4,661

Winchendon, MA Homes

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  • /25

    $390,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 2,151 Sq Ft

    32 Ash St, Winchendon, MA 01475

    Presenting a distinguished single-family residence constructed in 1854, offering 2151 square feet of refined living space. This property stands as a testament to enduring architectural integrity, meticulously preserved to offer a unique blend of historical charm and contemporary functionality. The residence encompasses three well-proportioned bedrooms, providing comfortable private

    Agent Photo

    Hometown Team

    Real Broker MA, LLC

    32 Ash St, Winchendon, MA 01475
  • /7

    $1,395

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    250 Spring Cir Unit 1, Winchendon, MA 01475

    The apartment is a few blocks away from the downtown area, which offers retail stores, CVS, Walgreens and much more, including the Town Hall, post office and police station.Tenant pays electric for heat/hot water/cooking and lights.One cat allowed and no dogs please.Parking off street for 2 carsCoin-op laundry in the buildingNO BROKER FEE OR APPLICATION FEEMANDATORY

    250 Spring Cir Unit 1, Winchendon, MA 01475
  • /37

    $580,000

    Sold Dec 22, 2025

    71 Woodlawn St, Winchendon, MA 01475

    • 3 Beds
    • 2 Baths
    • 1,628 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $356/SF
    • 20 Days On Market

    Current Estimated Value $473,655

    Last Listing Agent Paul Michaud Freedom Real Estate

    71 Woodlawn St, Winchendon, MA 01475
    • /42

      Est $490,020

      Not Listed For Sale

      23 Lincoln Ave, Winchendon, MA 01475

      • 3 Beds
      • 1.5 Baths
      • 2,494 Sq Ft
      • Built 1926
      23 Lincoln Ave, Winchendon, MA 01475

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Michelle Peterson Elm Grove Realty, LLC

  • /42

    $485,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,045 Sq Ft

    180 Spring St, Winchendon, MA 01475

    Completely refinished in 2023, this beautiful 4-bedroom, 2.5-bath home combines modern updates with a functional layout in a fantastic location. Just minutes from downtown shopping, restaurants, schools, and commuter routes, you'll enjoy the convenience of being close to everything while still having a backyard that feels surprisingly private. Step inside to an open-concept first floor where the

    Agent Photo

    Michelle Peterson

    Elm Grove Realty, LLC

    180 Spring St, Winchendon, MA 01475
  • /9

    $1,900 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    124-126 Lincoln Ave Unit 2, Winchendon, MA 01475

    Discover the potential for elevated living at 126 Lincoln Ave U:2, Winchendon, MA. This residential property, offering 1100 square feet of meticulously maintained living space, presents an inviting home environment, ready for immediate occupancy. This residence encompasses three well-proportioned bedrooms, providing ample private accommodations. The property includes one full bathroom, designed

    James Dickey Community Real Estate Property Management

    124-126 Lincoln Ave Unit 2, Winchendon, MA 01475
  • /42

    $555,000

    Sold May 08, 2026

    34 Prospect St, Winchendon, MA 01475

    • 5 Beds
    • 3 Baths
    • 2,498 Sq Ft
    • Built 1801

    Last Sold Summary

    • 1% Above List Price
    • $222/SF
    • 16 Days On Market

    Current Estimated Value $548,085

    Last Listing Agent Michelle Peterson Elm Grove Realty, LLC

    34 Prospect St, Winchendon, MA 01475
    • /38

      Est $366,349

      Not Listed For Sale

      46 Woodlawn Ave, Winchendon, MA 01475

      • 3 Beds
      • 1.5 Baths
      • 1,536 Sq Ft
      • Built 2005
      46 Woodlawn Ave, Winchendon, MA 01475

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Lana Kopsala Coldwell Banker Realty - Leominster

  • /28

    $250,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    26 Royalston Rd N, Winchendon, MA 01475

    Opportunity awaits with this 3-bedroom, 1.5-bath Cape situated on a sunny and spacious 0.69-acre lot. The first floor offers an eat-in kitchen, a front-to-back living room, a full bath, and a convenient first-floor primary bedroom. Upstairs, you'll find two additional bedrooms and a half bath, providing a functional layout. With some vision and updates, this property has the potential to become a

    Agent Photo

    Michelle Peterson

    Elm Grove Realty, LLC

    26 Royalston Rd N, Winchendon, MA 01475
  • /2

    $1,115

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    184 Lincoln Ave Unit 1R, Winchendon, MA 01475

