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!

185 Beartown Mountain Rd, Monterey, MA 01245

Price$4,500,000

Est. Mortgage: $/month

MLS Number 220508

  • Single Family
  • Village Berkshire - South
  • Year Built 2004
  • Bedrooms 4
  • Bathroom 4

Casually elegant and beautiful shingled eco-luxury mountaintop home with rare and extraordinary protected southerly long-range views, abutting 12000 acre Beartown State Forest. Carefully and exquisitely crafted, the gracious rooms feature four fireplaces with a hefty stone central core, mahogany windows and doors, and radiant heated wood floors. The horse barn has three generous stalls, a tack room, and caretaker's quarters. Horses enjoy organic pastures and an outdoor arena that could easily be a tennis court. The private setting and views are unmatched in the southern Berkshires, and the quality of construction speaks for itself.

Listed by BERKSHIRE PROPERTY AGENTS

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 A VisitAsk A QuestionMore Details

11 Wellman Rd, Monterey, MA 01245

Price$1,895,000

Est. Mortgage: $/month

MLS Number 224288

  • Single Family
  • Village Berkshire - South
  • Year Built 1932
  • Parking Spaces 5
  • Bedrooms 4

FIDDLETOP, MONTEREYAn elegant, iconic Berkshire estate located on a country lane in prime Monterey. The driveway takes you past open fields and towering oak and maple trees up the rolling hillside to the most perfect setting in the Berkshires. Distant views stretch out from the pool and beautifully landscaped grounds. Generous public rooms including a living room with wood-burning fireplace and French doors opening on to a stone floor 3 season porch, formal dining room with wood-burning fireplace, guest bath, butler's pantry, period kitchen with arched windows, a master suite with two full baths, guest suite with distant views, and two additional bedrooms. Renovate the guest suite in the detached garage for additional room. An extraordinary property and setting with limitless potential.

Listed by BROCKMAN REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 A VisitAsk A QuestionMore Details

Monterey, MA 01245

Price$1,750,000

Est. Mortgage: $/month

MLS Number 224494

  • Land
  • High School Mount Everett
  • Village Berkshire - South
  • Square Feet 661,696
  • Waterfront 1

UNIQUE MONTEREY LAKEFRONT PROPERTY-one of a kind opportunity! 15+ acre waterfront parcel on pristine Lake Garfield. Beautiful lake views off of quiet Hupi Rd with approximately 700' of water frontage on a motorboat accessible lake. Comprised of 2 lots - Lot #16 is 4.443 acres, Lot #15 is 10.738 acres - offered together at $1,750,000.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 A VisitAsk A QuestionMore Details

27 Stevens Lake Rd, Monterey, MA 01245

Price$1,299,500

Est. Mortgage: $/month

MLS Number 222454

  • Single Family
  • Village Berkshire - South
  • Year Built 1991
  • Parking Spaces 2
  • Bedrooms 5

STEVEN'S LAKE WATERFRONT! Perched on a knoll overlooking a serene body of water, this beautifully appointed home has commanding views of nature at its best! Offering 5 + bedrooms, 5 baths, dramatic great room with vaulted ceiling and stone fireplace, renovated kitchen, all orientated to a wraparound deck and an inviting screen porch. The lower level offers a spacious family room. HV/AC have been updated. Steven's Lake is a private community and a non motor boat lake with tennis court and is located 10 minutes from downtown Great Barrington.

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 A VisitAsk A QuestionMore Details

170 Gould Rd, Monterey, MA 01245

Price$1,150,000

Est. Mortgage: $/month

MLS Number 223800

  • Single Family
  • Village Berkshire - South
  • Year Built 1995
  • Parking Spaces 2
  • Bedrooms 5

A light, bright, very private contemporary country home, with an exquisite approach, on almost 14 acres of rolling meadows; featuring its own private swimming/trout pond, beach and dock. High ceilings and massive windows prevail, plus a 12 month glass porch, all overlooking a gorgeous setting. Designed for a large family, it offers an oversized master BR down, 3BRs + office upstairs and small gym on a lower level. Additional spacious guest apartment, with another master BR, bath and 2nd living room, can be an income producing rental, if desired. Located near skiing, hiking trails, the Monterey town beach boat ramp at Lake Garfield, and all the terrific Berkshire cultural venues. Many amenities; Verizon internet.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 A VisitAsk A QuestionMore Details

540 Main Rd, Monterey, MA 01245

Price$1,099,000

Est. Mortgage: $/month

MLS Number 217301

  • Land
  • High School Mount Everett
  • Village Berkshire - South
  • Square Feet 6,131,070
  • Waterfront 1

An outstanding 140+ acre property ideally located within walking distance to the center of Monterey, a terrific Southern Berkshire County Community, which is the 4th lowest real estate tax district in Massachusetts.This listing includes in excess of 1400 feet of frontage on two paved roads. Water views of a delightful 20 acre pond are also provided.Must be seen to be appreciated.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

540 Main Rd, Monterey, MA 01245

Price$1,099,000

Est. Mortgage: $/month

MLS Number 212666

  • Single Family
  • Village Berkshire - South
  • Year Built 1986
  • Parking Spaces 8
  • Bedrooms 3

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 is coming to the market for the first time in decades.

