An exceptional Italianate property where architectural distinction, craftsmanship, and a strong sense of place come together on more than 7.5 acres near Winchendons 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 artists 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.
Listed By
Agency Name: Morin Real Estate
Agent Name: Luxury Division Group
Agency Phone: 978-297-0961
Shown By
Agency Title: Better Homes and Gardens Real Estate The Masiello Group
Agency Phone: 800-741-1540
Choose a date and time to see 300 High St, Winchendon, MA 01475.
An agent will get in touch to confirm your request shortly.
Estimated Payment
$ 3,775.26 per month $2,670.68 Principal & Interest $754.58 Property Tax $350.00 Homeowner's InsuranceIf the email address was found in our system, your password has been sent. Please check your inbox.
Back to Login
300 High St | MLS# 73576380
This single family home located at 300 High St, Winchendon, MA 01475 is currently listed for sale with an asking price of $1,200,000. This property was built in 1923 and has 5 bedrooms and 3 full and 1 partial baths with 5456 sq. ft. Search Winchendon real estate on www.masiellogrouprealestate.com today.