Drawing upon a significant corporate and financial background, Jennifer is a skilled negotiator and consummate professional. She is a Gold Award winner at William Pitt Sotheby's International Realty and has proven negotiation skills and an understanding of real property investments and real estate transactions. Jennifer, a long-time resident of Old Lyme, serves on the Board of the Connecticut River Museum, and contributes her time and assistance to Child and Family Services, the Florence Griswold Museum and the Lyme Academy College of Fine Arts. She is also a member of the Old Lyme Country Club, Essex Yacht Club and the Black Hall Club
Drawing upon a significant corporate and financial background, Jennifer is a skilled negotiator and consummate professional. She is a Gold Award winner at William Pitt Sotheby's International Realty and has proven negotiation skills and an understanding of real property investments and real estate transactions. Jennifer, a long-time resident of Old Lyme, serves on the Board of the Connecticut River Museum, and contributes her time and assistance to Child and Family Services, the Florence Griswold Museum and the Lyme Academy College of Fine Arts. She is also a member of the Old Lyme Country Club, Essex Yacht Club and the Black Hall Club
Drawing upon a significant corporate and financial background, Jennifer is a skilled negotiator and consummate professional. She is a Gold Award winner at William Pitt Sotheby's International Realty and has proven negotiation skills and an understanding of real property investments and real estate transactions. Jennifer, a long-time resident of Old Lyme, serves on the Board of the Connecticut River Museum, and contributes her time and assistance to Child and Family Services, the Florence Griswold Museum and the Lyme Academy College of Fine Arts. She is also a member of the Old Lyme Country Club, Essex Yacht Club and the Black Hall Club
Read LessDr. and Mrs. Anthony Barri 9 Olivia Ln. Old Lyme, CT 06371 June 2, 2025 To Whom It May Concern, We are pleased to write this letter of recommendation for Jennifer Caulfield, who served as our real estate agent during the sale of our home in Old Lyme, Connecticut, with William Pitt Sotheby’s International Realty. With over 30 years of experience in the real estate industry, Jennifer brought a wealth of knowledge, dedication, and professionalism to the process, guiding us through a challenging market with care and commitment. Selling our five-bedroom home, listed from October 2024 to May 2025, proved to be a complex endeavor due to market conditions and pricing considerations. Throughout this period, Jennifer, demonstrated unwavering persistence, offering thoughtful strategies to position our property effectively. Her deep understanding of the Old Lyme community and its appeal to families and second-home buyers was evident in her efforts to highlight the home’s unique qualities. As a dear friend, she went above and beyond, maintaining open communication and providing personalized support during a lengthy process. While the sale was ultimately facilitated through a collaborative effort within her firm, with another agent bringing the buyer, Jennifer‘s role was instrumental in keeping the listing active and well-represented. Her professionalism and loyalty to our goals never wavered, and we are grateful for her partnership in achieving a successful sale. We confidently recommend Jennifer Caulfield] to anyone seeking a seasoned, client-focused real estate professional with a strong connection to the Old Lyme market. Her experience and dedication make her an asset to William Pitt Sotheby’s and to any client fortunate to work with her. Sincerely, Dr. and Mrs. Anthony Barri
My realtor with Sotheby's was terrific. She knew and understood what I wanted in a house and found it for me. I was delighted and would recommend her to all my friends,
Thanks to Jennifer Caulfield for help and encouragement in a long and complicated sale I felt she was always there for me
Jennifer Caulfield is professional, knowledegable, pragmatic and efficient. One of the best brokers I've ever worked with. Highly recommend her and WPSIR.
Mrs Caulfield was exceptional. She made the deal go through. What pro!!!
Recently I was responsible for the sale of an estate property. I contacted Jennifer Caulfield of William Pitt Sotheby's International to inquire about doing an appraisal and discuss marketing the property. From the first meeting until the sale, Jennifer's expertise and professionalism gave me complete confidence. She provided an impressive portfolio of William Pitt Sotheby's services and the proposed marketing strategy for the property. Her knowledge of the market and the unique features of the area and the home combined to bring about the sale to my complete satisfaction. Highly recommend!
My realtor, backed by the exceptional support and infrastructure at WPS's handled a unique property to the end with professionalism and extraordinary attention and care. Would recommend them to all.
Jennifer is a wonderful realtor. She helped us with three properties this year.
We have bought and sold 8 homes over the last 11 years because we were never able to find the right house in the right location. Old Saybrook and Essex have been our target but we’ve always “settled” nearby, unable to find the right house. Jennifer Caulfield brought us multiple offers on our sale and found the right house for us in the North Cove section of Old Saybrook. Right house. Right location. Right Agent.
Great agent! William Pitt has great reach, very broad.
Xun Mei Del Sesto of Sotheby's in Chicago researched agents in SECT for me. She is a friend and a consummate professional with charm and approachability. Jennifer Caulfield is elegant, smart with Xun Mei's other qualities. She managed to sell our very unique house despite the challenges of the pandemic. It had been with another broker for over a year and a half prior to my signing with Jennifer. There had been very little action or communication. Our experience with Sotheby's and Jennifer Caulfield was the opposite. Jennifer was attentive and encouraging and she closed the deal, finding us a lovely buyer who will appreciate the house as much as we did for 20 years. We would highly recommend Jennifer Caulfield and Sotheby's affiliates.
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