20

Winchendon, MA Homes for Sale

Section Image Section Image
  • /12

    $339,900

    • 4 Beds
    • 1 Bath
    • 1,203 Sq Ft

    20 Harvard St, Winchendon, MA 01475

    Opportunity for homeowner and investor, two lots /one house with a small garage and plenty of storage, potential to subdivide and sell additional land or build a second home or Adu or just enjoy playing and hosting on plenty of level grass with charming line of trees for some privacy! This Home boasts 4 bedrooms and plenty of space! The front porch is inviting and the neighborhood sought after!

    Agent Photo

    Kathy Perdue

    RE/MAX Synergy

    (351) 777-8796

    20 Harvard St, Winchendon, MA 01475
  • /29

    $399,999

    • 2 Beds
    • 2 Baths
    • 1,693 Sq Ft

    45 Phyllis Rd, Winchendon, MA 01475

    Welcome home to a well-maintained split in a quiet neighborhood offering comfort, value, and outdoor living. The property features solar panels for energy efficiency, along with a newer roof, windows, and vinyl siding for low-maintenance ownership. The yard extends well beyond the fenced-in area, offering additional space for recreation, gardening, or play. Enjoy nearby hiking and walking trails,

    Bessie Coutu Real Estate Exchange

    45 Phyllis Rd, Winchendon, MA 01475
  • /38

    $510,000

    • 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 24' x 24' 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
  • /30

    $629,999

    • 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

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    728 River St, Winchendon, MA 01475
  • /41

    $429,999

    • 4 Beds
    • 1 Bath
    • 1,824 Sq Ft

    495 Winchendon Rd, Ashburnham, MA 01430

    Prime Opportunity for Equestrians & Investors! This versatile property combines rural charm with business potential. This home offers 4-bedrooms, 1-bath featuring a walk-up attic, offering plenty of room to customize or expand. Adjacent to the home is a spacious barn equipped with tack room, storage hay loft, and three horse stalls—ready for immediate use. The property includes two separate

    Charlotte Marrocco-Mohler Berkshire Hathaway HomeServices Verani Realty

    495 Winchendon Rd, Ashburnham, MA 01430
  • /41

    $800,000

    • 3 Beds
    • 1.5 Baths
    • 1,733 Sq Ft

    750 Teel Rd, Winchendon, MA 01475

    ATTENTION DISCERNING BUYERS! EXTRAORDINARY WOODED ACREAGE FOR A CUSTOM-BUILT FUTURE! Bring your contractor and imagination to this rare offering featuring a 37+ acre wooded parcel complemented by an additional 3+ acres with an existing structure of limited utility offering redevelopment potential for a private estate, or thoughtfully designed compound, or an ideal setting for a horse farm. Enjoy

    Kathleen Edwards Keller Williams Realty Metropolitan

    750 Teel Rd, Winchendon, MA 01475
  • /32

    $298,000

    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    169 Spruce St, Winchendon, MA 01475

    Why pay rent when you can live here!! Wonderful Winchendon. Wow! This home has been updated and is ready for its new owners. NEW ROOF, ELECTRICAL, PLUMBING, FLOORING, LIGHTING , KICHEN AND BATH. Freshly painted interior. Kitchen with Quartz Countertops, new cabinets, new appliances, walk in pantry, dining area and open shelving. Home is pleasing to the eye with neutral colors and decor. Great

    Kathleen Walsh Keller Williams Realty North Central

    169 Spruce St, Winchendon, MA 01475
  • /42

    $1,500,000

    • 2 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    226 Lakeview Dr, Winchendon, MA 01475

    Luxury living on the lake! This stunning home built in 2023 set upon 75' of private sandy beach waterfrontage. A true rare find upon Lake Monomonac which spans Mass/NH. The owners left no thought out of this custom waterfront home. Enjoy living on one floor with views of the water everywhere you turn. Well designed kitchen with waterfall quartz counter tops, high end appliances and over sized

    Amy Reisert Borderline Realty

    226 Lakeview Dr, Winchendon, MA 01475
  • /11

    $409,000

    • 5 Beds
    • 2 Baths
    • 2,544 Sq Ft

    150-152 Mill Cir, Winchendon, MA 01475

    Investors or Owner Occupant buyers now has access to home ownership! The multi-family residence offers a unique investment opportunity Built in 1980, this property presents a chance to own a substantial residence with considerable potential. Duplex living with side by side units and separate driveways offers practical accommodations for residents, lending itself to a variety of configurations.

