This standout Victorian delivers the space, character, & updates buyers dream of. Enter into the grand foyer wrapped in original craftsmanship- woodwork, stair detail, hardwood floors, & a pellet-stove fireplace that immediately set the tone for the entire home. The main level offers oversized rooms, tall ceilings, pocket doors, & incredible natural light throughout each living & dining space. The updated kitchen blends perfectly w/ the era of the home & is complemented by a beautifully refreshed walk-in pantry w/ exceptional storage. Upstairs, you’ll find six bedrooms, giving u endless flexibility for guest rooms, offices, hobby spaces, or multigenerational living. The bathroom combines vintage charm & modern function w/ a tile shower & classic clawfoot tub. Need even more room? The walk-up attic & walk-out basement offer fantastic potential for storage or future expansion. Enjoy peace of mind w/a new boiler (2024). Homes with this level of detail, size, and care rarely come to market
Stunning 3-Bed, 2.5-Bath Colonial on 2.28 Private Acres! Step into this beautifully maintained home featuring a spacious open kitchen with breakfast bar, sun-filled living room with deck access, and formal dining with hardwood floors. The luxurious primary suite boasts a walk-in closet, bonus office space, and spa-like bath with Jacuzzi tub. Two additional bedrooms, serene backyard, 2-car garage, and storage shed complete this ideal retreat just minutes from outdoor recreation, shopping, and the NH border!
Unlock the full potential of this expansive farmhouse, offering generously sized rooms, a substantial lot, a huge garage, and plenty of storage — including a workshop above. The property has been cleaned out and de-leaded, but it now requires a comprehensive renovation. Bring your vision to life with this charming home, ideally located in a peaceful and desirable area. Featuring 4–5 bedrooms and 2 full bathrooms, the residence sits on a large lot with ample opportunities for expansion or customization. Whether you’re seeking to renovate, add value, or create your dream home, the possibilities are truly endless. Don’t miss this exceptional investment opportunity. Housing court approval required.
ATTENTION CONTRACTORS, FLIPPERS! COME BRING YOUR TOOLS AND IMAGINATION TO BRING THIS GEM BACK TO IT`S FULL POTENTIAL! THIS HOME BOASTS OF A NICE LARGE LIVING ROOM WITH HARDWOOD FLOORS, THREE BEDROOMS ON THE MAIN LEVEL WITH HARDWOOD FLOORS. THE THIRD BEDROOM DOES NOT HAVE A CLOSET! THERE IS A PANTRY OFF THE KITCHEN. A NEW BACK DECK THAT LEADS INTO THE KITCHEN. TWO FINISHED ROOMS IN LOWER LEVEL. JUST A SHORT DISTANCE TO TOWN, AND SCHOOLS. CLOSE TO THE NH LINE. SCHEDULE YOUR SHOWINGS TODAY!
Welcome to this updated home on a sought-after side street in Winchendon, where numerous upgrades have enhanced a spacious, inviting layout. The kitchen features abundant cabinets, ample counter space, with stainless steal appliances. While the dining room is large and filled with natural light, the living room offers a cozy fireplace for cool evenings. Both have gorgeous newly refinished hardwood floors. The first floor also includes a convenient bedroom, with two additional rooms that could serve as a private in-law suite or flexible living spaces, a full bath and another bonus room. Upstairs, you’ll find three generously sized bedrooms and a full bath, the primary with a large walk-in closet. The home includes a one-car garage underneath and an impressive deck perfect for entertaining, complemented by a large, level backyard ideal for gatherings and outdoor fun. The home has all new plumbing, mostly all new windows, new water heater, and the roof is approx 10 years old. Come see!
Welcome home to this 3-bedroom, 1.5-bath Colonial showcasing pride of ownership inside and out. Set on a nicely landscaped lot, this home offers an inviting first floor with an open dining room-to-kitchen layout featuring abundant cabinet and counter space. The kitchen flows seamlessly into the front-to-back family room, complete with direct access to the mahogany deck, patio, and hot tub—perfect for entertaining or relaxing outdoors. Enjoy the additional fire pit area for evening gatherings. A separate living room offers a cozy Harmen pellet insert and sitting area, while the remodeled half bath with laundry completes the main floor. The second level features a spacious main bedroom with walk-in closet, two additional bedrooms with new carpeting, and a remodeled full bath. The lower level provides ample storage space and is equipped with a generator hook-up. Additional updates include a new water system, new well bladder, new oil tank, and a convenient 2-car garage.
