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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!

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

$487,000

Excellent owner-occupied or investment opportunity at 132–134 Lincoln Ave in Winchendon! This recently renovated two-family sits on a spacious flat lot on a quiet side street, offering strong rental potential and comfortable living. The first-floor unit features 2 bedrooms with updated finishes, while the second-floor unit offers 3-bedroom potential or flexible bonus space perfect for a home office or additional living area. Both units showcase refreshed interiors with beautifully refinished hardwood floors and updated kitchens! The property includes a detached two-car garage, ample off-street parking, and a sizeable yard ideal for outdoor enjoyment. Separate utilities and a full basement provide added value and functionality. Whether you're looking to live in one unit and offset your mortgage or add to your portfolio, this move-in ready multi-family checks all the boxes. Open House Saturday April 18th, 11:30-1! Offers received, Highest and Best Deadline of Sunday April 19th at 2p.

5 Beds ⋅ 2 Baths ⋅ 73500927 MLS

Excellent owner-occupied or investment opportunity at 132–134 Lincoln Ave in Winchendon! This recently renovated two-family sits on a spacious flat lot on a quiet side street, offering strong rental potential and comfortable living. The first-floor unit features 2 bedrooms with updated finishes, while the second-floor unit offers 3-bedroom potential or flexible bonus space perfect for a home office or additional living area. Both units showcase refreshed interiors with beautifully refinished hardwood floors and updated kitchens! The property includes a detached two-car garage, ample off-street parking, and a sizeable yard ideal for outdoor enjoyment. Separate utilities and a full basement provide added value and functionality. Whether you're looking to live in one unit and offset your mortgage or add to your portfolio, this move-in ready multi-family checks all the boxes. Open House Saturday April 18th, 11:30-1! Offers received, Highest and Best Deadline of Sunday April 19th at 2p.

132-134 Lincoln Ave, Winchendon

$485,000

Tucked away on a peaceful dead-end road, this 2,600 sq ft home offers space, comfort, and a scenic setting. The main level features a sunlit living room with a striking brick fireplace, flowing into the dining area with sliders to the backyard. The kitchen is generously sized and offers an additional eating area. You will find 3 bedrooms on this floor, including a primary suite with private bath, plus another updated full bath. The lower level provides flexible living with a family room warmed by a pellet stove, a 4th bedroom, office, two additional bonus rooms, and laundry area. Outside, one will enjoy mature perennials, a vernal pool, quiet sounds of nature, and a circular driveway with plenty of parking. The oversized garage fits up to 4 cars tandemly and includes a large unfinished space above with exciting potential for an ADU (with town approval), artist studio, gym, or whatever suites your needs. New furnace 2023. House was just connected to town sewer! Beautifully maintained!

4 Beds ⋅ 2 Baths ⋅ 73511691 MLS

Tucked away on a peaceful dead-end road, this 2,600 sq ft home offers space, comfort, and a scenic setting. The main level features a sunlit living room with a striking brick fireplace, flowing into the dining area with sliders to the backyard. The kitchen is generously sized and offers an additional eating area. You will find 3 bedrooms on this floor, including a primary suite with private bath, plus another updated full bath. The lower level provides flexible living with a family room warmed by a pellet stove, a 4th bedroom, office, two additional bonus rooms, and laundry area. Outside, one will enjoy mature perennials, a vernal pool, quiet sounds of nature, and a circular driveway with plenty of parking. The oversized garage fits up to 4 cars tandemly and includes a large unfinished space above with exciting potential for an ADU (with town approval), artist studio, gym, or whatever suites your needs. New furnace 2023. House was just connected to town sewer! Beautifully maintained!

305 Benjamin St, Winchendon

$485,000

Welcome to this beautifully maintained 2021-built Colonial in Winchendon, MA, offering 1,664 sq ft of modern comfort and efficiency. This 3-bedroom, 2.5-bath home features granite countertops, a functional open layout, and thoughtful upgrades throughout. The updated basement provides additional flexible living space, while the whole-house well-water filtration system ensures quality and peace of mind. Enjoy the convenience of a one-car attached garage, solar panels for energy savings, and a septic system recently pumped in October 2025. Designed with safety in mind, the home includes an in-house fire prevention sprinkler system. Move-in ready and meticulously cared for, this property blends modern construction, efficiency, and everyday practicality in a desirable residential setting.

