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$3,900,000

Est. Mortgage: $/month

MLS Number 226469

  • Single Family
  • Village Berkshire - South
  • Year Built 2004
  • Bedrooms 5
  • Bathroom 5

Mountaintop Shingle Style home and horse farm built to last with southerly helicopter views over the Berkshires to the Litchfield Hills beyond, abutting 12,000 acre state forest. Classic contemporary styling inside and out with four stone fireplaces a large entertaining kitchen, and gracious flow through public rooms, porches, terraces and guest rooms. First and second floor master suites have their own outdoor intimate lounges and views. The residence was built as sustainable and non-toxic as possible with Mahogany windows and doors, and stone excavated from the site. The barn below has gener stalls and a wonderful guest or caretaker suite above - would make a great pool house and the outdoor arena could easily be a tennis court. Secluded yet nearby, with forever protected views,

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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11 Wellman Rd Monterey MA 01245

Price$1,850,000

Est. Mortgage: $/month

Pending

MLS Number 226109

  • Single Family
  • Address 11 Wellman Rd
  • Village Berkshire - South
  • Year Built 1932
  • Parking Spaces 5

FIDDLETOP Do you desire the utmost privacy without isolation? A timeless, gracious & distinguished home? Do you seek broad views, mature landscaping & tranquility? Are you seeking a 'forever' home?There's a simple reason this iconic property has only had 4 owners since it was built in 1932. All 4 could have lived in any number of wonderful homes in the Berkshires, but they did not. They chose Fiddletop. From the legendary conductor Eugene Ormandy to the the virtuoso violinist Zino Francescatti.Experience Fiddletop, spend time sitting in the gracious rooms watching the light skim the walls with the glow of the wood burning in the fireplace, or the sun reflected back on the mountains, & imagine how you can make this your 'forever' home... you will know you want to stay for decade

Listed by BROCKMAN REAL ESTATE, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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Hupi Rd 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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141 Stevens Lake Way Monterey MA 01245

Price$1,390,000

Est. Mortgage: $/month

MLS Number 226790

  • Single Family
  • Address 141 Stevens Lake Way
  • Village Berkshire - South
  • Year Built 1999
  • Parking Spaces 2

Gorgeous waterfront home on Peaceful Stevens Lake. This home is just minutes from downtown Great Barrington, Butternut and Beartown State Forest. Designed to be able to live on the first-level, this expansive open floor plan contains a cook's kitchen with Viking and Sub-Zero appliances, walk-in pantry, wood-burning fireplace and central A/C. There is a first-floor master suite as well as a separate in-law suite or perfect office/den. There is plenty of room (septic sized to accommodate 7 br) for multi-generational family/friends space upstairs as well as game room, studio/exercise room, a bunk room and full bath all on the lower level with walkout to the lake. A spectacular setting and home in a great location!

Listed by LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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527 Main Rd Monterey MA 01245

Price$1,295,000

Est. Mortgage: $/month

MLS Number 218925

  • Single Family
  • Address 527 Main Rd
  • Village Berkshire - South
  • Year Built 1963
  • Parking Spaces 3

Rare Lake Garfield home cantilevered over the lake. Lots of decks and glass.

Listed by BERKSHIRE REAL ESTATE CONNECTIONS

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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170 Gould Rd Monterey MA 01245

Price$1,150,000

Est. Mortgage: $/month

Pending

MLS Number 223800

  • Single Family
  • Address 170 Gould Rd
  • Village Berkshire - South
  • Year Built 1995
  • Parking Spaces 2

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 Fintan Hanley and Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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27 Stevens Lake Way Monterey MA 01245

Price$1,100,000

Est. Mortgage: $/month

MLS Number 226934

  • Single Family
  • Address 27 Stevens Lake Way
  • Village Berkshire - South
  • Year Built 1991
  • Parking Spaces 2

Privately set amid the trees with lovely, pristine lake views, this is a place to immerse yourself in nature, to enjoy cooking in the gourmet kitchen, to sunbathe on the deck, to gather in the great room and screened porch, to read by the fireplace after a day at Ski Butternut. Kayak or walk to the private Association beach, launch a canoe from your own mini-dock, stroll around this private, non-motor lake, or drive 10 minutes to Great Barrington for theater, restaurants, & shopping. This impeccable home, renovated with great attention to detail, offers it all, and with five bedrooms with en suite or shared baths, den with bath, & finished lower level, it provides ample space for friends, family and entertaining. This is the way the Berkshires are meant to be!

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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540 Main Rd Monterey MA 01245

Price$1,099,000

Est. Mortgage: $/month

MLS Number 212666

  • Single Family
  • Address 540 Main Rd
  • Village Berkshire - South
  • Year Built 1986
  • Parking Spaces 8

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 WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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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 George Cain of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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19 Buckingham Ln Monterey MA 01245

Price$1,050,000

Est. Mortgage: $/month

MLS Number 227504

  • Single Family
  • Address 19 Buckingham Ln
  • Village Berkshire - South
  • Year Built 1978
  • Bedrooms 3

Waterfront on Lake Garfield, this contemporary four-season home is tucked in a quiet cove with a wall of glass overlooking the lake. The Great Room leads to a large deck with remarkably pretty water views just steps from the lakeside lawn and private boat dock. Plenty of room for guests to spread out on three levels with a master suite, two guest bedrooms and 2.5 baths, along with a den and family room. The large family room has its own full bath so works as a big guest suite with views of the lake. The property is located at the end of private road not far from the town beach and within walking distance of Monterey village center, the new library, and soon to be new General Store. With central A/C and fiber internet, one may purchase in time to enjoy for the summer and work from home.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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.

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57 Art School Rd Monterey MA 01245

Price$999,999

Est. Mortgage: $/month

MLS Number 224294

  • Single Family
  • Address 57 Art School Rd
  • Village Berkshire - South
  • Year Built 1999
  • Bedrooms 6

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: 3.82% last updated on Jun 13, 2019
* 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.

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72 Beartown Mountain Rd Monterey MA 01245

Price$769,000

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. New Septic System installation will be financed by the seller from proceeds of the sale.''Virtual Tour''

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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