300 High St

Taxes: $9,055 (2025)

About this home

An exceptional Italianate property where architectural distinction, craftsmanship, and a strong sense of place come together on more than 7.5 acres near Winchendon’s historic Old Center. Commissioned as a country estate and conceived with accomplished early 20th-century design professionals, the property reflects a level of planning and execution rarely encountered today. Well-proportioned rooms, finely executed millwork, detailed finishes, and balanced scale create an atmosphere that feels substantial yet welcoming. The library offers a handsome setting for work or conversation, while the formal dining and living rooms reflect the artistry of an earlier era. A sun-filled conservatory with black-and-white tile, expansive windows, and French doors to the patio brings light and landscape into the home. Above, an artist’s studio with windows on three sides enjoys second-level views toward Mount Monadnock—an inspiring setting for painting, writing, music, or design. A separate service wing, historically designed for household staff, offers flexibility for live-in assistance, an au pair, guests, or broader household needs. Mature plantings, established trees, open lawn, and views toward Mount Monadnock contribute to a thoughtful relationship between home and landscape, reflecting the intentional character of the grounds. The abundant acreage offers possibilities for equestrian use, gardens, recreation, or outdoor living, while two surveyed lots provide additional options for future plans. The location offers convenient access to shopping, colleges and universities, and commuter rail service toward Greater Boston. The surrounding region offers four-season recreation, cultural amenities, lakes, conservation lands, and proximity to the mountains of southern New Hampshire. Spacious interiors, multiple gathering areas, and a natural connection to the outdoors create an inviting environment for daily life, longer stays, memorable gatherings, and every season. Rich in character and impressive in scale, this distinctive residence is defined by enduring design, luxuriant acreage, and a setting with presence. The Estate's accessibility and privacy create a rare balance of comfort, versatility, and connection to the wider region. Schedule a private showing today and experience firsthand what sets this home apart.

Property details

Sewer

Private

Style

Italianate

Water

City/Town Water

Cooling

Ductless Mini-Split System

Heating

Central Heat, Heat Pump, Individual, Pellet Stove, Wood Stove, Ductless Mini-Split System

Type

Detached

Flooring

Wood, Tile, Vinyl

Road type

Public

Appliances

Range, Wall Oven, Dishwasher, Disposal, Microwave, Countertop Range, Refrigerator, Washer, Dryer

Master Bath

Yes

Construction

Other (See Remarks)

Roof

Combination

Garage

Detached, Garage Door Opener, Heated, Storage, Work Area, Side Entry, Oversized Parking

Lot

Paved Drive, Cleared, Gentle Slope, Scenic View(s)

Parking

1-10 Spaces, Paved Driveway

Basement

Full, Partially Finished, Walk Out, Interior Access, Concrete Floor, Exterior Access

Electric

Common

Exterior

Patio, Gutters, Storage Shed, Decorative Lighting, Garden Area, Horses Permitted, Stone Wall

Interior

Security System, Cable Available, Walk-up Attic, French Doors, Elevator