    Looking for a 2-bedroom apartment for rent in Winchendon, MA with pet-friendly living and fewer monthly hassles?184 Lincoln Ave – Unit 1R offers 2 bedrooms and 1 bathroom, giving you the extra space you need for your household, home office, roommate, or other everyday needs.Enjoy the convenience of water, trash removal, and snow removal included, helping simplify your monthly

    184 Lincoln Ave Unit 1R, Winchendon, MA 01475
  • /42

    $870,000

    Sold Jan 15, 2026

    16 2nd St, Winchendon, MA 01475

    • 3 Beds
    • 2.5 Baths
    • 2,540 Sq Ft
    • Built 1959

    Last Sold Summary

    • 7% Below List Price
    • $343/SF
    • 28 Days On Market

    Current Estimated Value $860,913

    Last Listing Agent Robert Matewsky Keller Williams Realty North Central

    16 2nd St, Winchendon, MA 01475
    • /41

      Est $433,972

      Not Listed For Sale

      145 Bayberry Cir, Winchendon, MA 01475

      • 3 Beds
      • 2.5 Baths
      • 1,396 Sq Ft
      • Built 2014
      145 Bayberry Cir, Winchendon, MA 01475

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Kendra Dickinson Keller Williams Realty North Central

  • /4

    $330,000

    Pending
    • Land
    • 82.84 Acres
    • $3,984 per Acre

    0 Benjamin St, Winchendon, MA 01475

    This beautiful 82+ acres of heaven is awaiting its new owner to build their dream home. With its untouched forest and stone walls this property is nestled on the back roads of a quaint country town. Wake up every morning to the sounds of wildlife abound. Great outdoor attractions like Lake Dennison recreation area and The Winchendon Community Park are minutes down the road offering beautiful

    Agent Photo

    Michelle Peterson

    Elm Grove Realty, LLC

    0 Benjamin St, Winchendon, MA 01475
  • /36

    $4,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • House for Rent

    375 Hitchcock Rd, Winchendon, MA 01475

    Presenting like new (2024) Colonial home for rent in Winchendon's newest community of custom built homes!! Nearly 1900 square feet of perfect living space with an unparalleled country setting.. The home a flowing floorplan on the first floor and three ample sized bedrooms with ample closets, including a master bedroom suite with its own bathroom. Adding to the living space is an oversized deck

    Tim Damon Mercury Real Estate

    375 Hitchcock Rd, Winchendon, MA 01475
  • /25

    $394,000

    Sold Dec 17, 2025

    103 Maple St, Winchendon, MA 01475

    • 5 Beds
    • 2.5 Baths
    • 2,776 Sq Ft
    • Built 1885

    Last Sold Summary

    • 5% Below List Price
    • $142/SF
    • 43 Days On Market

    Current Estimated Value $405,137

    Last Listing Agent Wendy Poudrette Foster-Healey Real Estate

    103 Maple St, Winchendon, MA 01475
    • /4

      Not Listed For Sale

      678 Spring St, Winchendon, MA 01475

      • 2 Beds
      • Built 1988
      678 Spring St, Winchendon, MA 01475

      Last Sold Summary

      • 168 Days On Market

      Last Listing Agent Matthew Straight Coldwell Banker Realty - Leominster

  • /32

    $325,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,464 Sq Ft

    10 Jackson Ave, Winchendon, MA 01475

    Tucked into the heart of Winchendon, this inviting 2-bathroom, possible 4-bedroom home offers 1,465 square feet of warm, character-filled living space. Your first impression starts before you even step inside—the classic farmer's porch is the kind of spot made for enjoying morning and evening porch-sitting. Cross the threshold, and you're greeted by beautiful hardwood floors that make the home

    Kenton Jacobs Real Estate Exchange

    10 Jackson Ave, Winchendon, MA 01475
  • /22

    $1,450 Per Month

    • 2 Beds
    • 1 Bath
    • 650 Sq Ft
    • Apartment for Rent

    20-24 Walnut St Unit 3, Winchendon, MA 01475

    Renovated 2-Bedroom Apartment on Third Floor of Grand Victorian Colonial Multi-Family Home with tons of Charm. Nice Layout with 2- Good Sized Bedrooms at opposite ends of the Apartment. Walk through Galley Kitchen with Newer Appliances & Breakfast Nook, Living Room has Dining Alcove also. Gorgeous Refinished Hardwood Floors & Fresh Paint Throughout. 1 parking space in shared driveway during

    Mark Cirignano OmegaListings.com, Inc.

