Meet Our Agents

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Anthony Caropreso is a licensed Massachusetts Real Estate Broker. Born and raised in the Berkshires, he is knowledgeable of the area, schools,  cultural offerings and keeps informed on the business community.

Public Service:

• Currently serving as Corporator of  Adams Community Bank.
• Actively serving as a member of Lee Board of Assessors Chairman.
• 2000-2013, served as a member of the Lee Planning Board.
• 1997-2000, served as a member of the Lee Finance Committee.
• 1987-1997, served on the Lee Community  Development Corporation which developed Quarry Hill Business Park on  Rte. 102 in Lee and administered the Lee Small Business Loan Program.

Lisa Thomson-Kelley is a native of the Berkshires with three decades of experience. She has been the driving force behind many seamless, successful real estate transactions - earning her a reputation as a top-tier agent with the ability to secure the best outcomes for her clients. Since 1993, she has helped countless families, investors and second home buyers navigate the ever-changing market. Her clients don’t just buy homes, they make smart investments.

Growing up in the Berkshires, Lisa’s deep roots in the community have shaped her approach. Having raised her family in this beautiful region and continuing to live and work here, she brings an insider’s perspective and a heartfelt commitment to every neighborhood she serves. Beyond her professional success, Lisa is an active community leader, serving on multiple committees that give back to the Berkshires. Her passion and professionalism make her the go-to real estate expert for buyers, sellers, and investors alike. If you are looking for a real estate partner with the expertise, strategy, and heart to get you results, discover the difference and look no further than Lisa Kelley.

With deep roots in the Berkshires, I bring extensive knowledge and a passion for guiding buyers and sellers through every step of the real  estate process. My priority is to ensure that my clients feel confident and informed, whether finding the perfect home, making a sound  investment, or selling with ease. Known for my responsiveness, attention to detail, and problem-solving skills, I go the extra mile to make each transaction as smooth as possible.

Beyond real estate, I've been actively involved in my community for years. I served on the Planning Board for eight years before being elected Town Moderator and served on the board of Greenock Country Club  for six years. As the former Lee High Golf coach (2013-2018), I was  honored to lead my team to two Western Mass titles and earn Coach of the  Year twice.

My wife, Jen, and I love calling Lee home, where we raise our son, David, daughter Giana, and our standard poodle, Geno. Whether you're  looking for your first home, a second home in the Berkshires, or the  right buyer for your property, I'd love to help!

Jessie Carlino joined MacCaro in 2024.  While at MacCaro, she has earned her C2EX recognition and her Broker license.  With a strong background in hospitality, Jessie truly enjoys connecting with her clients and sharing her knowledge of the Berkshires. As a full-time Realtor, she enjoys working closely with her clients each step of the way through the buying and selling process. 

Jessie has always had a passion for the outdoors. She grew up skiing the local mountains and has spent the last 15 years hiking the Berkshires with her dog Molly. Through this she has gained appreciation and knowledge of what the Berkshires have to offer.  She and her husband Taylor reside in Pittsfield with their two sons, Giovanni and Luca.