85 Stockbridge Rd, Lee, MA 01238

Set on over 36 scenic acres in the heart of the Berkshires, this exceptional estate is a rare opportunity to own a thriving hospitality property with multiple components: a stately, welcoming country inn, a spacious owner/manager residence, and a profitable, versatile carriage house (priced and offered separately). With its blend of pastoral charm, New England heritage, and modern amenities, the property delivers a solid bottom line income with exceptional upside for future growth – whether through expansion, events, or enhanced guest offerings.

Listing includes two (2) parcels including Inn and Owner/Manager Home, and Barn

The elegant inn features 11 guest units, including 5 suites, 5 guest rooms, and a lovely private cottage. All accommodations have updated baths, some with soaking tubs, and select rooms include gas or wood-burning fireplaces. Generous common spaces—including a welcoming living room, dining room, sun / dining room, private sitting / TV room, guest pantry, and a heated swimming pool with surrounding patio—create a warm and memorable guest experience. The 36+ acre parcel offers abundant room for future development, from additional suites and guest cottages to event venues or curated outdoor activities. Behind the scenes are a large commercial kitchen, separate prep kitchen, and ample storage. An expansive historic 2-level barn (approximately 2500 square feet) currently used for storage offers spaces for several future opportunities.

Location

Perfectly situated to attract today’s traveler, the property lies in Lee, MA, at the cultural crossroads of the Berkshires—just minutes from Tanglewood, the Norman Rockwell Museum, Jacob’s Pillow, Shakespeare & Company, The Mount, and more. Renowned for arts, music festivals, outdoor recreation, skiing, and natural beauty, the region offers guests an unmatched blend of tranquility and accessibility. Visitors to the inn enjoy pastoral mountain views, meadows, fireplaces, heated outdoor amenities, and gourmet breakfasts.

Owner / Manager Residence (Included with sale of the inn)

A new owners / manager home is being built on property with plans for ample, gracious
private living and storage space as well as a lovely panoramic view of the property and
the beautiful Berkshire mountains in the distance. Spanning two levels, it will include 3 bedrooms, 3.5 baths, an office, and inviting kitchen, dining, and living spaces, along with private, scenic outdoor areas—balancing operational convenience with privacy.

Carriage House (Priced and Offered Separately)

Adjoining the estate on 1.75 acres, the expansive, charming carriage house contains 4 fully furnished and renovated upscale modern apartments currently operating as successful short-term and seasonal rentals. There are three 2-bedroom, 2-bath apartments and one 1-bedroom, 2-bath apartment. Each includes a living room, full modern kitchen, and dining area. All units are equipped with in-unit washers and dryers. Two units have private decks and two have patios. One apartment also includes a den and two gas fireplaces, adding comfort and appeal. Each unit is separately metered for utilities, ensuring operational efficiency and flexible ownership options. An attached 4-car garage offers additional guest parking or storage options. The second floor of the carriage house includes a large vacant space with high conversion potential—ideal for additional apartments, private suites, or support facilities.

The inn and owner’s residence are offered separately from the carriage house, though all may be acquired together to create a truly comprehensive Berkshires estate.