Berkshire, MA Homes

• 

  

  

  /56

  $3,600,000

  • 4 Beds
  • 3.5 Baths
  • 3,313 Sq Ft

  147 Hupi Rd, Monterey, MA 01245

  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

  147 Hupi Rd, Monterey, MA 01245
• 

  

  

  /47

  $1,750,000 Sold Jul 11, 2025

  • 2,300 Sq Ft
  • $761/SF
  • 1 Day On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  20 Lakeside Terrace, Monterey, MA 01245

  Fabulous Lakefront Family Retreat on Lake Garfield--an exceptional opportunity to own a year-round retreat in the heart of the Berkshires. Nestled in a serene location, this 4 BR, 3 BA gem offers 2,300 sq.ft. of lakefront living w/ all the comforts of home & the natural beauty of lakeside tranquility. Built in 1986 & thoughtfully updated over the years, this warm & inviting home features

  Claire Pollart LANCE VERMEULEN RE, INC

  20 Lakeside Terrace, Monterey, MA 01245
• 

  

  

  /39

  Est $916,807 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,900 Sq Ft

  205 Main Rd, Monterey, MA 01245

  205 Main Rd, Monterey, MA 01245
• 

  

  

  /32

  $1,149,000

  • 4 Beds
  • 2 Baths
  • 1,298 Sq Ft

  35 Bidwell Rd, Monterey, MA 01245

  A quintessential Lake Garfield home, originally built in the 1920s, now offers classic Berkshire lakefront living. With four bedrooms and two full baths, there's plenty of room for guests year-round. The property includes two parcels--one with the house, the other with a dock and the potential to build another home, creating a lakeside compound. Updates over the years include a roof, siding,

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  35 Bidwell Rd, Monterey, MA 01245
• 

  

  

  /63

  $620,000 Sold May 30, 2025

  • 2,117 Sq Ft
  • $293/SF
  • 187 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2000

  181 Main Rd, Great Barrington, MA 01230

  Meadowside is a custom built Segalla home that is a wonderful 3-bedroom, 2.5-bathroom contemporary home on 3.3 bucolic acres in Monterey. Open plan offers a half bath/ laundry room combo off the spacious kitchen, dining room, and living room that are just drenched in natural day light. Sleeping quarters have their own wing, down the hall are two good sized bedrooms, both contain large light

  David Carlson FAIRGROUND REAL ESTATE, INC

  181 Main Rd, Great Barrington, MA 01230
• 

  

  /53

  Est $2,234,470 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 6,217 Sq Ft

  6 Bidwell Rd, Monterey, MA 01245

  6 Bidwell Rd, Monterey, MA 01245
• 

  

  /36

  $850,000

  • 10 Beds
  • 4 Baths
  • 5,293 Sq Ft

  458 Monterey Rd, Great Barrington, MA 01230

  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

  458 Monterey Rd, Great Barrington, MA 01230
• 

  

  /57

  $1,525,000 Sold May 13, 2025

  • 3,495 Sq Ft
  • $436/SF
  • 190 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  112 Tyringham Rd, Monterey, MA 01245

  Situated on 2.4 acres, this gorgeous home is a short walk from Lake Garfield's public beach and close to the Berkshires' top attractions. Inside, 12-foot ceilings and an open floor plan create a lofty feel in the oversized kitchen and living area. A wide panoramic door (with a screen) leads to a massive deck, ideal for outdoor entertaining. The primary suite offers a large walk-in closet and

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  112 Tyringham Rd, Monterey, MA 01245
• 

  

  /39

  Est $432,484 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,424 Sq Ft

  335 Main Rd, Monterey, MA 01245

  335 Main Rd, Monterey, MA 01245
• 

  

  /84

  $2,399,990

  • 6 Beds
  • 5.5 Baths
  • 6,000 Sq Ft

  141 Stevens Lake Way, Monterey, MA 01245

  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

  141 Stevens Lake Way, Monterey, MA 01245
• 

  

  /32

  $1,375,960 Sold Mar 31, 2025

  • 2,754 Sq Ft
  • $500/SF
  • 199 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1997