3 Beds ⋅ 3 Baths ⋅ 73481771 MLS

Welcome to this beautifully maintained 2021-built Colonial in Winchendon, MA, offering 1,664 sq ft of modern comfort and efficiency. This 3-bedroom, 2.5-bath home features granite countertops, a functional open layout, and thoughtful upgrades throughout. The updated basement provides additional flexible living space, while the whole-house well-water filtration system ensures quality and peace of mind. Enjoy the convenience of a one-car attached garage, solar panels for energy savings, and a septic system recently pumped in October 2025. Designed with safety in mind, the home includes an in-house fire prevention sprinkler system. Move-in ready and meticulously cared for, this property blends modern construction, efficiency, and everyday practicality in a desirable residential setting.

7 Madison Ave, Winchendon

$484,900

Welcome to 46 Baldwinville State Road! 2024 built colonial on a 1.5 acre lot. This beautiful home consists of 3 bedrooms, the primary bedroom has 2 closets (1 walk in) and a full bath, luxury vinyl flooring throughout, slider going out to a wood deck, propane heating, central air, granite counter tops. Nothing to do but move in. Set up your private showing today!

3 Beds ⋅ 3 Baths ⋅ 73461683 MLS

Welcome to 46 Baldwinville State Road! 2024 built colonial on a 1.5 acre lot. This beautiful home consists of 3 bedrooms, the primary bedroom has 2 closets (1 walk in) and a full bath, luxury vinyl flooring throughout, slider going out to a wood deck, propane heating, central air, granite counter tops. Nothing to do but move in. Set up your private showing today!

46 Baldwinville State Road, Winchendon

$482,000

***OFFER DEADLINE ** 12PM ON TUESDAY MARCH 31st*** Welcome home to this lovely Colonial where comfort, style and thoughtful updates come together beautifully. The main level features a spacious living room and a fabulous kitchen layout with a cozy breakfast nook, enhanced by stainless steel smart appliances, cooktop and wall oven/microwave combo; perfect for the home chef enthusiast. Stylish gray cabinetry, high-end quartz countertops, classic subway tile backsplash and beautiful young flooring throughout the main level truly elevate the space. A bright and inviting dining area with sliders leads to the deck, creating a seamless indoor-outdoor connection. Both bathrooms have been tastefully updated with clean, cohesive finishes. Upstairs you’ll find three well-proportioned bedrooms, including a primary with a walk-in closet. Set on a generous lot, the property offers abundant off-street parking along with a spacious two-car attached garage.

3 Beds ⋅ 2 Baths ⋅ 73492712 MLS

***OFFER DEADLINE ** 12PM ON TUESDAY MARCH 31st*** Welcome home to this lovely Colonial where comfort, style and thoughtful updates come together beautifully. The main level features a spacious living room and a fabulous kitchen layout with a cozy breakfast nook, enhanced by stainless steel smart appliances, cooktop and wall oven/microwave combo; perfect for the home chef enthusiast. Stylish gray cabinetry, high-end quartz countertops, classic subway tile backsplash and beautiful young flooring throughout the main level truly elevate the space. A bright and inviting dining area with sliders leads to the deck, creating a seamless indoor-outdoor connection. Both bathrooms have been tastefully updated with clean, cohesive finishes. Upstairs you’ll find three well-proportioned bedrooms, including a primary with a walk-in closet. Set on a generous lot, the property offers abundant off-street parking along with a spacious two-car attached garage.

19 Madison Avenue, Winchendon

$475,000

Located in a commuter-friendly area, this charming 3-bedroom, 1.5-bath Colonial offers comfort, style, and thoughtful updates throughout. Step inside to a welcoming foyer that leads to a bright white kitchen featuring granite countertops, tile backsplash, stainless-steel appliances, and plenty of cabinet space. The kitchen flows into an open-concept dining room, creating a great space for everyday living and entertaining. Just beyond is the spacious living room with a cozy gas fireplace. Off the living room you’ll find a beautiful 3-season porch—perfect for relaxing and easily converted for year-round use with added heat. Upstairs are three comfortable bedrooms and a full bath. Outside, enjoy summer evenings on the generous deck, relaxing on the patio, or taking in the peaceful backyard. Additional highlights include an attached two-car garage and a heated basement with excellent potential for future finished space.

