Winchendon Center Real Estate

Welcome to Winchendon Center, a hidden gem nestled in the heart of Worcester County, Massachusetts. This charming community offers a perfect blend of small-town charm and modern convenience, making it an ideal place to call home.

Winchendon Center is rich in history, with roots dating back to the early 18th century. As you stroll through the picturesque streets, you’ll be captivated by the well-preserved architecture and the quaint ambiance that reflects the town's storied past. The center is home to a variety of local shops, delightful eateries, and community gathering spots, creating a vibrant atmosphere where neighbors become friends.

Nature enthusiasts will appreciate the abundance of outdoor activities available in and around Winchendon Center. The area boasts beautiful parks and scenic trails, perfect for hiking, biking, and leisurely walks. The nearby Lake Monomonac offers opportunities for fishing, boating, and picnicking, making it an excellent destination for family outings and weekend adventures.

Winchendon Center is also conveniently located, providing easy access to major highways and nearby cities. Whether you’re commuting to Worcester, Fitchburg, or beyond, you’ll find that this charming community strikes the perfect balance between tranquility and accessibility.

With its friendly atmosphere, rich history, and beautiful natural surroundings, Winchendon Center is not just a place to live; it’s a place to thrive. Explore the possibilities of making this enchanting town your new home, where community spirit and scenic beauty await at every turn.

Newest Listings in Winchendon Center

$445,000

5 Beds ⋅ 3 Baths ⋅ 73563079 MLS

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.

142 Pleasant St, Winchendon

Listing courtesy of Listing Agent: Noelle Medugno from Listing Office: Lamacchia Realty, Inc..

$418,000

6 Beds ⋅ 2 Baths ⋅ 73558512 MLS

Seller is now offering a $15,000 buyer closing-cost credit! This closing cost credit may be used toward eligible closing costs, prepaid expenses, or an interest-rate buy-down—helping qualified buyers reduce their upfront costs or potentially lower their monthly payment! 263 Front St. is a 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, this is a property you'll want to see.

263 Front St., Winchendon

Listing courtesy of Listing Agent: Leanne Roy from Listing Office: Keller Williams Realty North Central.

$180,000

73545020 MLS

Discover the potential of this versatile mixed-use parcel in a convenient Winchendon location. Offering excellent visibility and easy access, this property presents a unique opportunity for investors, developers, or business owners looking to bring their vision to life. Whether you're considering commercial, residential, or a mixed-use development (subject to local approvals), the possibilities are worth exploring. Located near downtown amenities, shopping, restaurants, schools, and major commuter routes, this property combines accessibility with future potential. Buyers are encouraged to perform their own due diligence regarding zoning, permitted uses, utilities, engineering, and approvals. Don't miss this opportunity to invest in a property with flexibility and long-term potential.

M-2 L-94 School St, Winchendon

Listing courtesy of Listing Agent: Vicki Christiansen from Listing Office: RE/MAX Town Square.

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.