Diana Bisselle

Licensed in CT, NY, and MA

#1 Team ~ Dollar Volume, WPSIR Litchfield County Brokerage offices 2025 

Diana Imperatore Bisselle's career is defined by the convergence of financial acuity and luxury real estate mastery. Having successfully navigated the complexities of global finance as an Emerging Markets Investment Professional, she has brought that same commanding expertise to the Tri-State area's beautiful and unique real estate landscape across CT, NY, and MA. This transition from Wall Street to Main Street is a testament to her belief in the power of "local expertise, global connections."

As a third-generation Connecticut resident, Diana’s understanding of Litchfield County and Fairfield Counties (CT), Dutchess and Columbia Counties (NY), and Berkshire County (MA) is both intrinsic and encyclopedic. Her deep roots in the regional brokerage community trace back to her family’s ownership of the esteemed Waugh Real Estate based in Sharon, CT, instilling a legacy of professional integrity and exceptional client service - values underpinning The Legacy Team, which she founded in their honor.

Diana’s real estate counsel is informed by two decades in international finance. Based in NYC, she served as an Emerging Markets Portfolio Manager and Equity Salesperson at leading global investment banks and a hedge fund, specializing in Russia, Eastern Europe, Turkey, and the Middle East. She holds a BA in International Relations and Soviet Studies from Boston University and a MA/MBA in Politics and Finance from NYU, offering clients a distinct advantage: market insight shaped by the rigor of global capital markets.

Now residing in Lakeville, CT (after twenty years in Old Greenwich and Darien) Diana serves as a key liason between Fairfield and Litchfield Counties. With deep familial roots in Millbrook, NY, she is also able to seamlessly cover Dutchess County as well.

Licensed in CT, NY, and MA, fluent in Russian, and supported by the global reach of Sotheby’s International Realty, she provides comprehensive, high-level representation. She is also a Board Member of the Lakeville Community Conservancy and the Institute for America Indian Studies.

AWARDS:

#1 Team in Dollar Volume, WPSIR Litchfield County Brokerage offices - 2025
#1 in Dollar Volume, Salisbury Brokerage - 2024
#1 Team (The Legacy Team at WPSIR) - 1H24
2023 RealTrends America's Best Real Estate Professionals
#1 in Dollar Volume, Salisbury Brokerage - 2022
Platinum Award - 2021, 2022, 2024, 2025
Diamond Award - 2020

DESIGNATIONS:
Resort and Second Home Property Specialist
Waterfront Property Specialist

SERVICE AREAS:
Sharon, CT
Salisbury, CT
Lakeville, CT
Kent, CT
Washington, CT
Millbrook, NY
Washington, NY
Ancram, NY

and much more!