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Known as “La Casa Azul,” this lovingly maintained ranch-style home welcomes you with an open-concept design that is perfect for family gatherings. The kitchen is a baker’s dream, featuring an oversized island which overlooks the dining and living room, granite countertops, and stainless-steel appliances. The primary bedroom offers its own private retreat, complete with a walk-in closet, a generously sized bathroom with a soaking tub and a separate stand-up shower, and also has a french door that leads onto the back deck, to enjoy a quiet evening before retreating to bed. Two additional bedrooms, a full bathroom, and a convenient laundry area complete the first floor. The daylight basement offers an office, work area, and a large partially finished room ready for the new owners to make their own while building sweat equity. Outside, the property features a two-car garage, storage shed, and an expansive back deck that provides plenty of space for entertaining. The yard is beautifully adorned with established perennials, adding charm and color throughout the seasons.

3 Beds ⋅ 2 Baths ⋅ 73588567 MLS

Known as “La Casa Azul,” this lovingly maintained ranch-style home welcomes you with an open-concept design that is perfect for family gatherings. The kitchen is a baker’s dream, featuring an oversized island which overlooks the dining and living room, granite countertops, and stainless-steel appliances. The primary bedroom offers its own private retreat, complete with a walk-in closet, a generously sized bathroom with a soaking tub and a separate stand-up shower, and also has a french door that leads onto the back deck, to enjoy a quiet evening before retreating to bed. Two additional bedrooms, a full bathroom, and a convenient laundry area complete the first floor. The daylight basement offers an office, work area, and a large partially finished room ready for the new owners to make their own while building sweat equity. Outside, the property features a two-car garage, storage shed, and an expansive back deck that provides plenty of space for entertaining. The yard is beautifully adorned with established perennials, adding charm and color throughout the seasons.

260 Ash St., Winchendon

$584,000

Beautiful, like-new, 4-year-old traditional Asher Colonial offering 1,828 sq. ft. on 4.13 private acres. This home boasts an upgraded brick walkway and large granite entry steps. The open-concept floor plan features a spacious kitchen with upgraded cabinets to the ceiling with crown molding, granite countertops, a granite island, and stainless steel appliances. The formal dining room is stunning! A front-to-back living room and half bath with laundry complete the first floor.A slider off the kitchen leads to a private deck overlooking the new above-ground pool and magnificent scenic views. The huge front-to-back primary suite features a walk-in closet, linen closet, and private full bath. Two generously sized bedrooms and a full bath complete the second floor. There is a large walk-out basement with French doors and high ceilings, perfect for a future finished space. Additional features include a 2-car attached garage, central air, Generac generator, and pool with equipment. Make this gorgeous Country Colonial, just minutes from downtown, shopping, and restaurants, your home today!

3 Beds ⋅ 3 Baths ⋅ 73588068 MLS

Beautiful, like-new, 4-year-old traditional Asher Colonial offering 1,828 sq. ft. on 4.13 private acres. This home boasts an upgraded brick walkway and large granite entry steps. The open-concept floor plan features a spacious kitchen with upgraded cabinets to the ceiling with crown molding, granite countertops, a granite island, and stainless steel appliances. The formal dining room is stunning! A front-to-back living room and half bath with laundry complete the first floor.A slider off the kitchen leads to a private deck overlooking the new above-ground pool and magnificent scenic views. The huge front-to-back primary suite features a walk-in closet, linen closet, and private full bath. Two generously sized bedrooms and a full bath complete the second floor. There is a large walk-out basement with French doors and high ceilings, perfect for a future finished space. Additional features include a 2-car attached garage, central air, Generac generator, and pool with equipment. Make this gorgeous Country Colonial, just minutes from downtown, shopping, and restaurants, your home today!

90 Royalston Rd N, Winchendon

$599,900

This historical former country club sits on 18.6 acres across two wooded parcels, with a stream. The interior offers approximately 3,400 square feet of living space with 4 bedrooms and 4 bathrooms. The great hall measures 48 feet by 25 feet and has beamed ceilings, wood paneled walls, hardwood floors, and a center brick fireplace with a wood stove, and the dining area shares the same room. Dining room furniture original to the home is included as a gift to buyers. The kitchen opens to the deck through French doors, with a center island, granite counters, a Sub-Zero refrigerator and freezer, two full size Miele ovens, and an espresso station. A butler's pantry connects to the kitchen and to the great hall through a swinging door, and it keeps its original glass front cabinets alongside granite counters, a sink, and a dishwasher. The second floor primary suite has wood paneled ceilings, a skylight, and a bathroom. The first floor residential wing has two additional bedrooms, each with a dedicated bathroom. A fourth bedroom would make a great library and has exclusive use of a large three season porch. The washer, dryer, dishwasher, and hybrid electric water heater date from 2023 to 2026. Heat is oil fired hot water baseboard with Nest thermostats, along with 200 amp electric service and a 30 amp outlet for recreational vehicles. Some air sealing and weatherization was completed in 2023, with insulation of the residential wing eaves now in progress. The home is served by town water and town sewer. This home is set at the end of a dead-end street, with access through stone columns that align with the craftsman bungalow style of the home and the impressive front entrance has a covered front porch with a full width stone base. There's also a back deck and a storage shed. The sellers have catalogued more than 70 species of birds on the property, along with fireflies and other wildlife. The driveway parks 12 or more vehicles. Buyers may want to explore allowed uses other than residential. Winchendon offers a vibrant main street, golf, tennis, a new outdoor amphitheater, trails, a 9+ mile paved bike path, and public and private schools. This wonderful and unique property is being listed as-is, with many projects completed, however the sellers are not able to make further repairs.

