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Winchendon, MA Homes for Sale

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  • /16

    $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
  • /42

    $389,500

    • 4 Beds
    • 2 Baths
    • 1,948 Sq Ft

    38 West St, Winchendon, MA 01475

    Fully Renovated 2-Family – Turnkey Investment Opportunity Beautifully updated and move-in ready, this side-by-side 2-family property has been thoughtfully renovated, offering a rare opportunity for both investors and owner-occupants. Each unit spans two floors and features modern finishes throughout. A separate heating system (installed in 2024) and brand-new oil tanks. Unit 1 offers an updated

    Piyarat Intachim-Kaufman Excelsior Realty

    38 West St, Winchendon, MA 01475
  • /35

    $579,900 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft

    40 Doyle Ave, Winchendon, MA 01475

    Welcome home to this beautifully maintained 3-year-old home that offers the perfect blend of modern comfort and peaceful country living! Situated on nearly 2.5 acres, this spacious 3 bed, 2.5 bath property delivers style and functionality. Come inside to discover a bright open concept kitchen, with maple cabinetry, granite countertops, SS appliances, LVP flooring flowing seamlessly into the

    The Knox Real Estate Team William Raveis R.E. & Home Services

    40 Doyle Ave, Winchendon, MA 01475
  • /15

    $484,900

    • 3 Beds
    • 1.5 Baths
    • 1,724 Sq Ft

    17 Town Farm Rd, Winchendon, MA 01475

    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

    Kathryn Buttrick Coldwell Banker Realty - Concord

    17 Town Farm Rd, Winchendon, MA 01475
  • /18

    $595,500

    • 3 Beds
    • 2.5 Baths
    • 2,050 Sq Ft

    42 Doyle Ave, Winchendon, MA 01475

    Welcome to this nearly new Colonial in desirable Doyle Estates! Set on 3.14 private acres, this 3-bedroom, 2.5-bath home offers over 2,000 sq ft of living space, including a finished basement. The open-concept kitchen and dining area feature stainless steel appliances, granite countertops, a center island, and maple cabinetry. The spacious living room includes a cozy gas fireplace, plus

    Musa Muzaaya The American Dream Real Estate

    42 Doyle Ave, Winchendon, MA 01475
  • /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
  • /12

    $389,900

    • 3 Beds
    • 1 Bath
    • 1,586 Sq Ft

    53 Town Farm Rd, Winchendon, MA 01475

    Welcome to this beautifully refreshed 3-bedroom, 1-bath split-level home, ideally situated on a level, wooded lot that offers both privacy and a natural backdrop. From the moment you step inside, you’ll be greeted by a bright, inviting interior, where freshly painted rooms throughout the main level create a crisp, modern canvas ready for your personal style. Designed for both comfort and

    Lisa Sheridan Coldwell Banker Realty

    53 Town Farm Rd, Winchendon, MA 01475
  • /41

    $349,900

    • 4 Beds
    • 1.5 Baths
    • 2,778 Sq Ft

    49 Juniper St, Winchendon, MA 01475

    OPEN HOUSE SUNDAY MAY 3RD 12PM-2PM. Classic Victorian on a quarter-acre lot in the heart of Winchendon — 4 bedrooms, 1.5 baths, and 2,788 square feet of genuine period character. Refinished hardwood floors throughout, original stained glass, pocket doors, fireplace, two staircases, walk-in pantry, and bay window sitting room. Updated kitchen with stainless appliances, first-floor laundry, and a

    Michael Tetreault The Tate Team

    49 Juniper St, Winchendon, MA 01475
  • /42

    $1,400,000

    • 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
  • /31

    $378,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 1,348 Sq Ft

    394 Front St, Winchendon, MA 01475

    Hard-to-find Village Colonial now ready for its next owner! This spacious 4-bedroom, 2 full bath home offers incredible value & charm throughout. Enjoy peace of mind with a newer metal roof (2018), replacement windows, vinyl siding, and brand new furnace installed in October 2025. The large Kitchen offers stainless steel appliances, updated cabinetry, and plenty of room to add a center

    Lisa Pete Acres Away Realty, Inc.

    394 Front St, Winchendon, MA 01475
  • /32

    $281,900

    • 2 Beds
    • 1 Bath
    • 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
  • /17

    $659,000

    • 10 Beds
    • 4 Baths
    • 3,818 Sq Ft

    10-12 School Square, Winchendon, MA 01475

    this large 4unit house located at center of the town, always fully rented, total monthly income; $6590, each tenant pay their own utilities. each unit has good size room. . the house will deliver with all the tenants because seller don't want to lose the rental income. only do showing on weekend. 4 years new roof. rare to find, great property created good cash flow, it won't last long.

    Jason Saphire www.HomeZu.com

    10-12 School Square, Winchendon, MA 01475
  • /6

    $120,000

    • Land
    • 11.78 Acres
    • $10,187 per Acre

    0 Mellen Rd, Winchendon, MA 01475

    If you’ve been searching for the perfect place to build but haven’t found the right fit, this property may be exactly what you’ve been waiting for. Opportunity to own over 11+ acres in a peaceful Winchendon setting, directly across from 174 acres of protected state forest land—offering immediate access to trails, wildlife, and year-round outdoor recreation right outside your door, while still

    Kristen Dodge LAER Realty Partners

    0 Mellen Rd, Winchendon, MA 01475
  • /30

    $400,000

    • 4 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    22 Prospect St, Winchendon, MA 01475

    This unique property is right for investers or for owner occupancy with rental income from the other unit. Property has several living options: 1) as a two family (as currently being used) or 2) potentially converted to a single family, whichever best suits your needs. Several updates include metal roofing, replacement windows, Peerless boilers with super store hot water. There is updated wiring

    Karl Seppa Media Realty Group Elite

    22 Prospect St, Winchendon, MA 01475
  • /7

    $70,000

    • Land
    • 1.11 Acres
    • $63,063 per Acre

    24 Old County Rd, Winchendon, MA 01475

    Location, location, location! Looking for that perfect location to build? This lot is just down the road from historic Old Centre and has easy access to Rt 140 and Downtown Winchendon, but the peace and quiet will make you think you are miles away! Land is surrounded by stone walls, driveway has been cut in, and well installed. Level land, sloping slightly upward in the back.

    Terry Lupien Morin Real Estate

    24 Old County Rd, Winchendon, MA 01475
  • /25

    $155,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    30 Carriage Ln, Winchendon, MA 01475

    Discover the ease of single-level living at 30 Carriage Lane. Built in 1986, this 1008 square foot mobile home offers a thoughtful layout designed for comfort and practicality. This residence features two well-proportioned bedrooms, one on each end of the home, providing comfortable personal retreats. The property also includes two bathrooms, ensuring convenience and privacy for residents and

    Terry Lupien Morin Real Estate

    30 Carriage Ln, Winchendon, MA 01475
  • /33

    $255,000

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

    33 East St, Winchendon, MA 01475

    WELCOME TO 33 EAST ST WINCHENDON. 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. JUST A SHORT DISTANCE TO TOWN, AND SCHOOLS. CLOSE TO THE NH LINE. SCHEDULE YOUR

    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

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 $428,444.
How many homes have sold over the last 12 months in Winchendon, MA?
112 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, 01436, 01468, 01368 and 01430.
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 6.37%, your estimated principal and interest payment would be $2,000 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $86K 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 Conant 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
$400,000
Median 2 Bedroom Sale Price
$225,000
Average Price Per Sq Ft
$252
Number of Homes for Sale
11
Last 12 months Home Sales
112
Months of Supply
1.20
Median List Price
$400,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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