Craig Della Penna, Realtor® | Northampton Real Estate, Amherst Real Estate, Florence Real Estate

     In 2003, I became a realtor with The Murphys Realtors. I focused on a special niche: the sale of houses near to rail trails, greenways, or other conservation lands. This unique real estate practice was recently featured in two national realtor trade magazines, a Boston Globe editorial, an article in the Wall Street Journal, and in United Airlines’ in-flight magazine, Hemispheres.
       I am consistently listed among the top performing realtors in the Five-College area of the Pioneer Valley because I bring innovation and creative marketing to the local real estate market. Earlier in the spring of 2013, I had my 5th book come out and also that same spring, a third book came out that featured some aspect of my creative marketing as a case-study. 

      For 20 years, I marketed rail freight, planned the start-up, and then operated two of the Northeast’s largest railroad-owned trans-loading facilities.   I have a background in RR history, and in 1994, was invited by a regional publisher to author a series of books on old rail lines and their conversion to bike and hike trails. I then got involved in the politics of how these conversions took place and in 1998, was hired by Rails-to-Trails Conservancy as a legislative agent and political organizer in the New England region.
       Because of this work, in their 10th anniversary issue, The Ride magazine named me as the most effective advocate for rail-to-trail issues on the Eastern Seaboard.  And for several years now, I an one of the country’s most in-demand public speakers on the subjects of how rail-to-trail projects impact residential real estate and how they foster sustainable economic development—improve communities. I have given over 1,200 lectures on these subjects in 19 states and Canadian provinces.  And I have helped advance the building of over 1,000 miles of rail trails in the past 15 years.          

         My wife Kathleen and I operate Sugar Maple Trailside Inn, a bed & breakfast located in a restored 1865 farmhouse-style home on Chestnut Street in Florence. The house sits eight (8) feet from southern New England’s first municipally built/operated rail trail. The renovation was recognized in 2003 with a Historical Preservation award by the City of Northampton and around the same time our house was featured on HGTV’s Restore America program. The B&B was also featured in Yankee Magazine’s "Best of New England” 70th Anniversary issue and we typically win "Best in the Valley."

          Because of my demonstrated interest in historic preservation, I am now on Northampton’s Historical Commission and the Board of Historic Northampton, Inc. My real estate practice has reflected this area as well because I’ve sold some of the most dramatic, famous AND historic properties in the Five College area.  Links to more info and all my businesses can be found  at or
Professional Realtor® through the National Association of Realtors®
Member of the Realtor Assoc. of the Pioneer Valley's Presidential Advisory Group for Green Initiatives
Member of the Massachusetts Association of Realtors®
Governor’s Bicycle Pedestrian Advisory Board
Former Co-chair of Mass Highway’s Trails & Greenways Taskforce
Former Chair of the East Coast Greenway’s Massachusetts Committee
Coordinator for the MassCentral Rail Trail Coalition
Member of the City of  Northampton's Historical Commission
Board member of Historic Northampton, Inc.
Board member of the Hampshire County Tourism Council
Board Member for Mass DCR’s Massachusetts Recreational Trail Advisory Board
Board Member for Friends of Schell Bridge, Inc.
Member of the Association of Pedestrian and Bicycle Professionals
Member of the Congress of New Urbanism
Advisory Board Member of the Massachusetts Bicycle Coalition [MassBike]
Professional Association of Innkeepers International


We’ve bought and sold properties before, in both Massachusetts and Maine.

"We’ve bought and sold properties before, in both Massachusetts and Maine, and have been

impressed with your responsiveness, your attention to detail, your willingness to market our

house, and your ability to sell it in a tough market. We have never had such a positive experience

with any other realtor!”
Susan M., Northampton, MA
He’s a complete package ..

"I worked with Craig as he helped my mom move to the area from Wisconsin, and as he helped 

me buy my house in Holyoke and sell my condo in Hatfield. With my mom, he helped her learn about

the community, find a service vendor for  everything, and even get some jobs started. He’s a

complete package: historian, community leader, advocate for so many things I value (community,

bike, the arts, neighborhoods, the environment), and he’s honest, able to handle the complex

emotions that arise  around home buying, a complete teddy bear, patient when he needs to be and

ferocious when we’re at the last straw. He is also wonderfully human- if there is any

communication snafu, he’s the first to take responsibility for where he may have contributed and

focus on what needs to happen next. He’s quite the gentleman, so you quickly realize that you

were really the source of the mix-up. He’s also so understanding when you mess up. He’s got

terrific taste in properties and I think he’s quick to "get” what you are looking for. Case in point,

both my mother and I bought the first house he showed us! I trust Craig  completely, and have so

enjoyed working with him over these past 5 years. Trust and expertise were so important when

selling an unusual and difficult condo in the new and tough condo market.”
Liesel D., Holyoke, MA
He sold it quickly and to qualified buyers...