3 Beds ⋅ 2 Baths ⋅ 73486452 MLS

Located in a commuter-friendly area, this charming 3-bedroom, 1.5-bath Colonial offers comfort, style, and thoughtful updates throughout. Step inside to a welcoming foyer that leads to a bright white kitchen featuring granite countertops, tile backsplash, stainless-steel appliances, and plenty of cabinet space. The kitchen flows into an open-concept dining room, creating a great space for everyday living and entertaining. Just beyond is the spacious living room with a cozy gas fireplace. Off the living room you’ll find a beautiful 3-season porch—perfect for relaxing and easily converted for year-round use with added heat. Upstairs are three comfortable bedrooms and a full bath. Outside, enjoy summer evenings on the generous deck, relaxing on the patio, or taking in the peaceful backyard. Additional highlights include an attached two-car garage and a heated basement with excellent potential for future finished space.

112 Baldwinville State Rd, Winchendon

$475,000

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.

3 Beds ⋅ 2 Baths ⋅ 73456492 MLS

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.

302 Ash St, Winchendon

$475,000

Three Newer Boilers with Super Store Hot water, All Newer Windows except for stained glass portholes, All Newer Wiring throughout the building with separate breaker boxes including common in basement and breaker boxes in each unit, Updated Plumbing throughout building and brick foundation has been repointed. Property offers off street parking in a neighborhood of multi-family and single family homes and a mile away from all downtown amenities. This property can be your investment money maker or your live in income producer to reduce or eliminate your mortgage payment. There is room for rent adjustments also. Come See.

8 Beds ⋅ 3 Baths ⋅ 73419470 MLS

Three Newer Boilers with Super Store Hot water, All Newer Windows except for stained glass portholes, All Newer Wiring throughout the building with separate breaker boxes including common in basement and breaker boxes in each unit, Updated Plumbing throughout building and brick foundation has been repointed. Property offers off street parking in a neighborhood of multi-family and single family homes and a mile away from all downtown amenities. This property can be your investment money maker or your live in income producer to reduce or eliminate your mortgage payment. There is room for rent adjustments also. Come See.

90 Linden St., Winchendon

$465,000

Great investment opportunity fully rented 4-family property offering 16 total rooms and 8 bedrooms. The building includes two first-floor apartments, four full bathrooms, and two spacious 3-bedroom units. One unit features an enclosed porch for added space. All units are heated by individual propane systems and have separate utilities. Coin-operated washer/dryer hookups only are in the basement. Off-street parking available. Current annual income exceeds $38,000, with tenants paying for all utilities except water and sewer. All units are occupied with one-year leases, which may be voided upon sale. Property has been owned by the same family for 45 years and is being sold as is. Solid income-producing assets with long-term ownership and strong rental history. Close to downtown offers a small-town experience with a mix of casual dining, local shops, community events, Winchendon Common Park with Performing Arts Amphitheater, paved walk/cycling trail.

8 Beds ⋅ 4 Baths ⋅ 73468504 MLS

Great investment opportunity fully rented 4-family property offering 16 total rooms and 8 bedrooms. The building includes two first-floor apartments, four full bathrooms, and two spacious 3-bedroom units. One unit features an enclosed porch for added space. All units are heated by individual propane systems and have separate utilities. Coin-operated washer/dryer hookups only are in the basement. Off-street parking available. Current annual income exceeds $38,000, with tenants paying for all utilities except water and sewer. All units are occupied with one-year leases, which may be voided upon sale. Property has been owned by the same family for 45 years and is being sold as is. Solid income-producing assets with long-term ownership and strong rental history. Close to downtown offers a small-town experience with a mix of casual dining, local shops, community events, Winchendon Common Park with Performing Arts Amphitheater, paved walk/cycling trail.

116 Maple Street, Winchendon

$460,000

Welcome to this charming Colonial-style home offering 6 rooms, 3 bedrooms, and 2.5 baths on a spacious 1-acre lot. The inviting 2-story foyer with a stunning palladium window sets the tone. Enjoy a fireplaced front-to-back living room with slider access to the deck, perfect for entertaining. The primary suite offers a private bath with a double-sink vanity. Additional features include a main level laundry room and a completely fenced backyard—ideal for pets or play. Conveniently located near Rte. 140. Enjoy privacy yet convenience.

3 Beds ⋅ 3 Baths ⋅ 73426261 MLS

Welcome to this charming Colonial-style home offering 6 rooms, 3 bedrooms, and 2.5 baths on a spacious 1-acre lot. The inviting 2-story foyer with a stunning palladium window sets the tone. Enjoy a fireplaced front-to-back living room with slider access to the deck, perfect for entertaining. The primary suite offers a private bath with a double-sink vanity. Additional features include a main level laundry room and a completely fenced backyard—ideal for pets or play. Conveniently located near Rte. 140. Enjoy privacy yet convenience.

