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323 Spring St, Winchendon
$370,000
2 Beds ⋅ 2 Baths ⋅ 73537527 MLS
Welcome to this beautifully remodeled single-family home that offers the perfect blend of turn-key convenience and classic warmth. Boasting 1,507 sq. ft. of bright, sun-drenched living space, the home features gorgeous hardwood and tile flooring throughout. The main level is designed for effortless living, offering an inviting living room, formal dining room, a brand-new kitchen, a full bath, and a dedicated laundry area. Plus, a fantastic main-floor bonus room serves as the ultimate dedicated at-home office! Upstairs, you'll find two spacious bedrooms and a convenient full bath. Relax on your welcoming front porch or take advantage of the 2-car attached garage and paved driveway. Perfectly nestled on a level lot, you are just steps away from local schools, parks, bike paths, and trails. This beautiful, move-in ready gem is an absolute must-see! Open House on Saturday, 6/27 from 12pm-1pm and Sunday 6/28 from 10am-11am.

323 Spring St, Winchendon

506 Central Street, Winchendon
$369,000
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

181 Goodrich Street, Winchendon
$366,000
2 Beds ⋅ 2 Baths ⋅ 73503358 MLS
Cute and cozy ranch peacefully nestled on a large corner lot in this great family neighborhood. This 2 bedroom home has 2 large paved driveways (coming in from both streets) with a finished basement (family room, 2 extra bedrooms and an extra 3/4 bath) and it's own entrance - great for future in-law potential, in home office, etc. Large back deck and very spacious storage shed (with electricity). First floor laundry room, updated bathrooms, ceramic tile floors, recessed lights, a 200 amp electrical panel and an updated kitchen (8 years). All kitchen appliances, washer, dryer, generator hookup and generator to convey. This home has a country feel but is not far from the downtown area with numerous amenities. A great environment for everyday living, this home is ready for your personal touches to make it your own. Call today!

181 Goodrich Street, Winchendon

71 Winter St, Winchendon
$360,000
4 Beds ⋅ 1 Baths ⋅ 73500431 MLS
Charming home near the heart of Winchendon Center, offering space, character, and a peaceful setting. Set on a .41-acre lot with a scenic stream, this property features a large, level yard and inviting outdoor spaces.A welcoming farmer’s porch leads into a bright living room with hardwood flooring, flowing into a dining area and updated kitchen with granite countertops and tiled backsplash. The layout offers flexibility with a first-floor bedroom and nearby full bath, while the second level includes a spacious primary bedroom and two additional bedrooms.Enjoy outdoor living on the back deck overlooking the yard and brook, along with a newly installed composite fence for added privacy. A storage shed provides additional utility, and the home is conveniently located near local shops, parks, and amenities.

71 Winter St, Winchendon

759 Brown Street, Winchendon
$355,000
3 Beds ⋅ 2 Baths ⋅ 73425866 MLS
Welcome home to this sweet and cozy ranch, perfectly situated on a spacious, level lot with a fenced-in yard—ideal for outdoor enjoyment, gardening, or simply relaxing. Inside, you’ll find 3 comfortable bedrooms, 1.5 baths, an updated kitchen, and both a welcoming living room/family room, providing plenty of space for everyone to spread out.Featuring nice flooring in much of the home, all that’s left to do is move in, unpack, and start making memories. Tucked away on a quiet road yet just minutes from shopping, dining, and everyday conveniences, this home offers the best of both peace and accessibility.For those who love the outdoors, Winchendon has so much to enjoy—spend a summer afternoon on beautiful Lake Monomonac, explore the trails and activities at Lake Dennison Recreation Area, or take a relaxing stroll or bike ride along the scenic Winchendon Rail Trail.Don’t miss your chance to make this delightful home yours!

759 Brown Street, Winchendon

70 Juniper St, Winchendon
$350,000
4 Beds ⋅ 1 Baths ⋅ 73569226 MLS
This beautifully updated single-family home offers the perfect blend of classic character and modern comfort in this established Winchendon neighborhood. Featuring 4 bedrooms and 1 full bathroom, this home has been thoughtfully refreshed and is ready for its next owners to move right in. The main level offers a welcoming layout with comfortable living spaces, an open kitchen, and convenient access to the rest of the home. Upstairs, you'll find well-appointed bedrooms with space for family, guests, or a home office. Outside, the approximately quarter-acre lot provides a manageable yard with room to enjoy the outdoors, garden, entertain, or simply relax. Located on a quiet, tree-lined street while remaining conveniently close to local schools, shopping, restaurants, recreation, and downtown Winchendon, this property offers an excellent opportunity for a first-time buyer, growing household, or anyone looking for a move-in-ready home. Seller offering a complimentary 1-year home warranty for buyers who close within 30 days of offer acceptance.