4 Beds ⋅ 4 Baths ⋅ 73587925 MLS

This historical former country club sits on 18.6 acres across two wooded parcels, with a stream. The interior offers approximately 3,400 square feet of living space with 4 bedrooms and 4 bathrooms. The great hall measures 48 feet by 25 feet and has beamed ceilings, wood paneled walls, hardwood floors, and a center brick fireplace with a wood stove, and the dining area shares the same room. Dining room furniture original to the home is included as a gift to buyers. The kitchen opens to the deck through French doors, with a center island, granite counters, a Sub-Zero refrigerator and freezer, two full size Miele ovens, and an espresso station. A butler's pantry connects to the kitchen and to the great hall through a swinging door, and it keeps its original glass front cabinets alongside granite counters, a sink, and a dishwasher. The second floor primary suite has wood paneled ceilings, a skylight, and a bathroom. The first floor residential wing has two additional bedrooms, each with a dedicated bathroom. A fourth bedroom would make a great library and has exclusive use of a large three season porch. The washer, dryer, dishwasher, and hybrid electric water heater date from 2023 to 2026. Heat is oil fired hot water baseboard with Nest thermostats, along with 200 amp electric service and a 30 amp outlet for recreational vehicles. Some air sealing and weatherization was completed in 2023, with insulation of the residential wing eaves now in progress. The home is served by town water and town sewer. This home is set at the end of a dead-end street, with access through stone columns that align with the craftsman bungalow style of the home and the impressive front entrance has a covered front porch with a full width stone base. There's also a back deck and a storage shed. The sellers have catalogued more than 70 species of birds on the property, along with fireflies and other wildlife. The driveway parks 12 or more vehicles. Buyers may want to explore allowed uses other than residential. Winchendon offers a vibrant main street, golf, tennis, a new outdoor amphitheater, trails, a 9+ mile paved bike path, and public and private schools. This wonderful and unique property is being listed as-is, with many projects completed, however the sellers are not able to make further repairs.

25 Fairbank Street, Winchendon

$224,900

Affordable, low-maintenance condo living in a convenient location! Enjoy your morning coffee or just unwind on the south-facing deck with a wooded view and covered by natural shade. Inside, you’ll find two spacious bedrooms, 1.5 baths, and a partially finished basement offering flexible space for a home office, recreation, or other inspirations. A wonderful opportunity for anyone looking for a cozy and convenient place to call home.

2 Beds ⋅ 2 Baths ⋅ 73587802 MLS ⋅ ['Banner Place'] BLDG.

Affordable, low-maintenance condo living in a convenient location! Enjoy your morning coffee or just unwind on the south-facing deck with a wooded view and covered by natural shade. Inside, you’ll find two spacious bedrooms, 1.5 baths, and a partially finished basement offering flexible space for a home office, recreation, or other inspirations. A wonderful opportunity for anyone looking for a cozy and convenient place to call home.

20 Banner Pl Unit C2, Winchendon

$499,900

Welcome to 13 Mechanic Street, a well-maintained true two-family property offering flexibility for owner-occupants, investors, multigenerational living, or those looking for additional rental income or whatever suits your desires. The property also offers a finished attic area with potential for an additional studio apartment. This property was substantially renovated approximately seven years ago, including being deleaded, updated plumbing and electrical systems, separately metered units, windows, roofing, Seperate heating systems, bathrooms, kitchen remodels, flooring, and more. A garage and usable yard space provide additional functionality and outdoor space. With its two-family layout, extensive updates, and additional potential, 13 Mechanic Street offers a versatile property with a variety of possible uses.

5 Beds ⋅ 3 Baths ⋅ 73587134 MLS

Welcome to 13 Mechanic Street, a well-maintained true two-family property offering flexibility for owner-occupants, investors, multigenerational living, or those looking for additional rental income or whatever suits your desires. The property also offers a finished attic area with potential for an additional studio apartment. This property was substantially renovated approximately seven years ago, including being deleaded, updated plumbing and electrical systems, separately metered units, windows, roofing, Seperate heating systems, bathrooms, kitchen remodels, flooring, and more. A garage and usable yard space provide additional functionality and outdoor space. With its two-family layout, extensive updates, and additional potential, 13 Mechanic Street offers a versatile property with a variety of possible uses.

13 Mechanic St, Winchendon

$290,000

This is a well-kept neat and clean cottage with expected irregularities. Many recent updates. The house has five rooms and one full bath, all on the first-floor level. It has three heating options, electric, Propane gas, or a pellet stove which is included in the price. The Propane gas heaters are new. The house only has a partial cellar with access through a floor hatch. The house is serviced by a recently installed septic system. The roof shingles are about 7 years old. The property is located at the end of a low traffic st. Great location. The lot is mostly cleared with lawn in the front and back.

