John Chakalos and Linda Carman: Murdered at Home and Missing at Sea

This is Part One of a three part series.

It was the morning of December 20, 2013 when Elaine Chakalos pulled into the driveway of the modest single-story home on Overlook Drive in Windsor, Connecticut. It had been a trying few weeks for the Chakaloses. Elaine’s mother, Rita Chakalos, passed away from a battle with cancer in November, and everyone was navigating their new reality without the matriarch of their family. 

Rita and her husband, 87-year old John Chakalos, were quite the fixtures in their local community, both in Windsor and in West Chesterfield, New Hampshire where they’d built a massive three-story home of over 15,000 square feet on 88-sprawling acres. Everyone who crossed paths with the couple knew two things about John and Rita Chakalos: that both had giving and charitable hearts, and that they had a lot of money to give.

But this home in Connecticut was quite the contrast to their New Hampshire mansion – a fraction of the size and not a single indoor swimming pool in sight. The Windsor house often served as an office space for John. Though he may have been 87-years old, the man still had a passion for his work. 

In court transcripts, another of John’s four daughters, Valerie, explained that she and her sisters were pretty much “planning his life” after Rita died. They encouraged him to stay nearby in Connecticut instead of up north at the New Hampshire estate, and were even planning to take him to look at new apartments in Connecticut, too. But for the time being he was in Windsor on Overlook Drive, where he’d been spending more time since Rita’s passing. 

About John Chakalos & Family

John Chakalos was best known for his development of nursing homes and extended care facilities throughout New England. Ever a family man, many of his properties were named after his daughters, Valerie Santillli, Elaine Chakalos, Charlene Gallagher and Linda Carman. 

There was Linda Manor Extended Care Facility in Leeds, Massachusetts and Charlene Manor Extended Care Facility in Greenfield, Massachusetts, among others.

Though he was closer to 90-years old every day, John was still active in his business endeavors. A co-developer he partnered with told the Daily Hampshire Gazette that John Chakalos was a dynamic, hard-working, larger-than-life figure who was at it every day. Quote, “He had a very strong work ethic and approached everything he did with an energy and enthusiasm that would belie his 87 years.” End quote.

In his younger days, John attended high school in Middletown, Connecticut, where he met the woman who would become his life-long companion, Rita Baranowski. Before the real estate ventures that turned into a vast portfolio of developments in multiple states, John enlisted in the U.S. Army where he served with distinction as a paratrooper during World War II. 

Multiple sources make reference of John’s favorite motto: Without family, you’ve got nothing; family is everything. That was the heart of who John was, his family and friends said. Dedicated to his wife, his children and grandchildren, as well as his nieces and nephews. John’s caring heart extended beyond his family, too. Charity and finding ways to give back to those in his community who needed it most was part of who he was. 

For nearly a decade, the Chakalos name was synonymous with holiday cheer. The West Chesterfield mansion on Pond Brook Road transformed each winter season into one of the most impressive private lights and decorations displays in the state, if not all of New England. The Sentinel Source reported that over 6 million lights adorned the property, lighting up the brick facade and blinking off the frozen winter snow. 

At first the light display started as John’s personal delight for his favorite holiday, though his family invited a local kindergarten class to come up to see the display. It soon after evolved into a public drive-thru event – anyone could come stare wide-eyed at the dazzling array of multicolored bulbs in exchange for a donation to a local food pantry. At its peak, the holiday lights event would bring in over a thousand bags of food and thousands of dollars – enough to carry the food bank for months.

The West Chesterfield house was used mostly as a place where John’s family, his daughters and grandchildren and the rest, could gather together to make memories. When he wasn’t in New Hampshire, John and Rita stayed in their Connecticut home, that modest dwelling on Overlook Drive that John ultimately planned to keep as an office. 

The issue of where John Chakalos really lived, where he legally established domicile, will play a substantial role in this case later on, but we’ll get there. 

Elaine stopped into her dad’s house in Windsor, Connecticut on Overlook Drive sometime around 8 o’clock in the morning of December 20, 2013 to check on her father, though I can’t be sure if it was part of her routine or if Elaine had any cause for concern that would warrant a visit. If she didn’t have cause for concern already, though, she certainly would as soon as she found her father in his bedroom. 

John Chakalos had been shot dead in his bed. 

The Story Continues on Dark Downeast

When the daughter of wealthy real estate developer John Chakalos walked into her father’s Connecticut home one morning in December 2013, it set into motion a long-term investigation of not one, but two suspicious deaths in the same family within a three year span. 

Investigators had a prime suspect for the murder of John Chakalos from the beginning, but it wasn’t until another member of the family disappeared under mysterious circumstances that the identity of that suspect was revealed.

Press play for Part I covering the background of two related cases, the murder of John Chaklos and the suspicious disappearance of Linda Carman.

The cases of John Chakalos and Linda Carman are active and on-going with developments as recent as early May 2022. In the next episode of Dark Downeast, I’ll dive deep into court records and explore some major questions central to both investigations: Who is Nathan Carman? Is he responsible for the death of his grandfather? Did Nathan intentionally sink his boat with his mother aboard? And why?

Episode Source Material

Court Documents Referenced and Cited

  • Search Warrant Affidavit by Detective Christopher Iovene, Middletown Police Department and Detective Sergeant William Freeman, Windsor Police Department, July 18, 2014