70 Juniper St, Winchendon

52 Peggi Lane, Winchendon
$350,000
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

257 Main Street, 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

64 Baldwinville State Rd, Winchendon
$350,000
3 Beds ⋅ 1 Baths ⋅ 73444600 MLS
Offer Deadline Monday 10/27 12pm. Welcome to this beautifully updated ranch offering comfort, efficiency, and modern style. Conveniently located near schools (public and private), parks, trails, Main Street, and Lake Dennison—perfect for hiking, fishing, biking, camping, and off-roading. This 3-bedroom, 1-bath home features newly installed windows that fill each room with natural light and showcase stunning white oak flooring. The kitchen offers quartz countertops and a clean, contemporary design ideal for everyday living. Enjoy a large, level backyard with privacy and mature blueberry bushes, plus a one-car garage, whole-house generator switch, and solar panels for energy savings. The unfinished basement provides great storage or future expansion potential. Thoughtfully maintained and move-in ready, this home blends small-town charm with modern convenience. Showings begin Friday, 10/17. Open House Saturday, 10/18 from 10:30 AM – 12 PM.

64 Baldwinville State Rd, Winchendon

34-36 Glenallen St, Winchendon
$350,000
6 Beds ⋅ 2 Baths ⋅ 73391215 MLS
Great opportunity to live rent-free—rent one unit and live in the other, or use it as a smart investment property! Updated custom bathrooms in both units and many upgrades throughout, including fresh paint and new flooring. Both units feature, large closets, and in-unit laundry hookups with range stove, refrigerator and microwave included. Enjoy a level backyard shaded by mature trees—perfect for relaxing or entertaining. A scenic bike and walking trail is just steps away, and the NH border is close by for easy shopping and access to lakes and recreation. Whether you're looking for extra income or a modern in-law setup, this property checks all the boxes. Live in one unit and rent the other, or enjoy space for extended family with total privacy. Turnkey, spacious, and in a fantastic location—this home is the one you’ve been waiting for! Don’t miss your chance to own this rare, gem with built-in versatility and value. Now with new updates!

34-36 Glenallen St, Winchendon

10 Jackson Ave., Winchendon
$340,000
4 Beds ⋅ 2 Baths ⋅ 73559752 MLS
Tucked into the heart of Winchendon, this inviting 2-bathroom, possible 4-bedroom home offers 1,465 square feet of warm, character-filled living space. Your first impression starts before you even step inside—the classic farmer's porch is the kind of spot made for enjoying morning and evening porch-sitting. Cross the threshold, and you're greeted by beautiful hardwood floors that make the home feel warm and inviting. The first-floor bathroom has been beautifully remodeled with a fresh, modern touch and features heated floors for added comfort. The first floor has high ceilings and tile flooring, making it perfect for a playroom.Upstairs, you will find a clawfoot tub and three rooms with wall-to-wall carpeting. One of the rooms does not have a closet, making it perfect for a home office.Outside, enjoy a small, level, fenced-in yard that's perfect for relaxing. Three off-street parking spots add everyday convenience that's hard to find in town. Did I mention the generator hookup, providing essential power when the electricity goes out?

10 Jackson Ave., Winchendon

34-36 West St, Winchendon
$340,000
4 Beds ⋅ 2 Baths ⋅ 73444327 MLS
Investors or owner-occupants, don’t miss this charming and well-maintained two-family home, perfectly situated for commuters. Each unit features 2 bedrooms, a welcoming living room, an eat-in kitchen, full bath, covered porch and back deck—ideal for comfortable living. The property has seen a large number of capital improvements within the last year to include; a new roof, new vinyl siding, one new boiler, 9 new windows, chimney replacement from the roof up, new front porch,some new flooring, and also had Mass Save insulate attic. The apartments have their own access to the divided basement allowing for additional storage. Each unit has their own parking spaces which allows for 2 vehicles on each side. The peaceful backyard offers a quiet outdoor space and the shed offers a place for outdoor tools. This versatile home is great for generating rental income, generational living or owner-occupancy. Don’t miss this fantastic opportunity—schedule your showing today!

34-36 West St, Winchendon

122 Hale St, Winchendon
$316,000
3 Beds ⋅ 1 Baths ⋅ 73453188 MLS
Welcome home to this beautiful, move-in ready gem just in time to celebrate the holiday season in your new home! The first-floor primary bedroom with double closets and convenient first-floor laundry make everyday living effortless. Upstairs, you’ll find two spacious additional bedrooms, perfect for family, guests, or that cozy home office you’ve been dreaming of. The sun-drenched living room offers a warm and inviting space, complete with a slider leading to the side yard—ideal for relaxing, entertaining, or enjoying peaceful evenings. Outdoor enthusiasts will love being just about a mile from Dunn State Park, offering endless opportunities for hiking, biking, swimming, and year-round recreation. Plus, enjoy the added convenience of being less than 15 minutes from the New Hampshire border! With a quick close possible and showings starting immediately, schedule your private tour today and be home for the holidays!