    20-24 Walnut St Unit 3, Winchendon, MA 01475
  • /42

    $644,000

    Sold Jan 20, 2026

    17 W Shore Dr, Ashburnham, MA 01430

    • 3 Beds
    • 3 Baths
    • 1,794 Sq Ft
    • Built 1983

    Last Sold Summary

    • 2% Below List Price
    • $359/SF
    • 61 Days On Market

    Current Estimated Value $34,680

    Last Listing Agent Nancy Day Berkshire Hathaway HomeServices Stephan Real Estate

    17 W Shore Dr, Ashburnham, MA 01430
    • /23

      Not Listed For Sale

      9 Crescent Rd, Winchendon, MA 01475

      • 2 Beds
      • 1 Bath
      • 1,103 Sq Ft
      • Built 1985
      9 Crescent Rd, Winchendon, MA 01475

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Terry Lupien Morin Real Estate

  • /35

    $539,000

    $46K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,924 Sq Ft

    6 Loon Rd, Winchendon, MA 01475

    BUYER OPPORTUNITY! Seller is offering up to $5,000 toward buyer closing costs! Move-in ready Colonial - privately set on 1.28 acres in one of Winchendon's desirable neighborhoods. Located on a cul-de-sac with just 3 homes, this property offers privacy, mature landscaping, perennial gardens and great curb appeal. A welcoming wraparound farmer's porch leads into a sun-filled interior with hardwood

    Cory Gracie LAER Realty Partners

    6 Loon Rd, Winchendon, MA 01475
  • /10

    $1,900 Per Month

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    322 Central St Unit 2, Winchendon, MA 01475

    Presenting 322 Central Street U:2 in Winchendon, MA, United States, this residential property offers a distinguished leasing opportunity within a locale of notable character. This residence, originally constructed in 1900, provides a unique canvas for refined living. The interior encompasses three thoughtfully designed bedrooms, each presenting an opportunity for personal comfort and repose

    Scott Bascom eXp Realty LLC

    322 Central St Unit 2, Winchendon, MA 01475
  • /34

    $400,000

    Sold Nov 25, 2025

    52 Belmont Ave, Winchendon, MA 01475

    • 4 Beds
    • 2.5 Baths
    • 2,306 Sq Ft
    • Built 1900

    Last Sold Summary

    • $173/SF
    • 5 Days On Market

    Current Estimated Value $418,617

    Last Listing Agent Laura Rice EXIT New Options Real Estate

    52 Belmont Ave, Winchendon, MA 01475
    • /30

      Not Listed For Sale

      5 Congress Rd, Winchendon, MA 01475

      • 2 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1985
      5 Congress Rd, Winchendon, MA 01475

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Michelle Peterson Elm Grove Realty, LLC

  • /20

    $429,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    33 W Shore Dr, Winchendon, MA 01475

    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

    Roman Deych Roman Deych

    33 W Shore Dr, Winchendon, MA 01475
  • /16

    $1,550 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Apartment for Rent

    17 Oak St Unit 1, Winchendon, MA 01475

    Spacious 1-bedroom, 1-bath apartment available for rent. This well-maintained unit offers comfortable living with parking for up to two vehicles.

    Kennia Mejia Realty ONE Group Nest

    17 Oak St Unit 1, Winchendon, MA 01475
  • /41

    $350,000

    Sold Nov 14, 2025

    34-36 Glenallen St, Winchendon, MA 01475

    • 6 Beds
    • 2 Baths
    • 2,204 Sq Ft
    • Built 1900

    Last Sold Summary

    • 22% Below List Price
    • $159/SF
    • 103 Days On Market

    Last Listing Agent Eric Machuca Results Realty

    34-36 Glenallen St, Winchendon, MA 01475
    • /20

      Not Listed For Sale

      1 Colonial Ln, Winchendon, MA 01475

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 2002
      1 Colonial Ln, Winchendon, MA 01475

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Michelle Peterson Elm Grove Realty, LLC

  • /40

    $399,999

    $18K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 2,289 Sq Ft

    263 Front St Unit 267, Winchendon, MA 01475

    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

    Leanne Roy Keller Williams Realty North Central

    263 Front St Unit 267, Winchendon, MA 01475
  • /33

    $388,000

    Sold Jan 27, 2026

    17 Town Farm Rd, Winchendon, MA 01475

    • 3 Beds
    • 1.5 Baths
    • 1,724 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Below List Price
    • $225/SF
    • 4 Days On Market

    Current Estimated Value $476,980

    Last Listing Agent Michael Allen Lamacchia Realty, Inc.

