Monterey, MA Homes for Sale

Welcome to a rare waterfront oasis offering over 650 feet of private frontage on the deepest part of Hayes Pond. Your private dock and beach area provide direct access to swimming, kayaking, and fishing, while a perfectly positioned gazebo is ideal for entertaining by the water. Inside, breathtaking water views grace every room through expansive windows. The open-concept design flows seamlessly

Tony Segalla LANCE VERMEULEN RE, INC

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

Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

Tucked away on a quiet 10.5-acre lot in low-tax Monterey, this stylish 1980's deck-style home offers 4 bedrooms and 2.5 bathrooms. There is also a bonus room/office in the primary suite and a den/family room downstairs. In the main living room, filled with character and light, you'll find a wood-burning fireplace and sliding doors that flow seamlessly to the the expansive back deck and screened

Kate Lascar COMPASS MASSACHUSETTS , LLC GB

This fully renovated 3-bedroom, 2-bath home on Peppermint Brook--an estuary of Lake Garfield--offers bright, open living with a seamless indoor/outdoor feel. Renovated in 2019 with thoughtful design, it includes a sleeping loft and a flexible third bedroom that can double as a den. Launch your kayak, canoe, or paddleboard right from the backyard into the brook, to the lake. While part of Sylvan

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard

Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Brookbend Condominiums were converted from a c.1790 former Inn, when Monterey was a bustling little village. Now it's a beautiful Hill Town with the best lake in the Berkshires - Lake Garfield.This lovely unit is flooded with light and quiet, located in back facing both south and west. In mint condition with a glassed heated porch, and a patio outside the door, summer and fall are filled with

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

Private Log Cabin Retreat on 18+ Acres with River Frontage -Escape to your own slice of secluded Berkshires with this classic log cabin set on over 18 private acres. Surrounded by nature, this home offers peaceful living with unmatched charm and character.A welcoming wrap-around porch invites you to relax and take in sweeping views of the property. Inside, the main floor features a dining room, a

Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Nestled in an idyllic, peaceful setting on nearly 26 acres this charming rustic log cabin offers the perfect blend of privacy, tranquility, and natural beauty. Located in a quiet, serene area, this home promises absolute solitude while being just moments away from the stunning waters of Lake Garfield, to which you have deeded rights w/shared dock. Whether you're seeking a year-round residence or

Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This Timber Fame (open floor plan) contemporary home features beautiful (wide-plank) pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the

George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

A rare Lake Garfield offering - this 3300sf home sits on over an acre with sweeping southerly views across the lake's widest point. The expansive great room--encompassing living, dining, and kitchen--opens to two-story lakeside decks, as do the sunroom and primary bedroom, and rooms below. Two guest bedrooms and another full bath complete the main level, which also features two built-in A/C

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

This rare find, located on the Great Barrington/Monterey line, offers the right buyer a unique opportunity to live, work, and play in the heart of the Berkshires. Situated on 4.32 acres, this 1958 ranch-style home has evolved over the years into a sprawling 5,200 square-foot property boasting endless potential. While it currently serves as an owner-operated wellness facility, an expansive

Cortney Dupont COHEN & WHITE ASSOCIATES

One of the oldest homes in Monterey, this stately Colonial built in 1750 sits proudly at the forefront of a picturesque 28-acre parcel across from a 12,000 acre state forest. Located on a quiet dirt road up from Lake Garfield, the property offers a storybook setting with mature gardens, two private ponds, and two brooks. The setting is rich with natural beauty.Inside, the home features three

Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

Discover Stevens Lake! This incredible property offers you a lifestyle that is unmatched in the modern world. The residence is perched overlooking the lake to experience spectacular sunrises. Entering from the garage there is a mud/laundry room which opens to the kitchen fit for any Chef. The kitchen features granite counters, Subzero and Viking appliances, a large pantry with an additional

Derek Strzepa NOCHER REALTY

Renovated beautifully in 2023, this contemporary home is on 3.31 acres , includes a .22-acre parcel on Lake Garfield. Built in 1987 this four bedroom, 3 bath contemporary home is nestled in a wooded grove approximately 1/2 mile from the public beach at Lake Garfield. Enter the light filled living area with 1/2 cathedral ceiling and fireplace. There is an efficient kitchen layout with access to a

Matt Carlino MACCARO REAL ESTATE

LAKE BUEL, NEW MARLBOROUGH COTTAGE!For the past 60 years this cottage has been a source of joy for the same family, now it is your turn. Affordable, simple, rustic three season cottage with deeded access to the lake. Well loved and nicely maintained, with updated kitchen, and a beautiful stone fireplace for those chilly evenings. Nice open plan Living/Dining area. Relax on the Deck or gather

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

LAKE LIVING DONE RIGHT! Year round retreat in the Lake Buel Community. Thoughtfully designed spaces, cozy & unpretentious. The living area, comfortable for family & guests, has vaulted ceiling and Gas Fireplace, making this home just as inviting in the cooler months. Kitchen is functional, attractive and updated. Simple lines, wainscoting, wood floors, ductless A/C units. The Sunroom is perfect

Helen Mullany HELEN MULLANY REAL ESTATE, LLC