Friday Front Porch Feature: A Family Home With Lots of Land
CHESHIRE, Mass. — Are you looking for a great family home with view of Mount Greylock? Then this is the home for you.
Our Friday Front Porch is a weekly feature spotlighting attractive homes for sale in Berkshire County. This week, we are showcasing 20 Pleasant View Drive.
There's a finished basement with an exercise room and workshop/mechanical area, and an attached two-car garage. The asking price is $849,000.
The home is listed with Moresi Real Estate Partners and we spoke with agent Sean Taylor, who also sat down with the owners, about this house.
What do you think makes this property a standout in the current market?
Taylor: What really makes this home special is the open floor plan — ideal for entertaining, cooking, or just relaxing with loved ones. You can unwind in the three-season room or cozy up by the double-sided, fieldstone fireplace. No matter where you are, inside or out, there's always a space to enjoy peace and comfort.
What was your first impression when you walked into the home?
The moment I walked in, I was struck by how beautiful every room is — thoughtfully designed, well-appointed, and full of charm. And those views! You can see in every direction, with some of the most stunning scenery in Berkshire County.
How would you describe the feel/atmosphere of the home?
The layout of this house is perfect for raising a family or hosting friends. The owners loved watching the sun rise and set over the property and spotting wildlife throughout the seasons. It has been a house filled with love, laughter, and happy memories — and they hope the new owners will feel the same warmth and joy.
What kind of buyer do you see this house being perfect for?
This home really suits so many lifestyles. Families will enjoy the big yard for sledding and the layout with the kids' rooms upstairs and the primary suite downstairs. It is also perfect for retirees who want the comfort of first-floor living with everything they need on one level. And for those looking for a getaway, it's close to favorites like Jiminy Peak, Mass MoCA, and Tanglewood — an ideal second home in the Berkshires.
Are there any standout design features and or recent renovations?
As the original owners, a lot of thought was put into every part of this home and it really shows. Recent renovations have enhanced the home's comfort and appeal. From the playroom and workout room in the basement to the open concept main floor and bright sunroom, every space was designed to be beautiful and practical for everyday living.
Do you know any unique stories about the home or its history?
The property has always had a special connection to its surroundings. The land this home sits on has been in the same family for over 150 years — a place full of stories, history and generations of care. Nestled on over 15 acres, the property continues to be a special spot where families and traditions can continue.
What do current owners love about this house?
The owners have loved everything about this house! They speak most fondly of the serenity and beauty surrounding the home. It's been a place filled with love, laughter, and family gatherings, where children grew up and memories were made. They have cherished the peaceful setting, the open spaces for entertaining, and the sense of warmth that fills every room.
What would you say to a buyer trying to imagine life in this space?
Imagine mornings filled with sunlight streaming into the house, coffee in the sunroom as wildlife stirs outside, and evenings gathered around the double-sided fireplace. This home was designed for connection — a place where family and friends come together, where laughter fills the rooms and where every season in the Berkshires feels special. With surrounding landowners maintaining large parcels, the home enjoys both privacy and the peaceful feeling of country living.
You can find out more about this house on its listing here.
*Front Porch Feature brings you an exclusive to some of the houses listed on our real estate page every week. Here we take a bit of a deeper dive into a certain house for sale and ask questions so you don't have to.
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