Monterey Real Estate

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!

179 Mt Hunger Monterey MA 01245

Monterey, MA179 Mt Hunger Rd

Price$4,290,000

Est. Mortgage: $/month

MLS Number 231972

  • Residential
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 8,374
  • Acreage 5.21

Casa tramonti.....House of the sunset...Life's reminder that whatever happens every day can end beautifully, says it all for this sophisticated contemporary, built by one of berkshire's premier builders. Offered for the first time, it has the necessary amenities of broadband fiber optic & great cell phone service. From the approach this home captures stunning westerly views to the catskills, keeping the viewer mesmerized with walls of glass. The sleek & sophisticated design of a most comfortable and ''livable'' space features open common living, decking for 80*, 5 br's en suite, an amazing sunroom & screened porch with waterfall sounds. A home theatre, gym & specimen plantings, organic vegetable garden, a multiple fruit orchard & fire pit to gather around.....Reason to never leave home!!

Listed by Mary Jane White and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

212-214 Blue Hill Rd Monterey MA 01245

Monterey, MA212-214 Blue Hill Rd Rd

Price$3,250,000

Est. Mortgage: $/month

MLS Number 234839

  • Residential
  • Bathroom 9
  • Bedrooms 7
  • Square Feet 6,510
  • Acreage 10.25

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. Built with reclaimed chestnut beams, the 3864 sq ft, 4 bed/4 bath, main home features an open, stylish first floor with sunset views, wood burning fireplaces, and multiple living areas. Upstairs, views abound from the primary bedroom and guest quarters. Down the hill, sits a spectacular contemporary barn conversion, with an open first floor, large screened porch, 3 beds, and 4 bath. Walk to beautiful benedict pond or hike the abutting appalachian trail. Low taxes. 10 min to gb.

Listed by Jared Kelly and L. Chapin Fish of BROCKMAN REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

99 Hupi Monterey MA 01245

Monterey, MA99 Hupi Rd

Price$2,250,000

Est. Mortgage: $/month

MLS Number 234858

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,300
  • Acreage 3.67

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. The great room has a wood burning fireplace and a large family room loft above. Owners may live fully on the main floor while guests occupy three bedrooms and two baths below, all with far-reaching views. Exquisite craftsmanship was employed in the creation of this house from the raised paneling to the landscaping. A rare find to have such incredible views and a dock on the lake. Central a/c and heated garage.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

57 Art School Monterey MA 01245

Monterey, MA57 Art School Rd

Price$1,300,000

Est. Mortgage: $/month

Pending

MLS Number 234824

  • Residential
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 4,468
  • Acreage 8.94

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. Downstairs there is 1 additional bedroom, full bath, billiard room, gym and family room. It even has a zip-line!!! Oversized garage. Generator, fiber optic internet and great rental potential. Low, low, monterey taxes. Minutes to monterey general store, lake garfield, great barrington, tanglewood and ski butternut. A true country escape !

Listed by Steven J. Weisz and Maggie C Merelle of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

540 Main Monterey MA 01245

Monterey, MA540 Main Rd

Price$1,100,000

Est. Mortgage: $/month

Pending

MLS Number 234715

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,379
  • Acreage 140.75

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.

Listed by George Cain of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

93 Brett Monterey MA 01245

Monterey, MA93 Brett Rd

Price$895,000

Est. Mortgage: $/month

MLS Number 234092

  • Land
  • Acreage 102

102 glorious monterey acresbordering 12,000 acre beartown state forest on 3 sides10 minutes to great barrington10 miles to stockbridgeinspiring, rare & private land with an ideal combination of open fields & forest. Sloping gradually up the mountain there are superb locations to build your dream home or homes with a sw exposure and the potential for distant views. Even rarer, this colonial-era farm borders what is now 12,000 acre beartown state forest with the appalachian trail, the knox trail, and benedict pond a hike away. Long road frontage equates to opportunity for up to 6 homes, if desired. This historic monterey farm is located in a truly unbeatable location with very low monterey taxes + a rustic original colonial farmhouse & barns. Fiber broadband on the way! Sold 'as is'

Listed by Jared Kelly and L. Chapin Fish of BROCKMAN REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

