SOLD SEP 23, 2026

Sold on sep 2026

$451,900

•

2,763

sq ft

142 Pleasant St, Winchendon, MA 01475

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About this home

Welcome to 142 Pleasant St! This spacious two-family home offers 5 bedrooms, 2.5 baths, and a versatile layout. Recent updates include refinished hardwood floors, new interior paint throughout, restored carpentry, updated light fixtures, and major electrical improvements. The kitchen features new quartz countertops and new appliances, while bathroom updates include new vanities and toilets. The third level includes a bonus room and bedroom, providing even more usable space. A two-level garage adds another unique feature, with a second floor, its own egress, and plenty of possibilities. Unit 2 is located on the second floor including 1 bedroom, living room, updated bathroom and updated kitchen with quartz countertops. Conveniently located near the center of Winchendon, with shops, dining, and local amenities nearby, along with the North Central Pathway, Whitney Pond, and Lake Dennison State Recreation Area. This property has character, thoughtful updates, flexible space, and plenty of potential for its next owner.

Multi-familyProperty Type

1870Year Built

0.25 acresLot Size

$164Price/Sq.Ft.

1 garage spacesParking

Listed by Noelle Medugno • Lamacchia Realty, Inc.

Listed by • Lamacchia Realty, Inc.

Bought with Dorisbel Baez • The Premium Group Real Estate

Redfin checked: a few seconds ago

•Source:MLS PIN #73563079

Redfin Estimate

$425,205

$27K since sold in September 2026$0 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 7.8% higher than the average sale price ($394K) of 6 comparable homes.

SOLD AUG 18, 2026
$375,000
A
4 beds2 baths2,111 sq ft
15 Juniper St, Winchendon, MA 01475
SOLD AUG 20, 2026
$381,900
B
4 beds2.5 baths2,001 sq ft
22 Prospect, Winchendon, MA 01475
SOLD JUL 20, 2026
$360,000
C
4 beds2 baths2,390 sq ft
34 Emerald St, Winchendon, MA 01475
SOLD DEC 17, 2025
$394,000
D
5 beds2.5 baths2,776 sq ft
103 Maple St, Winchendon, MA 01475
SOLD JUN 5, 2026
$487,000
E
5 beds2 baths2,331 sq ft
132-134 Lincoln Ave, Winchendon, MA 01475
SOLD SEP 17, 2026
$369,000
F
5 beds1.5 baths2,072 sq ft
506 Central St, Winchendon, MA 01475

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Market trends in 01475, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.9%

+1.0% MoM

Median sale price

$394K

$170 MoM

Avg. days on market

22d

9 days MoM

Recently sold homes

3 MoM

New listings for sale

$325,000
3 beds2 baths1,602 sq ft
411-413 River St, Winchendon, MA 01475
OPEN SAT, 10AM TO 12PM
$315,000
2 beds1 bath1,302 sq ft
4 Hale St, Winchendon, MA 01475
OPEN SAT, 10AM TO 11:30AM
$519,900
3 beds2.5 baths2,025 sq ft
71 Hapgood St, Winchendon, MA 01475
$379,900
3 beds2 baths2,692 sq ft
45 Joslin Rd, Winchendon, MA 01475
OPEN OCT 18, 1PM TO 3PM
$1,270,000
3 beds2.5 baths2,496 sq ft
55 Island Rd, Winchendon, MA 01475
$475,000
6 beds2.5 baths2,824 sq ft
20 Mechanic St, Winchendon, MA 01475
$1,200,000
5 beds3.5 baths5,456 sq ft
300 High St, Winchendon, MA 01475
$674,900
3 beds2 baths1,798 sq ft
35 Northern Heights Dr, Winchendon, MA 01475
OPEN SAT, 11AM TO 1PM
$385,000
3 beds1.5 baths1,264 sq ft
12 Baldwinville State Rd, Winchendon, MA 01475
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Sale and tax history for 142 Pleasant St

Sale History
Tax History

Date

Event

Price

MLS PIN #73563079

Sep 23, 2026

Sold

$451,900

$164/sq ft

Sep 7, 2026

Pending

—

Aug 24, 2026

Contingent

—

Aug 13, 2026

Listed

$445,000

$161/sq ft

MLS PIN #73297058

Dec 10, 2024

Sold

$319,000

$115/sq ft

Oct 24, 2024

Contingent

—

Oct 1, 2024

Listed

$349,900

$127/sq ft

+37

In the same family for 56 years, 142 Pleasant Street is an opportunity for buyers looking for a large home or a home with an apartment, with great potential for investors. The main house spans 3 floors, with large spacious rooms including kitchen, dining, living room, family room, 1/2 bath and a bedroom on the first floor. The second floor has 2 bedrooms and a full bath, and the third floor has a bedroom and sitting room. The apartment is on the second floor, with flexibility to be either 2 or 3 rooms (at 2 rooms, it would then lend a bedroom to the second floor of the main house). Vinyl windows/siding make for a low maintenance exterior. Seller believes some rooms have hardwoods under carpets. Lots of potential! With a flat yard on a side street location, this home has easy access to in-town amenities like Beals Memorial Library, the Historical Society, Post Office, Wendell P. Clark Memorial YMCA and businesses on Central Street. First showings at the open house: Friday, 10/4 5pm-7pm.

