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$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$590,000
5 Beds 3 Baths 73546210 MLS
This beautifully maintained 5 bedroom, 2 1/2 bath colonial boasts over 3400 sq ft. of living space. Built in 2016, this single-family residence offers spacious comfort and expansive outdoor living. The large open concept fist floor includes a modern kitchen with stainless steel appliances, granite countertops, a dual oven and center island with cooktop. A slider off the kitchen leads to a private deck with a patio fire pit and above ground pool just steps away.The property sits on a generous 5.49 acre lot, offering significant private outdoor space for recreation or quiet enjoyment. A two-car garage provides practical storage and parking solutions. This property offers a connection to nature, while only a 4 minute drive to Winchendon center with amenities such as restaurants and shopping.

365 Benjamin St, Winchendon

$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

$615,000
3 Beds 3 Baths 73544803 MLS
Immaculate, like new 1,828 sq. ft. colonial set on a private 4.13 acres. Welcome to 90 Royalston Road. Step inside to an inviting open-concept floor plan featuring a spacious kitchen with granite countertops, stainless steel appliances, an island, and cabinets with crown molding, a formal dining room, a front-to-back living room and a half bath with laundry. A slider off the kitchen leads to a private deck overlooking the above-ground pool and beautiful backyard. Upstairs, the front-to-back primary suite features a walk-in closet, linen closet and a private full bath. Two additional generously sized bedrooms and a full bath complete the second floor. Additional features include a two-car attached garage and central air. Enjoy peaceful country living just minutes from downtown, shopping, and restaurants. Welcome Home!

90 Royalston Rd N, Winchendon

$600,000
3 Beds 2 Baths 73541111 MLS
The money is in the details! 101 Royalston Rd N Winchendon This beautifully updated 3-bedroom,1.5 bath showcases quality craftsmanship throughout. Remodeled kitchen features a massive center island with seating, oversized sink, tile backsplash, tile flooring, double wall ovens, cooktop with range hood, wine refrigerator, pantry closets, & stainless-steel appliances. Front-to-back living room offers Teak flooring, leads to the composite deck overlooking the private backyard. Heated saltwater in-ground pool with gazebo & cabana, with fenced in yard. Upstairs a spacious primary bedroom with walk-in closet & Brazilian Chestnut hardwood flooring extending into the hallway & additional bedrooms. Custom built-ins for stellar dressing room or teen dream bedroom. Bath features a tiled walk-in shower & stone-top vanity. Finished lower level, Distinguished entertainment room with custom bar. 2-car attached, Mason Red Steel garage, & Reeds Ferry shed. Vivint 24/7 security system. New roof complete

101 Royalston Rd N, Winchendon

$349,000
3 Beds 2 Baths 73537312 MLS
Enjoy comfortable, low-maintenance living in desirable Glenwood Park, a welcoming and sought-after 55+ community! This spacious double wide manufactured Ranch offers 3 bedrooms and 2 full baths with an inviting open concept layout designed for easy everyday living. The heart of the home features a seamless flow between the kitchen, dining area, and living room. A separate mudroom with laundry adds convenience and provides direct access to the attached oversized two-car garage. Insulated and heated, the garage offers incredible flexibility for hobbies, projects, workshop space, or additional year-round enjoyment. Additional features include central A/C, crown molding throughout, a front porch, storage shed, and a low-maintenance yard so you can spend less time on upkeep and more time enjoying life. Move right in and enjoy easy one floor living! Quick closing is available.

52 Peggi Lane, Winchendon

$454,000
5 Beds 3 Baths 73530513 MLS
Step into a piece of Winchendon's rich history at 155 River St, a distinguished single-family residence built in 1890. With over 2000 square feet of thoughtfully designed living space, this home offers a unique blend of classic charm and contemporary comfort, perfect for those seeking a vibrant lifestyle. This expansive home features five well-proportioned bedrooms, providing ample private space for residents and guests alike. The three full bathrooms are placed for convenience and comfort. Set on a generous 16,335 square foot lot, the property offers an outdoor area for relaxation, recreation, or gardening pursuits. A single-car garage provides practical storage and parking solutions. Discover the unique character and endless possibilities of this remarkable Winchendon address.

155 River St, Winchendon

$330,000
73527138 MLS
This beautiful 82+ acres of heaven is awaiting its new owner to build their dream home. With its untouched forest and stone walls this property is nestled on the back roads of a quaint country town. Wake up every morning to the sounds of wildlife abound. Great outdoor attractions like Lake Dennison recreation area and The Winchendon Community Park are minutes down the road offering beautiful sites, biking, fishing, swimming, shows, and more. Winchendon offers a great downtown with a coffee shop, restaurants, antique stores, boutiques, and the YMCA. If you are looking for a place to retreat from the hustle and bustle of daily life, then this property might be the one to offer you the peace and serenity you are looking for. Property has roughly 2000 ft of road frontage on the unmaintained section of Benjamin St.

