CRAIG DELLA PENNA | NORTHAMPTON REALTOR

Northampton's Rail Trail & Historic Home Specialist

For more than 20 years, Craig Della Penna has helped buyers and sellers who value historic homes, walkable neighborhoods, rail trails, conservation land, and the unique lifestyle of the Pioneer Valley. His expertise goes far beyond real estate—it's rooted in preserving the places that make this region special.

100+

HISTORIC HOMES SOLD

2003

SERVING NORTHAMPTON SINCE

12k

MONTHLY READERS OF MY NEWSLETTER

FEATURED LISTING

310 South Street
Northampton, MA

WHY WORK WITH CRAIG

MORE THAN A REALTOR.

Craig isn't a generalist.

He has built a nationally recognized real estate practice around two passions:

  • Historic and antique homes

  • Homes near rail trails, bike paths, and conservation land

As one of the country's leading advocates for rail trail development, author of five books, and recipient of the National Association of REALTORS® Evergreen Award, Craig offers a perspective few Realtors can match.

Craig is also a Certified Residential Specialist (CRS). Only 2% of Realtors in a given marketplace have this designation. 

A landscape scene with a river flowing through a green valley, surrounded by trees and hills under a blue sky with some clouds, with two bridges crossing the river.
Host with gray hair smiling, standing in front of a promotional graphic for a show called 'Roads Less Travelled' featuring trees, a winding path, and people walking or biking.
A metal bridge crossing over a calm river, surrounded by lush green trees on a sunny day.

FEATURED SPECIALTIES

Historic Homes

Whether it's a Colonial, Victorian, farmhouse, or carefully restored antique home, Craig understands the character, craftsmanship, and challenges that come with owning historic properties.

Homes Along Rail Trails

Few Realtors know rail trails like Craig.

After spending years helping communities create rail trails throughout the Northeast, he built an entirely unique real estate niche helping buyers find homes that embrace active, connected living.

Walkable Village Living

Craig specializes in homes located near village centres, conservation land, walking paths, and neighborhoods that encourage a slower, community-focused lifestyle.

WHAT MY CLIENTS ARE SAYING

TESTIMONIALS

Homes I've Had the Privilege of Representing

Historic homes, village properties, and homes near some of New England's most beloved rail trails.