  142 Main Rd, Great Barrington, MA 01230

  On the Water in Monterey! This one owner Colonial styled residence is now on the market for the first time in 27 years. As part of the Steven's Lake private association, you can enjoy swimming and kayaking without the constant noise and the disruption of power boats. The screened porch and open area deck are idyllic for your own relaxation or for entertaining guests. With updating here and

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  142 Main Rd, Great Barrington, MA 01230
• 

  

  /28

  Est $504,356 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,776 Sq Ft

  346 Main Rd, Monterey, MA 01245

  346 Main Rd, Monterey, MA 01245
• 

  

  /40

  $1,590,000

  • 11 Beds
  • 12.5 Baths
  • 8,134 Sq Ft

  518 Main St, Great Barrington, MA 01230

  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

  518 Main St, Great Barrington, MA 01230
• 

  

  /46

  $690,000 Sold Jan 15, 2025

  • 1,750 Sq Ft
  • $394/SF
  • 201 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  241 Main Rd, Monterey, MA 01245

  ADDITIONAL 3.5 ACRE BUILDING LOT ABUTTING THIS PROPERTY FOR $70,000 with the sale of this home. Contemporary Log Cabin settled on 3.5 wooded Acres. This unique renovated log cabin offers you a peaceful quiet setting for you & your family to settle down. With 4 bedrooms and 2.5 baths privacy is assured and a open concept living room/kitchen area to gather. A wood burning fireplace for a quiet

  Matt Amstead FAIRGROUND REAL ESTATE, INC

  241 Main Rd, Monterey, MA 01245
• 

  

  /27

  Est $507,407 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,666 Sq Ft

  50 Hupi Rd, Monterey, MA 01245

  50 Hupi Rd, Monterey, MA 01245
• 

  

  /42

  $1,150,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,266 Sq Ft

  3 Stratford Ln, Monterey, MA 01245

  Lake life awaits! Contemporary year-round home lake views from all rooms & lake access on beautiful Lake Garfield! This 2,266 sq ft property features 3 BRs, 3 BAs, updated kitchen, & wood floors throughout most of the home. Heat pumps provide economical heating & cooling. Spacious den/music room & study on walkout lower level. Set on 1.3 acres, w/ plenty of room for gardens & tons of deck space

  Claire Pollart LANCE VERMEULEN RE, INC

  3 Stratford Ln, Monterey, MA 01245
• 

  

  /26

  $590,000 Sold Jan 13, 2025

  • 1,248 Sq Ft
  • $473/SF
  • 65 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  85 Pixley Rd, Great Barrington, MA 01230

  Immaculate and renovated home in Monterey very near the Lake Buel public boat launch. Minutes to downtown Great Barrington, Ski Butternut and so much more. Move right into this lovely home. This light and bright home has a cathedral ceiling living room with a wood burning fireplace. All on one level for easy living. Primary with half bath plus two additional bedrooms and full bath. The open

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  85 Pixley Rd, Great Barrington, MA 01230
• 

  

  /40

  Est $1,286,319 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,487 Sq Ft

  605 Main Rd, Monterey, MA 01245

  605 Main Rd, Monterey, MA 01245
• 

  /2

  $155,000

  • Land
  • 5 Acres
  • $29,580 per Acre

  104 Hupi Rd, Monterey, MA 01245

  Ready to build a new custom home with all your personal touches! Views of Lake Garfield. Close to downtown Monterey. Fresh 5 acre parcel to construct a magnificent home in the Berkshires!

  Cristian Sanchez COHEN & WHITE ASSOCIATES

  104 Hupi Rd, Monterey, MA 01245
• 

  

  /7

  $40,000 Sold Dec 23, 2024

  • Land
  • 3.12 Acres
  • $12,821 per Acre

  • 110 Days On Market

  0 Broderick Rd, Monterey, MA 01245

  A private sloped, wooded lot in Monterey with deeded access to Lake Garfield, including dock rights! This sloped parcel on 3.12 acres offers plenty of room for a home built to take advantage of lake views. Build your three-season home in a tranquil area of the Berkshires, where you can put down roots and become a part of the community.

