Diana Bisselle

Diana Bisselle

Licensed Real Estate Salesperson

Member of The Legacy Team at William Pitt Sotheby's International Realty
Diana Bisselle
  • M
19 Main Street
PO Box 667
Salisbury, CT 06068

Years in Business

Properties Sold

Last Year's Sales Volume

About Me About Me

From traveling the world as an Emerging Markets Investment Professional to navigating the winding country roads of Litchfield County, Diana Imperatore Bisselle truly embodies the phrase "local expertise, global connections".

As a resident of Lakeville, CT, Diana has deep roots in, and an unparalleled understanding of, the local real estate market. Born and raised in neighboring Sharon, CT, her parents Philip and Dobrila Waugh founded Waugh Real Estate, a well-known local brokerage covering the Tri-State area for over 30 years. This exposure has instilled in her the importance of superior client service and professional integrity - core values that define The Legacy Team recently launched by Diana and her husband Andrew.

Prior to and complementing her real estate career, Diana worked in New York City for several international investment banks and a hedge fund specializing in Russia, Eastern Europe, Turkey and the Middle East as both an Equity Salesperson and Emerging Markets Portfolio Manager. She has an undergraduate degree in International Relations and Soviet Studies from Boston University and an MA/MBA in Politics and Finance from NYU. 

During her 20+ years in finance, she lived in both Old Greenwich and Darien allowing her to be well-versed in both Litchfield and Fairfield County. She is often found liaising between the two counties, leveraging the resources of the many Sotheby's offices from the coastline to the Litchfield Hills. This is further enhanced by a robust global network unique to Sotheby's.

Diana has been an involved parent at Pear Tree Point School in Darien, Indian Mountain School in Lakeville and Kent School in Kent, CT. She is on the Board of the Lakeville Community Conservancy.

Licensed in CT, NY and MA. Fluent in Russian.

  • Languages Spoken English, Russian
  • Born In Sharon, CT
  • Lives In Lakeville, CT
  • Passion Exploring the world & Ancient Architectural Wonders
  • Interests Travel, Golf, Ballet & Art
93 & 107 Amenia Union Road, Sharon, CT

My Awards

  • ~ #1 in Dollar Volume, Salisbury Brokerage - 2022
  • ~ Platinum Award - 2022
  • ~ Platinum Award - 2021
  • ~ Diamond Award - 2020
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My Listings and Sales

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Testimonials (14)

Diana Bisselle is a wonderful agent and a lovely person. She was patient and helpful throughout our house search. We really came to like her very much. We have already recommended her to two of our friends. Thank you Stephen Scheer
We love Diana. She is great. Jon Birge Miriam Birge
Hiring Diana to help with my house hunt was the best decision. She is professional and responsive (a breath of fresh air!), and her calm demeanor and sharp wit and kept the stresses of buying my home light and manageable. Everyone should have the pleasure of working with Diana! Emma O'Brian
I would recommend Diana Bisselle to anyone! She was a pleasure to work with and helped us through buying our first home. Megan Reed & Nathaniel Bekoe
Diana Bisselle is the absolutely most knowledgeable, responsive, kind, personable, and patient agent we have worked with in over 40 years of purchasing real estate. It was truly a pleasure to work with her. William Pitt/Julia B. Fee Sotheby’s is extraordinarily fortunate to have Diana as part of their team. Thomas Hays
Outstanding! Our Agent Diana Bisselle supported and mentored us with professional perfection and compassion through a complex sale. If the bar is set at a 10, this team was a 20! I honestly don’t think I could have traveled the “sell journey” without Diana’s exceptional partnership. Thank you! Thank you! Lynne Calhoun
If first impressions are anything, Diana is a best-case win for your company. From our first phone call to the moment she escorted me to the lawyer's office, I was always met with a pleasant, calming, smile; exacting knowledge of the area (used mainly to gently guide me away from seeing properties she knew would not be a good fit for me); professionalism; accessibility; and the constant feeling that I could trust her guidance every step of the way. I know whom I'll be calling in the future. Thank you. David Beahm
Diana is brilliant. She has a lovely, engaging personality that matches her professionalism and clear expertise in the CT real estate market. We were so pleased and fortunate to work with her. Lawrence & Joan Hathaway
Diana was a godsend! She took a difficult situation in hand, with competence and foresight at every turn. Her advice was always on target. Her capacity for diplomacy is extraordinary. She is a consummate professional. I am grateful. James Lipton
Diana Bisselle was wonderful. When we first showed her the house, she saw it's special qualities exactly as we did. We were amazed at the work she did for us, & the house was sold much quicker than we had anticipated. We credit Diana for this. She made the entire process painless for us, from start to finish. We will highly recommend her in the future. Clark & Claire Smith Clark & Claire Smith
Diana Bisselle was amazing for us, from start to finish. She saw the special qualities of our house, the property, & its location exactly as we did, before we even told her what we found special about it. We will highly recommend Diana to anyone we know that may sell their house in the future. Clark & Claire Smith
Diana Bissell, our Sotheby's agent, was fantastic throughout the entire process. Always there to answer every question regardless of the nature of the inquiry. In that regard, I would like to change your question to "How likely is it that you would recommend Diana Bissell to a friend or colleague?" Extremely likely and without reservation. Having bought or sold 6 houses in our lifetime, Diana is by far the best agent we have ever had. Sincerely, Eric and Elise Cieplik Eric & Elise Cieplik
Diana is an excellent and thoughtful agent. Ronald & Judith Frost
Working with Diana was an absolute pleasure throughout the entire process, from initial viewing to closing. Dealing with a Foreclosure property was complicated and daunting, but Diana was extremely dedicated to our vision of preserving an 1860's farmhouse. Diana aggressively pursued potential problems to find solutions, whether it was researching town hall records, site visits, or local guidance. As a Sharon resident, Diana really cares about the community as well as her clients and it genuinely shows. I would highly recommend working with Diana Bisselle on any project. Sincerely, Tom & Lizzie Thoma Pillar & Elizabeth Gill

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6 refreshing homes with great indoor pools…    


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  • Diana Bisselle

    Diana Bisselle

    Licensed Real Estate Salesperson
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