The Vassall and Craigie estates contained land and outbuildings for farming.

The Longfellow gardens consisted mainly of decorative flower gardens and, at the north of a property, a "woodland walk".

There was a pond on the property (originally between the two houses now directly to the west) which the children especially enjoyed.

Henry Longfellow had a formal garden designed based on a pattern he had seen.

He combined formal gardens and open areas to allow for ample outdoor living space for his family.

He later added a balustrade to the front yard.

Alice Longfellow worked with two landscape architects, Martha Brookes Hutcheson (1904-05) and Ellen Biddle Shipman (1923-1925) to restore the family garden. She also added a pergola and sundial.