Benjamin St., Winchendon

$350,000
2 Beds 2 Baths 73525143 MLS
Welcome home to this meticulously maintained colonial offering 2 bedrooms, 1.5 baths, and a spacious detached 2-car garage. The bright, cabinet-packed eat-in kitchen features custom built-ins and a generous dining area. Natural light fills the living room, creating a warm, inviting space. The first floor includes a large full bath with laundry hookup, new vinyl flooring, and a mudroom with two closets. Upstairs are two bedrooms with new carpet, ample closets, and pull-down attic access. Enjoy the screened three-season porch for dining or relaxing. Outside, a 24×24 garage with new doors and openers, plus a 14×8 shed, provides excellent storage. The private backyard is a hidden gem. Minutes to Lake Dennison for swimming, camping, and recreation. Video tour available.

257 Main Street, Winchendon

$549,000
3 Beds 3 Baths 73520335 MLS
* PRICE REDUCED nearly $20,000! MOTIVATED SELLER relocating for work & ready for an offer! * Don't miss this opportunity to own this beautiful Colonial in one of Winchendon's most desirable neighborhoods. Set on 1.28 acres on a cul-de-sac with just three homes, this property offers privacy, mature landscaping & exceptional curb appeal. Inside you'll find an open foyer, hardwood floors throughout, a sun-filled layout, a living room with a gas fireplace plus a separate front-to-back family room. The eat-in kitchen features granite countertops, a center island, a breakfast bar & newer stainless steel appliances. Relax on the wraparound farmers porch or entertain on the back deck overlooking perennial gardens. Upstairs offers 3 bedrooms, including a primary suite with a walk-in closet & spa-like bathroom. Additional features include 2nd-floor laundry, a 2-car garage, shed, Buderus heating system and a 2021 roof. Easy to show!

6 Loon Road, Winchendon

$482,000
3 Beds 2 Baths 73511173 MLS
Room for everyone in this commodious colonial in picturesque Winchendon, MA! With almost 3500 sf of living area, 3BR/1.5BA, bonus rooms on the first floor (in-law?) and heated basement there's plenty of areas for living AND the fun extras! Oversized windows let in plenty of sunshine and the stainless steel applianced kitchen was recently remodeled! Main roof is 3 years old, hot and cold outdoor spicket, and there is even a generator hook-up! Spacious 1+ acre lot with shed, 2 parking areas, above ground pool and additional areas for picnics, volley ball, corn hole, etc! Winchendon is a thriving community with many natural and cultural amenities including a recreational trail, YMCA with pool and outdoor track, library, an artists' mecca, amphitheater with events throughout the year and in the area are box-store shopping, mountains, skiing, hiking, colleges, universities, hospitals and a Purple Line T stop!

35 Royalston Rd N, Winchendon

$200,000
4 Beds 1 Baths 73500136 MLS
Back on market after frozen pipes this winter. This is now a short sale. This MUST be a cash or 203k loan purchase. The pictures do not depict the current condition. This charming cape-style home is priced to sell and features four bedrooms, a large kitchen with an open concept to the dining area that has sliders to a back deck, overlooking a spacious yard. The living room is ample in size and great for entertaining. One of the bedrooms upstairs passes through to another. There are two separate staircases to the upstairs bedrooms. The backyard is secluded, quiet, and offers great space for a play area and gardening. Centrally located and versatile, it’s an excellent opportunity for comfortable family living, or a small home-based business or office setup. . New windows in 2017.

118 Spring St, Winchendon

$120,000
73491734 MLS
If you’ve been searching for the perfect place to build but haven’t found the right fit, this property may be exactly what you’ve been waiting for. Opportunity to own over 11+ acres in a peaceful Winchendon setting, directly across from 174 acres of protected state forest land—offering immediate access to trails, wildlife, and year-round outdoor recreation right outside your door, while still being just minutes to Lake Dennison Recreation Area and convenient access to Route 12. This property offers a rare combination of privacy, natural surroundings, and a head start toward future development, with a portion of the lot already cleared and a roughed-in driveway providing access to a potential homesite, along with previous perc testing completed to offer added confidence as you plan your build. Whether you’re looking to build a private residence, create a retreat, or invest in land with long-term potential, this parcel offers flexibility and opportunity in a truly special setting.

Mellen Rd, Winchendon

$385,000
3 Baths 73484914 MLS
This is a fantastic opportunity for someone who wants multiple streams of income. The building offers a two-bedroom apartment that would be great for owner-occupant use or revenue production, and a 95-seat restaurant in operation for 20 years. The restaurant has proven to be a staple in the community, serving breakfast, lunch, and dinner, as well as hosting many private functions, which is no surprise, as this building has been a place to gather since the prohibitions in the 1930's. Consider many options: continue as a thriving restaurant/bar, convert to multi-family housing (town approval required), or reimagine as office space, a bewery, a gift shop, or a creative venue. Upgrades during the current ownership include a commercial-grade septic system, electric upgrades, new water heaters, and an oil tank. This is a turnkey opportunity with immediate cash flow or limitless redevelopment potential.

61 - 63 Glenallen St, Winchendon

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