Excellent opportunity to own a spacious two-family home with the added benefit of rental income. The 1st unit offers three-bedrooms, full bath, a comfortable living room, dining area, and generously sized kitchen with access to the back porch. The second unit features two bedrooms, a full bath, living and dining areas, and a functional kitchen. Both units have separate heat and electricity, also access to basement storage. Additional it includes a fenced backyard, detached garage, and off-street parking. Conveniently located near the town center and local amenities. A great option for owner-occupants or investors!
Welcome to 142 Pleasant St! This spacious two-family home offers 5 bedrooms, 2.5 baths, and a versatile layout. Recent updates include refinished hardwood floors, new interior paint throughout, restored carpentry, updated light fixtures, and major electrical improvements. The kitchen features new quartz countertops and new appliances, while bathroom updates include new vanities and toilets. The third level includes a bonus room and bedroom, providing even more usable space. A two-level garage adds another unique feature, with a second floor, its own egress, and plenty of possibilities. Unit 2 is located on the second floor including 1 bedroom, living room, updated bathroom and updated kitchen with quartz countertops. Conveniently located near the center of Winchendon, with shops, dining, and local amenities nearby, along with the North Central Pathway, Whitney Pond, and Lake Dennison State Recreation Area. This property has character, thoughtful updates, flexible space, and plenty of potential for its next owner.
Welcome to this well-maintained two-family home offering the perfect blend of charm, space, and investment potential. Each expansive unit features 3 bedrooms, bright and inviting living areas, spacious kitchens, and an abundance of natural light, creating comfortable spaces for both owners and tenants alike. Thoughtfully updated over the years, including two brand-new boilers installed in 2026, this property offers the ideal opportunity for an owner-occupant seeking supplemental rental income or an investor looking to add a turnkey duplex to their portfolio. Ideally situated in a convenient in-town location close to shopping, dining, schools, parks, and commuter routes, this versatile property delivers both lifestyle and long-term value. Whether you're starting your investment journey or growing an established portfolio, 263 Front Street is a property you'll want to see.
Investor opportunity awaits in a great location! This sold-as-is, 2 family property on a corner lot offers potential for those looking to bring new life to a home w/ character, spacious layouts & plenty of upside. Please note: there is currently no power at the property, & this is not a bank-owned sale. Featuring 2 separate units, this property provides flexible living space for future tenants. Both units offer multiple fireplaces, original built-ins & original details that showcase the home’s character. Additional features include a side covered porch, private rear deck & off-street parking. Located close to local shops, restaurants & several local ponds along with nearby Lake Dennison Recreation Area, offering a swimming beach, fishing, picnic areas, boat ramp access, camping, & miles of trails. Great opportunity for investors, contractors, or buyers looking for a project w/ potential. Sold-as-is.
this large 4unit house located at center of the town, always fully rented, total monthly income; $6590, each tenant pay their own utilities. each unit has good size room. . the house will deliver with all the tenants because seller don't want to lose the rental income. only do showing on weekend. 4 years new roof. rare to find, great property created good cash flow, it won't last long.

Winchendon is located in Massachusetts. Winchendon, Massachusetts has a population of 10,371. Winchendon is less family-centric than the surrounding county with 27.84% of the households containing married families with children. The county average for households married with children is 31.47%.
The median household income in Winchendon, Massachusetts is $84,120. The median household income for the surrounding county is $81,660 compared to the national median of $69,021. The median age of people living in Winchendon is 39.2 years.
The average high temperature in July is 79.6 degrees, with an average low temperature in January of 10.3 degrees. The average rainfall is approximately 47.4 inches per year, with 66.6 inches of snow per year.