Year

Property tax

Land + Additions

Assessment*

2023

$3,491 (+8.2%)

$30,000 + $230,500

$260,500

2022

$3,226 (−1.3%)

$37,800 + $175,700

$213,500

2021

$3,268 (−2.4%)

$34,400 + $173,500

$207,900

2020

$3,347 (+5.3%)

$32,100 + $173,500

$205,600

2019

$3,178 (+7.3%)

$29,700 + $160,500

$190,200

2018

$2,963 (−2.5%)

$27,700 + $143,100

$170,800

2017

$3,039 (+5.7%)

$32,500 + $136,600

$169,100

2016

$2,874 (+4.2%)

$30,900 + $134,000

$164,900

2015

$2,757 (+6.4%)

$30,900 + $134,000

$164,900

2014

$2,592 (+11.6%)

$32,700 + $129,700

$162,400

2013

$2,323 (−0.4%)

$34,800 + $120,800

$155,600

2012

$2,333 (+3.3%)

$37,900 + $116,500

$154,400

2011

$2,259 (−5.9%)

$40,200 + $120,500

$160,700

2010

$2,400 (+0.1%)

$40,200 + $141,600

$181,800

2009

$2,397

$40,200 + $157,400

$197,600

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.25 Acres

Year renovated

—

Sq. Ft.

2,763

Year built

1870

Style

Multi-Family (2-4 Unit)

County

Worcester County

APN

3494249

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 1
# of Covered Spaces: 1
Open Parking Spaces: 4
Parking Spaces: 5
Parking Features: Paved Drive, Off Street, Paved

Interior

Virtural Tour Information
Virtual Tour 1 (External Link)

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 1

Basement Information
Basement: Interior Entry, Sump Pump, Unfinished

Laundry Information
Laundry Features: Washer & Dryer Hookup

Appliances
Appliances: Range, Oven, Dishwasher, Refrigerator

Interior Features
# of Rooms (Total): 13
Window Features: Box/Bay/Bow Window(s)
Flooring: Wood, Vinyl, Carpet, Hardwood, Tile
Interior Features: Cathedral/Vaulted Ceilings, Crown Molding, Stone/Granite/Solid Counters, Upgraded Countertops, Bathroom With Tub & Shower, Remodeled, Living Room, Dining Room, Kitchen, Family Room, Laundry Room

Unit #1 Information
# of Levels: 3
# of Floors: 1
Lease: N

Unit #2 Information
# of Levels: 1
# of Floors: 2
Lease: N

Exterior

Building Information
Building Area (Total): 2,763
Foundation Details: Stone
Stories (Total): 4
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Roof: Shingle
Patio And Porch Features: Porch

Property Information
PropertySubType: Multi Family
Above Grade Finished Area: 2763
Levels: 4

Lot Information
Lot Size (Acres): 0.25
Lot Features: Corner Lot
Road Surface Type: Paved
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $3,996
Tax Year: 2025

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers

Heating & Cooling
Has Heating
Heating: Steam, Oil
Heating Units: 1

Location

School Information
Middle Or Junior School: Murdock Middle School
High School: Murdock High School

Location Information
Directions: Route 12 or Route 202 to Spring/Front St to Pleasant St.
UnparsedAddress: 142 Pleasant St, Winchendon MA 01475

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Park, Walk/Jog Trails, Bike Path, Conservation Area, House of Worship, Public School

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 2,763
Stories: 2.0
Lot Size: 0.25 acres
Style: Multi-Family (2-4 Unit)
Year Built: 1870
Year Renovated: —
County: Worcester County
APN: 3494249

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
StandardStatus: Closed

Around this home

Schools

Toy Town Elementary School

Public 3-5 • Assigned • 0.3mi

4/10

Murdock Middle School

Public 6-8 • Assigned • 1.0mi

5/10

Murdock High School

Public 9-12 • Assigned • 1.0mi

3/10

Provided by GreatSchools

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

3/10 Heat Factor

8 days above 91° expected this year, 18 days in 30 years

4/10 Wind Factor

17% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winchendon, MA • 01475

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

83/ 100

Very good sunlight

Sunscore

This home ranks in the top 14% for direct sun exposure in Winchendon. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9 hrs

5.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$404,000 – $489,000

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Home values near 142 Pleasant St

Data from public records.

Address	Redfin Estimate
151 Pleasant Street, Winchendon, MA 5 Beds \| 2 Baths \| 1767 Sq. Ft.	$284,812
163 Pleasant Street, Winchendon, MA 4 Beds \| 2 Baths \| 1620 Sq. Ft.	$330,526

Address	Redfin Estimate
145 Pleasant Street, Winchendon, MA 4 Beds \| 2 Baths \| 2488 Sq. Ft.	$415,464
96 Pleasant Street, Winchendon, MA 4 Beds \| 1.5 Baths \| 1667 Sq. Ft.	$330,941

Address	Redfin Estimate
148 Pleasant Street, Winchendon, MA 5 Beds \| 3 Baths \| 2544 Sq. Ft.	$313,279
88 Pleasant Street, Winchendon, MA 3 Beds \| 1.5 Baths \| 1969 Sq. Ft.	$359,584

Property information provided by MLS PIN when last listed in 2026. This data may not match . Learn more.

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