    Peter Costa Spencer Home Realty

    150-152 Mill Cir, Winchendon, MA 01475
  • /26

    $215,900

    • 3 Beds
    • 1 Bath
    • 1,267 Sq Ft

    97 Pearl St, Winchendon, MA 01475

    Come on out and be the first to see this charming 3 bedroom home in quite family neighborhood. Large 2 car garage/barn with secondary large shed of workshop. Large private parcel of land. Nestled at 97 Pearl St, Winchendon, MA, this single-family residence in Worcester County presents a remarkable canvas for those with a vision, offering a compelling investment opportunity. This property invites

    Kenneth Maston Parkhill Realty Group

    97 Pearl St, Winchendon, MA 01475
  • /15

    $339,900

    • 3 Beds
    • 1 Bath
    • 1,340 Sq Ft

    16 Maple Place, Winchendon, MA 01475

    Well maintained 3 bedroom home in a great location. Bright and sunny 1st floor with a large living room. Spacious kitchen. Extra room for office space or den. 3 full sized bedrooms. Beautiful full bath. New septic. Move right in and start the new year in your new home. Seller willing to buydown the mortgage rate of this home. PLEASE SET UP APPTS THRU SHOWINGTIME.

    Tyler Scaglione Cameron Real Estate Group

    16 Maple Place, Winchendon, MA 01475
  • /32

    $289,900 Open Sat 1PM - 3PM

    • 2 Beds
    • 1.5 Baths
    • 919 Sq Ft

    31 Webster St, Winchendon, MA 01475

    Welcome home to this beautifully remodeled single-family gem in the heart of Winchendon, MA. This charming two-bedroom, one-bath home blends modern finishes with comfortable living, making it truly move-in ready. Step inside to discover an updated interior featuring stylish upgrades, fresh finishes, and a thoughtfully designed layout that maximizes both space and natural light.Outside, you’ll

    Scott Bascom eXp Realty

    31 Webster St, Winchendon, MA 01475
  • /30

    $138,000

    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft

    11 Colonial Ln, Winchendon, MA 01475

    Welcome to this well-maintained 2-bedroom, 1.5-bath manufactured home located in the peaceful 55+ community of Glenwood Park. Designed for comfortable single-level living, this home offers a spacious living room with high ceilings and abundant natural light, creating an open and airy feel. The eat-in kitchen features an adjacent mud room with access to a generous deck overlooking a tranquil,

    Carole Norton Real Estate Exchange

    11 Colonial Ln, Winchendon, MA 01475
  • /42

    $489,900

    • 4 Beds
    • 2 Baths
    • 1,923 Sq Ft

    46 Juniper St, Winchendon, MA 01475

    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

    Kimberly Clark RE/MAX Vision

    46 Juniper St, Winchendon, MA 01475
  • /8

    $475,000

    • 8 Beds
    • 4 Baths
    • 3,891 Sq Ft

    116 Maple St, Winchendon, MA 01475

    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.

    Brenda Albert LAER Realty Partners

    116 Maple St, Winchendon, MA 01475
  • /13

    $390,000

    • 4 Beds
    • 2 Baths
    • 2,242 Sq Ft

    19 Chestnut St, Winchendon, MA 01475

    Currently configured as a multi-unit residence but could be converted to a single-unit dwelling for larger household. Nice condition. Clean. Much updating over the years. Both apartment empty. Upstairs 4-bedroom unit currently available for new owner's Immediate use. Downstairs, 1 bedroom apartment empty and ready for immediate use.. House has bricked facade street faced room that possibly could

    Jonathan Minerick homecoin.com

    19 Chestnut St, Winchendon, MA 01475
  • /37

    $229,000

    • 4 Beds
    • 2 Baths
    • 3,360 Sq Ft

    35 School St, Winchendon, MA 01475

    Unlock the full potential of this expansive farmhouse, offering generously sized rooms, a substantial lot, a huge garage, and plenty of storage — including a workshop above. The property has been cleaned out and de-leaded, but it now requires a comprehensive renovation. Bring your vision to life with this charming home, ideally located in a peaceful and desirable area. Featuring 4–5 bedrooms and

    Eugene Clements Clements Realty Group

    35 School St, Winchendon, MA 01475
  • /27

    $269,000

    • 3 Beds
    • 1 Bath
    • 1,728 Sq Ft

    33 East St, Winchendon, MA 01475

    ATTENTION CONTRACTORS, FLIPPERS! COME BRING YOUR TOOLS AND IMAGINATION TO BRING THIS GEM BACK TO IT`S FULL POTENTIAL! THIS HOME BOASTS OF A NICE LARGE LIVING ROOM WITH HARDWOOD FLOORS, THREE BEDROOMS ON THE MAIN LEVEL WITH HARDWOOD FLOORS. THE THIRD BEDROOM DOES NOT HAVE A CLOSET! THERE IS A PANTRY OFF THE KITCHEN. A NEW BACK DECK THAT LEADS INTO THE KITCHEN. TWO FINISHED ROOMS IN LOWER LEVEL.