2 Beds ⋅ 1 Baths ⋅ 73586262 MLS

This is a well-kept neat and clean cottage with expected irregularities. Many recent updates. The house has five rooms and one full bath, all on the first-floor level. It has three heating options, electric, Propane gas, or a pellet stove which is included in the price. The Propane gas heaters are new. The house only has a partial cellar with access through a floor hatch. The house is serviced by a recently installed septic system. The roof shingles are about 7 years old. The property is located at the end of a low traffic st. Great location. The lot is mostly cleared with lawn in the front and back.

123 Franklin St, Winchendon

$489,900

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 1.05 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.

3 Beds ⋅ 3 Baths ⋅ 73585536 MLS

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 1.05 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.

Lot 2 River St, Winchendon

$325,000

Great opportunity for owner occupants or investors with this side-by-side two family home! The spacious 2-bedroom owner’s unit has seen numerous updates, including an updated kitchen and bathroom, newer plumbing and electrical, insulation, and a new oil tank. The first floor features a living room, dining room, kitchen, pantry, and three-season porch, with a mix of hardwood, tile, and newer LVP flooring. Upstairs are two bedrooms with newer flooring plus a versatile foyer/flex space ideal for a home office or study area. The second unit is a 1-bedroom residence with its own electrical panel, propane heat, and hot water, providing an established source of rental income. Utilities are currently included in the rent, while the separate systems offer flexibility for future rental arrangements. Town water and sewer, off-street parking, and a fenced in backyard complete the property. Whether you’re looking to owner occupy while offsetting your mortgage with rental income or add another multi-family to your portfolio, this property offers plenty of possibilities!

3 Beds ⋅ 2 Baths ⋅ 73584981 MLS

Great opportunity for owner occupants or investors with this side-by-side two family home! The spacious 2-bedroom owner’s unit has seen numerous updates, including an updated kitchen and bathroom, newer plumbing and electrical, insulation, and a new oil tank. The first floor features a living room, dining room, kitchen, pantry, and three-season porch, with a mix of hardwood, tile, and newer LVP flooring. Upstairs are two bedrooms with newer flooring plus a versatile foyer/flex space ideal for a home office or study area. The second unit is a 1-bedroom residence with its own electrical panel, propane heat, and hot water, providing an established source of rental income. Utilities are currently included in the rent, while the separate systems offer flexibility for future rental arrangements. Town water and sewer, off-street parking, and a fenced in backyard complete the property. Whether you’re looking to owner occupy while offsetting your mortgage with rental income or add another multi-family to your portfolio, this property offers plenty of possibilities!

411-413 River St, Winchendon

$315,000

Welcome home to 4 Hale St in Winchendon, MA. This 1910 ranch sits on a corner lot and offers single-level living, with hardwood floors, French doors, and classic character throughout.The main bedroom features a walk-in closet and dressing area, and a bonus room with washer/dryer hookups adds everyday convenience. A walk-up attic offers extra storage or future potential.Outside, enjoy the composite deck or unwind by the fire pit on the spacious, private lot. The home is ready for its next owner's updates and personal touches, an opportunity to build equity in a desirable Winchendon location.

2 Beds ⋅ 1 Baths ⋅ 73584873 MLS

Welcome home to 4 Hale St in Winchendon, MA. This 1910 ranch sits on a corner lot and offers single-level living, with hardwood floors, French doors, and classic character throughout.The main bedroom features a walk-in closet and dressing area, and a bonus room with washer/dryer hookups adds everyday convenience. A walk-up attic offers extra storage or future potential.Outside, enjoy the composite deck or unwind by the fire pit on the spacious, private lot. The home is ready for its next owner's updates and personal touches, an opportunity to build equity in a desirable Winchendon location.

4 Hale St, Winchendon

$509,900

This beautiful home and property in a quiet Winchendon neighborhood is ready for its new owners! When you walk into the house through the front door you'll be captivated by the bright, airy atmosphere and thoughtfully designed living space. You are greeted by a spacious living room, with a pellet stove, great for cozying up on cool nights. Adjacent to the living room is the formal dining area which effortlessly connects to the kitchen making it easy for gatherings. The kitchen has cabinetry, custom built-ins, and a peninsula, a great breakfast nook. The standout feature is the sunroom, which is bathed in natural light. Heading upstairs, you'll find a full bath and three generously sized bedrooms. The main bedroom has a large walk-in closet and is a cozy retreat. The finished basement is an incredible bonus offering a multitude of possibilities. Enjoy summers grilling on the back deck, night relaxing in the screened in back patio, or rocking on the front porch. Recent upgrades include: Updated well(hydro blasted) 2025, Outside piping was upgraded(flex piping) 2025.

3 Beds ⋅ 3 Baths ⋅ 73583622 MLS

This beautiful home and property in a quiet Winchendon neighborhood is ready for its new owners! When you walk into the house through the front door you'll be captivated by the bright, airy atmosphere and thoughtfully designed living space. You are greeted by a spacious living room, with a pellet stove, great for cozying up on cool nights. Adjacent to the living room is the formal dining area which effortlessly connects to the kitchen making it easy for gatherings. The kitchen has cabinetry, custom built-ins, and a peninsula, a great breakfast nook. The standout feature is the sunroom, which is bathed in natural light. Heading upstairs, you'll find a full bath and three generously sized bedrooms. The main bedroom has a large walk-in closet and is a cozy retreat. The finished basement is an incredible bonus offering a multitude of possibilities. Enjoy summers grilling on the back deck, night relaxing in the screened in back patio, or rocking on the front porch. Recent upgrades include: Updated well(hydro blasted) 2025, Outside piping was upgraded(flex piping) 2025.

