Chapin Fish: A Legacy of Dedication and Excellence in Berkshire Real Estate
With over 20 years of experience and a reputation for outstanding results, Chapin Fish has become a trusted leader in Berkshire real estate. Formerly the Broker-Owner of Brockman Real Estate—a boutique firm synonymous with luxury properties in the Berkshires—Chapin is now proud to align with William Pitt Sotheby’s International Realty, the world's premier luxury real estate brokerage. This partnership combines his unparalleled local expertise and client dedication with Sotheby’s global reach and marketing power, reinforcing his commitment to delivering exceptional results.
Chapin’s approach is grounded in genuine care, active listening, and a dedication to his clients’ success. Over the years, his clients have chosen him not only for his expertise but also for his ability to navigate both the happiest and most challenging transitions with empathy and professionalism.
A Proven Track Record
Chapin’s portfolio features an impressive array of transactions, including significant estates, waterfront retreats, historic homes, and complex land parcels. With nearly 400 transactions and over $218 million in sales, he ranks among the top brokers in the Berkshires. Yet, for Chapin, success is measured by the relationships he builds and the trust his clients place in him—not just the numbers.
A Foundation of Values
Chapin credits his mentors, Bill Brockman and Jack Jefferson, for shaping his approach to real estate. Bill’s philosophy that "real estate is about listening to people and appreciating their needs" remains at the heart of Chapin’s work. These values have helped Chapin become one of the top-performing brokers in the region over the past two decades.
Deep Roots and Community Commitment
A native of a historic maritime village on Long Island, Chapin’s life has been enriched by diverse experiences—from studying in Sweden to traveling across six continents. He holds a degree from Washington University in St. Louis and has pursued careers in both the travel industry and professional acting. Twenty years ago, Chapin returned to his New England roots, where his family’s history dates back to 1640, and settled in Sandisfield with his husband and three children.
Chapin is deeply committed...
Chapin Fish: A Legacy of Dedication and Excellence in Berkshire Real Estate
With over 20 years of experience and a reputation for outstanding results, Chapin Fish has become a trusted leader in Berkshire real estate. Formerly the Broker-Owner of Brockman Real Estate—a boutique firm synonymous with luxury properties in the Berkshires—Chapin is now proud to align with William Pitt Sotheby’s International Realty, the world's premier luxury real estate brokerage. This partnership combines his unparalleled local expertise and client dedication with Sotheby’s global reach and marketing power, reinforcing his commitment to delivering exceptional results.
Chapin’s approach is grounded in genuine care, active listening, and a dedication to his clients’ success. Over the years, his clients have chosen him not only for his expertise but also for his ability to navigate both the happiest and most challenging transitions with empathy and professionalism.
A Proven Track Record
Chapin’s portfolio features an impressive array of transactions, including significant estates, waterfront retreats, historic homes, and complex land parcels. With nearly 400 transactions and over $218 million in sales, he ranks among the top brokers in the Berkshires. Yet, for Chapin, success is measured by the relationships he builds and the trust his clients place in him—not just the numbers.
A Foundation of Values
Chapin credits his mentors, Bill Brockman and Jack Jefferson, for shaping his approach to real estate. Bill’s philosophy that "real estate is about listening to people and appreciating their needs" remains at the heart of Chapin’s work. These values have helped Chapin become one of the top-performing brokers in the region over the past two decades.
Deep Roots and Community Commitment
A native of a historic maritime village on Long Island, Chapin’s life has been enriched by diverse experiences—from studying in Sweden to traveling across six continents. He holds a degree from Washington University in St. Louis and has pursued careers in both the travel industry and professional acting. Twenty years ago, Chapin returned to his New England roots, where his family’s history dates back to 1640, and settled in Sandisfield with his husband and three children.
Chapin is deeply committed to his community. He has served as a volunteer firefighter for nearly two decades, as a trustee of the Bidwell House Museum since 2008, and was a President of the Berkshire County Board of Realtors. He and his family are also restoring the historic Monterey General Store, aiming to create a vibrant community hub that honors its 18th-century legacy while looking to the future.
A Life Built on Relationships
At the core of Chapin’s career is a strong belief in fairness, decency, and generosity. His work is built on referrals and a reputation for integrity. Whether helping a family find their dream home or guiding a seller through a complex transaction, Chapin approaches each client with dedication and care, making him a partner you can trust in any real estate journey.
