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:

  • Tumbled marble flooringsoaring wood ceilings, and rich copper accents throughout—including a copper soaking tub and farm sink
  • An open-concept great room anchored by a wood-burning furnace, supplementing the efficient radiant heat system
  • Expansive wraparound deck overlooking rolling meadows, a bass-stocked pond, and a private wilderness dotted with charming bridges
  • Direct indoor access to the attached stable wing, seamlessly connecting home and horse

Equestrian Facilities:

  • Five-stall barn integrated with the main houseEquestrian retreat
  • Radiant-heated tack room, feed room, and wash area
  • Multiple paddockspastures, and a dressage ring complete with viewing deck
  • Miles of private wooded trails, perfect for riding, hiking, or seasonal recreation

Additional Structures & Features:

  • Detached 2-car garage with heated workshop/studio above—ideal for creative pursuits or guest overflow
  • 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 spaceEquestrian retreatFinished acreage
  • Third matching outbuilding for hay or general storage, all echoing the estate’s signature bear motif woven throughout the architecture
  • 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.


🗝️ Offered by private showing only.
📑 Proof of funds or lender pre-approval required for appointment.

From Zillow

Leave a Reply

Your email address will not be published. Required fields are marked *