71 Hapgood, Winchendon

$379,900

So much more than what you find in your traditional split-entry style home!!! A beautiful sunken Great Room in the back of this home for privacy offering cathedral ceilings, skylights, brick hearth, laminate flooring and sliding glass doors leading to a deck! 2 bathrooms (one with walk-in shower)! A front-to-back family room in the basement! Master bedroom has a walk-in closet! 3rd bedroom is on the lower level. Need a den or home office? Living room French Doors lead to a sunken den, office or maybe a playroom? Priced low because some work still remains to be done. This home will not meet FHA, FmHA or VA requirements. Above ground pool conveys but needs work. Located on a beautiful country road yet just minutes to downtown Winchendon and Routes 12, 202, 140 and 2! A travelers DREAM to live in the country with over an acre yet have good highway access! Title 5 passed!! Still time to be in your home before the upcoming holidays if you hurry!!

3 Beds ⋅ 2 Baths ⋅ 73583584 MLS

So much more than what you find in your traditional split-entry style home!!! A beautiful sunken Great Room in the back of this home for privacy offering cathedral ceilings, skylights, brick hearth, laminate flooring and sliding glass doors leading to a deck! 2 bathrooms (one with walk-in shower)! A front-to-back family room in the basement! Master bedroom has a walk-in closet! 3rd bedroom is on the lower level. Need a den or home office? Living room French Doors lead to a sunken den, office or maybe a playroom? Priced low because some work still remains to be done. This home will not meet FHA, FmHA or VA requirements. Above ground pool conveys but needs work. Located on a beautiful country road yet just minutes to downtown Winchendon and Routes 12, 202, 140 and 2! A travelers DREAM to live in the country with over an acre yet have good highway access! Title 5 passed!! Still time to be in your home before the upcoming holidays if you hurry!!

45 Joslin Road, Winchendon

$475,000

Welcome to 20 Mechanic Street! This true two-family property offers a total of 6 bedrooms and 2 full bathrooms, with each unit featuring 3 bedrooms and 1 full bath. Extensively renovated approximately five years ago, the property was taken down to the studs and rebuilt with major updates throughout. Improvements include updated electrical and plumbing, spray foam insulation in the walls and floors, updated kitchens and bathrooms, newer water heaters, and mini-split systems providing heating and cooling in each unit. The exterior has also been updated with a newer roof, siding, and windows—all completed within the last five years. With extensive improvements already completed and two spacious 3-bedroom units, this property offers an excellent opportunity to add a substantially updated multifamily to your real estate portfolio.

6 Beds ⋅ 3 Baths ⋅ 73581438 MLS

Welcome to 20 Mechanic Street! This true two-family property offers a total of 6 bedrooms and 2 full bathrooms, with each unit featuring 3 bedrooms and 1 full bath. Extensively renovated approximately five years ago, the property was taken down to the studs and rebuilt with major updates throughout. Improvements include updated electrical and plumbing, spray foam insulation in the walls and floors, updated kitchens and bathrooms, newer water heaters, and mini-split systems providing heating and cooling in each unit. The exterior has also been updated with a newer roof, siding, and windows—all completed within the last five years. With extensive improvements already completed and two spacious 3-bedroom units, this property offers an excellent opportunity to add a substantially updated multifamily to your real estate portfolio.

20 Mechanic St, Winchendon

$674,900

Some homes are meant to be lived in, others are meant to be explored, and this one happens to be both! Nearly 25 acres surround this inviting ranch at the end of a quiet cul-de-sac, with private trails, Whitney Pond along the rear boundary, and room to enjoy life on your own terms! Step inside to an open-concept living area where the living room, dining area, and kitchen connect effortlessly. Hardwood floors run throughout, while sliders fill the space with natural light and whisk you out to the charming deck. The living room fireplace adds warmth and character, while three bedrooms provide comfortable space for everyone. Downstairs, a propane stove warms the expansive basement, offering tons of versatile space for a family room, game area, workshop, gym, hobbies, or whatever you envision. Outside is where this property really shines. 24+ acres of mature woods create a private backdrop, with more than a mile of trails winding through the land for hiking, cross-country skiing, snowmobiling, power sports, hunting, and exploring. Direct access to the former Boston & Maine Railroad corridor and groomed snowmobile trails adds even more four-season recreation. Approximately 360 feet of Whitney Pond frontage stretches along the rear property boundary, bringing fishing, kayaking, wildlife watching, and peaceful waterfront moments close to home. Eight established garden beds, a chicken-coop area, garden shed, screened gazebo, and dedicated RV/camper parking add even more ways to enjoy the land. The oversized garage setup is equally impressive, with a 24' x 36' three-car barn/garage plus heated 24' x 24' attached and detached two-car garages, providing space for up to seven vehicles along with equipment, projects, and storage. Recent improvements include a new roof with transferable 50-year warranty, replaced well system, whole-house water radon mitigation system, EcoFlow backup power system, and newer high efficiency boiler. There’s a lot to discover here, and pictures can only tell part of the story. Come experience the space, privacy, and possibilities for yourself! Your next adventure awaits!