Chapin Fish: A Legacy of Dedication and Excellence in Berkshire Real Estate
With over 20 years of experience and a reputation for outstanding results, Chapin Fish has become a trusted leader in Berkshire real estate. Formerly the Broker-Owner of Brockman Real Estate—a boutique firm synonymous with luxury properties in the Berkshires—Chapin is now proud to align with William Pitt Sotheby’s International Realty, the world's premier luxury real estate brokerage. This partnership combines his unparalleled local expertise and client dedication with Sotheby’s global reach and marketing power, reinforcing his commitment to delivering exceptional results.
Chapin’s approach is grounded in genuine care, active listening, and a dedication to his clients’ success. Over the years, his clients have chosen him not only for his expertise but also for his ability to navigate both the happiest and most challenging transitions with empathy and professionalism.
A Proven Track Record
Chapin’s portfolio features an impressive array of transactions, including significant estates, waterfront retreats, historic homes, and complex land parcels. With nearly 400 transactions and over $218 million in sales, he ranks among the top brokers in the Berkshires. Yet, for Chapin, success is measured by the relationships he builds and the trust his clients place in him—not just the numbers.
A Foundation of Values
Chapin credits his mentors, Bill Brockman and Jack Jefferson, for shaping his approach to real estate. Bill’s philosophy that "real estate is about listening to people and appreciating their needs" remains at the heart of Chapin’s work. These values have helped Chapin become one of the top-performing brokers in the region over the past two decades.
Deep Roots and Community Commitment
A native of a historic maritime village on Long Island, Chapin’s life has been enriched by diverse experiences—from studying in Sweden to traveling across six continents. He holds a degree from Washington University in St. Louis and has pursued careers in both the travel industry and professional acting. Twenty years ago, Chapin returned to his New England roots, where his family’s history dates back to 1640, and settled in Sandisfield with his husband and three children.
Chapin is deeply committed to his community. He has served as a volunteer firefighter for nearly two decades, as a trustee of the Bidwell House Museum since 2008, and was a President of the Berkshire County Board of Realtors. He and his family are also restoring the historic Monterey General Store, aiming to create a vibrant community hub that honors its 18th-century legacy while looking to the future.
A Life Built on Relationships
At the core of Chapin’s career is a strong belief in fairness, decency, and generosity. His work is built on referrals and a reputation for integrity. Whether helping a family find their dream home or guiding a seller through a complex transaction, Chapin approaches each client with dedication and care, making him a partner you can trust in any real estate journey.
Read Less
Working with Chapin Fish was hands-down one of the best decisions we've ever made. From the very beginning, he was more than just a realtor—he was a true partner in helping us find our forever home. His deep knowledge of the market and ability to navigate every step with care and confidence made the entire process smooth and enjoyable. But what really sets Chapin apart is how his commitment doesn't end when the papers are signed. He continues to check in on us, offering support and making sure we’re fully settled—even going so far as to deliver an AC unit during a heatwave, just to make sure we were comfortable. That level of thoughtfulness and integrity is incredibly rare. If you're looking for someone who’s not only skilled but genuinely cares, Chapin is the person you want by your side. He’s knowledgeable, trustworthy, and kind—and we absolutely recommend him to anyone seeking a home and a great experience.
Chapin went above and beyond!
Chapin did an amazing job, in many ways, starting with finding us the "needle in haystack" perfect property for us. He was instrumental is helping solve an issue that came up early in negotiations with the seller's agent and was with us every step of the way. I can't say enough nice things about him.
As a first time homeowner, Chapin made this process easeful and informative. His warm welcoming energy during the initial tour was carried throughout the entire process until closing. He made himself available for any questions or follow-up that was needed. I would highly recommend him to work with anyone looking to purchase a home.
Where to begin? Chapin Fish is such a special human being and throughout our entire journey with our real estate I found myself thinking of him more as a best friend than just as our agent. Our situation was extremely challenging and almost impossible at times, I never imagined that things would work out as well as they did and as quickly. Chapin goes above and beyond what one could expect, he invests his entire energy and is completely transparent, professional and authentic. His expertise, his wisdom, his style and opinions are all so helpful almost miraculous at times. Graceful, Dedicated and True are words that I would use to describe Chapin, although he is so much more. It's hard to relate everything that makes Chapin so special because he is such a one of a kind treasure and the list would be endless. If we had known he was so wonderful maybe we would have not moved! We look forward to continuing our friendship with Chapin into the future and we highly recommend his services, you'll be amazed! We call him the 'Real Estate Whisperer' Chapin, you're awesome, we are so very grateful for everything you've done for us. -Lisa&Rick
Chapin was great to deal with. Had a great experience.
