21 Jackson Ave, Winchendon, MA 01475
Property image
Property image
OFF MARKET

21 Jackson Ave
Winchendon, MA 01475

  • 5 Beds
  • 2 Baths
  • 2,020 sqft (on 0.47 acres)

$366,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $2,315/mo*
Refinance Your Home

$366,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $2,315/mo*
Refinance Your Home
5 Beds
2 Baths
2,020 sqft
(on 0.47 acres)

Home Value

Trulia Estimate
$366K
Since last month
Decreased$6K (-1.6%)
Since last year
Increased$24K (+7.1%)
Since last sale
Increased$255K (+231.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +408% in the last 10 years
MonthEstimated value
2026
August 2026$365K
July 2026$369K
June 2026$371K
May 2026$370K
April 2026$372K
March 2026$362K
February 2026$361K
January 2026$354K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
101-103 Linden St, Winchendon, MA
0.17
Multi-Family Home
$425,000
12/09/25
4
2
2,370
46 Juniper St, Winchendon, MA
0.14
Multi-Family Home
$440,000
03/19/26
4
2
1,923
8 Highland St, Winchendon, MA
0.32
Multi-Family Home
$407,500
11/21/25
4
2
1,914
132-134 Lincoln Ave, Winchendon, MA
0.35
Multi-Family Home
$487,000
06/05/26
5
2
2,331
103 Maple St, Winchendon, MA
0.25
Multi-Family Home
$394,000
12/17/25
5
2.5
2,776
90 Linden St, Winchendon, MA
0.16
Multi-Family Home
$475,000
12/03/25
8
3
3,044
174-174 Mill St #176, Winchendon, MA
0.55
Multi-Family Home
$417,000
12/12/25
6
2
2,400
116 Maple St, Winchendon, MA
0.24
Multi-Family Home
$465,000
04/28/26
8
4
3,891
38-40 West St, Winchendon, MA
0.71
Multi-Family Home
$389,500
07/23/26
4
2
1,948
15-17 Oak St, Winchendon, MA
0.50
Multi-Family Home
$549,900
10/01/25
5
4
3,744

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
19 Jackson Ave, Winchendon, MA 01475
0.01
$357,300
4
2
1,922
Off Market
83 Juniper St, Winchendon, MA 01475
0.04
$374,100
3
2
1,589
Off Market
10 Jackson Ave, Winchendon, MA 01475
0.05
$325,000
4
2
1,464
For Sale
66 Juniper St, Winchendon, MA 01475
0.09
$352,500
3
1
1,582
Off Market
62 Juniper St, Winchendon, MA 01475
0.10
$313,500
3
1
1,610
Off Market
19-21 East St, Winchendon, MA 01475
0.10
-
6
2
2,440
Off Market
376 Central St, Winchendon, MA 01475
0.10
$478,100
4
2
1,526
Off Market
3 Winter St, Winchendon, MA 01475
0.12
$430,300
3
2
1,724
Off Market
31 Webster St, Winchendon, MA 01475
0.13
$278,000
2
1
919
Recently Sold
17 Winter St, Winchendon, MA 01475
0.13
$383,500
3
1
1,701
Off Market
46 Juniper St, Winchendon, MA 01475
0.14
$440,000
4
2
1,923
Recently Sold
29 Winter St, Winchendon, MA 01475
0.14
$373,000
3
1.5
2,128
Recently Sold

Local Information

  • Map ViewExplore the area around 21 Jackson Ave.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1910
Lot Size
0.47 acres
Living Area
2,020 sqft
Price/Sqft
$181

About this House

Nice opportunity to build some Sweat Equity with this spacious Two Family on a Lot that is large enough to SUB DIVIDE and is high and dry with town water/sewer should be very easy to build on and is mostly cleared already. Heat and electric is on . Tenant on the 2nd floor and 1st floor is vacant with the walls ready for paint and it could use some new flooring in a couple rooms. Wide pine flooring in the Living room. Needs some exterior work won't pass fha but should be fine for conventional loans . Property " Sold As Is."
21 Jackson Ave, Winchendon, MA 01475 is a 5 bedroom, 2 bathroom, 2,020 sqft multi-family built in 1910. It last sold for $110,000 on Mar 8, 2019. It is currently off market. The Trulia Estimate is $366,000, with a rent estimate of $2,072/month.

Home Details for 21 Jackson Ave

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Shingle

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Multi Family

Community

Units in Building: 2

Lot Information

Lot Area: 0.47 acres

Price and Tax history

DateEventPrice
Mar 8, 2019
Source: N/A
Sold
$110,000
Feb 4, 2019
Source: Agent Provided
Pending
$125,000
Feb 1, 2019
Source: Agent Provided
PendingToActive
$125,000
Jan 23, 2019
Source: Agent Provided
Pending
$125,000
Nov 29, 2018
Source: Agent Provided
PriceChange
$125,000
Price decreased by 4%

Market trends in Winchendon

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
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Around this home

What Locals Say about Winchendon

At least 32 Trulia users voted on each feature.

  • 87 % Say parking is easy

  • 85 % Say it's dog friendly

  • 81 % Say kids play outside

  • 80 % Say car is needed

  • 75 % Say yards are well-kept

  • 74 % Say there's holiday spirit

  • 64 % Say people would walk alone at night

  • 63 % Say it's quiet

  • 59 % Say there are sidewalks

  • 55 % Say neighbors are friendly

  • 50 % Say there's wildlife

  • 50 % Say they plan to stay for at least 5 years

  • 45 % Say streets are well-lit

  • 36 % Say there are community events

  • 34 % Say it's walkable to restaurants

  • 14 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Ingrid Ochoa
    "There are families and parks and the people are very nice! My neighbors are amazing! They never bother or complain about my chickens "
    0
    Flag
  • Christina R.
    "On my street almost every house has a dog. There are many dog owners walking their dogs on my street as well."
    1
    Flag
  • Laurie T.
    "neighbors shoot off fireworks in the summer and plow each others driveways we grow gardens and share our crops"
    0
    Flag
  • Gonzalezem0324
    "there are many families in our neighborhood very quiet and calm feels very safe to walk our dogs very friendly neighbors "
    6
    Flag
  • Jessica K.
    "All the neighbors that live on my block are very nice. if we needed a hand or help they would help with no issues. each neighbor knows me by a 1st name basis. "
    3
    Flag
  • jackblair
    "Quiet area of older homes well maintained. Within walking distance of public schools and town shopping. Fire department two blocks away. Wonderful retirement, assisted living home beautifully maintained nearby. Crime free and sade."
    3
    Flag
  • Jackson
    "I live here. The people are solid and friendly and community minded."
    2
    Flag
  • Michael C.
    "lower taxes, good community, great history to live in."
    3
    Flag

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Apartments for Rent

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Homes for sale near 21 Jackson Ave

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Off Market Homes Near 21 Jackson Ave

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Frequently asked questions about 21 Jackson Ave

  • What is 21 Jackson Ave estimated to be worth?
    Trulia's estimated value for 21 Jackson Ave in Winchendon, MA is $366,000.
  • What is the price history for 21 Jackson Ave?
    21 Jackson Ave in Winchendon, MA last sold for $110,000 in March 2019.
  • Is Winchendon a buyer's or seller's market?
    Winchendon is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Winchendon?
    Residents describe Winchendon, MA as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Winchendon, MA.