39 Winter St, Winchendon, MA 01475
Property image
Property image
OFF MARKET

39 Winter St
Winchendon, MA 01475

  • 4 Beds
  • 1.5 Baths
  • 1,714 sqft (on 0.26 acres)

$385,000

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $2,425/mo*
Refinance Your Home

$385,000

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $2,425/mo*
Refinance Your Home
4 Beds
1.5 Baths
1,714 sqft
(on 0.26 acres)

Home Value

Trulia Estimate
$385K
Since last month
Decreased$5K (-1.2%)
Since last year
Increased$14K (+3.7%)
Since last sale
Increased$219K (+131.9%)
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 +128% in the last 10 years
MonthEstimated value
2026
August 2026$385K
July 2026$389K
June 2026$390K
May 2026$391K
April 2026$390K
March 2026$380K
February 2026$376K
January 2026$363K
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
29 Winter St, Winchendon, MA
0.02
Single-Family Home
$373,000
03/13/26
3
1.5
2,128
70 Juniper St, Winchendon, MA
0.23
Single-Family Home
$201,140
06/12/26
3
1
1,525
108 Highland St, Winchendon, MA
0.11
Single-Family Home
$440,000
01/21/26
4
2
2,067
33 East St, Winchendon, MA
0.10
Single-Family Home
$281,000
07/08/26
3
1
1,728
50 East St, Winchendon, MA
0.09
Single-Family Home
$375,000
07/10/26
3
1.5
1,445
71 Winter St, Winchendon, MA
0.08
Single-Family Home
$360,000
06/01/26
4
1
1,470
52 Belmont Ave, Winchendon, MA
0.04
Single-Family Home
$400,000
11/25/25
4
2.5
2,306
80 North St, Winchendon, MA
0.18
Single-Family Home
$80,000
08/21/25
3
1
956
22 Woodlawn St, Winchendon, MA
0.35
Single-Family Home
$371,000
09/17/25
3
2
1,888
13 Woodlawn St, Winchendon, MA
0.38
Single-Family Home
$360,000
11/12/25
3
2
1,567

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
29 Winter St, Winchendon, MA 01475
0.02
$373,000
3
1.5
2,128
Recently Sold
17 Winter St, Winchendon, MA 01475
0.04
$383,500
3
1
1,701
Off Market
52 Belmont Ave, Winchendon, MA 01475
0.04
$400,000
4
2.5
2,306
Recently Sold
12-14 Belmont Ave, Winchendon, MA 01475
0.08
-
4
2
2,392
Off Market
3 Winter St, Winchendon, MA 01475
0.08
$430,300
3
2
1,724
Off Market
50 East St, Winchendon, MA 01475
0.09
$375,000
3
1.5
1,445
Recently Sold
71 Winter St, Winchendon, MA 01475
0.08
$360,000
4
1
1,470
Recently Sold
33 East St, Winchendon, MA 01475
0.10
$281,000
3
1
1,728
Recently Sold
19-21 East St, Winchendon, MA 01475
0.11
-
6
2
2,440
Off Market
108 Highland St, Winchendon, MA 01475
0.11
$440,000
4
2
2,067
Recently Sold
20 Harvard St, Winchendon, MA 01475
0.11
-
4
1
1,203
Off Market
46 North St, Winchendon, MA 01475
0.14
$336,700
4
1.5
1,914
Off Market

Local Information

  • Map ViewExplore the area around 39 Winter St.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1900
Lot Size
0.26 acres
Living Area
1,714 sqft
Price/Sqft
$225

About this House

The place you've been waiting for to call home-sweet-home and just in time for the upcoming holiday season!! This 4- BR home boasts some of the most incredible hardwood and pine flooring and natural woodwork! HUGE walk-in pantry off kitchen! Laundry room off the kitchen that leads to the multi-level BARN!! Baths on both 1st and 2nd levels! A lovely bay area in LR to enjoy reading your favorite book! Pellet stove connection in den or BR #5. Skylights in master bedroom with TONS of storage space! Home exterior, including front porch detail, freshly painted yellow with white/green accents! Barn, of course, is barn red!!! Owners have paid the sewer betterment for you, too!! Home ownership doesn't get much better than this folks!! Owners have enjoyed this home for many years...and now it's your turn!! And did I say you could be home for the holidays?
39 Winter St, Winchendon, MA 01475 is a 4 bedroom, 2 bathroom, 1,714 sqft single-family home built in 1900. It last sold for $166,000 on Dec 17, 2015. It is currently off market. The Trulia Estimate is $385,000, with a rent estimate of $2,919/month.

Home Details for 39 Winter St

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Dec 17, 2015
Source: N/A
Sold
$166,000
Nov 14, 2015
Source: Agent Provided
Pending
$172,500
Oct 10, 2015
Source: Agent Provided
PriceChange
$172,500
Price decreased by 6%
Sep 29, 2015
Source: Agent Provided
Listed For Sale
$183,900
Mar 27, 1997
Source: N/A
Sold
$94,000

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
Skip to last item
  • Results are loading
Skip to first item

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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Air Conditioning

Homes for sale near 39 Winter St

Skip to last item
Skip to first item

Off Market Homes Near 39 Winter St

Skip to last item
Skip to first item

Frequently asked questions about 39 Winter St

  • What is 39 Winter St estimated to be worth?
    Trulia's estimated value for 39 Winter St in Winchendon, MA is $385,000.
  • What is the price history for 39 Winter St?
    39 Winter St in Winchendon, MA last sold for $166,000 in December 2015.
  • 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.
  • How big is the lot at 39 Winter St?
    The lot at 39 Winter St in Winchendon, MA is about 0.26 acres (11,325 sq ft).