5 Cross Rd, Winchendon

$460,000

Welcome home to this beautiful 3-bedroom, 2.5-bath new construction colonial . The open-concept first floor features a bright living area that flows seamlessly into a stylish kitchen with granite countertops and quality finishes. Upstairs you’ll find three spacious bedrooms, including a primary suite with en-suite bath and generous closet space. Enjoy year-round comfort with central air conditioning and forced hot air heating. A full basement and attached garage provide plenty of storage and convenience. Home to be completed in the next 30 days.

3 Beds ⋅ 3 Baths ⋅ 73425417 MLS

Welcome home to this beautiful 3-bedroom, 2.5-bath new construction colonial . The open-concept first floor features a bright living area that flows seamlessly into a stylish kitchen with granite countertops and quality finishes. Upstairs you’ll find three spacious bedrooms, including a primary suite with en-suite bath and generous closet space. Enjoy year-round comfort with central air conditioning and forced hot air heating. A full basement and attached garage provide plenty of storage and convenience. Home to be completed in the next 30 days.

102 Pearl Street, Winchendon

$457,000

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.

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

$451,900

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.

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

$451,000

Welcome to this well-maintained 3-bedroom, 3-bath home, perfectly situated at the end of a dead-end street offering privacy and natural beauty. Set on a nicely landscaped lot with perennial gardens and stone walls, this property provides a peaceful retreat surrounded by woods on the sides and back. You'll love the fenced backyard, patio, and a dedicated area perfect for a hobby farm. Inside, the home features a bright and open kitchen with stainless steel appliances and maple cabinets, flowing into a large front-to-back living room with gleaming hardwood floors throughout. A spacious 3-season room with soaring cathedral ceilings overlooks the private wooded backyard—ideal for relaxing or entertaining. The lower level offers a partially finished space, perfect for additional living. This serene and private property is perfect for those seeking space, comfort, and a connection to nature—all while being close to modern conveniences.

3 Beds ⋅ 3 Baths ⋅ 73423495 MLS

Welcome to this well-maintained 3-bedroom, 3-bath home, perfectly situated at the end of a dead-end street offering privacy and natural beauty. Set on a nicely landscaped lot with perennial gardens and stone walls, this property provides a peaceful retreat surrounded by woods on the sides and back. You'll love the fenced backyard, patio, and a dedicated area perfect for a hobby farm. Inside, the home features a bright and open kitchen with stainless steel appliances and maple cabinets, flowing into a large front-to-back living room with gleaming hardwood floors throughout. A spacious 3-season room with soaring cathedral ceilings overlooks the private wooded backyard—ideal for relaxing or entertaining. The lower level offers a partially finished space, perfect for additional living. This serene and private property is perfect for those seeking space, comfort, and a connection to nature—all while being close to modern conveniences.

155 Converse Dr, Winchendon

$450,000

This warm and welcoming updated colonial home offers plenty of room with over 1,700 square feet! It sits on over 2 acres and features 3-bedrooms with 1.5-bathrooms. With a cozy fireplace and sliders that open to a large walk-out deck overlooking a wooded backyard it is a relaxing home. The partially finished walk-out lower level provides flexible space ideal for a home office, playroom, gym, or additional living area. The property features 3/4-enclosed carport. Serene country living with in town rail trail! Please schedule through Showingtime!

3 Beds ⋅ 2 Baths ⋅ 73515470 MLS

This warm and welcoming updated colonial home offers plenty of room with over 1,700 square feet! It sits on over 2 acres and features 3-bedrooms with 1.5-bathrooms. With a cozy fireplace and sliders that open to a large walk-out deck overlooking a wooded backyard it is a relaxing home. The partially finished walk-out lower level provides flexible space ideal for a home office, playroom, gym, or additional living area. The property features 3/4-enclosed carport. Serene country living with in town rail trail! Please schedule through Showingtime!

