114 Beachside Avenue in Westport, CT: Setting the Bar for Luxury Living on Connecticut’s Gold Coast

Set on nearly seven acres of prized waterfront along Westport’s Beachside Avenue, 114 Beachside has long been one of the most recognizable and talked-about properties on Connecticut’s Gold Coast. Once home to television icons and a senior member of the U.S. Treasury, the estate is now in the hands of Gary and Peggy Reiner—who have made it the site of Westport’s most ambitious residential build in decades.

The home’s modern history begins in the mid-1980s, when talk show pioneer Phil Donahue and his wife, actress Marlo Thomas, purchased the property as a weekend and summer retreat from Manhattan. With over 8,400 square feet of living space in a Tudor revival-style main house, sweeping lawns, and a private stretch of beach on Long Island Sound, the property became part of the fabric of Westport’s so-called “Hollywood of the East.” Neighbors included Paul Newman and Joanne Woodward, Don Imus, and Martha Stewart.

Donahue and Thomas held the home for nearly two decades before selling it in 2006 for a then-record-setting $25 million to financier Herbert M. Allison Jr., a veteran of Wall Street and Washington. Allison had just completed a high-profile run as CEO of TIAA and would go on to lead Fannie Mae during the housing crisis and serve as Assistant Secretary of the Treasury under President Obama, where he oversaw the $700 billion bank bailout program.

Following Allison’s death in 2013, the estate was listed for sale. Despite its pedigree and location, the house lingered on the market for years, drawing no serious buyers.

That changed in 2020, when Gary and Peggy Reiner purchased the property for $16.5 million—roughly half the original listing price. Though the original Tudor was still standing, its best days were long behind it. The Reiners saw the value not in the structure, but in the land itself.

Gary Reiner brings a sharp strategic mind to every venture. After beginning his career at Boston Consulting Group, where he became a partner focused on tech-sector strategy, Reiner joined General Electric in 1991. Over nearly two decades, he rose to become the company’s Chief Information Officer and helped lead its Six Sigma transformation. Since 2010, he has served as an Operating Partner at General Atlantic, the global growth equity firm, where he advises and supports a range of high-growth technology companies. He holds board seats at Citigroup, Hewlett-Packard, and multiple General Atlantic portfolio companies, and has long been active in nonprofit work, including a decade on the board of Norwalk Hospital.

The new home, now complete, spans nearly 20,000 square feet across multiple finished levels. The first floor alone comprises more than 10,000 square feet, complemented by a spacious upper story and finished attic spaces. The home includes 28 rooms in total including 8 bedrooms, 8 full bathrooms, and 3 half baths.

Design-wise, the exterior pays subtle homage to traditional coastal architecture while leaning into a clean, modern silhouette. Inside, 12-foot ceilings give the home a sense of openness and scale. Materials include wide-plank hardwood, stone and tile flooring, and custom wood paneling. The kitchen and bathrooms are finished with contemporary, high-end fixtures. Five fireplaces anchor key living areas, while an indoor pool, hot tub, outdoor shower, and expansive stone patio maximize year-round enjoyment of the waterfront setting.

Mechanical systems are state-of-the-art: a gas-powered HydroAir system provides heat, supported by central air conditioning and a whole-house generator. A three-level elevator, sprinkler system, and smart-home automation are also integrated throughout the property.

Supporting structures include a garage, carport, canopy, and manicured outdoor spaces designed for entertaining and relaxation—all with commanding views of the Sound.