122 Hale St, Winchendon

14 Benjamin St, Winchendon
$315,000
2 Beds ⋅ 2 Baths ⋅ 73571993 MLS
Welcome to this charming Cape, offering a warm and inviting layout filled with natural light and character. The main level features a spacious open concept kitchen with tile floors and a cozy breakfast nook, creating a comfortable space for everyday living and entertaining. A welcoming mudroom provides convenient access to the home, while the bright living room and additional bonus room offer flexible space. First-floor laundry is conveniently located in the half bath. A beautiful staircase serves as a centerpiece of the home, highlighted by a large window that fills the space with natural light. Upstairs, you’ll find two generously sized bedrooms, each with closet space, along with a full bathroom conveniently between them. Outside enjoy the large, fully fenced backyard. Additional updates include a new roof in 2021 and a new hot water tank in 2024. With its charming details, functional layout, spacious yard, and thoughtful updates, this Cape is ready to welcome its next owner. Schedule your showing and come see all this home has to offer!

14 Benjamin St, Winchendon

145 Spruce St, Winchendon
$300,000
3 Beds ⋅ 1 Baths ⋅ 73466330 MLS
This charming single-family home in Winchendon offering comfort, updates, and a convenient location close to downtown amenities. This well-maintained property features 3 bedrooms and 1 full bathroom. The updated kitchen offers new cabinets, dishwasher, microwave, an electric stove, and a desirable walk-in pantry for added storage and functionality. The first-floor bathroom includes a walk-in shower and laundry hookups. Recent updates include new flooring, fresh interior paint, newly installed windows. The home features FHW by oil heat and an electric hot water heater installed in 2025. Exterior highlights include off-street paved parking for two cars, a covered porch perfect for summer enjoyment, and a spacious backyard ideal for outdoor activities. Images may be digitally enhanced and virtually staged to demonstrate layout and potential; furnishings not included. Conveniently located near

145 Spruce St, Winchendon

169 Spruce Street, Winchendon
$296,000
2 Beds ⋅ 1 Baths ⋅ 73495033 MLS
Why rent when you can move right into this fully remodeled low-maintenance home!! Situated at the end of a quiet street this home has been thoughtfully updated to reduce future expenses: ROOF, ELECTRICAL, PLUMBING, FLOORING, CARPET, KITCHEN and BATH are ALL NEW!. A sunny, fully insulated three-season room welcomes you into the kitchen featuring quartz countertops, new cabinets & appliances with a walk-in pantry for extra storage. The new bath features tiled floor and shower/tub with space for laundry. Fresh neutral paint throughout creates a clean, modern backdrop to personalize. All main utilities located on the first floor with an energy-efficient layout to keep bills down. Separate area for boiler and additional storage in attached shed. Rear yard to be hydroseeded prior to closing. A great condo alternative with more space and fewer surprises — move in with confidence!

169 Spruce Street, Winchendon

33 East St, Winchendon
$281,000
3 Beds ⋅ 1 Baths ⋅ 73525386 MLS
Opportunity awaits in Winchendon - own instead of renting! Conveniently located near the NH border, this affordable 3BR 1BA home offers convenient one-level living w/hardwood floors in most rooms & a spacious, open dining/living room perfect for everyday use. The kitchen features a pantry for added storage & the newer deck offers a great spot to enjoy the outdoors with a manageable yard for outdoor play and entertaining. A full basement provides plenty of storage space, plus two partially finished rooms that may offer potential for future expansion, home office space, hobby areas, or additional finished living area w/proper approvals. For the savvy handy buyer, this could be a great opportunity to bring your ideas, put in some sweat equity & update to your liking while owning instead of renting! Looking for an investment or flip? This could be a quick summer project to refresh & list for the fall. Motivated sellers say come see and bring an offer - quick closing possible!

33 East St, Winchendon

31 Webster St, Winchendon
$278,000
2 Beds ⋅ 1 Baths ⋅ 73473970 MLS
Welcome home to this beautifully remodeled single-family gem in the heart of Winchendon, MA. This charming two-bedroom, one-bath home blends modern finishes with comfortable living, making it truly move-in ready. Step inside to discover an updated interior featuring stylish upgrades, fresh finishes, and a thoughtfully designed layout that maximizes both space and natural light. Outside, you’ll find an exceptionally large backyard—perfect for entertaining, gardening, relaxing, or future expansion. Whether you envision summer gatherings, a play area, or a peaceful retreat, this outdoor space offers endless possibilities. Conveniently located while still offering privacy and room to breathe, this home is an ideal choice for first-time buyers, downsizers, or anyone looking for a turnkey property in a welcoming community. Don’t miss the opportunity to own this beautifully updated home with modern appeal and a generous yard in Winchendon.

31 Webster St, Winchendon

137 Spruce St, Winchendon
$275,000
2 Beds ⋅ 2 Baths ⋅ 73534409 MLS
Conveniently located close to downtown Winchendon, this 2-bedroom, 1.5-bath home offers a practical layout and easy access to local amenities. Start your mornings relaxing on the covered side porch before entering into the eat in kitchen, with a good-sized living room featuring updated flooring and first-floor laundry for added convenience. Upstairs you’ll find two bedrooms and a full bath. Outside, enjoy a manageable yard with space for gardening, pets, or outdoor relaxation. Take advantage of all that Winchendon has to offer, including direct access to the new bike/walking path, the growing downtown area, community events, Lake Dennison recreation area, and the new Community Park Amphitheater featuring concerts and seasonal events throughout the year. Bring your ideas and make this home your own!

137 Spruce St, Winchendon

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