Sugarbush Real Estate gets new ownership

May 27, 2026  |  By Waterbury Roundabout

After decades of leadership from longtime owners Cindy Carr and Brian Shea, the independent Sugarbush Real Estate brokerage firm has changed hands.

New owners Dan Cypress and Jessica Bridge also own Element Real Estate and Heney Realtors.

The transition went into effect this month and reflects a thoughtful, long-term plan to preserve the character and values of Sugarbush Real Estate while introducing state-of-the-art tools and expanded support to help the company evolve for the future, according to the owners’ announcement. 

Founded by Cindy Carr in 1969, Sugarbush Real Estate has long been known for its deep local roots, relationships, and commitment to the Mad River Valley community. Carr and Shea said they looked for successors to continue in that spirit and to ensure that the firm would have the resources and technology needed in today’s market. 

“This decision was about making sure Sugarbush Real Estate continues to thrive as an independent brokerage while giving our agents and clients even more support moving forward,” Carr said.

Sugarbush Real Estate will continue operating independently under its own name, leadership, and identity, while benefiting from additional operational support and modern infrastructure behind the scenes. 

Clients and the community will not see many significant impacts from the ownership change. Agents will remain in place along with local leadership. Shea will continue in his role as Principal Broker, and Carr will remain actively involved with the brokerage and its clients. 

“There’s a deep level of trust here that’s been built over generations,” Cypress said. “Our goal is to strengthen that foundation with best-in-class marketing, state-of-the-art technology, and operational support that helps agents work more efficiently and clients feel even more informed and connected throughout the process.” 

Improvements the new ownership foresees over time will focus on upgrading technology, digital marketing, client communication and the firm’s website. 

A key priority will be maintaining the local connections and attention to detail. “People still want local knowledge and real relationships,” Bridge said. “What’s exciting is being able to pair that personal connection with modern systems and technology that make the experience smoother, more responsive, and more transparent for everyone involved.”