Recently Viewed Properties

Sales Associate

Contact Me

Get Pre-Approved Today

with our affiliated lender
NMLS#: 1598647

Connect with Annie


International President's Circle  What's this?

More about Annie Jessup


A lifelong resident of the Boston area, Annie has established herself as a leading agent in Westwood, Dedham, Brookline and the surrounding towns. Annie joined the Hammond Residential Wellesley office in 2001 working with buyers and sellers in the western suburbs. She achieved success quickly as a real estate agent by listening carefully to the needs of her clients and providing them with solid information and good advice.

Annie moved to Westwood more than 18 years ago with her husband and their then-growing family. It was a natural fit when Hammond Residential opened a Westwood Office in 2014 that Annie take on a new expanded role as its Assistant Manager. Still working with her buyer and seller clients, she had an added interest in the growth of the new office and this has been a benefit that Annie enjoyed taking a part it in. In 2016 when Coldwell Banker Residential Brokerage acquired Hammond Annie returned to the CBRB Wellesley office as a top producing agent. Consistently selling over 12 million in real estate each year. Annie's energy, enthusiasm, and integrity have all contributed to her continued success.

In her spare time she is an active member of her community. Annie is currently on the Board of the Westwood Historical Society and Fox Hill Garden Club. She graduated from Newton Country Day School of the Sacred Heart and Providence College.


“You are one of the hardest working and most resourceful agents I've ever worked with. With your efforts, we quickly had our home under agreement after a long, drawn out failed attempt with another firm. I would use you every time and strongly recommend your services to anyone that truly wants a real estate professional. Thank you for all you did for us.“

- Julie and Craig, February 2016

“Thanks Annie, we enjoyed working with you as well and were very pleased with the outcome. I know at the time we mentioned to a few of our friends that we had used you and were very pleased. We would for sure recommend them to you. “

- Matt R., October 2015

"Annie was pivotal in selling our home in 2012. We were also looking in the same town, and finding neighborhoods we liked and attempting to sell at the same time was difficult, to say the least. She was professional, confidential, courteous, and she definitely knew the market. We would absolutely recommend her!"

- Ellen O., October 2015

“Thanks for everything. We have not been involved in a lot of real estate sales, but you two were an order of magnitude better than any other agents we have used. We will certainly recommend you to anyone else we learn wants to sell a property, and would be glad to serve as a reference for you anytime.”

- Jim and Judy P., December 2013