    17 Town Farm Rd, Winchendon, MA 01475
    • /42

      Not Listed For Sale

      14 School Square, Winchendon, MA 01475

      • 8 Beds
      • 3.5 Baths
      • 3,437 Sq Ft
      • Built 1900
      14 School Square, Winchendon, MA 01475

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Michelle Peterson Elm Grove Realty, LLC

  • /23

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,110 Sq Ft

    262 West St, Winchendon, MA 01475

    OFFER DEADLINE OF WEDNESDAY, SEPTEMBER 2ND AT 6:00 P.M. Charming single level residence in tranquil setting! This inviting property, built in 1950, consists of three bedrooms, one full bath, family room, living room and eat-in kitchen set on 1.03 acres of land. An enclosed porch provides a relaxing setting with which to enjoy the private backyard. A paved driveway leads to the single car garage,

    Terry Lupien Morin Real Estate

    262 West St, Winchendon, MA 01475
  • /33

    $400,000

    Sold Apr 30, 2026

    250 Teel Rd, Winchendon, MA 01475

    • 3 Beds
    • 1 Bath
    • 1,375 Sq Ft
    • Built 1999

    Last Sold Summary

    • 8% Above List Price
    • $291/SF
    • 6 Days On Market

    Current Estimated Value $407,881

    Last Listing Agent Laura Rice EXIT New Options Real Estate

    250 Teel Rd, Winchendon, MA 01475
    • /9

      Not Listed For Sale

      0 Mill Glen Rd, Winchendon, MA 01475

      0 Mill Glen Rd, Winchendon, MA 01475

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Lisa Durant Coldwell Banker Realty - Leominster

  • /31

    $390,000

    Pending
    • 4 Beds
    • 1 Bath
    • 1,802 Sq Ft

    114 Glenallen St, Winchendon, MA 01475

    OPEN HOUSE Saturday 8/15 NOON to 2pm!! 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

    Edwin Ahearn Lamacchia Realty, Inc.

    114 Glenallen St, Winchendon, MA 01475
  • /29

    $395,000

    Sold Jun 24, 2026

    53 Town Farm Rd, Winchendon, MA 01475

    • 3 Beds
    • 1 Bath
    • 1,586 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Above List Price
    • $249/SF
    • 4 Days On Market

    Current Estimated Value $393,213

    Last Listing Agent Lisa Sheridan Coldwell Banker Realty

    53 Town Farm Rd, Winchendon, MA 01475
    • /6

      Not Listed For Sale

      0 Beachview Dr, Winchendon, MA 01475

      0 Beachview Dr, Winchendon, MA 01475

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Kenny Leva Gibson Sotheby's International Realty

  • /15

    $309,900

    $90K PRICE DROP
    • 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. One-year American Home Shield Warranty included. PLEASE SET UP APPTS

    Tyler Scaglione Cameron Real Estate Group

    16 Maple Place, Winchendon, MA 01475
  • /15

    $315,000

    Sold Apr 09, 2026

    93 High St, Winchendon, MA 01475

    • 4 Beds
    • 1.5 Baths
    • 1,868 Sq Ft
    • Built 1850

    Last Sold Summary

    • 6% Below List Price
    • $169/SF
    • 6 Days On Market

    Current Estimated Value $323,412

    Last Listing Agent Bonnie Stone Stone Farm Real Estate, LLC

    93 High St, Winchendon, MA 01475
    • /15

      Est $449,609

      Not Listed For Sale

      7 Linden St, Winchendon, MA 01475

      • 3 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2017
      7 Linden St, Winchendon, MA 01475

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Suraj Tamrakar Keynova Group LLC

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$412,500
Median Single Family Sale Price
$410,000
Median Townhouse Sale Price
$380,000
Median 2 Bedroom Sale Price
$323,000
Median 1 Bedroom Sale Price
$117,500
Average Price Per Sq Ft
$254
Number of Homes for Sale
11
Last 12 months Home Sales
108
Months of Supply
1.20
Median List Price
$415,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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