  Richard Needelman BISHOP WEST REAL ESTATE

  0 Broderick Rd, Monterey, MA 01245
• 

  

  /35

  Est $3,020,386 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,044 Sq Ft

  14 Bidwell Rd, Monterey, MA 01245

  14 Bidwell Rd, Monterey, MA 01245
• 

  

  /6

  $157,999

  • Land
  • 6 Acres
  • $27,719 per Acre

  8 Brook Ln, Monterey, MA 01245

  Nestled in the heart of the Berkshires, this 5.7-acre wooded lot offers privacy, tranquility, and endless potential. With no HOA restrictions, this oversized parcel is ideal for your dream getaway or year-round retreat. Located directly across from Lake Buel and just a 5-minute drive to Butternut Ski Resort, it's a prime spot for both winter sports lovers and summer lakegoers. Enjoy the best of

  Steven Bintz PlatLabs, LLC

  8 Brook Ln, Monterey, MA 01245
• 

  

  /56

  $2,150,000 Sold Dec 16, 2024

  • 3,615 Sq Ft
  • $595/SF
  • 167 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1910

  17 Cronk Rd, Great Barrington, MA 01230

  An unusual and wonderful early barn conversion, originally built in the 1700s and converted to a house around 1910. The current owner has renovated and added onto it thoughtfully and completely. A large open space with lots of windows, a huge stone fireplace and a cathedral ceiling define the living a dining rooms. The kitchen was enlarged and remodeled in 2012 with Wolf and SubZero appliances,

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  17 Cronk Rd, Great Barrington, MA 01230
• 

  

  /6

  Est $336,910 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,151 Sq Ft

  29 Swann Rd, Monterey, MA 01245

  29 Swann Rd, Monterey, MA 01245
• 

  

  /11

  $295,000

  • Land
  • 3.00 Acres
  • $98,333 per Acre

  10 Art School Rd, Monterey, MA 01245

  Lovely partially developed 3 acre parcel on the most desirable and private Art School Rd. Prime location in Monterey approximately 0.8 miles to Lake Garfield, and with potential view of pond on abutting property. There is an old cottage on the property which needs to be torn down prior to building. Established dirt driveway and well are in place.

  Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  10 Art School Rd, Monterey, MA 01245
• 

  

  /46

  $2,100,000 Sold Nov 25, 2024

  • 2,600 Sq Ft
  • $808/SF
  • 65 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2017

  40 Sylvan Rd, Monterey, MA 01245

  This 2017 waterfront home on Lake Garfield has seen very gentle use over the past six years. Featuring three bedrooms and four baths, it offers five sleeping rooms on three fully finished levels. The south-facing great room and the family room below both boast gas fireplaces, radiant heat, and air conditioning. The open kitchen is outfitted with premium SubZero, Wolf, and Asko appliances. Six

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  40 Sylvan Rd, Monterey, MA 01245
• 

  

  /15

  Est $477,276 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,800 Sq Ft

  19 Broderick Rd, Monterey, MA 01245

  19 Broderick Rd, Monterey, MA 01245
• 

  

  /3

  $80,000

  • Land
  • 3.41 Acres
  • $23,460 per Acre

  1 Main Rd, Monterey, MA 01245

  Don't miss your chance to own this great parcel with 3.41 acres of prime land with approximately 230' of frontage. Great location 10 minutes from Lee outlets and the pike, and 20 minutes to Tanglewood. This is a great opportunity for someone looking to build a home or a builder looking to build a home. Adjoining buildable parcel with over 16 acres also available for sale (MLS #73386997)

  Tracy Barber Real Broker MA, LLC

  1 Main Rd, Monterey, MA 01245
• 

  

  /46

  $5,600,000 Sold Nov 12, 2024

  • 9,300 Sq Ft
  • $602/SF
  • 9 Days On Market

  • 8 Beds
  • 6.5 Baths
  • Built 2006

  29 Fairview Rd, Monterey, MA 01245

  CROW HOUSE - An Enchanting Private Stone-and-Timber Compound in Monterey.One of Berkshire County's most atmospheric and luxurious properties, this stone-and-timber 52-acre compound, which abuts thirteen thousand acres of protected State Forest, is a magical world unto itself. A winding driveway through horse pastures leads under a Porte cochere to a European-style courtyard, where a pergola

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  29 Fairview Rd, Monterey, MA 01245
• 

  

  /32

  Est $501,266 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,236 Sq Ft

  56 Brett Rd, Monterey, MA 01245

  56 Brett Rd, Monterey, MA 01245
• 

  