Life Long Memories Await at this Beautiful Waterfront House on Desirable Lake Monomonac! Inviting Open layout with Vaulted Ceilings, Tons of natural light , Lots of cabinet space w/ center island , quartz counters undermount cabinet lighting. Large master suite over looking the water. 6 ft whirlpool tub in the master bath, walk-in closet. NEW HEATED In-Ground Salt Water Pool "FIBERGLASS " lifetime installed by Snyder pools. Huge Stamped Concrete patio, beautiful stone walls. Wiring in place for a mJacuzzi under the covered deck and enjoy the glorious sunsets off the the large covered porch overlooking the lake . Nice beach area in a quiet cove . The house is abt 90% new with new footings and foundation . Energy Certificate . Just a small section of the existing house was saved. Has a beautiful yard . New Drainage, New Drilled Well!! Perfect house for entertaining and tranquility. Massive finished walk-out basement . Lots of natural light. Time to get settled in for the Summer!!
WELL LOVED AND CARED FOR FAMILY HOME NEW TO THE MARKET! This gorgeous colonial holds 100+ years beautiful memories and history. Original woodwork, flooring that features bullet molding throughout. The first floor offers spacious eat in kitchen ,newer stainless appliances with cozy pantry, laundry room and 1/2 bath. Open ,Sun filled Living and Dinning room with hardwood flooring, built ins and Office/Den space. Extra wide original molding staircase, stain glass window leads to second floor. Three bedrooms with plenty of closet storage space with new carpets. Mudroom for extra convenience and storage. Charming, freshly painted front porch. Oversize, 2 car garage with new doors. Located on a quiet side street. Close to schools, shopping and downtown.
Welcome to this charming 2-bedroom, 1.5-bath mobile home in the peaceful 55+ community of Glenwood Park in Winchendon. This home features a spacious living room with high ceilings and natural light, an eat-in kitchen with a mud room that gives access to a generous deck surrounded by tranquil wooded scenery. The primary bedroom features double closets for ample storage and the second bedroom has an attached half bath, ideal for guests. Outside, a large shed provides excellent outdoor storage. The paved driveway has parking for two vehicles, and the lot is nicely wooded, offering privacy with nature’s backdrop in a serene retirement friendly neighborhood. Minutes from local amenities yet nestled in a quiet park setting.
Discover easy, move-in-ready living at 35 Hillside Drive, a fully updated 3-bedroom, 1.5-bath split-level home just steps from Lake Monomonac. This home features a new roof, brand new kitchen with quartz countertops, stainless-steel appliances, and a center island. The main level offers brand new engineered hardwood flooring, recessed lighting, and a new slider leading to a private back deck and wooded yard. All bedrooms include updated Pergo flooring, and the primary bedroom has its own half bath. A finished basement adds valuable extra living space ideal for a family room, home office, or gym. Additional features include an attached two-car garage, fresh paint throughout, modern lighting, and direct access to hiking trails and just a few steps to water access. With major updates complete, a peaceful location, and a quick close available, this move-in-ready home offers incredible value near the lake. OPEN HOUSE Sat 11/22 11-12:30pm!!!
This brand new 3-bedroom, 2.5-bath Colonial on 4.8 wooded acres is under construction. Quality built 3 bedroom, 2.5 bath home offers 1,652’ of living area with an oversized attached 1-car garage. The inviting farmer’s porch with composite decking leads into an open-concept first floor with 9' ceilings and featuring the kitchen with granite countertops, an island and dining area with access to a 12x12 deck overlooking the private backyard. Upstairs includes a primary suite with full bath and walk-in closet, two additional bedrooms, a full bathroom and a convenient laundry area. The full walk-out basement offers potential for future living space. Buyers still have time to customize interior finishes. Doyle Estates—where quality, comfort, and privacy come together in this new neighborhood. Completed and staged model home available for viewing. No HOA fee. What a great way to start 2026!
