John Dewey Academy, MA homes for sale & real estate

John Dewey Academy, MA Homes for Sale

Charming Renovated Cottage – Great Barrington, MA Beautifully updated 2-bedroom Four Square-style cottage in the desirable "The Hill" neighborhood. This turnkey home features a brand-new kitchen, freshly painted interior, refinished hardwood floors, and energy-efficient Anderson windows throughout. The exterior has been professionally restored and painted, while a newly fenced garden creates a private outdoor oasis. Off-street parking adds everyday convenience. Ideally located just minutes from downtown Great Barrington, Lake Mansfield, and preserved nature trails, this cottage offers easy access to shopping, dining, and year-round cultural and recreational attractions. Whet

John Dewey Academy, MA Homes for Sale

BRIDGERTOWN Investment opportunity or live with income potential. This 2 unit in-town has a 3 bedroom 1 bath on the 1st floor apartment and a 1 bedroom 1 bath on the 2nd floor with room to expand to in the 3rd floor attic space. Walk to town of Great Barrington with all it has to offer, 1/2 block to Co-op and Main St. Utilities are included in rent as electric and heat is combined. 1 car garage attached with more storage. Washer and dryer in basement.

John Dewey Academy, MA Homes for Sale

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion—with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision—be it modern apartments, stylish offices, ret

John Dewey Academy, MA Homes for Sale

The iconic Wainwright Inn, built in 1766, is ideally located on Main Street in Great Barrington, the largest town & hub of the famous Berkshires vacation destination in Western Massachusetts. The Inn consists of a main house with 9 guest suites & a spacious owner's suite, & a carriage house with an apartment & two additional guest suites. In pristine condition, the current owners have improved the property significantly to include: AC system, new kitchen, structural upgrades, new parking lot and landscaping. Solid income and occupancy history. Known for its beauty, the Inn features spacious public rooms with high ceilings, fireplaces and historical details intact, and