Winchendon Real Estate

Welcome to Winchendon, Massachusetts – a charming town nestled in the heart of Worcester County, where the beauty of nature meets the warmth of a close-knit community. Known for its rich history and picturesque landscapes, Winchendon offers a serene escape from the hustle and bustle of city life while providing all the conveniences of modern living.

As you explore Winchendon, you’ll be captivated by its quaint downtown area, filled with unique shops, delightful eateries, and friendly faces. The town boasts a strong sense of community, with numerous events throughout the year that bring residents together, from seasonal festivals to farmers’ markets. Families will appreciate the excellent school system and the abundance of recreational opportunities, including parks, hiking trails, and nearby lakes perfect for fishing and boating.

Nature enthusiasts will find solace in the stunning surroundings, with the lush greenery of the Monadnock Region beckoning outdoor adventures. Whether you’re hiking in the nearby woods or enjoying a leisurely stroll along the scenic streets, Winchendon’s natural beauty is sure to inspire.

With a rich tapestry of history, culture, and community spirit, Winchendon is more than just a place to live; it’s a place to thrive. Whether you’re looking to buy your first home, retire in peace, or invest in a growing market, Winchendon offers a variety of real estate options to suit every lifestyle. Come discover the charm of Winchendon – where your dream home awaits!

Newest Listings in Winchendon

$449,000

3 Beds ⋅ 3 Baths ⋅ 73554607 MLS

Newer constriction with DEEDED BEACH RIGHTS to Sunset Lake. Rear boundary borders thousands of conservation acres with endless ATV and snowmobile trails. Seasonal views of the lake. Town water! 3 BD + office, 2 ½ baths house with DEEDED BEACH RIGHTS to Sunset Lake. Master BD with master bath. Good size kitchen and dinning room. Washer/dryer (hook up) on the 1st floor. Ashburnham mailing address but Winchendon public schools. Use Ashnburnham for GPS

33 W Shore Drive, Winchendon

Listing courtesy of Listing Agent: Roman Deych from Listing Office: Roman Deych.

$299,000

7 Beds ⋅ 5 Baths ⋅ 73554552 MLS

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.

179 Front St, Winchendon

Listing courtesy of Listing Agent: Blood Team from Listing Office: Keller Williams Realty - Merrimack.

$409,900

73554498 MLS

An excellent opportunity to purchase a highly visible building in downtown Winchendon! First floor has been used by a successful real estate company since 1992. Spacious second floor apartment yields $1,550/month rent. Second floor tenant is month to month and pays their own electric and heat (electric baseboard). First floor offers FHA heat and central air conditioning! Recent improvements include roof, paved driveway, electrical and plumbing!! Custom office furniture on first floor will convey. A fantastic investment and business opportunity!!

215 Central Street, Winchendon

Listing courtesy of Listing Agent: Nancy Macomber from Listing Office: Sparks Real Estate.

$485,000

4 Beds ⋅ 3 Baths ⋅ 73554031 MLS

Completely refinished in 2023, this beautiful 4-bedroom, 2.5-bath home combines modern updates with a functional layout in a fantastic location. Just minutes from downtown shopping, restaurants, schools, and commuter routes, you'll enjoy the convenience of being close to everything while still having a backyard that feels surprisingly private. Step inside to an open-concept first floor where the living room, dining area, and kitchen flow together, making the space perfect for everyday living and entertaining. The living room features a coffered ceiling and a large picture window that fills the home with natural light. The kitchen offers plenty of cabinet space, granite countertops, a beautiful tile backsplash, and a center island overlooking the dining area, making it easy to stay connected with family and guests while preparing meals. The first-floor primary suite is a standout feature, offering a spacious bedroom, walk-in closet, and a beautifully finished private bath complete with a double vanity, soaking tub, and walk-in glass shower. A half bath rounds out the first floor. Upstairs you'll find three generously sized bedrooms, all with great closet space, along with a full bath and a separate laundry room for added convenience. Outside, the level, three-quarter fenced backyard is ready to enjoy. Spend summer evenings on the stone patio gathered around the built-in fire pit, while the storage shed and detached one-car garage provide plenty of room for your tools, lawn equipment, and extra storage. Whether you're hosting friends, letting kids or pets play, or simply enjoying a quiet evening outdoors, this backyard offers plenty of space to make it your own. With its extensive updates, spacious floor plan, and desirable location, this move-in-ready home is one you won't want to miss.

