Kevin Caulfield

Managing Director


About Kevin

Kevin Caulfield has over 15 years of experience in the Boston real estate market. He has distinguished himself as a top agent, consistently being recognized by “Boston’s Top 20” as one of the premier brokers in the city.

Throughout his career, Kevin has been involved in over $400 million of real estate transactions. Specializing in residential brokerage services, Kevin works extensively with developers and investors. After co-founding Charlesgate Realty Group in 2003, Kevin has continued to build his business through the likes of Coldwell Banker and Campion & Company.

While developing a loyal client base, Kevin has led his team to increased sales volume every single year since 2001, including the recession. Kevin focuses on providing elite level service to his customers, and has completed transactions in every neighborhood throughout the city of Boston.

A graduate of Boston College, Kevin was a member of the Men’s Ice Hockey Team from 1996-2000. He continues to support ice hockey as a mentor in the Boston College Student-Athlete Mentor Program, and was an Assistant Ice Hockey Coach at Thayer Academy. He also serves on the Executive Board for Thayer Academy’s Alumni Association.

Kevin was a longtime resident of the South End. He now resides in Hingham with his wife Kate and their three daughters.

Adam Smith



About Adam

A lifetime Boston-area resident, Adam Smith brings over seven years of experience in the areas of marketing, sales, and development to his position at Compass. Adam is a licensed real estate agent and has been involved in over $110 million in real estate transactions since entering the industry in 2015.

Adam has spent the last two years working alongside top agent Kevin Caulfield at Campion & Company. Prior to Campion, he spent three years working on Commonwealth Avenue at Boston University. While at BU, Adam held various roles in fundraising and development, overseeing the entire annual fund for BU Athletics, focusing on giving strategies, solicitations, special events, and stewardship.

Known by many for his strong integrity, attention to detail, and work ethic, Adam prides himself on a client-first approach to service and problem solving. A former NCAA Division-III football student-athlete, Adam completed his bachelor’s degree at the University of Connecticut and master’s degree at Springfield College. Adam and his wife Leigha currently reside on the South Shore.

Jeannie Crane



About Jeannie

Jeannie Crane is a licensed Real Estate Salesperson with a multi-faceted real estate background and has joined Compass as a member of the Caulfield Properties Team.

Jeannie has served as a vital bridge between owners, clients and developers in pre-planning, marketing and preparation for numerous small, med and large scale developments, gaining strong ties to the Boston community.

Jeannie is excited to pair her background in development, marketing and leasing to achieve aggressive goals and focuses on new strategic opportunities within the operations of the Caulfield Properties Team. Jeannie will leverage Compass’ cutting edge technology, global resources and network to elevate the team’s success.

In her work she displays creative energy, positive and engaging attitude while collaborating with a vast array of clientele. She is recognized for her attention to detail and going above and beyond in every interaction. Jeannie demonstrates extraordinary sales skills along with her commitment to providing exceptional service to prospective buyers and clients.

Prior to real estate, Jeannie had a successful career at Fidelity Investments. Jeannie worked in Corporate Affairs as the Director of Corporate Sponsorships and Special Events. Traveling nationally and internationally Jeannie gained a strong client and community relationship network that has carried throughout her career.

Jeannie is a graduate of Boston College and resides in Boston.

Eve Szerlip



About Eve

Eve Szerlip is a licensed Real Estate Salesperson. Prior to joining the Caulfield Properties Team, Eve studied Finance at Miami University’s Farmer School of Business. Upon graduation, Eve knew she wanted to pursue a career in Real Estate. The fast-pace climate and relationship-centric industry immediately drew her in!

Dave Spina



About Dave

Dave Spina joins the Caulfield Properties Team as a Licensed Real Estate Salesperson. Dave is the General Manager of Jiffy On Demand, a home maintenance application, in the Greater Boston area. Dave deals with service professionals, clients, and marketing on a daily basis giving him a creative insight into cutting-edge technology and the Boston housing market. Dave is a driven, tenacious, and positive person who prior to his real estate ventures was a professional hockey player for 13 years (7 years NHL/AHL organizations and 6 years in Europe). He graduated in 2005 with a degree in Economics from Boston College and now resides in Needham, Massachusetts with his wife Megan and children Evelyn and Harvey.

Cassandra Svolis



About Cassandra

Cassandra Svolis is a licensed Real Estate Salesperson with the Caulfield Properties Team. As a Massachusetts native with strong family ties to Real Estate and Architecture, the transition to a career in Real Estate was an organic one.

After six years in New York City, Cassandra moved to Boston, where she worked as the Director of Marketing for a liquid alternatives shop, bringing successful change to the company in her three year tenure. While gaining valuable industry experience and knowledge, ultimately this path was not fulfilling and brought Cassandra to realize her true passions lie in her roots. Cassandra is thrilled to bring her passion and knowledge together, while finding joy in guiding clients to find their next home.

Cassandra graduated from Lasell College in Newton, Massachusetts with a degree in Marketing. She currently lives in Beacon Hill and enjoys finding the best restaurants in Boston with friends, and fitting in some travel whenever and wherever she can.