Fife'n Drum

Kent is one of the most affluent and desirable towns in northwest Connecticut, attracting a mix of full-time residents, second-home owners, and retirees seeking both privacy and lifestyle. Its bucolic setting along the Housatonic River and the Berkshire foothills has long made it a retreat for high-net-worth individuals from New York City and beyond. Many properties in Kent are large country estates, weekend retreats, or luxury homes set on expansive acreage, reflecting the town’s strong base of wealthy homeowners and its reputation as a discreet, upscale destination. The town’s historic village center offers boutique shopping, art galleries, fine dining, and cultural attractions that cater to a discerning resident and visitor base. Anchored by the prestigious Kent School and nearby private boarding schools, the area draws families and investors who value both exclusivity and community stability. This demographic strength supports not only the residential market but also creates durable demand for quality retail, hospitality, and service-oriented commercial space. With its combination of scenic beauty, cultural cachet, and affluent population, Kent continues to rank among Connecticut’s premier small towns. Its proximity to New York City—less than two hours by car—further cements its status as a weekend haven and long-term investment market for the region’s most sophisticated crowd.Northeast Private Client Group is pleased to exclusively present 53 and 59 North Main Street, the Fife ’n Drum Restaurant and Inn in downtown Kent, Connecticut. The offering comprises two adjacent parcels: a 4,159-square-foot restaurant at 53 North Main Street and a 4,156-square-foot country inn and gift shop at 59 North Main Street. The Fife ’n Drum has been a Kent institution for more than fifty years, family-owned and operated since it opened in 1973. Its upscale dining and award-winning Wine Cellar draw loyal locals and visitors from across the region. Ownership has reinvested throughout: the Glass Room was added in 2003, and the restaurant has since taken a new roof and upgraded mechanical systems. A one-bedroom apartment occupies the second floor. Next door, the Fife ’n Drum Country Inn and Gift Shop keeps ten guestrooms, with a retail shop across much of the first floor. It is one of the few lodging options in downtown Kent. A new owner can modernize the rooms and reposition the inn for higher revenue, and the gift shop could become an additional guest suite, a lobby or an amenity space. Kent draws full-time residents and weekend visitors from across the Northeast for its scenery, arts community and dining. The property sits less than one mile from Kent School and within walking distance of the village’s shops, galleries and museums. All qualified parties are invited to request the full offering package.