3 Beds ⋅ 2 Baths ⋅ 73580203 MLS

Some homes are meant to be lived in, others are meant to be explored, and this one happens to be both! Nearly 25 acres surround this inviting ranch at the end of a quiet cul-de-sac, with private trails, Whitney Pond along the rear boundary, and room to enjoy life on your own terms! Step inside to an open-concept living area where the living room, dining area, and kitchen connect effortlessly. Hardwood floors run throughout, while sliders fill the space with natural light and whisk you out to the charming deck. The living room fireplace adds warmth and character, while three bedrooms provide comfortable space for everyone. Downstairs, a propane stove warms the expansive basement, offering tons of versatile space for a family room, game area, workshop, gym, hobbies, or whatever you envision. Outside is where this property really shines. 24+ acres of mature woods create a private backdrop, with more than a mile of trails winding through the land for hiking, cross-country skiing, snowmobiling, power sports, hunting, and exploring. Direct access to the former Boston & Maine Railroad corridor and groomed snowmobile trails adds even more four-season recreation. Approximately 360 feet of Whitney Pond frontage stretches along the rear property boundary, bringing fishing, kayaking, wildlife watching, and peaceful waterfront moments close to home. Eight established garden beds, a chicken-coop area, garden shed, screened gazebo, and dedicated RV/camper parking add even more ways to enjoy the land. The oversized garage setup is equally impressive, with a 24' x 36' three-car barn/garage plus heated 24' x 24' attached and detached two-car garages, providing space for up to seven vehicles along with equipment, projects, and storage. Recent improvements include a new roof with transferable 50-year warranty, replaced well system, whole-house water radon mitigation system, EcoFlow backup power system, and newer high efficiency boiler. There’s a lot to discover here, and pictures can only tell part of the story. Come experience the space, privacy, and possibilities for yourself! Your next adventure awaits!

35 Northern Heights Dr, Winchendon

$600,000

New home to be built on a quiet country road with few neighbors on a wooded 1 acre lot. Inside is a welcoming foyer with built ins, and a wide open first floor plan that will satisfy huge family gatherings making entertaining easy. The kitchen features Maple cabinets with soft close doors and drawers, granite tops, an oversized island and of course our custom lighting package with under cabinet and toe kick lights. There is a dining area and a living room, but the 12x24 family room is the bonus living area that sets this home apart from others. Upstairs are 2 guest bedrooms with and a common bathroom with linen closet. Master suite features cathedral ceiling, large walk in closet and a double vanity in the master bath. Enjoy the outside from either the front farmers porch framed with rough sawn timbers, or the 10x12 rear deck. There is a 2 car garage, central A/C, the lot will be landscaped and the driveway paved. Construction starts soon, so secure it now and be involved with every detail of your new home.

3 Beds ⋅ 3 Baths ⋅ 73579681 MLS

New home to be built on a quiet country road with few neighbors on a wooded 1 acre lot. Inside is a welcoming foyer with built ins, and a wide open first floor plan that will satisfy huge family gatherings making entertaining easy. The kitchen features Maple cabinets with soft close doors and drawers, granite tops, an oversized island and of course our custom lighting package with under cabinet and toe kick lights. There is a dining area and a living room, but the 12x24 family room is the bonus living area that sets this home apart from others. Upstairs are 2 guest bedrooms with and a common bathroom with linen closet. Master suite features cathedral ceiling, large walk in closet and a double vanity in the master bath. Enjoy the outside from either the front farmers porch framed with rough sawn timbers, or the 10x12 rear deck. There is a 2 car garage, central A/C, the lot will be landscaped and the driveway paved. Construction starts soon, so secure it now and be involved with every detail of your new home.

24 Old County Rd, Winchendon

$385,000

***Open House Saturday (10/10) 12-2*** Welcome home to this charming ranch offering comfortable one-level living and a wonderful blend of updates, character, and outdoor space. Whether you're purchasing your first home or looking to downsize, this lovingly maintained property is ready to welcome its next owner. The home features three bedrooms and one-and-a-half baths, with the smaller third bedroom currently being used as a spacious walk-in closet—providing excellent flexibility for storage, a home office, nursery, or guest space. The primary bedroom features new carpet and a screened porch. Outside, you'll find a large backyard surrounded by mature trees, offering plenty of room to relax, garden, entertain, or simply enjoy the privacy of your own outdoor space. The established garden adds even more charm and potential for those who enjoy gardening and outdoor living. A nature lovers dream, only two minutes from Lake Dennison, six minutes from Otter River, and close to multiple hiking trails.

