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Lindsay Britton
REALTOR®
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300 High St, Winchendon, MA 01475

$1,200,000
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New to the Market Active
BEDS5 BATHS3 full 1 partial SQUARE FEET5,456 MLS#73576380
STATUSActive PROPERTY TYPEResidential - Single Family

Property Description

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.

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 lindsaybritton.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Concrete
Cooling: Ductless
Fireplaces: 6
Garage: 4
Heating: Central, Steam, Oil, Pellet Stove, Wood Stove, Ductless
Home Style: Italianate
Lot Size: 7.66 Acres
Roof Type: Tile
Taxes: $9,055
Year Built: 1923

Amenities

Bathroom - Half
Coffered Ceiling(s)
Closet
Lighting - Overhead
Crown Molding
Closet/Cabinets - Custom Built
Decorative Molding
Bathroom - Full
Attic Access
Ceiling Fan(s)
Sunken
Window Seat
Bathroom
Entry Hall
Library
Live-in Help Quarters
Walk-up Attic
Elevator
Patio
Rain Gutters
Storage
Decorative Lighting
Garden
Horses Permitted
Stone Wall

Feature Descriptions

Appliances: Tankless Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Building Area Total: 5456
Community Features: Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Laundromat, Bike Path, Conservation Area, House of Worship, Private School, Public School, T-Station, University, Other
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Dining Room: Wood / Coal / Pellet Stove, Flooring - Hardwood, Chair Rail, Lighting - Overhead, Crown Molding, Decorative Molding
Door Features: Pocket Door, French Doors
Electric: Other (See Remarks)
Elevator: Y
Exterior: See Remarks
Fireplace Features: Bedroom
Fireplace Y/N: Yes
Flooring: Wood, Tile, Vinyl, Flooring - Vinyl, Flooring - Stone/Ceramic Tile, Flooring - Hardwood
Frontage: 1150.00
GarageY/N: Yes
HeatingY/N: 1
HorseY/N: Yes
Kitchen: Flooring - Hardwood, Dining Area, Pantry, Stainless Steel Appliances, Lighting - Overhead
Laundry: Electric Dryer Hookup, Exterior Access, Sink, In Basement
Living Room: Wood / Coal / Pellet Stove, Beamed Ceilings, Flooring - Hardwood, French Doors, Cable Hookup, Crown Molding, Decorative Molding
Lot Features: Cleared, Gentle Sloping
Master Bathroom: Yes
Master Bedroom: Bathroom - Full, Wood / Coal / Pellet Stove, Flooring - Hardwood, French Doors
Open Parking Y/N: Yes
Parcel Number: M:8A3 B:0 L:7,3495583
Parking Features: Detached, Garage Door Opener, Heated Garage, Storage, Workshop in Garage, Garage Faces Side, Oversized, Paved Drive, Off Street, Paved
Parking Total: 8
Patio And Porch: Patio
Rooms Total: 12
Security: yes
Security Features: Security System
Sewer: Public Sewer
Special View Info: Scenic View(s)
Utilities: for Gas Range, for Electric Oven, for Electric Dryer
Water: Public
Waterfront Features: Lake/Pond, Beach Ownership(Public)

Local Schools

High School: Murdock
Middle School: Murdock
Elementary School: Toy Town

Listed By / Shown By

Listed By

Agency Name: Morin Real Estate
Agent Name: Luxury Division Group
Agency Phone: 978-297-0961

Shown By

Agent Name: Lindsay Britton
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 3,775.26 per month $2,670.68 Principal & Interest $754.58 Property Tax $350.00 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 09/22/2026. The listing information on this page last changed on 09/22/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 09/22/2026 7:30:31 AM EST) or MLSPIN MLS (last updated Tue 09/22/2026 7:06:10 AM EST) or Prime MLS (last updated Mon 09/21/2026 11:33:00 PM EST) or MREIS (last updated Tue 09/22/2026 2:05:13 AM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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