Winchendon, MA Homes

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  /41

  $415,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,914 Sq Ft

  8 Highland St, Winchendon, MA 01475

  Investors or Owner occupied take notice!!! This is a beautifully updated two family on a side street just a short distance from downtown, and the new amphitheater. The first unit is on the first floor and has 1 bdrm, living room, an eat-in kitchen, pantry, and a full bath with laundry. The second unit is two levels. The first level has 1 bdrm, kitchen, dining/living room combo, 3/4 bath, and

  

  Michelle Peterson

  Elm Grove Realty, LLC

  (351) 300-7320

  8 Highland St, Winchendon, MA 01475
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  /42

  $489,900 Sold Sep 29, 2025

  • 1,568 Sq Ft
  • $312/SF
  • 7 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2005

  32 Old County Rd, Winchendon, MA 01475

  Tucked back from the road for full privacy, this beautifully maintained 3-bedroom, 1.5-bath colonial offers the perfect blend of comfort and updates. The 1st-floor features a spacious living room, an open-concept kitchen with stainless steel appliances and peninsula seating, a freshly remodeled 1/2 bath and a bright dining area. Upstairs, you’ll find 3 generously sized bedrooms and a full

  Benjamin Hause Keller Williams Realty North Central

  32 Old County Rd, Winchendon, MA 01475
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  /42

  Est $386,394 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft

  10 Hale St, Winchendon, MA 01475

  10 Hale St, Winchendon, MA 01475
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  /10

  $549,900 Open Sat 12PM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,652 Sq Ft

  371 Hitchcock Rd, Winchendon, MA 01475

  This brand new 3-bedroom, 2.5-bath Colonial on 4.8 wooded acres is under construction. Quality built 3 bedroom, 2.5 bath home offers 1,652’ of living area with an oversized attached 1-car garage. The inviting farmer’s porch with composite decking leads into an open-concept first floor featuring the kitchen with granite countertops, an island and dining area with access to a 12x12 deck overlooking

  

  Cory Gracie

  LAER Realty Partners

  (351) 222-8835

  371 Hitchcock Rd, Winchendon, MA 01475
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  /35

  $411,000 Sold Sep 26, 2025

  • 1,584 Sq Ft
  • $259/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1985

  195 Holly Dr, Gardner, MA 01440

  Looking for your perfect first home or just an amazing place you’ll love? This property has it all! Set on a large lot with a huge yard and a spacious deck, it’s ideal for barbecues, morning coffee, or evening drinks. Beautiful French doors off the kitchen fill the space with natural light and open right onto the deck, creating a seamless indoor-outdoor flow. The kitchen opens to the family

  Laura Urbec BA Property & Lifestyle Advisors

  195 Holly Dr, Gardner, MA 01440
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  /40

  Est $618,891 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,410 Sq Ft

  75 Monomonac Rd W, Winchendon, MA 01475

  75 Monomonac Rd W, Winchendon, MA 01475
• 

  

  /18

  $420,000

  • 4 Beds
  • 1 Bath
  • 1,343 Sq Ft

  706 Brown St, Winchendon, MA 01475

  Nestled in the charming town of Winchendon, Massachusetts, the single family residence at 706 Brown St presents an opportunity to invest in a property with considerable potential. Built in 1983, this home offers a solid foundation for creating the living space you have always envisioned. The heart of this single family residence is undoubtedly its expansive lot, spanning 88,165 square feet, which

  Thomas Pultorak Foster-Healey Real Estate

  706 Brown St, Winchendon, MA 01475
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  /42

  $550,000 Sold Sep 26, 2025

  • 2,866 Sq Ft
  • $192/SF
  • 67 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1986

  19 Otter River Rd, Winchendon, MA 01475

  NEW CARPET CREDIT!!! MOTIVATED SELLER!!! BRING OFFERS!!! This stunning country home sits on an expansive 1.7-acre lot, offering plenty of space for outdoor entertaining. The 2800 st ft. interior features two large living areas with cozy fireplaces, and a recently updated kitchen includes newer cabinets, black granite countertops, stainless steel appliances, and tile flooring. A formal dining

  Michelle Peterson Elm Grove Realty, LLC

  19 Otter River Rd, Winchendon, MA 01475
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  /42

  Est $742,432 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,785 Sq Ft

  26 Lakeview Dr, Winchendon, MA 01475

  26 Lakeview Dr, Winchendon, MA 01475
• 

  

  /15

  $379,900 Open Sat 1PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,536 Sq Ft