3 Beds ⋅ 2 Baths ⋅ 73579662 MLS

***Open House Saturday (10/10) 12-2*** Welcome home to this charming ranch offering comfortable one-level living and a wonderful blend of updates, character, and outdoor space. Whether you're purchasing your first home or looking to downsize, this lovingly maintained property is ready to welcome its next owner. The home features three bedrooms and one-and-a-half baths, with the smaller third bedroom currently being used as a spacious walk-in closet—providing excellent flexibility for storage, a home office, nursery, or guest space. The primary bedroom features new carpet and a screened porch. Outside, you'll find a large backyard surrounded by mature trees, offering plenty of room to relax, garden, entertain, or simply enjoy the privacy of your own outdoor space. The established garden adds even more charm and potential for those who enjoy gardening and outdoor living. A nature lovers dream, only two minutes from Lake Dennison, six minutes from Otter River, and close to multiple hiking trails.

12 Baldwinville State Rd, Winchendon

$475,000

Fully occupied 4 family in great location on a corner lot of dead end street. Simple layout with 2, 1 bedroom apartments on first floor. The second floor has a 1 bedroom apartment and a 2 bedroom apartment with access to a den on 3rd floor. Additional 30x30 garage with 2 doors is included in 2 bedroom rent. Each units has a forced hot water furnace with tankless hot water and designated oil tank, so tenants pay all heat and hot water. All roofs including flat roof on garage replaced in last 8 years. Nice back yard offers just enough space for outdoor enjoyment.

5 Beds ⋅ 4 Baths ⋅ 73578492 MLS

Fully occupied 4 family in great location on a corner lot of dead end street. Simple layout with 2, 1 bedroom apartments on first floor. The second floor has a 1 bedroom apartment and a 2 bedroom apartment with access to a den on 3rd floor. Additional 30x30 garage with 2 doors is included in 2 bedroom rent. Each units has a forced hot water furnace with tankless hot water and designated oil tank, so tenants pay all heat and hot water. All roofs including flat roof on garage replaced in last 8 years. Nice back yard offers just enough space for outdoor enjoyment.

324 Front St, Winchendon

$464,900

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 1.05 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.

3 Beds ⋅ 3 Baths ⋅ 73574967 MLS

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 1.05 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.

Lot 1 River St, Winchendon

$425,000

Welcome to this exceptional, updated Ranch offering an impressive finished lower level with an office/guest room, and an oversized 19x52 heated garage with room for a workshop, recreational vehicles, hobbies and more! This home features a newly finished lower level, offering an inviting and sophisticated extension of the home’s living space and is designed for both entertaining and everyday enjoyment. The spacious entertainment room features a striking tiled pellet stove surround, creating a warm focal point, along with a custom two-tier wood slab bar, wet bar and full-size refrigerator. An office/guest room offers flexible space for a variety of needs, while a beautifully appointed bathroom with a shower completes this impressive level. All lower level work is fully permitted. On the main level, the spacious updated kitchen invites everyone to gather around the granite island. The generous dining area provides plenty of space to linger over meals and entertain, while the large living room, complete with a tiled fireplace, offers a comfortable space to relax and enjoy time together. This bright and cheery home has 2 bedrooms and a full bathroom on the main floor. The expansive level backyard provides room to gather, play, garden etc. Two sheds provides storage for yard supplies and outdoor equipment. This property is in a Home Business Zone (town approval required). This meticulously maintained and move in ready home, offers an exceptional combination of living space that truly sets it apart!

2 Beds ⋅ 2 Baths ⋅ 73574438 MLS

Welcome to this exceptional, updated Ranch offering an impressive finished lower level with an office/guest room, and an oversized 19x52 heated garage with room for a workshop, recreational vehicles, hobbies and more! This home features a newly finished lower level, offering an inviting and sophisticated extension of the home’s living space and is designed for both entertaining and everyday enjoyment. The spacious entertainment room features a striking tiled pellet stove surround, creating a warm focal point, along with a custom two-tier wood slab bar, wet bar and full-size refrigerator. An office/guest room offers flexible space for a variety of needs, while a beautifully appointed bathroom with a shower completes this impressive level. All lower level work is fully permitted. On the main level, the spacious updated kitchen invites everyone to gather around the granite island. The generous dining area provides plenty of space to linger over meals and entertain, while the large living room, complete with a tiled fireplace, offers a comfortable space to relax and enjoy time together. This bright and cheery home has 2 bedrooms and a full bathroom on the main floor. The expansive level backyard provides room to gather, play, garden etc. Two sheds provides storage for yard supplies and outdoor equipment. This property is in a Home Business Zone (town approval required). This meticulously maintained and move in ready home, offers an exceptional combination of living space that truly sets it apart!

125 Baldwinville State Rd, Winchendon

$385,000

There’s something special about a Village Colonial: the character, the generous rooms and the feeling of being connected to the heart of town. Welcome to 374 Front Street, where you’ll find all of that, plus a floor plan with plenty of room to make it your own. The spacious 15x15 eat-in kitchen, with newer appliances and hardwood floors, is made for morning coffee, weeknight dinners and conversations around the table. A separate dining room gives you great space to celebrate holidays and gatherings, while the oversized 21x15 living room offers plenty of space to gather and relax. Need flexibility? A first-floor bedroom/separate office create options for guests, working from home, a playroom or hobby space, plus additional open space between the dining room and living room. Upstairs are three more generously sized bedrooms, including a 15x14 primary bedroom and a 13x13 bedroom with a walk-in closet. Wood floors (mix of hardwood, Douglas Fir and Pine) run throughout much of the home, and second-floor laundry keeps everyday chores conveniently close to the bedrooms. Outside, enjoy a level backyard with room for gardening, games, summer cookouts or simply relaxing at home. The porch adds another spot to sit back and enjoy the neighborhood, while the newer 2024 roof is an important update already taken care of. Best of all, you’re close to the heart of Winchendon, with local shops, dining, Beals Memorial Library and community activities nearby. Outdoor adventures are easy to find too, from the North Central Pathway and Winchendon Community Park to nearby Lake Dennison and Otter River. If you’ve been waiting for a home with character, space to spread out and the convenience of village living, this one deserves a closer look.