Brand new Colonial set on 4.5 acres in the beautiful Doyle Estates neighborhood. This quality-built home offers 1,834 sq. ft. of stylish living space. The open-concept layout features luxury vinyl plank flooring, a spacious living room and a convenient mudroom with a custom bench, storage, and half bath. The kitchen will have quartz countertops, maple cabinetry and an island perfect for entertaining, while the dining area opens to a 12x14 deck overlooking the peaceful backyard. Upstairs, the luxurious primary suite includes a tray ceiling, sitting area, dual-sink bathroom and barn door to a walk-in closet. Two additional bedrooms, a full bath and laundry room complete the second floor. Enjoy central A/C, an attached 2-car garage, and a walk-out basement ready for future expansion. Doyle Estates—where quality, comfort, and privacy come together in this new neighborhood. This house is ready for buyers personal interior selections! Late December completion.
Here’s your opportunity to get into this coveted 55+ park! Built in 2007, this youngster has all the modern conveniences & layout, plus an extra-wide carport and extra-thick skirting to help keep things nice and cozy in winter. Being on an elevated lot means you have a lush, verdure view right from your kitchen window! And storage shed for all the garden gadgets. The Glenwood neighborhood is located a mere 5 miles from groceries & other shopping just over the line in New Hampshire. Further up the road are exclusive New Hampshire offerings such as Mt. Monadnock and Cathedral of the Pines. Head south a couple of miles to the Winchendon Community Park with its stunning amphitheater overlooking the water & robust event calendar. Downtown amenities include expanded recreational trail, YMCA, library and delightful local eateries and gift shops. A fabulous home in a wonderfully quaint New England town. Don't miss the Open House this Saturday 12/13 from 9AM-11AM! DON’T WAIT ON THIS ONE!
27 Cottage St, Winchendon, MA, presents a single-family residence, newly built and ready to welcome its first residents. This new home offers the promise of modern living within a peaceful setting. The residence features three bedrooms, providing comfortable accommodations for rest and relaxation. Two full bathrooms and one-half bathroom offer convenience and functionality, ensuring that the needs of everyday living are met with ease and style. With a living area of 1400 square feet, the home provides a practical and inviting space for both intimate gatherings and quiet moments of reflection. The ample lot size of 1.9 acres offers a sense of openness and connection with nature. This single-family residence at Lot 1 Cottage St is a fantastic opportunity to create the lifestyle you have always desired. End of October completion date
21 Cottage St, Winchendon, MA, presents a single-family home, newly built and ready to welcome its first residents. This new home offers the promise of modern living within a peaceful setting. The residence features three bedrooms, providing comfortable accommodations for rest and relaxation. Two full bathrooms and one-half bathroom offer convenience and functionality, ensuring that the needs of everyday living are met with ease and style. With a living area of 1400 square feet, the home provides a practical and inviting space for both intimate gatherings and quiet moments of reflection. The ample lot size of 1.9 acres offers a sense of openness and connection with nature. This single-family residence is a fantastic opportunity to create the lifestyle you have always desired. End of October completion date
Follow the long, picturesque driveway and discover a world of privacy, luxury, and calm complete with a pool, outdoor jacuzzi, encompassed in 24 acres of land. Spanning approximately 2,289 square feet, this home features 3 bedrooms, 2 full baths, an office, a family room and a generous 2 car garage. Step inside to a beautiful open concept living area featuring vaulted ceilings and a seamless flow between the kitchen and living room. The living area extends into a stunning sunroom filled with natural light from multiple windows and skylights, a perfect space for year round relaxation. Designed with privacy in mind, the primary suite occupies its own wing of the home, featuring a en-suite bath, a spacious walk in closet and a versatile office space. The backyard oasis features a in-ground pool surrounded by mature trees for privacy, with a spacious deck and gazebo perfect for entertaining. Every detail of this home was designed to offer the perfect blend of comfort and privacy.