  1135 Alger St, Winchendon, MA 01475

  Open House this Saturday, November 8th from 1:00 to 2:00. Welcome to this charming 22-year-young Colonial tucked away on just over an acre of serene, wooded privacy. Featuring three spacious bedrooms and 11⁄2 bathrooms, the home offers front-to-back living & dining rooms, creating warm and inviting spaces for gathering and everyday living. On the first floor, enjoy the flexible room—perfect as an

  Wendy Poudrette Foster-Healey Real Estate

  1135 Alger St, Winchendon, MA 01475
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  /32

  $480,000 Sold Sep 25, 2025

  • 1,654 Sq Ft
  • $290/SF
  • 23 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1998

  48 Baldwinville Rd, Winchendon, MA 01475

  *8/24 OPEN HOUSE CANCELED* This 3 bedroom split-level home offers the perfect blend of privacy and functionality. Set on almost 8 acres, the property features a sprawling yard. Inside, the kitchen is equipped with new stainless steel appliances and a cozy dine-in seating area. The spacious family room showcases wood flooring, while a formal dining area offers flexibility to serve as an additional

  Christy Nault Central Mass Real Estate

  48 Baldwinville Rd, Winchendon, MA 01475
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  /42

  Est $518,082 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,064 Sq Ft

  265 Monomonac Rd W, Winchendon, MA 01475

  265 Monomonac Rd W, Winchendon, MA 01475
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  /32

  $449,900 Open Sat 11AM - 12PM

  • 3 Beds
  • 1.5 Baths
  • 1,715 Sq Ft

  35 Hillside Dr, Winchendon, MA 01475

  Welcome to 35 Hillside Drive, a beautifully updated 3-bedroom, 1.5-bath split-level home offering comfort, style, and privacy just steps from Lake Monomonac. This move-in-ready property features a new roof, new kitchen with stainless steel appliances, quartz countertops, and a spacious island ideal for everyday living and entertaining. The main level showcases engineered hardwood flooring,

  Timea Godor LAER Realty Partners

  35 Hillside Dr, Winchendon, MA 01475
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  /25

  $455,000 Sold Sep 23, 2025

  • 1,668 Sq Ft
  • $273/SF
  • 4 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  15 Cottage St, Winchendon, MA 01475

  Sun filled colonial in quiet Winchendon location. This home has been rehabbed from top to bottom, featuring 1,668 sq ft of open concept living with 4 bedrooms. New wrap around porch and deck, freshly painted with updated electric, lighting and plumbing, new flooring, new kitchen with granite countertops, new insulation, and 6 new energy efficient mini-splits that provide heat and air conditioning

  Paul Collette Keller Williams Realty North Central

  15 Cottage St, Winchendon, MA 01475
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  /30

  Est $412,764 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 834 Sq Ft

  5 1st St, Winchendon, MA 01475

  5 1st St, Winchendon, MA 01475
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  /42

  $649,999

  • 3 Beds
  • 3 Baths
  • 1,794 Sq Ft

  17 W Shore Dr, Ashburnham, MA 01430

  Stunning A-frame home overlooking Sunset Lake offers a rare blend of natural beauty, modern updates, and exceptional privacy. The moment you arrive, the floor-to-ceiling window wall captures your attention, perfectly framing views of the New England landscape. Expansive deck extends the living space outdoors, providing the ideal setting for entertaining, sun bathing, or enjoy the sun rising over

  Nancy Day Berkshire Hathaway HomeServices Stephan Real Estate

  17 W Shore Dr, Ashburnham, MA 01430
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  /13

  $371,000 Sold Sep 17, 2025

  • 1,888 Sq Ft
  • $197/SF
  • 44 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  22 Woodlawn St, Winchendon, MA 01475

  MOVE RIGHT IN!! Everything has been done for you! This bright and sunny open plan kitchen, dining and living room has cathedral ceilings and feels nice and big! The three bedrooms are large and you have the bonus of 2 full bathrooms a new roof, flooring and fresh paint throughout! This will not last long, see it today!

  Nilton Lisboa Lisboa Realty

  22 Woodlawn St, Winchendon, MA 01475
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  /22

  Est $354,657 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 558 Sq Ft

  85 4th St, Winchendon, MA 01475

  85 4th St, Winchendon, MA 01475
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  /12

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft

  21 Cottage St, Winchendon, MA 01475

  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

  Paul Collette Keller Williams Realty North Central

  21 Cottage St, Winchendon, MA 01475
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  /35

  $406,000 Sold Sep 08, 2025

  • 1,700 Sq Ft
  • $239/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1920

  353 Front St, Winchendon, MA 01475

  THIS 4 BEDROOM 2 FULL BATH HOME HAS BEEN COMPLETELY COSMETICALLY UPDATED FLOORS, KITCHEN, BATHS, NEW CUSTOM LIGHTING, THIS HOME HAS LOTS OF CHARACTER, FIRST FLOOR CONSIST OF FOYER/MUDROOM, LAUNDRY ROOM,LARGE LIVING ROOM WITH WAINSCOATING,DECORATIVE CEILINGS, LVP & TILE FLOORING ,MAIN SUITE VAULTED CEILINGS ,WALK-IN SHOWER, CUSTOM TILE, OVERSIZE TUB, KITCHEN WITH STAINLESS APPLIANCES, QUARTZ

