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.

CONTACT CRAIG

100+

HISTORIC HOMES SOLD

2003

SERVING NORTHAMPTON SINCE

12k

MONTHLY READERS OF MY NEWSLETTER

FEATURED LISTING

310 South Street Northampton, MA

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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.

MORE ABOUT CRAIG

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.

MY PODCAST

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.

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WHAT MY CLIENTS ARE SAYING

TESTIMONIALS

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CLIENT

Ken and Susan R., Northampton, MA

CLIENT

"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.”

CLIENT

Peter W., Ashfield, MA

CLIENT

"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 four!”

CLIENT

Kristen W., Northampton, MA

CLIENT

"I worked with Craig Della Penna, 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.”

CLIENT

MORE 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.

View More Historic Sold Homes

A blue Victorian-style house with a turret and white trim, surrounded by a well-maintained garden and trees.

A green house with a metal roof, two leafless trees in front, an American flag, and a mailbox.

A two-story house with light gray siding, a covered front porch with white railings, numerous windows, and a chimney, surrounded by green trees and bushes under a bright blue sky.

Front view of a white Victorian-style house with decorative trim, black shutters, and a porch with two green chairs.

Yellow two-story house with a front porch and lush green lawn.

Yellow house with white trim, front garden with flower boxes, white picket fence, and a lamp post in the yard.

A two-story house with pink siding, blue shutters, and a wraparound porch, surrounded by a green lawn and trees.

Rural scene with two barns and a house, power lines, and a paved road in the foreground, surrounded by green grass and trees.

A brick house surrounded by green trees and bushes, with a gravel pathway leading to it.

A two-story blue house with white trim, a front porch with white railing, hanging flower baskets, and a well-maintained yard with shrubs and a wooden fence.

A two-story red house with white window shutters and a black roof, surrounded by trees and bushes, on a grassy lawn with a paved street in front.

A large, ornate, Victorian-style house with a steep roof, tower, and wraparound porch, surrounded by green trees and bushes.

An aerial view of a light green house with a gray roof surrounded by trees, shrubs, and a grassy yard, with a driveway and an American flag in the background.

A brick house with a red roof surrounded by trees and shrubs, with a grassy yard in front.

A two-story house with beige siding, white trim, green shutters, and a front porch with white columns, surrounded by trees and greenery.

A purple, two-story house with a front porch, located on a residential street with trees and power lines visible.

A two-story brick house with white trim and a front porch, surrounded by green bushes and plants under a partly cloudy sky.

A large white house with a porch, multiple windows, and a brown roof, surrounded by trees and situated on a grassy area.

A three-story blue house with black shutters on the windows, a white front door with steps, and surrounded by trees and a lawn.

A white two-story house with black shutters, a gabled roof, and a front porch surrounded by snow.

A two-story blue house with gray shutters, a front porch, and a white picket fence in a suburban neighborhood under a clear blue sky.

Green house with screened porch and decorative trim, surrounded by trees and plants.

A two-story green house with a sign labeled 'The Chalet' in a wooded area with snow on the ground.

A red two-story house with green shutters, a small front porch, and a large lawn, set in a wooded area with blue sky and leafless trees.

A large three-story house painted black with multiple windows, brick chimneys, and a wooden front door with steps leading up to it, surrounded by a grassy yard and leafless trees.

Two-story house under construction, with a front porch supported by four columns, partially finished siding, and surrounded by green trees.

White two-story house with green shutters, a front porch with decorative trim, and a driveway with a parked car, surrounded by trees.

A two-story white house with black shutters and a red barn with a small window under a blue sky.

A two-story white house with red shutters, surrounded by greenery, with a lawn and trees in front.

Yellow Victorian-style house with a front porch, surrounded by green trees and lawn, with a detached garage and a driveway.

A large, historic stone house with a porch and multiple windows, surrounded by a lawn and trees, under a partly cloudy sky.

A two-story light blue house with white trim, surrounded by trees and a green lawn, under a cloudy sky.

A large two-story house with dark brown wooden siding, brick accents, multiple windows, and a front porch, surrounded by trees and shrubs, with a driveway in front.

A two-story brick house with a pitched roof and dormer window, front steps, two large bushes flanking the entrance, and a well-maintained lawn.

A large, vintage yellow house with white trim and a wrap-around porch, surrounded by green lawn and trees in the background.

Yellow and purple two-story house with outdoor staircase, surrounded by trees and greenery

A beige multi-story house with white trim, surrounded by a landscaped yard with flower beds and a stone pathway, under a partly cloudy sky.

A two-story yellow house with a porch and green shutters, located on a street with leafless trees in the background.

White two-story house with black shutters, leafless trees, and a front yard with bushes on a sunny day

White multi-story house with black shutters, front yard with bushes and flowers, and a sidewalk in front.

A gray, three-story Victorian house with a front porch, multiple windows, surrounded by trees and grass.

A large, two-story house with yellow siding, black shutters, and a red foundation, surrounded by green grass and trees.