  /39

  $795,000

  • 3 Beds
  • 3 Baths
  • 2,634 Sq Ft

  350 Beartown Mountain Rd, Monterey, MA 01245

  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

  350 Beartown Mountain Rd, Monterey, MA 01245
• 

  

  /28

  $700,000 Sold Nov 08, 2024

  • 1,850 Sq Ft
  • $378/SF
  • 40 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1975

  77 New Marlboro Rd, Monterey, MA 01245

  Our team calls this dreamy Berkshires home ''The Fairy Tale House.'' As you approach via the winding drive, the third-floor roof peeks over goldenrod and wildflowers. Perched on a hillside with mountain views, the 4-bedroom, 3.5-bath home on 5 acres has a unique facade, surrounded by wild and groomed gardens, grape vines, and hydrangeas. Inside, the Great Room boasts dark wood beams, a stone

  John Panzer ELYSE HARNEY REAL ESTATE

  77 New Marlboro Rd, Monterey, MA 01245
• 

  

  /57

  Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 2,616 Sq Ft

  53 Stevens Lake Way, Great Barrington, MA 01230

  53 Stevens Lake Way, Great Barrington, MA 01230
• 

  

  /9

  $109,900

  • Land
  • 26 Acres
  • $4,268 per Acre

  0 W Hubbard Rd, Sandisfield, MA 01255

  Discover the possibilities nestled in the heart of the Berkshires--just 20 minutes from the charm and culture of Great Barrington. This picturesque lot offers a rare combination of natural beauty and practical readiness, with a completed perc test and engineered septic designs already in place. Whether you're envisioning a peaceful weekend escape or a cozy, year-round haven, this is the perfect

  Andreea Duta BISHOP WEST REAL ESTATE

  0 W Hubbard Rd, Sandisfield, MA 01255
• 

  

  /27

  $412,000 Sold Nov 01, 2024

  • 1,008 Sq Ft
  • $409/SF
  • 146 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1945

  91 Fairview Rd, Monterey, MA 01245

  A quintessential Berkshire four-season cabin, secluded on an elevated parcel within biking distance to Lake Garfield and the town beach. Two families enjoyed this home for decades, having recently replaced windows and installed a new roof on both the house and two-car garage. The large living room has a fieldstone wood-burning fireplace with even enough room for overflow guests. The sweet eat-in

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  91 Fairview Rd, Monterey, MA 01245
• 

  

  /41

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,595 Sq Ft

  352 Monterey Rd, Monterey, MA 01245

  352 Monterey Rd, Monterey, MA 01245
• 

  

  /78

  $795,000

  • 4 Beds
  • 3 Baths
  • 1,956 Sq Ft

  139 Tyringham Rd, Monterey, MA 01245

  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

  139 Tyringham Rd, Monterey, MA 01245
• 

  

  /10

  $199,000 Sold Sep 20, 2024

  • Land
  • 2.78 Acres
  • $71,712 per Acre

  • 290 Days On Market

  Unlisted Address

  LOVE THESE VIEWS! Big sky and mountains in the distance. Prime land at a very affordable price on one of the nicest roads in Monterey; a naturally beautiful town with a rural feel, yet close to Great Barrington, culturally rich & with many recreational opportunities. This building parcel offers many aspects that distinguish this land and make it a cut above the rest: Wide road frontage

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  Unlisted Address
• 

  

  /42

  Est $950,943 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,590 Sq Ft

  19 Art School Rd, Monterey, MA 01245

  19 Art School Rd, Monterey, MA 01245
• 

  

  /8

  $68,000

  • Land
  • 1.10 Acres
  • $61,818 per Acre

  0 Norwalk Acres Rd Unit 242782, Monterey, MA 01245

  Start building your Berkshire Dream home today! Grab your hiking shoes, bike, and skis, or if you're looking for theater, dance, or music-Norwalk Acres is a stone's throw away from Lake Garfield, Butternut Basin Ski Area, Beartown State Forest, the Appalachian Trail as well as Shakespeare & Co., Barrington Stage Co, The Mahaiwe Performing Arts Center, Jacobs Pillow, and Tanglewood. Are you ready

  Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

  0 Norwalk Acres Rd Unit 242782, Monterey, MA 01245

Showing Results 1 - 40, Page 1 of 18