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Homes in the Southernmost Berkshire Towns

The shortest distance between New York City and relaxation brings you to these charming houses in the area's southernmost town.


One of the nicest homes in the desirable Otis Wood Lands
383 Deer Run
Sandisfield, Mass.

4 Beds/2 ½ Baths/2350 sqft
Offered by Jeff Wilkinson, Southern Berkshire Realty, 413-269-7600

BEAUTIFUL-Simply one of the nicest homes in Otis Wood Lands. Big, light-filled great room, huge screened porch, convenient kitchen & main-level master suite w/whirlpool. Nice den with a wood stove plus 3 good-sized guest bedrooms. Very quiet location abutting a state forest with miles of hiking and cross country ski trails. Located in desirable Otis Wood Lands with a private lake & beach, club house & fitness center, pool & tennis. Conveniently located near Tanglewood, Jacobs Pillow and most other popular Berkshire destinations, yet only 2 3/4 hrs to NYC or 2 hrs to Boston.


East Country Living in The Berkshires
110 Mill River-GB Road
New Marlborough, Mass.

2 Beds/1 Bath/1438 sqft
Offered by Dan Alden, William Pitt Sotheby’s, 413-335-9300

Picture-perfect Greek Revival farmhouse just a short stroll to the bucolic village of Mill River. An ideal country pied-a-terre, this home has been tastefully updated to offer the quintessential Berkshire getaway experience for all seasons. The first floor features an inviting sunroom, bright living and dining area with pellet stove, cook’s kitchen with family room and a full first-floor bath with laundry. The second floor offers two bedrooms, full bath and bonus nook. Exterior features include beautiful trees and landscaping, bluestone patio with stone walls and a privately fenced back yard. 15 minutes to downtown Great Barrington, skiing at Butternut, walking and biking distance to some of the most beautiful trails and rivers of the Berkshires, all just 2.5 hrs to NYC and Boston metro areas.


Walk to Town: Great Barrington
69 Castle Street
Great Barrington, Mass.

3 Beds/2 Baths/1320 sqft
Offered by Helen Mullany, Helen Mullany Real Estate LLC, 413-429-7733

In-town convenience, this carriage house has beautiful porches, wood floors, kitchen with granite and stainless steel, three bedrooms, and good work and hobby space. Yoga studio, bandstand, restaurants, farmers market just out your door. Walking distance from NYC bus. Private fenced-in backyard with fire pit and deck off the living room to enjoy.


Casual & Sophisticated with the most Amazing Views & more
927 Boardman Street
Sheffield, Mass.

5 Beds/3 ½ Baths/3679 sqft
Offered by Stone House Properties, 413-528-4211

This magical property is an ideal blend of country comfort with hip chic style. The ease and elegance were designed for those desiring a casual Berkshire lifestyle. The floor plan is perfect for gathering friends & the attention to detail is evident the minute you walk in the door ~ prepare to be wowed! The kitchen is awe inspiring as the focal point of the house and will entice even the most novice of cooks! Cathedral ceiling, exposed preserved beams, pizza oven, & LaCanche range are just a few of the highlights. The wall of glass from the living room takes in the VIEW and has a fireplace for cool Berkshire evenings. The property and VIEWS are breathtaking and the wide open skies showcase the surrounding fields, mountains, pond, and DRAMATIC NIGHTLY SUNSETS. STUNNING!



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Ideally situated in the heart of downtown Stockbridge, and move-in ready

Elle Villetto and Jared Kelly of William Pitt Sotheby’s International Realty offer an 1860 colonial home, stylishly updated and move-in ready. See it now and be in before the summer!

A minimalist condo with maximum light

We often referred to this project as the “house of glass” because there is glass everywhere.

Berkshire region real estate sales

Weekly real estate transactions for Berkshire County in Massachusetts, Litchfield County in Connecticut, and Columbia County in New York.

The Edge Is Free To Read.

But Not To Produce.