  Julia Cotter Golden Key Realty, LLC

  353 Front St, Winchendon, MA 01475
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  /24

  Est $417,667 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  100 Mill Cir, Winchendon, MA 01475

  100 Mill Cir, Winchendon, MA 01475
• 

  

  /19

  $439,900

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft

  27 Cottage St, Winchendon, MA 01475

  27 Cottage St, Winchendon, MA, presents a single-family residence, newly built and ready to welcome its first residents. This new home offers the promise of modern living within a peaceful setting. The residence features three bedrooms, providing comfortable accommodations for rest and relaxation. Two full bathrooms and one-half bathroom offer convenience and functionality, ensuring that the

  Paul Collette Keller Williams Realty North Central

  27 Cottage St, Winchendon, MA 01475
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  /42

  $409,000 Sold Sep 08, 2025

  • 1,872 Sq Ft
  • $218/SF
  • 13 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1986

  1170-1172 Alger St, Winchendon, MA 01475

  Welcome to this charming 2-Family Home in scenic Winchendon, MA! Nestled amidst the natural beauty of North-Central Massachusetts (near NH), this attractive & maintained multi-family residence is a true gem in the area and offers a fantastic investment or potential owner-occupied opportunity. Both units are currently rented – one on a month-to-month basis with long-term tenants who wish to stay,

  Derrick Bonnah Thumbprint Realty, LLC

  1170-1172 Alger St, Winchendon, MA 01475
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  /32

  Est $483,112 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,328 Sq Ft

  46 Beachview Dr, Winchendon, MA 01475

  46 Beachview Dr, Winchendon, MA 01475
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  /28

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,289 Sq Ft

  728 River St, Winchendon, MA 01475

  Follow the long, picturesque driveway and discover a world of privacy, luxury, and calm complete with a pool, outdoor jacuzzi, encompassed in 24 acres of land. Spanning approximately 2,289 square feet, this home features 3 bedrooms, 2 full baths, an office, a family room and a generous 2 car garage. Step inside to a beautiful open concept living area featuring vaulted ceilings and a seamless flow

  Ricardo Rodriguez Coldwell Banker Realty - Boston

  728 River St, Winchendon, MA 01475
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  /38

  $340,000 Sold Aug 29, 2025

  • 1,536 Sq Ft
  • $221/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2005

  46 Woodlawn Ave, Winchendon, MA 01475

  OFFER DEADLINE WEDNESDAY - July 16th @ 12 NOON --- 3-bedroom, 1.5-bath Colonial nestled on just over a half-acre lot on a quiet dead-end street—offering a peaceful setting with the convenience of nearby amenities. Located close to downtown, shopping, schools, Lake Dennison recreation area, and the New Hampshire border, this home is ideal for both commuters and outdoor enthusiasts.The first floor

  Lana Kopsala Coldwell Banker Realty - Leominster

  46 Woodlawn Ave, Winchendon, MA 01475
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  /41

  Est $441,209 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,098 Sq Ft

  68 Gardner Rd, Winchendon, MA 01475

  68 Gardner Rd, Winchendon, MA 01475
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  /38

  $525,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 2,070 Sq Ft

  330 Benjamin St, Winchendon, MA 01475

  Welcome to this charming ranch-style home nestled on over 3 acres of picturesque land. Enter to a spacious formal living & dining area, filled w/ natural light through a large picture window. A comfortable den w/ fireplace & sliding glass doors opens to your back deck. The kitchen boasts a farmhouse sink & a dining area w/ a bay window overlooking your vast backyard. This home offers a convenient

  Leslie Tondreau Lamacchia Realty, Inc.