4 Beds ⋅ 2 Baths ⋅ 73571805 MLS

There’s something special about a Village Colonial: the character, the generous rooms and the feeling of being connected to the heart of town. Welcome to 374 Front Street, where you’ll find all of that, plus a floor plan with plenty of room to make it your own. The spacious 15x15 eat-in kitchen, with newer appliances and hardwood floors, is made for morning coffee, weeknight dinners and conversations around the table. A separate dining room gives you great space to celebrate holidays and gatherings, while the oversized 21x15 living room offers plenty of space to gather and relax. Need flexibility? A first-floor bedroom/separate office create options for guests, working from home, a playroom or hobby space, plus additional open space between the dining room and living room. Upstairs are three more generously sized bedrooms, including a 15x14 primary bedroom and a 13x13 bedroom with a walk-in closet. Wood floors (mix of hardwood, Douglas Fir and Pine) run throughout much of the home, and second-floor laundry keeps everyday chores conveniently close to the bedrooms. Outside, enjoy a level backyard with room for gardening, games, summer cookouts or simply relaxing at home. The porch adds another spot to sit back and enjoy the neighborhood, while the newer 2024 roof is an important update already taken care of. Best of all, you’re close to the heart of Winchendon, with local shops, dining, Beals Memorial Library and community activities nearby. Outdoor adventures are easy to find too, from the North Central Pathway and Winchendon Community Park to nearby Lake Dennison and Otter River. If you’ve been waiting for a home with character, space to spread out and the convenience of village living, this one deserves a closer look.

374 Front Street, Winchendon

$385,000

A true diamond in the rough, this home has great bones, great space, and a lot of potential for a variety of prospective buyers. Situated conveniently on Tannery Pond, only a few minutes to downtown Winchendon, this property is zoned for a two family but currently being used as a single family. All systems - heat, hot water, and electric - are in great shape. Worry-free solar panels are owned, not leased. A recent renovation to the kitchen has added value, but there is much more opportunity to live comfortably yet build more equity. This house has amazing possibilities, and as a single home or a duplex allows for a rare vesatility for a new owner. Schedule a showing today!

4 Beds ⋅ 2 Baths ⋅ 73571155 MLS

A true diamond in the rough, this home has great bones, great space, and a lot of potential for a variety of prospective buyers. Situated conveniently on Tannery Pond, only a few minutes to downtown Winchendon, this property is zoned for a two family but currently being used as a single family. All systems - heat, hot water, and electric - are in great shape. Worry-free solar panels are owned, not leased. A recent renovation to the kitchen has added value, but there is much more opportunity to live comfortably yet build more equity. This house has amazing possibilities, and as a single home or a duplex allows for a rare vesatility for a new owner. Schedule a showing today!

33-35 Beech St., Winchendon

$409,900

Welcome home to this beautifully renovated property in Winchendon! Completely transformed with thoughtful updates throughout, this inviting home offers a fresh, modern feel while maintaining plenty of warmth and charm. Soaring ceilings and luxury vinyl flooring create a bright, spacious atmosphere, while the updated kitchen features beautiful quartz countertops and stainless steel appliances.The home offers two beautifully finished full bathrooms—one conveniently located on the first floor and a second adjoining the primary bedroom on the second floor. With stylish finishes, comfortable living spaces, and extensive renovations already complete, all that's left to do is unpack and settle in.Beautifully updated and truly move-in ready—come see all this Winchendon home has to offer! Seller is willing to credit the Buyer $5000 in closing costs!

3 Beds ⋅ 2 Baths ⋅ 73568807 MLS

Welcome home to this beautifully renovated property in Winchendon! Completely transformed with thoughtful updates throughout, this inviting home offers a fresh, modern feel while maintaining plenty of warmth and charm. Soaring ceilings and luxury vinyl flooring create a bright, spacious atmosphere, while the updated kitchen features beautiful quartz countertops and stainless steel appliances.The home offers two beautifully finished full bathrooms—one conveniently located on the first floor and a second adjoining the primary bedroom on the second floor. With stylish finishes, comfortable living spaces, and extensive renovations already complete, all that's left to do is unpack and settle in.Beautifully updated and truly move-in ready—come see all this Winchendon home has to offer! Seller is willing to credit the Buyer $5000 in closing costs!

