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: 3.6% last updated on Aug 15, 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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50 Mt Hunger Estates Rd Monterey MA 01245

Price$2,200,000

Est. Mortgage: $/month

MLS Number 228340

  • Single Family
  • Village Berkshire - South
  • Year Built 2006
  • Parking Spaces 2
  • Bedrooms 7

Quintessential Berkshire Lodge.View of Lake Garfield and distant mountain ranges from every room, on more then 16 acres. Enter this home through double glass doors to a vaulted beam ceiling living room with stone fireplace. French doors to deck overlooking lake and views. Main floor consists of dining room for 10, open gourmet kitchen with granite counters, family room with wood burning fireplace and screened dining porch. Master bedroom wing, includes fireplace and spacious bath with jet tub and free standing shower. Wood paneled library w/fireplace. Separate guest wing with 2 bedrooms, full bath, powder room, laundry room. 2 car garage.Separate guest floor include family room and full kitchen, firepl. 4 bedrooms, hobby room, 2 full baths, second laundry.Whole house auto generator.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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: 3.6% last updated on Aug 15, 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: 3.6% last updated on Aug 15, 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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 Rd Monterey MA 01245

Price$995,000

Est. Mortgage: $/month

Pending

MLS Number 226934

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

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. Privately set amid the trees with lovely, pristine lake views and easy lake access, 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 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: 3.6% last updated on Aug 15, 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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93 Brett Rd Monterey MA 01245

Price$995,000

Est. Mortgage: $/month

MLS Number 227997

  • Land
  • High School Mount Everett
  • Village Berkshire - South
  • Acreage 102
  • Square Feet 4,443,120

NEW TO MARKET! First time offered in 50 years! Circa 1840 colonial farmhouse & barns ready for restoration. Truly incredible & exceptionally rare land with the perfect combination of open fields and forest gradually sloping up the mountainside with a South & West exposure. Even rarer, this colonial-era farm borders what is now 12,000 acre Beartown State Forest with the Appalachian Trail and the Knox Trail a relatively short hike away, as well as ponds within the State Forest. Often these large tracts of land that remain are in the distant hill towns, but this historic Monterey farm is just 10 minutes and 6 miles from the dining, and shopping of downtown Great Barrington, named the 'Best Small town in America'' by Smithsonian Magazine. 8 Bedrooms, rich character, very low Monterey taxes!

Listed by BROCKMAN REAL ESTATE, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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93 Brett Rd Monterey MA 01245

Price$995,000

Est. Mortgage: $/month

MLS Number 227996

  • Single Family
  • Address 93 Brett Rd
  • Village Berkshire - South
  • Year Built 1840
  • Bedrooms 8

NEW TO MARKET! First time offered in 50 years! Circa 1840 colonial farmhouse & barns ready for restoration. Truly incredible & exceptionally rare land with the perfect combination of open fields and forest gradually sloping up the mountainside with a South & West exposure. Even rarer, this colonial-era farm borders what is now 12,000 acre Beartown State Forest with the Appalachian Trail and the Knox Trail a relatively short hike away, as well as ponds within the State Forest. Often these large tracts of land that remain are in the distant hill towns, but this historic Monterey farm is just 10 minutes and 6 miles from the dining, and shopping of downtown Great Barrington, named the 'Best Small town in America'' by Smithsonian Magazine. 8 Bedrooms, rich character, very low Monterey taxes!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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Mt Hunger Rd Monterey MA 01245

Price$975,000

Est. Mortgage: $/month

MLS Number 228208

  • Land
  • Co Listing Office Id 210
  • High School Mount Everett
  • Village Berkshire - South
  • Acreage 193.7

Almost two hundred of beautiful wooded acres close to Lake Garfield and center of Monterey. The lot can be purchased as one 193 acre lot or four smaller, 46-50 acre lots.

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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$975,000

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: 3.6% last updated on Aug 15, 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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38 Elephant Rock Rd Monterey MA 01245

Price$850,000

Est. Mortgage: $/month

MLS Number 228342

  • Single Family
  • Address 38 Elephant Rock Rd
  • Village Berkshire - South
  • Year Built 1984
  • Bedrooms 3

Charming, sunny and airy unique three-story home with a master bedroom, two small bunk rooms and one bathroom on beautiful Lake Garfield. Open, stacked, loft-like spaces provide a unique ''tree-house'' experience. Enjoy south-facing lake access and all-day sunbathing on 30-foot dock with a separate floating raft. The naturally wooded environment with hundred-year old hemlocks, mountain laurel and other native species, provide privacy and contribute to deep, no-weed swimming. The property features two outdoor decks for lounging or watching sunsets. Enjoy alfresco dining on the upper deck and on chilly evenings, relax next to the living room wood-burning fireplace, or stoke up the wood stove in the kitchen/dining room. Epic lake views from every room over the best lake in Berkshire County.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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