17 Town Farm Rd, Winchendon

$440,000

Motivated Seller! Turn-Key Income Machine ready for Tenants or perfect for owner occupant. Gutted down to the studs and Fully remodeled & renovated 2-Family: Live in One Unit, Pay Mortgage with the Other! Delivered Vacant, Separately Metered Utilities, In-Unit Laundry, New Systems including Rinnai Combi propane boilers, all new electrical and plumbing through out, New Siding, New Roof, New Life! Both units feature 2 Bedrooms and 1 full bath. Eat-in Kitchens offer generous cabinet space, granite counter tops, New SS appliances. Detached 2 car garage features brand new garage Doors, Roof and Siding. Energy efficient, Meeting HERS index requirements! Close proximity to Down town, YMCA, RT 140 & RT 2, NH state line for tax free shopping, Golf course and public transportation.

4 Beds ⋅ 2 Baths ⋅ 73470589 MLS

Motivated Seller! Turn-Key Income Machine ready for Tenants or perfect for owner occupant. Gutted down to the studs and Fully remodeled & renovated 2-Family: Live in One Unit, Pay Mortgage with the Other! Delivered Vacant, Separately Metered Utilities, In-Unit Laundry, New Systems including Rinnai Combi propane boilers, all new electrical and plumbing through out, New Siding, New Roof, New Life! Both units feature 2 Bedrooms and 1 full bath. Eat-in Kitchens offer generous cabinet space, granite counter tops, New SS appliances. Detached 2 car garage features brand new garage Doors, Roof and Siding. Energy efficient, Meeting HERS index requirements! Close proximity to Down town, YMCA, RT 140 & RT 2, NH state line for tax free shopping, Golf course and public transportation.

46 Juniper St, Winchendon

$440,000

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!

4 Beds ⋅ 2 Baths ⋅ 73457281 MLS

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!

108 Highland St, Winchendon

$440,000

Discover easy, move-in-ready living at 35 Hillside Dr, 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

3 Beds ⋅ 2 Baths ⋅ 73451043 MLS

Discover easy, move-in-ready living at 35 Hillside Dr, 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

35 Hillside Dr, Winchendon

$440,000

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. Home is 100% complete

3 Beds ⋅ 3 Baths ⋅ 73442863 MLS

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. Home is 100% complete

21 Cottage St, Winchendon

$435,000

Highly desirable newer ranch-style home featuring 3 bedrooms, 2 full baths, a 2-car garage, and a spacious 1.98-acre lot. The updated kitchen boasts granite countertops, a center island, recessed lighting, and stainless steel appliances. A front-to-back living room opens to a deck overlooking the fenced backyard. The main bedroom offers a private full bath, with first-floor laundry and two additional generously sized bedrooms. The oversized 2-car garage includes automatic door openers, complemented by 2 sheds for extra storage and a large, level backyard perfect for summer activities. Enjoy central A/C, a brand-new 3-bedroom septic system, a full basement, and low-maintenance vinyl siding. Conveniently located near commuter routes, shopping, and the Winchendon Rail Trail, this is a wonderful place to call home.

3 Beds ⋅ 2 Baths ⋅ 73519889 MLS

Highly desirable newer ranch-style home featuring 3 bedrooms, 2 full baths, a 2-car garage, and a spacious 1.98-acre lot. The updated kitchen boasts granite countertops, a center island, recessed lighting, and stainless steel appliances. A front-to-back living room opens to a deck overlooking the fenced backyard. The main bedroom offers a private full bath, with first-floor laundry and two additional generously sized bedrooms. The oversized 2-car garage includes automatic door openers, complemented by 2 sheds for extra storage and a large, level backyard perfect for summer activities. Enjoy central A/C, a brand-new 3-bedroom septic system, a full basement, and low-maintenance vinyl siding. Conveniently located near commuter routes, shopping, and the Winchendon Rail Trail, this is a wonderful place to call home.

151 Gardner Rd, Winchendon

$435,000

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

6 Beds ⋅ 2 Baths ⋅ 73459563 MLS

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

53 Grove St, Winchendon

$430,000

Tucked away on over 2 private acres surrounded by woods, 365 Mellen Rd offers peace, privacy, and plenty of potential. This 3-bed, 1.5-bath Cape features 1,148 sqft of living space, a 2-car attached garage with a huge loft perfect for storage or a future ADU, and a big paved driveway with ample parking. Major updates give peace of mind including a 1-year-old roof, 2-year-old heating system, newer windows, and a brand-new water system with updated well parts. Inside you’ll find a functional layout with an eat-in kitchen, cozy living room, and natural light throughout. The lot is a true retreat with room to roam, entertain, or simply enjoy the quiet setting. Move-in ready with strong mechanicals, this property is ideal for anyone looking to enjoy country living with space to grow.