16 Winter Pl, Winchendon

$380,000

OPEN HOUSE Saturday 10/10 NOON to 2pm!! Priced UNDER APPRAISED VALUE! Welcome home to this sun-filled, open-concept home! The bright first-floor living space features hardwood floors and a picturesque window that flows seamlessly into the eat-in kitchen with ample cabinet storage. Head right into the family room featuring a vaulted ceiling and a stunning picture window overlooking your serene backyard. Down the hallway, you’ll find two comfortable bedrooms and a full bath. The fully finished lower level adds incredible living space, offering two additional bedrooms and a versatile bonus room—perfect for a home office, gym, or playroom! Head outside to your private, wooded backyard complete with a patio, convenient storage shed, and an inground pool perfect for summer fun. Whether relaxing in your private backyard sanctuary or exploring nature at the nearby Monomonac Hill Conservation Area, this property offers the perfect mix of comfort and outdoor adventure! Peace of mind comes with a brand new roof and brand new 4 bedroom septic system! Your private backyard paradise awaits—schedule your showing today and start making memories!

4 Beds ⋅ 1 Baths ⋅ 73563203 MLS

OPEN HOUSE Saturday 10/10 NOON to 2pm!! Priced UNDER APPRAISED VALUE! Welcome home to this sun-filled, open-concept home! The bright first-floor living space features hardwood floors and a picturesque window that flows seamlessly into the eat-in kitchen with ample cabinet storage. Head right into the family room featuring a vaulted ceiling and a stunning picture window overlooking your serene backyard. Down the hallway, you’ll find two comfortable bedrooms and a full bath. The fully finished lower level adds incredible living space, offering two additional bedrooms and a versatile bonus room—perfect for a home office, gym, or playroom! Head outside to your private, wooded backyard complete with a patio, convenient storage shed, and an inground pool perfect for summer fun. Whether relaxing in your private backyard sanctuary or exploring nature at the nearby Monomonac Hill Conservation Area, this property offers the perfect mix of comfort and outdoor adventure! Peace of mind comes with a brand new roof and brand new 4 bedroom septic system! Your private backyard paradise awaits—schedule your showing today and start making memories!

114 Glenallen Street, Winchendon

$375,000

263 Front St. is a well-maintained two-family home offering the perfect blend of charm, space, and investment potential. Each expansive unit features 3 bedrooms, bright and inviting living areas, spacious kitchens, and an abundance of natural light, creating comfortable spaces for both owners and tenants alike. Thoughtfully updated over the years, including two brand-new boilers installed in 2026, this property offers the ideal opportunity for an owner-occupant seeking supplemental rental income or an investor looking to add a turnkey duplex to their portfolio. Ideally situated in a convenient in-town location close to shopping, dining, schools, parks, and commuter routes, this versatile property delivers both lifestyle and long-term value. Whether you're starting your investment journey or growing an established portfolio, this is a property you'll want to see.

6 Beds ⋅ 2 Baths ⋅ 73558512 MLS

263 Front St. is a well-maintained two-family home offering the perfect blend of charm, space, and investment potential. Each expansive unit features 3 bedrooms, bright and inviting living areas, spacious kitchens, and an abundance of natural light, creating comfortable spaces for both owners and tenants alike. Thoughtfully updated over the years, including two brand-new boilers installed in 2026, this property offers the ideal opportunity for an owner-occupant seeking supplemental rental income or an investor looking to add a turnkey duplex to their portfolio. Ideally situated in a convenient in-town location close to shopping, dining, schools, parks, and commuter routes, this versatile property delivers both lifestyle and long-term value. Whether you're starting your investment journey or growing an established portfolio, this is a property you'll want to see.

263 Front St., Winchendon

$409,000

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

4 Beds ⋅ 3 Baths ⋅ 73554607 MLS

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

33 W Shore Drive, Winchendon

$299,000

Investor opportunity awaits in a great location! This sold-as-is, 2 family property on a corner lot offers potential for those looking to bring new life to a home w/ character, spacious layouts & plenty of upside. Please note: there is currently no power at the property, & this is not a bank-owned sale. Featuring 2 separate units, this property provides flexible living space for future tenants. Both units offer multiple fireplaces, original built-ins & original details that showcase the home’s character. Additional features include a side covered porch, private rear deck & off-street parking. Located close to local shops, restaurants & several local ponds along with nearby Lake Dennison Recreation Area, offering a swimming beach, fishing, picnic areas, boat ramp access, camping, & miles of trails. Great opportunity for investors, contractors, or buyers looking for a project w/ potential. Sold-as-is.

7 Beds ⋅ 5 Baths ⋅ 73554552 MLS

Investor opportunity awaits in a great location! This sold-as-is, 2 family property on a corner lot offers potential for those looking to bring new life to a home w/ character, spacious layouts & plenty of upside. Please note: there is currently no power at the property, & this is not a bank-owned sale. Featuring 2 separate units, this property provides flexible living space for future tenants. Both units offer multiple fireplaces, original built-ins & original details that showcase the home’s character. Additional features include a side covered porch, private rear deck & off-street parking. Located close to local shops, restaurants & several local ponds along with nearby Lake Dennison Recreation Area, offering a swimming beach, fishing, picnic areas, boat ramp access, camping, & miles of trails. Great opportunity for investors, contractors, or buyers looking for a project w/ potential. Sold-as-is.

179 Front St, Winchendon

$434,000

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

5 Beds ⋅ 3 Baths ⋅ 73530513 MLS

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

155 River St, Winchendon