Listed by George Cain of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

57 Art School Rd, Monterey, MA 01245

Price$1,090,000

Est. Mortgage: $/month

MLS Number 224294

  • Single Family
  • Village Berkshire - South
  • Year Built 1999
  • Bedrooms 6
  • Bathroom 5

This expanded custom stone Contemporary Post and Beam home, is sited in a private meadow on 8.94 acres in the beautiful Monterey countryside. A half mile +/- to the beach at Lake Garfield. The 5-bedroom, 4500 square foot residence has a high level of craftsmanship in a classic Berkshire Post and Beam vernacular designed for modern living. The large chef's kitchen has an open floor plan with soaring ceilings and a wall of windows overlooking the Gunite pool and lush acres. The rooms transition in size from intimate dining and office to the large great room, and include full wet bar. The first floor master has two walk in closets and a bath you dream about. A recreation area with family room, exercise area, and game room are on the lower level with another bedroom and full bath.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 A VisitAsk A QuestionMore Details

72 Beartown Mountain Rd, Monterey, MA 01245

Price$785,000

Est. Mortgage: $/month

MLS Number 223604

  • Multi-Family
  • Village Berkshire - South
  • Acreage 2.1
  • Bedrooms 5
  • Square Feet 4,832

This very unique, immaculate, splendidly updated family compound/legal 2-family w/income producing opportunity, surrounded by plush green lawn is located on an enchanted country lane in Monterey, MA. Walk to Lake Garfield sandy beach, hike the trails in Beartown State Forest, Ski Butternut and enjoy Great Barrington, Stockbridge and Lenox shops galleries & restaurants, all within a short drive. This very special property consists of 2 attached homes; the large historic home, together with the classy newer addition, plus detached, oversized 2-car garage. Both homes are updated to today standard & maintained with extraordinary touch of class. Included brand new, 5br Septic System, the seller financed installation from proceeds of the sale. Please don't miss viewing the ''Virtual Tour''.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

72 Beartown Mountain Rd, Monterey, MA 01245

Price$785,000

Est. Mortgage: $/month

MLS Number 223602

  • Single Family
  • Village Berkshire - South
  • Year Built 1800
  • Parking Spaces 2
  • Bedrooms 5

Very unique, splendidly updated family compound/legal 2-family with income producing opportunity, a magical place surrounded by lovely gardens, located on an enchanted country lane in Monterey, MA. Walk to the Lake Garfield sandy beach, Hike the trails in Beartown State Forest, Ski Butternut and enjoy all that Great Barrington, Stockbridge and Lenox offer; restaurants, shops, galleries, all within a short drive. This very special property consists of 2 attached homes plus oversized 2-car garage; the larger historic home, together with the classy newer addition, both homes updated to today standard and maintained with extraordinary touch of class. The price has recently been reduced, including a brand new, 5br Septic System, financed by the seller from proceeds of the sale.''Virtual Tour''.

Listed by Dagmar Kubes of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

16 Bidwell Rd, Monterey, MA 01245

Price$749,000

Est. Mortgage: $/month

MLS Number 225318

  • Single Family
  • Village Berkshire - South
  • Year Built 1950
  • Bedrooms 3
  • Bathroom 2

Wonderful Berkshire waterfront home on Lake Garfield. 3 Bedrooms + Den, 2 full Baths. Open plan Living Room, Dining Room and Kitchen. Over an acre of Land. Well cared for, and in move-in condition. New Dock, new Roof and new Paint. (Title V done, as well). Low, low Monterey Taxes. Close to all Berkshire attractions and easy access to the Taconic & Mass Pike. A rare opportunity to own and enjoy lakefront living...

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 A VisitAsk A QuestionMore Details

Monterey, MA 01245

Price$599,000

Est. Mortgage: $/month

MLS Number 224179

  • Single Family
  • Village Berkshire - South
  • Year Built 1971
  • Bedrooms 4
  • Bathroom 2

22 ACRES WITH THE VACATION HOME YOU ALWAYS DREAMED OF. Imagine summers relaxing on your screened porch or sipping a cool drink on your front porch. Winters skiing at Berkshires favorite ski area, Eight minutes away.Then coming home and warming up by the wood burning fireplace.Lot's of room fro family and friends. This home nestled on 22+ acres of land set away from road for privacy yet only eleven minutes to Great Barrington.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 A VisitAsk A QuestionMore Details