3 Beds ⋅ 2 Baths ⋅ 73440616 MLS

Tucked away on over 2 private acres surrounded by woods, 365 Mellen Rd offers peace, privacy, and plenty of potential. This 3-bed, 1.5-bath Cape features 1,148 sqft of living space, a 2-car attached garage with a huge loft perfect for storage or a future ADU, and a big paved driveway with ample parking. Major updates give peace of mind including a 1-year-old roof, 2-year-old heating system, newer windows, and a brand-new water system with updated well parts. Inside you’ll find a functional layout with an eat-in kitchen, cozy living room, and natural light throughout. The lot is a true retreat with room to roam, entertain, or simply enjoy the quiet setting. Move-in ready with strong mechanicals, this property is ideal for anyone looking to enjoy country living with space to grow.

365 Mellen Rd, Winchendon

$430,000

This charming oversized 3-bedroom ranch is on a quiet dead-end street, just minutes to town. This beautifully maintained home features a spacious living room with a cozy fireplace and a generous picture window that fills the space with natural light. The amazing family room boasts cathedral ceilings and a wood stove, creating a warm, inviting enviornment for gatherings and cozy nights. The kitchen though compact, is well equipped with everything you need, and it sits adjacent to the dining area. The primary bedroom includes an updated en-suite bath, a true haven. Hardwood floors flow through much of the home, adding warmth and timeless appeal. Handicap-accessible doors and hallways provide easy accessibility. If more room is needed, the basement offers ample space to finish into additional living areas. Enjoy the inground pool area, ideal for entertaining next summer. There is single-car garage and two driveways. The perrenial gardens are an added bonus! New Septic being intalled!

3 Beds ⋅ 2 Baths ⋅ 73435246 MLS

This charming oversized 3-bedroom ranch is on a quiet dead-end street, just minutes to town. This beautifully maintained home features a spacious living room with a cozy fireplace and a generous picture window that fills the space with natural light. The amazing family room boasts cathedral ceilings and a wood stove, creating a warm, inviting enviornment for gatherings and cozy nights. The kitchen though compact, is well equipped with everything you need, and it sits adjacent to the dining area. The primary bedroom includes an updated en-suite bath, a true haven. Hardwood floors flow through much of the home, adding warmth and timeless appeal. Handicap-accessible doors and hallways provide easy accessibility. If more room is needed, the basement offers ample space to finish into additional living areas. Enjoy the inground pool area, ideal for entertaining next summer. There is single-car garage and two driveways. The perrenial gardens are an added bonus! New Septic being intalled!

24 Vaine St, Winchendon

$425,000

Discover the allure of 736 Central St. in Winchendon, MA, a charming single-family log home built in 1994 offering 1481 square feet on two levels of thoughtfully designed living space and approximately 360 sq/ft of mostly finish living space in basement with 1/2 bath. This property presents an open floor plan with loft living area, a good size heated family/4 season room. The home features a 34x8 farmers porch for your enjoyment and relaxing with a swing, two inviting bedrooms and a loft area providing additional personal space for your needs and imagination, perhaps a home office. Complementing these are a full bathroom and an additional half bathroom, ensuring convenience for both residents and guests. The first floor half bath has hookups for a full size washer and dryer for added convenience. Kitchen boasts a walkin pantry for added storage. Set on an expansive 2.05 acre lot, the property offers generous outdoor possibilities. A newer heated and well-insulated two-car garage provides practical storage and protection for vehicles along with rear garage door opens to service part of basement along with 2 storage sheds. This is more than a house; it's a foundation for your future memories. We invite you to explore the possibilities of making this exceptional property your own. For all you snowmobile and hiking enthusiasts, there is acess to a Rail Trail that goes into New Hampshire and beyond or near by Lake Monomonac. While being situated in a quiet, private spot, you're just a 3 minute drive from the downtown area. This home comes with gas-fiired electric gererater and whole house connection. Some photos are before furniture was removed. It's ready to go and a quick closing is possible.