Welcome to this 3-bedroom, 2.5-bath Colonial situated on Bayberry Circle! Enjoy a fenced-in backyard perfect for outdoor entertaining, complete with an above-ground pool and back deck or relax out on the inviting front porch. The first floor offers a welcoming open floor plan featuring a spacious living room and a modern kitchen with a center island, granite countertops, and an adjoining dining area—ideal for everyday living and gatherings. Upstairs, you’ll find the main bedroom with a full bath and walk-in closet, along with two additional bedrooms and another full bath. Luxury vinyl plank flooring throughout. The full walkout basement provides excellent potential for future expansion or ample storage. A wonderful home offering comfort, style, and room to grow!
Welcome to this charming ranch-style home nestled on over 3 acres of picturesque land. Enter to a spacious formal living & dining area, filled w/ natural light through a large picture window. A comfortable den w/ fireplace & sliding glass doors opens to your back deck. The kitchen boasts a farmhouse sink & a dining area w/ a bay window overlooking your vast backyard. This home offers a convenient laundry room w/ access to a walk-up attic for easy storage. The primary bedroom features recessed lighting, a walk-in closet & a private bath, while two additional bedrooms & a second full bath provide plenty of space for family or guests. Enjoy the bright three-season sunroom or head down to the versatile partially finished walkout lower level, complete w/ a full bath & sauna plus a huge workshop. Outdoors, you’ll find mature apple trees, gardening area plus two electrified sheds. Additional highlights include central air, central vacuum, and the peaceful privacy of your expansive lot.
Nestled on a large 6.47 acre lot in the charming town of Winchendon, this new home offers a unique opportunity to embrace refined country living in a private setting. This attractive property is ready to welcome you. The kitchen is a culinary dream, featuring a large kitchen island that serves as a natural gathering place, complemented by sleek stone countertops and stylish cabinets that provide ample storage, while a tasteful backsplash adds a touch of sophistication. The bright and airy living room invites relaxation and conversation. With three bedrooms and two full bathrooms, plus a half bathroom, this residence provides comfortable accommodation for everyday living. The convenience of a paved driveway and two-car garage ensures secure parking and additional storage space. All in convenient Winchendon location, close to downtown, schools and shopping.
Inviting and spacious, this home offers a fantastic layout for everyday living and entertaining. Enter into the front-to-back living room featuring hardwood floors, a cozy fireplace, and a sliding glass door that opens to your back deck. The updated kitchen boasts a breakfast bar, black stainless steel appliances, and flows seamlessly into the formal dining room with hardwood floors—perfect for hosting gatherings. A convenient half bath completes the main level. Upstairs, discover a large family room with a vaulted ceiling, skylights, and a gas fireplace, along with three comfortable bedrooms, a full bath, and a versatile office. Outside, enjoy your own backyard retreat with a spacious deck, an in-ground pool, and a storage shed. A paved driveway and two-car attached garage add ease and functionality to this exceptional property. Don't miss the chance to make this house YOUR home!
Beautifully renovated 4-bedroom, 1.5-bath home in Winchendon featuring a brand-new kitchen with quartz countertops, stainless steel appliances, center island, and built-in wine rack. Enjoy the open layout with brand-new flooring throughout, complemented by modern updates including new electrical, new heating system, and new roof. The spacious bedrooms offer plenty of natural light, while the updated bathrooms add a touch of style and convenience. Outdoor living is made easy with new front and rear decks, perfect for relaxing or entertaining. This move-in ready property combines classic charm with modern upgrades, offering peace of mind and comfort for years to come. Don’t miss the opportunity to own this turnkey home!
Spacious Colonial on Over 4 Acres of Tranquility. Enjoy 2,648 sq ft of comfortable living space nestled on 4.13 private acres in a serene, natural setting. Built in 2004, this 7-room, 3-bedroom, 2-bath Colonial offers a flexible layout and plenty of charm. The expansive 28' x 22' living/family room is great for gathering, while the formal dining room and den—both with hardwood floors—add elegance and warmth. The den also features a cozy propane fireplace, perfect for New England evenings.The large kitchen includes a breakfast area, ideal for casual dining or entertaining. Unwind in the main bath’s spa tub. Additional highlights include a 2-car attached garage and close proximity to outdoor recreation—Lake Dennison and Otter River are minutes away.Whether you're looking to move right in or update the home to match your vision, this property offers exceptional value—delivering space, privacy, and location at a price well below similar listings in the area.
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.
