142 Pleasant St, Winchendon MA 01475
Winchendon, MA 01475 • Winchendon Center
$445,000
Est. $2,783/month
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Open House Schedule
16
Aug
Sunday, August 16
11:00 AM - 12:30 PM EDT
15
Aug
Saturday, August 15
11:00 AM - 12:30 PM EDT
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.
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Property History
Property Timeline
Listed for Sale
Aug 13, 2026
$445,000
Original listing
Agent: Noelle Medugno
Office: Lamacchia Realty, Inc.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/13/2026 | 🏠 Listed for Sale | $445,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $3,996 | $340,100 |
Financial Details
Annual Property Tax
$3,996
Tax Year 2025
Assessed Value
$340,100
Facts & Features
1 Car Garage
Home Facts
Type
Residential Income
Style
Multi Family
Year Built
1870
Living Area
2,763 sq ft
Lot Size
0.25 acres
Stories
4
Bedrooms
5
Full Baths
2
Half Baths
1
Total Rooms
13
Investment Metrics
Units
2
Unit 1 Rent
— · N
Unit 2 Rent
— · N
Interior
Heating
Steam, Oil
Cooling
None
Flooring
Wood, Vinyl, Carpet, Hardwood, Tile
Appliances
Range, Oven, Dishwasher, Refrigerator
Fireplace
None
Basement
Interior Entry, Sump Pump, Unfinished
Laundry
Washer & Dryer Hookup
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
Exterior
Construction
None
Architecture
None
Roof
Shingle
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
Porch
Parking
Garage Spaces
1
Has Garage
Yes
Features
Paved Drive, Off Street, Paved
Total Spaces
5
Utilities
Electric
Circuit Breakers
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$3,996
Assessed Value
$340,100
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Asbestos-containing Material In Basement. Buyer/buyer Agent To Perform Due Diligence.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Worcester
Property Overview
Property Type
Multi Family
Listing Type
For Sale
Year Built
1870
Bedrooms
5
Full Bathrooms
2
Half Bathrooms
1
Living Area
2,763 sq ft
Total Rooms
13
Stories
4
Levels
4
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,763 sq ft above grade
Display Options
Outdoor Areas
Patio & porchPorch
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood, Vinyl, Carpet, Hardwood, Tile
Appliances:
Range, Oven, Dishwasher, Refrigerator
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
Windows:
Box/Bay/Bow Window(s)
Basement:
Interior Entry, Sump Pump, Unfinished
Laundry:
Washer & Dryer Hookup
Security:
Construction & Materials
Year Built:
1870
Structure Type:
Exterior Materials:
Roof:
Shingle
Foundation:
Stone
Stories:
4
Heating, Cooling & Utilities
Heating:
Steam, Oil
Heating Zones:
1
Cooling:
Hot Water:
Oil
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Porch
Fencing:
Other Structures:
Lot Features:
Corner Lot
Road Surface:
Paved
Parking & Garage
Garage Spaces:
1
Total Parking Spaces:
5
Parking Features:
Paved Drive, Off Street, Paved
Nearby Schools
School District
Winchendon School District local
F
School Safety
2024-25
5.3%
Above Average
5.1%
Suspensions
0.7%
In-School
0.2%
Emergency
0.2% below state avg
Elementary Schools
3 schools
C
Toy Town Elementary School
0.4 mi
|
#621 of 824
|
Score: 39.6
Dropped 30 spots from last year
-18.6 below state avg
292 students
Moderate
Grades 03-05
Winchendon PreSchool Program
0.9 mi
90 students
Moderate
Grades PK
Memorial School
0.9 mi
268 students
Moderate
Grades K-02
Middle Schools
1 school
C-
Murdock Middle School
1.0 mi
|
#302 of 352
|
Score: 31.1
Improved 63 spots from last year
-27.2 below state avg
281 students
Moderate
Rising School
Grades 06-08
High Schools
3 schools
The Winchendon School
0.8 mi
Grades 08-12
C-
Murdock High School
1.0 mi
|
#280 of 346
|
Score: 43.2
Improved 13 spots from last year
-15 below state avg
256 students
Moderate
14 sports
• 494 athletes
College Ready Curriculum
Grades 09-12
B
Murdock Academy for Success
1.0 mi
|
#183 of 346
|
Score: 69.8
Same rank as last year
1 students
Less Diverse
College Ready Curriculum
Grades 06-12
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Monthly Payment Breakdown
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Homeowners Insurance
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95% Interest
Year 15
50/50
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95% Principal
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Location
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Neighborhood
Winchendon Center
142 Pleasant St, Winchendon MA 01475
Winchendon, MA 01475
Listing Information
Listing Agent
Noelle Medugno
Listing Office
Lamacchia Realty, Inc.
Office Phone
978-993-3600
Agent MLS ID
CN243406
Office MLS ID
AN6314
Listing Data Updated
Aug 13, 2026 6:52 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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