93 Brett Monterey MA 01245

Monterey, MA93 Brett Rd

Price$895,000

Est. Mortgage: $/month

MLS Number 234093

  • Residential
  • Bathroom 3
  • Bedrooms 8
  • Square Feet 3,536
  • Acreage 102

102 glorious monterey acresbordering 12,000 acre beartown state forest on 3 sides10 minutes to great barrington10 miles to stockbridgeinspiring, rare & private land with an ideal combination of open fields & forest. Sloping gradually up the mountain there are superb locations to build your dream home or homes with a sw exposure and the potential for distant views. Even rarer, this colonial-era farm borders what is now 12,000 acre beartown state forest with the appalachian trail, the knox trail, and benedict pond a hike away. Long road frontage equates to opportunity for up to 6 homes, if desired. This historic monterey farm is located in a truly unbeatable location with very low monterey taxes + a rustic original colonial farmhouse & barns. Fiber broadband on the way! Sold 'as is'

Listed by L. Chapin Fish and Jared Kelly of BROCKMAN REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

255 Hupi Monterey MA 01245

Monterey, MA255 Hupi Rd

Price$795,000

Est. Mortgage: $/month

MLS Number 234435

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,500
  • Acreage 8.46

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. A terrific layout for hosting guests, as the walkout lower level has a guest bedroom, a large game/media/office or family room, along with a full bath, so may be an entire teen or guest suite. The second floor houses the primary bedroom, a guest bedroom and a large family bathroom. The spotless two-car garage was built in 2019. This is a wonderful neighborhood for walking, nearby access to the lake, beartown state forest and the appalachian trail.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Beartown Mountain Monterey MA 01245

Monterey, MABeartown Mountain Rd

Price$775,000

Est. Mortgage: $/month

MLS Number 231812

  • Land
  • Acreage 77.72

Looking to build a family compound or a large private estate? Look no further! 77+/- sprawling wooded acres abutting state forest with 1800+ ft of usable road frontage. This property could be developed into multiple building sites or developed into a residential estate. The possibilities are endless!

Listed by Lance Vermeulen and Antonio M Segalla of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

235 Main Monterey MA 01245

Monterey, MA235 Main Rd

Price$689,000

Est. Mortgage: $/month

MLS Number 234404

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 4,000
  • Acreage 2.75

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. The large finished space on the lower level off the oversized garage could be the the perfect in law suite with its own entrance or a place for the kids to chill. With many outdoor decks and garden areas to enjoy, this monterey home is the perfect full time or part time home for lots of people to enjoy.

Listed by Timothy Lovett and Fintan T Hanley of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

664 Main Monterey MA 01245

Monterey, MA664 Main Rd

Price$599,000

Est. Mortgage: $/month

Pending

MLS Number 234778

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,464
  • Acreage 5.83

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. Large den/office w/ access from the kitchen or entry, full bath w/ carrara marble floors & subway tile. The second floor has four bedrooms w/ oak floors, a large primary bedroom w/ a big bathroom w/ tub & shower & twin vanities. Floor is limestone & walls are limestone & ceramic. There are three more bedrooms & a hall bath w/ tile floor. The full walk-out basement is easily finished for additional space. High speed internet via fiber optic. Close to the town beach on beautiful lake garfield.

Listed by Jeff Wilkinson of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

26 Seven Arts Monterey MA 01245

Monterey, MA26 Seven Arts Rd

Price$595,000

Est. Mortgage: $/month

MLS Number 234050

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,660
  • Acreage 0.53

Don't let this lake buel cottage slip through your fingers! Waterfront properties in south county are few & far between. This 4-bedroom, 2-full bath lake cottage getaway has been in the same family for generations. Enjoy this wonderful gathering place for family & friends on hot summer days and all the other days in between. Beautiful stone fireplace & vaulted ceilings in the cozy living room. Multiple skylights and windows to allow plenty of natural sunlight in. Sliding glass doors off of the living room leads onto a deck for entertaining, grilling, and simply relaxing. All just steps away from your own private dock on lake buel!

Listed by William Morrow of WHEELER & TAYLOR REALTY CO., INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of July 27, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.