We were very happy that we listed our Berkshire property with Chapin He handled the listing as a true professional.
Chapin was helpful, thoughtful, and enthusiastic about the listing. I appreciate the guidance we were given during the process.
Excellent and professional
We worked with Jared Kelly as our buyer's agent. Jared was fantastic: thoughtful, responsive, and well informed about all of the issues. He also referred us to a great inspector and r.e. atty to represent us at the closing. We highly recommend working with Jared.
Chapin Fish is an extraordinary real estate broker; intelligent, thoughtful, and has an acute understanding of the real estate market in the Berkshire area. We faced various complications while preparing for the sale of our historic house. Chapin advised us and carried us through them all with remarkable support and grace. He is a pleasure to work with and a top notch professional.
Our realtor, Chapin Fish, understood our goals and tailored his recommendations accordingly. He did not waste our time by having us look at properties that did not meet our criteria. He is very knowledgeable about the area and was able to steer us away from properties that did not meet our needs. Chapin was responsive and researched questions we had. I would trust Chapin with any future real estate dealings.
| 4 Beds | 4/1 Baths | 3,100 Sqft | 5.13 Acres |
Step onto a property as striking as the Berkshires themselves—where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The...
| 21.3 Acres |
OWN THE ENTIRE NORTH SHORE OF a 10 ACRE POND. Tucked into the quiet SE corner of the Berkshires, this is a property where the pace of the world seems to slow. 21.3 acres in all,...
| 3 Beds | 2/1 Baths | 3,443 Sqft | 65.16 Acres |
They don't build love at first sight anymore, either. But Sky Hill Farm - a genuine 1798 Federal colonial in Tyringham Valley - has been creating that exact feeling for over...
| 5 Beds | 6/1 Baths | 7,331 Sqft | 7.3 Acres |
Luxe lake living at its finest! Rarely does a large waterfront estate come to the Berkshires' market, let alone one recently built and exquisitely executed. 707 Stratford Rd...
| 7 Beds | 9/1 Baths | 9,500 Sqft | 11.05 Acres |
| 4 Beds | 4/1 Baths | 5,800 Sqft | 12.35 Acres |
Spectacular Contemporary Atop the Berkshires Masterful architecture. Epic views. Coming to the market for the first time, this stunning contemporary fulfills every wish list....
| 13 Beds | 9/2 Baths | 9,587 Sqft | 119.56 Acres |
MORNINGSIDE, TYRINGHAM A spectacular estate dating back to the Tyringham Shakers. An extraordinary, & unique opportunity to own a part of Berkshire history. Overlooking Tyringham...
| 8 Beds | 6/1 Baths | 7,492 Sqft | 91 Acres |
Contemporary 5 BR estate home, reno'd 2014, pool, pool hse, & 3BR guest quarters over carriage barn. Incl. is 7 Dellea, a 2 bedroom ranch, 1,292 sf + finished basement rms. Pastoral...
| 8 Beds | 6/1 Baths | 5,000 Sqft | 10 Acres |
AN EXQUISITE, FULLY REMODELED CONTEMPORARY HOME & ESTATE Rarely does a property come on to market that offers all the features today's discriminating buyer is seeking. This is...
| 12 Beds | 8/1 Baths | 7,931 Sqft | 433 Acres |
| 12 Beds | 8/1 Baths | 7,931 Sqft | 433 Acres |
| 5 Beds | 5/1 Baths | 5,600 Sqft | 12.3 Acres |
CHANTERWOOD: BERKSHIRE WATERFRONT ESTATE ON GOOSE POND-ONE OF NEW ENGLAND'S FINEST LAKES! 300' of shoreline + private sandy beach, dock, privacy, & 12 acres divided into 3 parcels...
| 4 Beds | 5/2 Baths | 6,600 Sqft | 26.57 Acres |
Many dream of converting a historic barn into a country house. A barn tells a story, has a past, and the old beams, posts and boards have a patina and a magic which new construction...
| 4 Beds | 5/2 Baths | 6,600 Sqft | 26.57 Acres |
Sell Your Home
