Bear Hill Estate | Over 100-Acre Equestrian Retreat at the CT/MA Border

Private • Purpose-Built • Unmatched Serenity
For those who belong to the land, Bear Hill Estate is a rare and extraordinary offering—a 100+ acre legacy property designed for connection: to nature, to animals, and to the soul. Located at the confluence of Connecticut and Massachusetts, with seamless access to I-395, I-84, and the Mass Pike, this fully realized lifestyle compound caters to equestrians, creatives, homesteaders, and lovers of the outdoors.
At the heart of the estate sits a custom-crafted log home, built from hand-felled white pine logs sourced from Nova Scotia. Even the cabinetry was built there, ensuring material integrity and artisanal continuity from forest to finish. This 3-bedroom, 2.5-bath home is a work of craftsmanship, imbued with organic luxury and thoughtful detail.
Main Residence Features:
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Tumbled marble flooring, soaring wood ceilings, and rich copper accents throughout—including a copper soaking tub and farm sink
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An open-concept great room anchored by a wood-burning furnace, supplementing the efficient radiant heat system
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Expansive wraparound deck overlooking rolling meadows, a bass-stocked pond, and a private wilderness dotted with charming bridges
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Direct indoor access to the attached stable wing, seamlessly connecting home and horse
Equestrian Facilities:
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Five-stall barn integrated with the main house
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Radiant-heated tack room, feed room, and wash area
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Multiple paddocks, pastures, and a dressage ring complete with viewing deck
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Miles of private wooded trails, perfect for riding, hiking, or seasonal recreation
Additional Structures & Features:
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Detached 2-car garage with heated workshop/studio above—ideal for creative pursuits or guest overflow
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The Landing: A multi-functional outbuilding with 400-amp electrical service, oversized bay door, full workshop space, and a finished upstairs suite with private deck—perfect for a home office, studio, or retreat space
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Third matching outbuilding for hay or general storage, all echoing the estate’s signature bear motif woven throughout the architecture
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An engineered foundation in place for a future luxury residence, with detailed architectural plans available for visionaries ready to expand
The Lifestyle:
Bear Hill Estate is a purpose-built sanctuary, where land stewardship, fine craftsmanship, and wild beauty converge. Whether you are training show horses, stewarding land, crafting art, or simply seeking a self-contained rural escape, this estate delivers.
Complete privacy is matched by ease of access, with major commuter routes nearby and regional amenities within easy reach—including Worcester, Sturbridge, and the Berkshires.
From Zillow