About Me About Me

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


My Awards

  • Platinum Award, 2020, 2021
  • Gold Award, 2022

My Listings and Sales

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Testimonials (8)

Jennifer Caulfield is professional, knowledegable, pragmatic and efficient. One of the best brokers I've ever worked with. Highly recommend her and WPSIR. Kathryn Hunter
Mrs Caulfield was exceptional. She made the deal go through. What pro!!! David McDermott
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! Barbara Aubin
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. Robert Zdon
Jennifer is a wonderful realtor. She helped us with three properties this year. Timothy & Robin D'Albenas
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. Barbara & Charles Coffery
Great agent! William Pitt has great reach, very broad. Rosemary Petersen
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. Timothy & Katherine Love

Additional Communities

East Lyme
Old Saybrook

Jennifer Caulfield in the News


William Pitt Sotheby’s International Realty Agents Honored with Awards for Sales in 2021…

Cottages & Gardens

Tour a $4.85M Waterfront Estate in Old Lyme Dotted with Elegant Cottages…

CT Insider

Former shoreline sheep barn and ‘upside-down house’ listed for $5.5M…

Connecticut Cottages & Gardens

Deeds & Don’ts…

Contact Me

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    Jennifer Caulfield

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