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!

Monterey MA 01245

Monterey, MA

Price$5,500,000

Est. Mortgage: $/month

Pending

MLS Number 243798

  • Residential
  • Bathroom 7
  • Bedrooms 8
  • Square Feet 9,300
  • Acreage 51.55

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 draped in wisteria links the entrances to the five-bedroom, five-bath main house, the three-bedroom, two-bath guest house and a terrace with an outdoor dining pavilion.

Listed by Timothy Lovett and Fintan Hanley of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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40 Sylvan Road Monterey MA 01245

Monterey, MA40 Sylvan Road

Price$2,395,000

Est. Mortgage: $/month

Pending

MLS Number 244119

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,600
  • Acreage 0.37

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 rooms provide direct access to the deck and patio with stunning lake views. Additional features include fiber internet, a whole house generator, a private dock, an easy-care metal roof, and hardy-plank shingle siding. Lake garfield, the premier recreational lake in the southern berkshires, rarely has homes available on the market, making this a unique opportunity. Offered mostly furnished.

Listed by Fintan Hanley and Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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17 Cronk Road Monterey MA 01245

Monterey, MA17 Cronk Road

Price$2,150,000

Est. Mortgage: $/month

Pending

MLS Number 242978

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,615
  • Acreage 27.97

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, and cherry cabinets. With five bedrooms and four and a half baths on two levels, all but one of the bedrooms are ensuite. The very creative and bright primary bedroom, up a few steps from the second floor, also has a cathedral ceiling and gorgeous built-ins. This romantic property contains a large field, lawns, woodland and huge ponds; a virtual national geographic display of bird and animal life.

Listed by Timothy Lovett and Fintan Hanley of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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112 Tyringham Road Monterey MA 01245

Monterey, MA112 Tyringham Road

Price$1,695,000

Est. Mortgage: $/month

MLS Number 244558

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,495
  • Acreage 2.4

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 luxurious wet room for a private retreat. On the opposite side, two additional bedrooms, a shared bathroom, and laundry provide convenience. The finished lower fully walkout level includes a family room with a bar, a fourth bedroom, and a full bath - ideal as an in-law suite. An oversized two-car ev-ready garage connects directly to the suite. Energy efficient with a solar-ready roof and central ac.

Listed by Timothy Lovett of Compass Massachusetts,LLC ((617) 610-6496)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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142 Main Road Monterey MA 01245

Monterey, MA142 Main Road

Price$1,450,000

Est. Mortgage: $/month

MLS Number 244203

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,754
  • Acreage 2.96

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. Although listed as a 3 bedroom home, there are 5 distinct sleeping areas and the screened porch and open area deck are idyllic for your own relaxation or for entertaining guests. With a little updating here and there, the investment in this home will pay very handsome dividends. Opportunities like this one do not come along very often.

Listed by George Cain of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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617 Main Road Monterey MA 01245

Monterey, MA617 Main Road

Price$1,198,000

Est. Mortgage: $/month

MLS Number 244470

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,830
  • Acreage 2

Built in 1850, this historic home has beautiful mountain views, mature landscaping and deeded access to lake garfield! This home boasts a wood burning fireplace in lr, a sunny den (potential conversion to primary suite), dr and half bath/laundry on 1st floor. The second floor has 4 br/2 full ba, with a sleeping porch with mountain views. The finished attic offers ample storage and is perfect for a home office and gym. The two story 2 car garage offers an ev charger and a partially finished 2nd floor that can be easily converted into a separate apartment. The home has been lovingly updated with new windows, doors and fixtures throughout, refurbished floors, a backup generator, and a comprehensive lead abatement. Enjoy the large outdoor deck complete with shower and hot tub. Special!

Listed by Steven J. Weisz of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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139 Tyringham Road Monterey MA 01245

Monterey, MA139 Tyringham Road

Price$949,000

Est. Mortgage: $/month

MLS Number 244696

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 1,956
  • Acreage 3.31

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 charming, screened porch and an incredibly spacious deck. Two bedrooms and a full bath complete this main floor. The second floor consists of two spacious bedrooms each with its own bath. The primary bedroom has a large walk-in closet and a juliet balcony overlooking the backyard. Please read the supplemental remarks to learn more about the house & lake lo

Listed by Matt Carlino of MACCARO REAL ESTATE ((413) 243-4647)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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10 Phelps Road Monterey MA 01245

Monterey, MA10 Phelps Road

Price$899,000

Est. Mortgage: $/month

MLS Number 242946

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,297
  • Acreage 0.32

Idyllic, bright cottage, recently renovated and expanded, situated on an inlet of lake garfield. Drop your kayak in the water and be on the lake in minutes, or relax on your private screened porch. This home has so much to offer and was renovated with great thought and attention to detail, with high end finishes throughout.An open floor plan encourages gathering, while adding to the ease of the home. Three bedrooms and a sleeping loft provide ample space for guests, while the cozy feel of the home also makes it a perfect getaway from the hustle and bustle of daily life.To top it off, the property has deeded rights to lad's beach association, with the opportunity to apply for a boat slip, and access to the sandy beach and swimming.Come see this absolute gem for yourself!

Listed by Lauren Rosen and Lance Vermeulen of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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6 Tyringham Road Monterey MA 01245

Monterey, MA6 Tyringham Road

Price$799,000

Est. Mortgage: $/month

MLS Number 243992

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4,188
  • Acreage 1.1

C1780 classic colonial residence with a scenic view of a quaint berkshires village. Passionate about historic homes, the ledgehurst estate is a worthy project waiting for it's next chapter. Sitting atop a hill overlooking the village of monterey. Owned by the bidwell family, founders of monterey, and run as a boarding house in the 1900s. Later returned to a private estate with a grand indoor pool surrounded by sliding glass doors, a master bedroom balcony, heated brick floor, bar, grill, and sauna. The original horse barn remains, now filled with classic automobiles, plus a detached garage and a home garage. 4 bdrms, 3.5 baths. Sunny living, dining, and office spaces. Central fireplace. Bucolic setting in the village and one mile to lake garfield. Close to all the berkshires has to offer

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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241 Main Road Monterey MA 01245

Monterey, MA241 Main Road

Price$730,000

Est. Mortgage: $/month

MLS Number 243215

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 1,750
  • Acreage 3.5

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 night inside or get some fresh air and listen to the nearby river outside on the screen porch, you will not have a hard time finding a place to relax. With all new systems and a new modern renovation this home is move in ready!

Listed by Matt Amstead and Eric Steuernagle of FAIRGROUND REAL ESTATE,INC ((413) 717-0276)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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77 New Marlboro Road Monterey MA 01245

Monterey, MA77 New Marlboro Road

Price$725,000

Est. Mortgage: $/month

Pending

MLS Number 244273

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 1,850
  • Acreage 5.01

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 hearth, and antique windows. Upstairs, cozy bedrooms bask in natural light. The remodeled kitchen, pink sunroom, and spacious dining room add charm. Just 7 minutes from the southfield store and close to outdoor activities like paddling, hiking, and skiing.

Listed by John G Panzer of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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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85 Pixley Road Monterey MA 01230

Monterey, MA85 Pixley Road

Price$625,000

Est. Mortgage: $/month

MLS Number 244416

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,248
  • Acreage 2.6

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 kitchen has granite counters and stainless appliances. So much to love. French doors from the living room to a nice rear deck overlooking the fire pit. Good rental history.

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 2024
* 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 November 4, 2024 . 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.