180 Spring St, Winchendon

Listing courtesy of Listing Agent: Michelle Peterson from Listing Office: Elm Grove Realty, LLC.

$359,000

5 Beds ⋅ 2 Baths ⋅ 73553845 MLS

For more than 50 years, this home has been lovingly cared for by the same family. Beautiful solid wood kitchen cabinets, woodwork, and trim hand-crafted by the homeowner. Hardwood floors have been preserved under the plush carpeting throughout most rooms. (can be seen in the upstairs closet) Plenty of closet space, storage, and built-ins and 10ft ceilings found throughout the house. The first floor features an eat-in kitchen, dining room, living room, half bath, office, and a four season sunroom surrounded by windows. The 2nd floor offers three spacious bedrooms, a full bath, built in cabinets, and a laundry chute. The walk-out basement has two finished rooms, a laundry area with a utility sink and access to the garage & backyard. This corner lot includes plenty of parking with two driveways, a one-car garage, and a storage shed. The location is close restaurants and shopping in both MA and NH. Find Lake Dennison nearby for outdoor recreation and public beach access, The Winchendon School, a private boarding & day campus for students, the North Central Pathway rail trail for biking, or the amphitheater at Winchendon Community Park for live music by the water. Stop by to see what this home has to offer!

506 Central Street, Winchendon

Listing courtesy of Listing Agent: Kim Tabor from Listing Office: Coldwell Banker Realty - Leominster.

$450,000

4 Beds ⋅ 3 Baths ⋅ 73550549 MLS

Endless possibilities await! Originally built as a single-family home, this property offers the opportunity to restore it to a spacious 4-bedroom residence while enjoying over 6 acres of flat, usable land on a scenic country road just minutes from the New Hampshire border. Perfect for those dreaming of a small homestead, hobby farm, or simply room to spread out, the property features a large two-story barn, two open fields, private wooded acreage, and Robbins Brook flowing through the land. Currently configured as a 3-family, it also presents the potential for rental income while planning future renovations. Property is being sold as is. Seller will not provide Title V. Buyers are responsible for their own due diligence. Also listed as a Multi Family MLS #73550523

60 Robbins Rd, Winchendon

Listing courtesy of Listing Agent: Brenda Albert from Listing Office: LAER Realty Partners.

$450,000

4 Beds ⋅ 3 Baths ⋅ 73550523 MLS

Opportunity awaits with this unique 3-family property set on over 6 acres of flat, usable land on a scenic country road just minutes from the New Hampshire border. Whether you're seeking an owner-occupied investment, income property, or a small homestead, this property offers exceptional potential. Originally built as a single-family home, it could be converted into a spacious 4-bedroom residence. Features include a large two-story barn, two large open fields, private wooded area, and Robbins Brook flowing through the property, creating a picturesque setting for farming, gardening, or recreation. Property is being sold as is. Seller will not provide Title V. Buyers are responsible for their own due diligence. Also see MLS #73550549 - Single Family.

60 Robbins Rd, Winchendon

Listing courtesy of Listing Agent: Brenda Albert from Listing Office: LAER Realty Partners.

$449,000

3 Beds ⋅ 2 Baths ⋅ 73550476 MLS

Set on a sprawling 2.69-acre lot, this inviting Cape offers the perfect blend of comfort, space, and country charm. The bright, airy kitchen features stainless steel appliances, abundant cabinet and countertop space, and sliders leading to the deck—ideal for seamless indoor-outdoor living. A spacious family room showcases a stunning wood-paneled, beamed ceiling and a classic brick fireplace, creating a warm and welcoming gathering space. The open living and dining rooms provide an easy flow for everyday living and entertaining. Two bedrooms are conveniently located on the second floor, offering privacy from the main living areas while a 1st floor bedroom completes the package. Outside, enjoy the expansive yard complete with a barn/stable, an attached garage, and plenty of off-street parking, providing endless possibilities for hobbies, storage, animals, or outdoor enjoyment.