"A collaborator and consultant to our "Friends of the Canal Walk” advocacy group led to  hiring

Craig to sell my Amherst house last year. He sold it quickly and to qualified buyers who seemed

respectful of the architectural features of the home and preserving the traditional neighborhood.”
Nancy S., Holyoke, MA
... he helped me sell my house in record time, and he helped me buy a new place.

"I recommend Craig- he helped me sell my house in record time, and he helped me buy a new

place. I’m very happy with Craig!”
Catherine R., Northampton, MA
We bought our first home through Craig and we were very satisfied with his professional

approach and knowledge.

"Craig Della Penna has done an exceptional job for us. We bought our first house through Craig

back in 2006, and were very satisfied with his professional approach and knowledge. Needless to

say, when we started looking for our next house, Craig was the first person we called. After

spending a little time with Craig, you will see he has a wealth of information about real estate in

the Pioneer Valley to help you with any questions. And if he doesn’t know the answer, he follows

up within a day.”
Matt and Tammi K., Northampton, MA
Craig helped me in each step of buying my house.

"Craig helped me in each step of buying my house. His knowledge of the buying/selling process

made things go very smoothly. His suggestions and referrals were solid, which made the

inspection and mortgage application procedures go along without a hitch. I always felt he was on

my side.”
Kathy S., Northampton, MA
Helpful and supportive during difficult times.

"Great information. Very responsive. Helpful and supportive during difficult times.”
Maureen F., Northampton, MA
Craig has served as both my listing agent and buyer agent.

"Craig has served as both my seller and buyer agent. As a seller agent, he was helpful in advising

me on some minor home improvements that would make my house more salable. As a buyer agent,

he has patiently shown me houses over the  years, until I found one. After the house inspection, he

handled getting contractors to provide repair estimates. This helped free me of tasks for which I

had no time and in negotiations with the seller over the price and repairs.”
Phil L., Northampton, MA
Keeping the buyer off the roller coaster.

"Craig put in time with me over several years before I finally decided on a property. The purchase

turned out to be a bumpy road, but Craig did well living up to his motto of "keeping the buyer off

the roller coaster.”’
Dale R., Holyoke, MA
I was very happy with Craig.

"He did a good job being patient with us while we struggled with the process of purchasing a

multi-family house.”
Brooke S., Northampton, MA
He is a delight to work with, never once made us feel pressured. I would highly recommend him.

"Craig is fantastic! He recognized that our needs were very specific and he very patiently took us

to many houses until we found the right one. He is a delight to work with, never once making us

feel pressured. I would very highly recommend him.”
Susan B., Whately, MA
Craig was definitely the best at communication, honesty, and market analysis.

"I worked with Craig Della Penna, Murphy’s agent this April and May, and I cannot give him

enough praise. Not only did he do an incredible job selling my house in a difficult market and town,

but he always made me feel supported during the process. I have worked with many real  estate

agents and agencies during my  life, and Craig was definitely the best at communication, honesty,

and market analysis. The best part is that Craig is always honest with you, even if it is not

something you want to hear. I highly recommend that anyone looking for an agent within a 45

minute radius of Northampton works with Craig (I was 45 minutes from Northampton), whether

you are a buyer or seller. You won’t find a better realtor or agency.”
Kristen W., Northampton, MA
My wife and I would recommend Craig in a heartbeat!

"He’s honest, and he offered advice, guidance, and reassurance as we searched for and eventually

settled on an antique home which had a "difficult” seller and a lengthy closing process. Craig was

such a pleasure and an absolute professional. He comes highly recommended from this family of

Peter W., Ashfield, MA

"Craig went above and beyond in every way. He was incredibly knowledgeable and helpful. We

were so impressed by his attention, knowledge, and support. We sing his praises regularly and

already consider him to be a friend.”
Ken and Susan R., Northampton, MA

My Active Properties

My Recently Sold Properties