    John Keefe Keller Williams Realty-Merrimack

    33 East St, Winchendon, MA 01475
  • /3

    $525,000

    • Land
    • 9 Acres
    • $58,333 per Acre

    Lot 187 Gardner Ma, Winchendon, MA 01475

    Located on the 140Corridor used by 10,965 cars daily, according to MassDOT, with 3-phase power and approximately 315’ to the Route 12 & 140 junction and municipal water access. Are you looking for a site for a retail or convenience store? Maybe a service shop like a barber, tailoring, print shop or dry cleaner? It seems the zoning allows for these as well as a restaurant, movie theater, bowling

    Karissa Moore K&G Realty Services, LLC

    Lot 187 Gardner Ma, Winchendon, MA 01475
  • /42

    $800,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2.5 Baths
    • 2,650 Sq Ft

    1 Roberts Way, Winchendon, MA 01475

    FEBRUARY PRICE DROP—$25K reduction brings this stunning 2025 Westminster new construction to $800,000. Why wait for spring and compete with the rush when you can move in NOW? 2,650 square feet: a showstopper kitchen with 8' island, pantry closet, quartz counters, subway tile backsplash, Bosch appliances & induction range. Cathedral-ceiling family room with a fireplace flows into open-plan living,

    Jennifer Shenk Keller Williams Realty North Central

    1 Roberts Way, Winchendon, MA 01475

Why Live in Winchendon

Winchendon, Massachusetts, a small community with a rich industrial history, is known for its historic homes and the enduring legacy of its toy manufacturing past, earning it the nickname "Toy Town." The town's historical charm is preserved through attractions like the Winchendon Historical Society, which offers ghost tours and themed escape rooms, and the Murdock-Whitney House and Isaac Morse House, the latter of which doubles as a toy museum and retro ice cream shop. Community events such as the Taste of Winchendon and the Fall Festival draw residents together with food trucks, live music, and family-friendly activities. Housing in Winchendon ranges from historic homes dating back to the 1750s to more contemporary developments from the 1980s, with a mix of single-family homes and multifamily developments. Central Street is the hub of local commerce, featuring a variety of dining options, including Christos Place and Two Foxes Farm Pizza, as well as a locally-owned hardware store that supports community outreach. Winchendon Community Park and other green spaces provide residents with ample opportunities for outdoor recreation, including fishing at Whitney Pond and exploring the North Central Pathway. While the local schools have average ratings, the community spirit and historical allure make Winchendon a unique place to call home. Located along U.S. Route 202, Winchendon offers commuting options to nearby towns like Gardner and Leominster, with Worcester 45 miles to the south.

Frequently Asked Questions

What is the average home price in Winchendon, MA?
Homes for sale in Winchendon, MA have an average home price of $427,069.
How many homes have sold over the last 12 months in Winchendon, MA?
113 homes have sold in Winchendon, MA over the last 12 months.
What are the most popular zip codes in Winchendon, MA?
The most popular zip codes in Winchendon, MA include 01475, 01430, 01436, 01468 and 01440.
How much do you need to make to afford a house in Winchendon?
The median home price in Winchendon is $400,000. If you put a 20% down payment of $80,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $1,980 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $85K a year to afford the median home price in Winchendon. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Winchendon, MA?
Winchendon, MA has highly rated public and private schools. Some of the best schools in Winchendon based on Niche Grades are The Winchendon School, Memorial and Oakmont Regional High School. Browse all the schools in Winchendon, MA to learn more.

Home Trends in Winchendon, MA

Housing Trends

Median Sale Price
$410,000
Median Single Family Sale Price
$410,000
Median Townhouse Sale Price
$380,000
Median 2 Bedroom Sale Price
$220,000
Average Price Per Sq Ft
$250
Number of Homes for Sale
13
Last 12 months Home Sales
113
Months of Supply
1.40
Median List Price
$400,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
5%
How to Buy a Home How to Finance a Home How to Sell a Home