Public Remarks: Sometimes fairy tales do come true... Tucked away on five private acres in Monterey, this singular handcrafted Berkshire cottage feels as though it emerged from a storybook. Natural-edge wood siding, steep rooflines, a massive fieldstone chimney and a tower-like upper level rise from a landscape of hydrangeas, woodland and a grape-covered arbor. Inside, the house is an irresistible mix of rustic character and thoughtful updates. Original wood floors, reclaimed hand-hewn beams, paneled walls, arched doors and unexpected architectural details give each room its own identity. The dramatic great room is the heart of the house, where soaring volume, exposed beams, richly paneled walls and an immense fieldstone fireplace create a space that feels far removed from everyday life. French doors open to a stone patio, while an open staircase rises through the room to the upper level, adding to the home's storybook quality. A sun-filled pink living room offers a dreamy contrast - soft, light-filled and wrapped in windows overlooking the hydrangeas and surrounding woods. A pleasing counterpoint to the darker, more rustic great room, it is an inviting place to read, relax or gather. A remodeled kitchen combines form and function, with white cabinetry, stone counters, a farmhouse sink, center island and a stunning commercial-style range beneath a stainless-steel hood. The adjoining dining room creates an easy flow for entertaining. Four bedrooms are arranged in two separate wings, offering privacy and flexibility. The south wing begins with a first-floor bedroom and bath, continues upstairs to a second bedroom with a newly added bath, and culminates in a third-floor office tucked beneath the peaked roof. On the opposite side of the house, in the north wing, two additional bedrooms each enjoy their own bath. Thoughtful bathroom updates, including the addition of the upstairs bath, bring modern comfort while remaining true to the character of the home. The story continues outdoors. Hydrangeas spill across the front of the house, mature grapevines climb the arbor, and lawns fade into woods and wild garden areas. The west-facing hillside brings seasonal mountain views through the trees, along with places to dine outdoors, wander, garden or simply enjoy the quiet. Private and quietly tucked away, yet only about 15 minutes from Great Barrington, with access to Monterey's Lake Garfield town beach and close to the lakes, trails, and outdoor recreation that make this part of the Berkshires so appealing. Low Monterey taxes and high speed Internet on site.
Single-familyProperty Type
1975Year Built
5.1 acresLot Size
$467Price/Sq.Ft.
Listed by Elle Villetto• WILLIAM PITT SOTHEBY'S - LENOX
Listed by Jared Kelly• WILLIAM PITT SOTHEBY'S - GT BARRINGTON
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.
BCMLS #216320
Dec 9, 2016
Listing Removed
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Jul 16, 2016
Listed
$475,000
$253/sq ft
As the MLS and public records start to fill up, we'll list the details here.
Public record
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Single Family Residential
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Berkshire County
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Last updated by owner on Sep 18, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
2/10 Heat Factor
7 days above 89° expected this year, 16 days in 30 years
4/10 Wind Factor
13% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Monterey, MA • 01245
Average low and high temperatures (°F)
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48
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77
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73
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41
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Sun exposure
86/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9 hrs
4.8 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 77 New Marlboro Rd
$874,178
$4,822 under list price of $879K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $320K to $975K.