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

$382,900

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

39 Winter St, Winchendon, MA 01475

Est. Refi. Payment $2,616/mo*
Refinance Your Home
Currently Off Market - Sold Dec 17, 2015 for $166,000

Home Value

Trulia Estimate
$383K
Since last month
Decreased$2K (-0.5%)
Since last year
Increased$23K (+6.4%)
Since last sale
Increased$216K (+130.2%)
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 +120% in the last 10 years
MonthEstimated value
2026
October 2026$382K
September 2026$383K
August 2026$384K
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
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
70 Juniper St, Winchendon, MA
0.22
Single-Family Home
$350,000
09/30/26
4
1
1,603
506 Central St, Winchendon, MA
0.14
Single-Family Home
$369,000
09/17/26
5
1.5
2,072
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
15 Juniper St, Winchendon, MA
0.32
Single-Family Home
$375,000
08/18/26
4
2
2,111
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
14 Winter Pl, Winchendon, MA 01475
0.03
$331,500
2
1
1,461
Off Market
51 Winter St, Winchendon, MA 01475
0.03
$401,700
5
2
1,874
Off Market
38 Winter St, Winchendon, MA 01475
0.03
$336,400
3
1
1,182
Off Market
46 Belmont Ave, Winchendon, MA 01475
0.04
$297,900
4
2
1,152
Off Market
10 Winter Pl, Winchendon, MA 01475
0.04
$356,700
3
1
1,472
Off Market
17 Winter St, Winchendon, MA 01475
0.04
$378,000
3
1
1,701
Off Market
54 Belmont Ave, Winchendon, MA 01475
0.04
$382,600
3
2
1,500
Off Market
52 Belmont Ave, Winchendon, MA 01475
0.04
$403,900
4
2.5
2,306
Off Market
52 Winter St, Winchendon, MA 01475
0.05
$332,100
4
2
1,680
Off Market
36 Belmont Ave, Winchendon, MA 01475
0.05
$424,100
3
2
2,520
Off Market
463-465 Central St, Winchendon, MA 01475
0.05
$372,800
6
2
2,762
Off Market
453 Central St, Winchendon, MA 01475
0.05
$396,800
3
2
2,245
Off Market
16 Winter Pl, Winchendon, MA 01475
0.05
$409,900
3
2
1,320
For Sale
62 Belmont Ave, Winchendon, MA 01475
0.05
$331,100
3
1
1,525
Off Market
459 Central St, Winchendon, MA 01475
0.05
$368,800
4
1.5
1,522
Off Market
445 Central St, Winchendon, MA 01475
0.06
$473,000
2
2
3,232
Off Market
51 Belmont St, Winchendon, MA 01475
0.06
-
-
-
-
Off Market
16-016 Winter Pl, Winchendon, MA 01475
0.06
-
-
-
-
Off Market
26 Belmont Ave, Winchendon, MA 01475
0.06
$452,300
4
3
3,723
Off Market

Local Information

  • Map ViewExplore the area around 39 Winter St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1900
0.26 acre lot
1,714 sqft
$223/sqft

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $382,900, with a rent estimate of $2,893/month.

Home Details for 39 Winter St

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: OilHeating Fuel: Oil
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 August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
1MoM

Around this home

What Locals Say about Winchendon

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 74% say there's holiday spirit
  • 59% say there are sidewalks
  • 55% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
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

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 $382,900.
  • 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).

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