Jennifer Caulfield

Jennifer Caulfield About Jennifer

Realtor

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 MORE

Our agents are recognized in the communities they serve for their deep knowledge, expert guidance and commitment to excellence.

  • Office Location Essex
  • Licensed In Connecticut
  • Languages Spoken English
  • Communities Old Saybrook, Old Lyme, Lyme, Essex

The Property Journey

Nothing compares to the level of exposure we generate for our listings.

Agent Awards

  • Gold Award, 2022, 2023
  • Platinum Award, 2020, 2021

My Listings and Solds

Loading listings...

double quote
Endorsements
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, Claudia Weicker
double quote
Endorsements
Thanks to Jennifer Caulfield for help and encouragement in a long and complicated sale I felt she was always there for me Rosemary Willis
double quote
Endorsements
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
double quote
Endorsements
Mrs Caulfield was exceptional. She made the deal go through. What pro!!! David McDermott
double quote
Endorsements
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
double quote
Endorsements
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
double quote
Endorsements
Jennifer is a wonderful realtor. She helped us with three properties this year. Timothy & Robin D'Albenas
double quote
Endorsements
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
double quote
Endorsements
Great agent! William Pitt has great reach, very broad. Rosemary Petersen
double quote
Endorsements
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

COMMUNITIES
LISTINGS
East Lyme
120
COMMUNITIES
LISTINGS
Old Saybrook
99

In The News

Zip06

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

READ MORE

Cottages & Gardens

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

READ MORE

CT Insider

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

READ MORE
  • Jennifer Caulfield

    Jennifer Caulfield

    Realtor
    M.
    Essex
    13 Main Street
    Essex, CT 06426

Contact

  • This field is for validation purposes and should be left unchanged.

QR Download Link

Scan to download agent info

  • Contact
CONTACT ME
Sign Up For Updates

Subscribe to receive the latest real estate market updates, exclusive new listings, architecture & design inspiration and more.