2 Beds ⋅ 3 Baths ⋅ 73570387 MLS

Discover the allure of 736 Central St. in Winchendon, MA, a charming single-family log home built in 1994 offering 1481 square feet on two levels of thoughtfully designed living space and approximately 360 sq/ft of mostly finish living space in basement with 1/2 bath. This property presents an open floor plan with loft living area, a good size heated family/4 season room. The home features a 34x8 farmers porch for your enjoyment and relaxing with a swing, two inviting bedrooms and a loft area providing additional personal space for your needs and imagination, perhaps a home office. Complementing these are a full bathroom and an additional half bathroom, ensuring convenience for both residents and guests. The first floor half bath has hookups for a full size washer and dryer for added convenience. Kitchen boasts a walkin pantry for added storage. Set on an expansive 2.05 acre lot, the property offers generous outdoor possibilities. A newer heated and well-insulated two-car garage provides practical storage and protection for vehicles along with rear garage door opens to service part of basement along with 2 storage sheds. This is more than a house; it's a foundation for your future memories. We invite you to explore the possibilities of making this exceptional property your own. For all you snowmobile and hiking enthusiasts, there is acess to a Rail Trail that goes into New Hampshire and beyond or near by Lake Monomonac. While being situated in a quiet, private spot, you're just a 3 minute drive from the downtown area. This home comes with gas-fiired electric gererater and whole house connection. Some photos are before furniture was removed. It's ready to go and a quick closing is possible.

736 Central St., Winchendon

$425,000

Nestled in the heart of Winchendon, 101-103 Linden Street is a welcoming two-family home full of charm and versatility. Each apartment offers large rooms with 2 bedrooms and bath. The first-floor unit includes a bonus room that’s perfect as a home office, guest room, or extra bedroom. Both eat-in kitchens are large, have been updated with granite and newer cabinets, and offer plenty of cabinet and pantry space. The finished third floor offers even more bonus space for a playroom, studio, or private getaway. Each unit has its own laundry. With over 2,300 square feet (not including the 3rd floor) and on a generous lot, this classic multi family home combines charm, space, and opportunity—whether you’re looking to live in one unit and rent the other, or invest in a great property in a great location. Second floor apartment lease recently renewed, first floor empty and available. Updated boilers, hot water heaters, and panels. This great investment will not last, don't miss your chance!

4 Beds ⋅ 2 Baths ⋅ 73440841 MLS

Nestled in the heart of Winchendon, 101-103 Linden Street is a welcoming two-family home full of charm and versatility. Each apartment offers large rooms with 2 bedrooms and bath. The first-floor unit includes a bonus room that’s perfect as a home office, guest room, or extra bedroom. Both eat-in kitchens are large, have been updated with granite and newer cabinets, and offer plenty of cabinet and pantry space. The finished third floor offers even more bonus space for a playroom, studio, or private getaway. Each unit has its own laundry. With over 2,300 square feet (not including the 3rd floor) and on a generous lot, this classic multi family home combines charm, space, and opportunity—whether you’re looking to live in one unit and rent the other, or invest in a great property in a great location. Second floor apartment lease recently renewed, first floor empty and available. Updated boilers, hot water heaters, and panels. This great investment will not last, don't miss your chance!

101-103 Linden St, Winchendon

$425,000

Located on one of the nicest streets in Winchendon, this classic colonial offers comfortable living and room for expansion. Situated on a little over an acre of land, abutting Whitney Pond - waterfront property without the waterfront price! Upon entering the front to back living room, you will be greeted by refinished hardwood floors, fresh paint, brick fireplace and energy saving pellet stove. Sliders to the private enclosed porch overlook the wooded backyard. Half bath with laundry is a convenience. Large dining room opens to kitchen with amazing pantry! Upstairs, 3 bedrooms (with new carpeting) and 2 full baths complete the floorplan. The walkout basement could be finished for more living space. Attached 2 car garage makes life easier when coming home with groceries, etc. Come make it yours!

3 Beds ⋅ 3 Baths ⋅ 73409626 MLS

Located on one of the nicest streets in Winchendon, this classic colonial offers comfortable living and room for expansion. Situated on a little over an acre of land, abutting Whitney Pond - waterfront property without the waterfront price! Upon entering the front to back living room, you will be greeted by refinished hardwood floors, fresh paint, brick fireplace and energy saving pellet stove. Sliders to the private enclosed porch overlook the wooded backyard. Half bath with laundry is a convenience. Large dining room opens to kitchen with amazing pantry! Upstairs, 3 bedrooms (with new carpeting) and 2 full baths complete the floorplan. The walkout basement could be finished for more living space. Attached 2 car garage makes life easier when coming home with groceries, etc. Come make it yours!

