a pool, guest house, boathouse, spa, expansive terraces integrated with gardens and a deep water pier for a boat. Flanked with imported floor-to-ceiling glass doors and windows, the property's features emphasize its "seamless" indoor/outdoor living. Additionally, the home has over 13,000 square feet of living space.
The eight-bedroom, 11.5-bathroom home at 45 Binney Lane is currently listed at $35.5 million and is presented by Amanda J. Miller and Ellen Mosher of Houlihan Lawrence.

An aerial view of the property at 97 Pecksland Road.
The 19-acre property on Pecksland Road sits in the heart of mid-country Greenwich and is home to a 2009 custom built "grand estate," according to the listing. The home has a gated entrance and a long, dramatic driveway leading to the main home that emphasizes privacy with the size of the lot.
The estate is fit with oversized living rooms and bar areas for entertaining, multiple offices, a full library, wine cellar, golf simulation room, children play space, gym and a kennel room that can fit three large dogs. There is a three-car garage and a three-car "porte cohcere," or covered entrance area for cars. Additionally, the listing writes there is a "car collectors dream" in the lower level of the home that can hold up to 30 cars. The outside features a double pool and spa. There is a two-bedroom guest house adjacent to the pool.
The Pecksland Road estate has 10 bedrooms, 14 full bathrooms and five half bathrooms and is on the market for $33.8 million. The listing belongs to Rob Johnson of Brown Harris Stevens CT, LLC.

An aerial overview of the estate at 30 Field Point Dr.
The estate at 30 Field Point Drive in Greenwich is a Georgian Colonial style home with only two previous owners, according to the listing. Sitting on about 6.4 acres, the property features two smaller subdivided areas of land for a guest house and cottage that flank the driveway. The home has design features like a columned terrace that allows residents to overlook their property, marble finishes, raised wainscoting and the library features a doorway from the Grosvenor House in London.
The 11-bedroom, nine-bathroom and two-half-bathroom home is currently listed for $30 million and is listed by Brown Harris Stevens CT, LLC.

The exterior of the property at 15 Dairy Rd.
The property at 15 Dairy Road in Greenwich sits on over five acres of gated land. The tree-lined driveway leads up to the main property where the finishes blend the old and the new, according to the listing. Giant metal-framed windows throughout the home allow for plenty of light to come in, and the living spaces are finished with onyx countertops and wood details throughout.
The waterfront home features three floors plus a basement level, and bedrooms on the third floor of the property havce views of the Long Island Sound and the New York City skyline.The various floors of the property can be accessed by elevator. The home also has a media/movie room, a gym, a library and a connecting underground hallway to the pool house.
Outside, the property is equipped with an indoor lap pool with retractable cover, sound system, bar area, gas fireplace and powered screens. There is also a tennis court on site.
This nine-bedroom, nine-bathroom and four-half-bathroom home is on the market for $29.95 million and the listing belongs to Rob Johnson of Brown Harris Stevens CT, LLC.

An aerial view of the waterfront property at 21 Vista Dr.
The property at 21 Vista Drive in Greenwich boasts over five acres of land and 750 feet of private shoreline. The estate is located within the exclusive Indian Harbor Association that gives residents the security of a guarded gate house and was once owned by former President Donald Trump. The home has been on and off market and is currently listed at its lowest price yet.
The finishes of the home are "grandiose" and "elegant," according to the listing, and unique features of the home include an indoor lap pool, a seperate outdoor pool overlooking the waterfront, a great room with 20 foot ceilings, "flat and expansive" front and rear yards, a tennis court and a deep water dock.
The home, which is on the market for $29.9 million, boasts 24 bedrooms, 15 full bathrooms and three half bathrooms. The listing belongs to Rob Johnson of Brown Harris Stevens CT, LLC.

Double H Farm, located at 11 Old Stagecoach Road in Ridgefield, will host a sneak preview of a multimillion dollar barn. The event, to be held on Aug. 24, will benefit the Semper Fi Fund. The barn will be featured on the Polo America Barn Tour.
The property at 7-11 Old Stagecoach Road in Ridgefield — also named "Double H Farm" — is a unique equestrian compound that sits on 87 acres of land in Faifield County.
The main home is four stories, and the property as a whole is "outfitted with resort-like amenities," according to the listing. The land holds, two additional renovated homes, two barns with stalls for over 40 horses, a trophy lounge, a "party barn" for events, paddocks with run-in sheds, two covered hot walkers, staff apartments, a pool, tennis court, indoor and outdoor riding rings and a jumping derby field.
The home has five bedrooms, six full bathrooms and three half bathrooms and is currently on the market for $28 million, represented by Krissy Blake of Sotheby's International Realty.

A rendering of the final design for 1 Indian Chase Drive in Greenwich.
The estate on 1 Indian Chase Drive in Greenwich sits above Indian Harbor and boasts 295 feet of private waterfront. The home, which has been renovated to a contemporary style, features a waterside entertaining deck, boathouse and floating dock, according to the listing. Floor to ceiling glass windows and doors make for indoor/outdoor living and give the home multiple views of the Long Island Sound.
Features of the home include dine-in wine cellar, home theater and wellness center. Outside, the home boats a tennis court, a two-bedroom cottage and pool with a spa.
This seven-bedroom, eight-full-bathroom and three-half-bathroom home is on the market for just under $28 million. 1 Indian Chase Drive is currently listed at $27.95 million and is represented by Leslie McElwreath of Sotheby's International Realty.