  330 Benjamin St, Winchendon, MA 01475
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  /42

  $465,000 Sold Aug 29, 2025

  • 2,494 Sq Ft
  • $186/SF
  • 73 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1926

  23 Lincoln Ave, Winchendon, MA 01475

  SELLER SAYS SELL!!!! Tudor-style home looks like something straight out of a storybook. Upon entering, you're welcomed into an elegant foyer with gleaming hardwood floors. French doors lead to a formal living room featuring a cozy fireplace, while just beyond is a formal dining room with beautiful built-in cabinets. The sunk-in family room offers ample space for entertaining and opens directly

  Michelle Peterson Elm Grove Realty, LLC

  23 Lincoln Ave, Winchendon, MA 01475
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  /38

  Est $389,355 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  628 Teel Rd, Winchendon, MA 01475

  628 Teel Rd, Winchendon, MA 01475
• 

  

  /20

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,067 Sq Ft

  67 Hill St, Winchendon, MA 01475

  Nestled on a large 6.47 acre lot in the charming town of Winchendon, this new home offers a unique opportunity to embrace refined country living in a private setting. This attractive property is ready to welcome you. The kitchen is a culinary dream, featuring a large kitchen island that serves as a natural gathering place, complemented by sleek stone countertops and stylish cabinets that provide

  Paul Collette Keller Williams Realty North Central

  67 Hill St, Winchendon, MA 01475
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  /17

  $245,000 Sold Aug 25, 2025

  • 1,078 Sq Ft
  • $227/SF
  • 69 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  47 Beech St, Winchendon, MA 01475

  Discover the possibilities with this cozy 3-bedroom, 1.5-bath home, perfectly situated on a scenic lot where the backyard almost meets Miller's River and Mason & Parker Pond. Whether you're looking to create your dream home or invest in a renovation project, this property offers the perfect canvas. Inside, you'll find a functional layout with plenty of natural light and space to reimagine each

  Paula Valente Real Estate Exchange

  47 Beech St, Winchendon, MA 01475
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  /4

  Est $460,107 Not Listed For Sale

  • 2 Beds

  291 Ash St, Winchendon, MA 01475

  291 Ash St, Winchendon, MA 01475
• 

  

  /38

  $455,000

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  80 Elmwood Rd, Winchendon, MA 01475

  Welcome to 80 Elmwood Rd! A beautifully maintained 3-bedroom, 2.5-bath young colonial built in 2017. Step inside to find gleaming hardwood floors, a spacious open layout, and a stylish kitchen featuring granite countertops and plenty of closet storage on the 1st floor. The inviting dining area is accented with modern wood paneling, creating a perfect space for gatherings. Upstairs, you'll find

  Adrian Olivera Keller Williams Realty North Central

  80 Elmwood Rd, Winchendon, MA 01475
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  /36

  $400,000 Sold Aug 22, 2025

  • 1,120 Sq Ft
  • $357/SF
  • 26 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1964

  556 N Central St, Winchendon, MA 01475

  Charming Ranch situated on nearly an acre lot (0.98). This inviting home offers two bedrooms and an office, a recently updated bathroom, newer roof, and 1 car garage! Step inside to discover beautiful hardwood floors throughout with the exception of the kitchen and the recently renovated bathroom, which boasts elegant tile flooring, enhancing the warmth and character of the home, Enjoy the

  Kelly Yakuben Liberty Real Estate

  556 N Central St, Winchendon, MA 01475
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  /34

  Est $439,877 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,914 Sq Ft

  25 Cross Rd, Winchendon, MA 01475

  25 Cross Rd, Winchendon, MA 01475
• 

  

  /24

  $440,000

  • 3 Beds
  • 2.5 Baths
  • 1,666 Sq Ft

  160 Lakeshore Dr, Winchendon, MA 01475

  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.

  Terry Lupien Morin Real Estate

  160 Lakeshore Dr, Winchendon, MA 01475
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  /12

  $80,000 Sold Aug 21, 2025

  • 956 Sq Ft
  • $84/SF
  • 1 Day On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  80 North St, Winchendon, MA 01475

  One-family owned for decades, this diamond in the rough is ready to be brought back to its charm. First floor has kitchen, living room and full bath and three bedrooms on second floor. Located on a fairly level lot close to area amenities, shopping and the New Hampshire border.

  Wendy Poudrette Foster-Healey Real Estate

  80 North St, Winchendon, MA 01475
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  /41

  Est $504,859 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  26 Toy Town Ln, Winchendon, MA 01475

  26 Toy Town Ln, Winchendon, MA 01475
• 

  

  /36

  $530,000

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  21 Sibley Rd, Winchendon, MA 01475

  Spacious Colonial on Over 4 Acres of Tranquility. Enjoy 2,648 sq ft of comfortable living space nestled on 4.13 private acres in a serene, natural setting. Built in 2004, this 7-room, 3-bedroom, 2-bath Colonial offers a flexible layout and plenty of charm. The expansive 28' x 22' living/family room is great for gathering, while the formal dining room and den—both with hardwood floors—add elegance

  Brian Forgues Elm Grove Realty, LLC

  21 Sibley Rd, Winchendon, MA 01475

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