Communities – Monterey

In it’s history the town was mostly known for its sawmills, but today it is a rural community, known more for its recreational areas in the state forests and along Lake Garfield. Much of the northwest corner of town is dominated by Mount Wilcox and the lower portion of Beartown State Forest. The state forest is crossed by the Appalachian Trail, which crosses from Great Barrington, below the peak of the mountain and on to Sky Hill in Tyringham.

Search new real estate in the Berkshires town of Monterey, MA. Discover hundreds of current listings, including lakeside homes, luxury estates, and residential land. Love what you see? Register with us to save your favorites, and receive notifications when similar properties are listed. Contact us to see any of the homes below!

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40 Sandisfield Rd, Monterey, Massachusetts 01245

Residential For Sale

1Bedroom(s)
1Bathroom(s)
21Picture(s)
704Sqft
SWEET LITTLE COTTAGE WITH MEADOW AND MATURE TREES, LOCATED IN MONTEREY CLOSE TO LAKE GARFIELD, SKI SLOPES AND NUMEROUS HIKING TRAILS. THE COTTAGE HAS A NEW ROOF AND POTENTIAL FOR FURTHER EXPANSION. THE OUTBUILDING HAS POTENTIAL AS A STUDIO OR WORKSHOP. EXCELLENT PROXIMITY TO THE CENTER OF MONTEREY AND JUST 9 MILES TO CENTER OF GREAT BARRINGTON.
$299,000

0 West Rd, Monterey, Massachusetts 01245

Land For Sale

2Picture(s)
2.28Acre
Sweet wooded building lot in a quiet community. Close to Lake Buel, Butternut and Great Barrington.
$75,000

409 Monterey Rd, Great Barrington, Massachusetts 01230

Land For Sale

7Picture(s)
4.71Acre
A great potential investment property. Build your own ''dream ski chalet''! 4.7 acres and 493 feet of road frontage on Monterey Rd. This property is walking distance to Butternut ski resort- Contains a gutted out (fire damaged) main house, and two outbuildings- restorative or new building potential. We have acquired new approved septic plans.
$210,000

0 Lake Ave, Monterey, Massachusetts 01245

Land For Sale

2Picture(s)
0.77Acre
Sweet wooded building lot in a quiet community. Close to Lake Buel, Butternut and Great Barrington. Additional land is available.
$50,000

0 West Rd, Monterey, Massachusetts 01245

Land For Sale

2Picture(s)
0.41Acre
Sweet wooded building lot in a quiet community. Close to Lake Buel, Butternut and Great Barrington. Come Build your dream home! Additional land is available.
$50,000

99 Hupi Rd, Monterey, Massachusetts 01245

Residential For Sale

4Bedroom(s)
4Bathroom(s)
43Picture(s)
3,300Sqft
A waterfront dock on Lake Garfield comes with this Contemporary Craftsman home perched on Mount Hunger with extraordinary panoramic views over the lake all the way to the Catskill Mountains. As spotless as the day it was built, it's hard to step away from the view enjoyed by almost every room on three floors including the screened porch and deck that spans the length of the house.
$2,250,000

212-214 Blue Hill Rd Rd, Monterey, Massachusetts 01245

Residential For Sale

7Bedroom(s)
9Bathroom(s)
80Picture(s)
6,510Sqft
SUPERB COUNTRY ESTATE WITH 2 HOMES AND WESTERLY VIEWS.This is, simply put, one of the best locations in the Berkshires. Set on bucolic, beautiful, Blue Hill Rd, surrounded by Beartown State Forest, this magnificent property boasts two compelling homes, a paddock, a stream-fed swim pond, and a hand-hewn log cabin.
$3,250,000

57 Art School Rd, Monterey, Massachusetts 01245

Residential For Sale

6Bedroom(s)
6Bathroom(s)
53Picture(s)
4,468Sqft
Private Country Estate with Pool. Sunny and wonderful open plan Great Room with stone fireplace and gourmet Kitchen. Celebrate in the intimate Dining Room or the double sized custom Screened Patio overlooking the Pool. Private Office. Primary Bedroom Suite, including Laundry on the Main Floor. Upstairs there are 4 Bedrooms and 2 full Baths.
$1,300,000

664 Main Rd, Monterey, Massachusetts 01245

Residential For Sale

4Bedroom(s)
3Bathroom(s)
19Picture(s)
2,464Sqft
Lovingly remodeled neo-colonial on 5.8 acres in wonderful Monterey. Set far back from the road & very quiet. Spacious open plan kitchen, dining & living area. Kitchen has ample quartz counters, new stainless appliances & slate floors. The dining/living areas have 6'' oak flooring. Big rear deck.
$599,000

540 Main Rd, Monterey, Massachusetts 01245

Residential For Sale

3Bedroom(s)
2Bathroom(s)
8.00Parking(s)
26Picture(s)
2,379Sqft
This outstanding 140+ acre property, with a picturesque 2,379SF Cape, is located very close to the center of Monterey, a terrific Southern Berkshire County Community. Several well-maintained outbuildings add to the utilitarian value of this expansive one-of-a-kind property, which includes a 20 acres pond, hiking trails, and frontage on two paved roads.
$1,100,000

255 Hupi Rd, Monterey, Massachusetts 01245

Residential For Sale

3Bedroom(s)
3Bathroom(s)
26Picture(s)
2,500Sqft
Located on a beautiful and quiet side road just a walk or bike ride away from Monterey Town Beach this lovely three story, three bedroom, three bath home abuts town-owned Brewer Pond property. The exterior was newly painted last summer and the inside is fresh, white and bright.
$795,000

235 Main Rd, Monterey, Massachusetts 01245

Residential For Sale

3Bedroom(s)
4Bathroom(s)
37Picture(s)
4,000Sqft
Location and space make this home a desirable property for the buyer with lots of family and friends. The large open plan living space and kitchen is the perfect setting for social gatherings. Steps down to the den offers yet another space for the overflowing guests to enjoy. Bedrooms are very well proportioned and separated from one another for privacy.
$689,000
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