Highest & Best due June 9th by 6 PM. Loved by the same family for generations, this year-round Lake Damond waterfront property is ready for its next chapter. Offering 125 feet of lake frontage, this 4 bedroom, one bath home is tucked into a wooded setting for privacy while still providing plenty of open, sunny space to enjoy the water. The main level features an open living, dining, kitchen area w/ a bank of windows overlooking the lake, access to the expansive deck, 2 first floor bedrooms, a 1st floor bath w/ shower, and workshop/utility/storage room. Upstairs are 2 additional bedrooms. Outdoor features include swimming, non-motorized boating, dock, 3 outbuildings, and access to the association’s private beach and play ground. Improvements include a metal roof, Well, replacement windows, and fuel oil tank. Property is being sold furnished & strictly AS IS, WHERE IS. Septic is operational but its assumed the system will need replacement. Cash buyer/rehab loan likely due to septic.
Tucked away on a dead-end street in the foothills of the Berkshires, this thoughtfully designed Cape offers space, flexibility, and a setting that feels like a retreat. Set back on 2.73 acres with scenic views, the open floor plan invites easy everyday living and effortless entertaining. The main level features a primary suite with a private bath, walk-in closet, and its own balcony for quiet morning coffee or unwinding at the end of the day. A first-floor laundry room adds convenience, while the dining area flows into a kitchen with granite counters and seating—perfect for gathering and conversation. A home office or flex room completes the first floor, offering options for work, hobbies, or guests. Upstairs, you’ll find four additional bedrooms plus access to a bonus space with a separate entrance from the garage—ideal for future expansion or creative use. The walk-out basement includes partially finished space with radiant floors, cold storage, and additional potential.
The equestrian elegance of this property starts at the gated driveway. Perched on the hill is a fully equipped custom built multi use barn entirely heated by radiant floor heat & includes 8 stalls w/auto waterers perfect for breeders or veterinarian. Includes kit, office, W&D & bath. Also included is a heated equip shed and workshop, heated drive through aisle for large trucks, wash stalls & more. The grounds include 8 paddocks with waterers , an exercise track, 3 lg pastures w/ hydrants. A second barn offers 12 addl stalls. The Meticulously kept grounds is professionally landscaped and a covered wraparound porch to greets guests. Kitchen has quartz counters, GE Profile appliances & a slider to large patio perfect for entertaining. Gas Fireplace in Livingroom, hardwood floors w/cherry inlay. Sweeping staircase to second floor w/4 bedrooms and a grand primary en suite with a private entrance. Whole house generator, central vac & 3 car garage. SEE VIDEO & ATTACHMENT FOR FULL DETAIL

Chesterfield is located in Massachusetts. Chesterfield, Massachusetts 01012has a population of 1,087. Chesterfield 01012 is more family-centric than the surrounding county with 28.67% of the households containing married families with children. The county average for households married with children is 27.29%.
The median household income in Chesterfield, Massachusetts 01012 is $80,156. The median household income for the surrounding county is $76,959 compared to the national median of $69,021. The median age of people living in Chesterfield 01012 is 49 years.
The average high temperature in July is 79.5 degrees, with an average low temperature in January of 10.4 degrees. The average rainfall is approximately 51.8 inches per year, with 77.1 inches of snow per year.