160 Lakeshore Drive, Winchendon

$420,000

Welcome to this well-maintained 2-bedroom, 2-bath split-level ranch situated on just over a half-acre of fully fenced land. Built in 1994, this home offers the benefits of newer construction and a thoughtfully designed layout with approximately 1,460 square feet of comfortable living space. The bright and functional floor plan makes the most of every square foot, providing easy everyday living and entertaining. Step outside and enjoy your private backyard retreat complete with a hot tub and plenty of room for pets, gardening, gatherings, or simply relaxing. Conveniently located near local amenities while offering a peaceful setting, this move-in-ready home is ideal for first-time buyers, downsizers, or anyone looking for low-maintenance living with outdoor space to enjoy.Showings begin at the Open House on Saturday, June 20th from 2:30 PM to 4:00 PM.

4 Beds ⋅ 2 Baths ⋅ 73538595 MLS

Welcome to this well-maintained 2-bedroom, 2-bath split-level ranch situated on just over a half-acre of fully fenced land. Built in 1994, this home offers the benefits of newer construction and a thoughtfully designed layout with approximately 1,460 square feet of comfortable living space. The bright and functional floor plan makes the most of every square foot, providing easy everyday living and entertaining. Step outside and enjoy your private backyard retreat complete with a hot tub and plenty of room for pets, gardening, gatherings, or simply relaxing. Conveniently located near local amenities while offering a peaceful setting, this move-in-ready home is ideal for first-time buyers, downsizers, or anyone looking for low-maintenance living with outdoor space to enjoy.Showings begin at the Open House on Saturday, June 20th from 2:30 PM to 4:00 PM.

164 Lincoln Ave, Winchendon

$417,000

This beautifully renovated 6-bedroom, 2-bath duplex is bright, sun-filled, and fully updated with newer features throughout. The first floor unit consists of an updated 3-bedrooms and 1 bathroom. It also features ample storage. The second floor unit includes 3 bedrooms, 1 bathroom, a washer/dryer hookup, ample parking with a private entrance, and a spacious backyard—perfect for both winter activities and warmer months. Solar panels have been installed on the property. This property is perfect for an investor or owner occupant! Private showings are available. Contact us today to schedule a viewing!

6 Beds ⋅ 2 Baths ⋅ 73446617 MLS

This beautifully renovated 6-bedroom, 2-bath duplex is bright, sun-filled, and fully updated with newer features throughout. The first floor unit consists of an updated 3-bedrooms and 1 bathroom. It also features ample storage. The second floor unit includes 3 bedrooms, 1 bathroom, a washer/dryer hookup, ample parking with a private entrance, and a spacious backyard—perfect for both winter activities and warmer months. Solar panels have been installed on the property. This property is perfect for an investor or owner occupant! Private showings are available. Contact us today to schedule a viewing!

174-176 Mill St, Winchendon

$415,000

Are you looking for a cozy home with a private backyard? This property features a light-filled living room that flows into an open-concept dining area. A sliding door leads to a large deck overlooking the acreage, perfect for unwinding or entertaining guests. The updated galley kitchen features stainless steel appliances and a glass-tile backsplash behind the countertops. The main floor offers a master bedroom with luxury vinyl flooring and ample closet space, two additional bedrooms with similar features, and a full bathroom. The lower level includes an office with separate exterior access, a utility and workshop area, additional storage, and access to a one-car garage. Outside, there is a large storage shed along with a fire pit for three-season enjoyment. The property offers space and tranquillity while remaining close to highway access, trails, and a conservation area; Lake Dennison and No. Central Pathway & Rail Trail. A new roof (2020). Don't miss out on this property!

3 Beds ⋅ 1 Baths ⋅ 73493265 MLS

Are you looking for a cozy home with a private backyard? This property features a light-filled living room that flows into an open-concept dining area. A sliding door leads to a large deck overlooking the acreage, perfect for unwinding or entertaining guests. The updated galley kitchen features stainless steel appliances and a glass-tile backsplash behind the countertops. The main floor offers a master bedroom with luxury vinyl flooring and ample closet space, two additional bedrooms with similar features, and a full bathroom. The lower level includes an office with separate exterior access, a utility and workshop area, additional storage, and access to a one-car garage. Outside, there is a large storage shed along with a fire pit for three-season enjoyment. The property offers space and tranquillity while remaining close to highway access, trails, and a conservation area; Lake Dennison and No. Central Pathway & Rail Trail. A new roof (2020). Don't miss out on this property!

266 West Street, Winchendon

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