45 Town Farm Road, Winchendon

Listing courtesy of Listing Agent: Corrie Ann Carbone-Patricelli from Listing Office: Lamacchia Realty, Inc..

$344,900

4 Beds ⋅ 2 Baths ⋅ 73550098 MLS

**OFFER DEADLINE- Monday 7/20/26 @ 5pm** Charm and character from 1870 with all the right updates in mind! This 2,111 square foot single-family home delivers historic character with genuinely useful, flexible space. Four bedrooms offer plenty of room to spread out, work from home, host guests, or set up that hobby space you've been dreaming about. The layout adapts to however you want to live in it. The standout? A first-floor bathroom that goes well beyond the basics — oversized and outfitted with a full laundry area, making everyday routines effortless and giving the first floor a smart, functional flow. 15 Juniper St is a rare chance to own a piece of Winchendon's history without sacrificing modern convenience. Fresh paint throughout and oil tank replaced in 2026. Close to downtown, dining, bike path, amphitheater, schools and playgrounds.

15 Juniper St, Winchendon

Listing courtesy of Listing Agent: Diana Boutell from Listing Office: Lamacchia Realty, Inc..

$250,000

3 Beds ⋅ 2 Baths ⋅ 73549049 MLS

Opportunity awaits with this 3-bedroom, 1.5-bath Cape situated on a sunny and spacious 0.69-acre lot. The first floor offers an eat-in kitchen, a front-to-back living room, a full bath, and a convenient first-floor primary bedroom. Upstairs, you'll find two additional bedrooms and a half bath, providing a functional layout. With some vision and updates, this property has the potential to become a wonderful place to call home and is an excellent opportunity for buyers looking to build equity. Being sold as is, this home is best suited for cash or 203k financing, as it will not qualify for CONV, FHA, VA, or USDA financing, as is. If you're searching for a property with potential on a generous lot, this could be the one you've been waiting for. Seller will consider installing a new septic and fixing the bathroom plumbing to pass conventional financing with a sales price of $285k or greater.

26 Royalston Rd. North, Winchendon

Listing courtesy of Listing Agent: Michelle Peterson from Listing Office: Elm Grove Realty, LLC.

$484,900

3 Beds ⋅ 3 Baths ⋅ 73547936 MLS

Tucked into a peaceful wooded setting, this inviting Colonial offers the privacy, flexibility, and outdoor space that make everyday life feel like a retreat. Imagine morning coffee on the deck surrounded by trees, summer gatherings overlooking the expansive yard, or quiet evenings by the fireplace after a long day. The bright, comfortable interior has been thoughtfully refreshed with attractive updates while maintaining a warm, welcoming feel throughout. A versatile additional room offers flexible space for a home office, hobbies, recreation, or other uses. Downstairs, the partially finished walkout level creates even more room to relax and opens to a patio where the backyard becomes a natural extension of the home. A large garage, newer shed, and generous grounds provide outstanding space for recreation, projects, and storage. Private yet convenient, this is a home designed to be enjoyed both inside and out. Schedule a showing today and experience everything this home has to offer!

309 Ash Street, Winchendon

Listing courtesy of Listing Agent: Miller Real Estate Group from Listing Office: Keller Williams Pinnacle Central.

$390,000

3 Beds ⋅ 2 Baths ⋅ 73547144 MLS

Presenting a distinguished single-family residence constructed in 1854, offering 2151 square feet of refined living space. This property stands as a testament to enduring architectural integrity, meticulously preserved to offer a unique blend of historical charm and contemporary functionality. The residence encompasses three well-proportioned bedrooms, providing comfortable private accommodations, including a large walk-in off the primary. Complementing these are one full bathroom on the second floor and one-half bathroom with laundry on the first floor. Further enhancing the property's appeal is a two-car garage, providing secure parking and additional storage solutions. The generous lot, spanning 29621 square feet, offers ample exterior space for various outdoor pursuits and landscaping possibilities including a built-in pool for those HOT summer days.

32 Ash St, Winchendon

Listing courtesy of Listing Agent: Hometown Team from Listing Office: Real Broker MA, LLC.

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