142 Pleasant St Winchendon, MA ^$ 445,000

142 Pleasant St

^$ 445,000

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Open House 8/15 11am - 12:30pm

142 Pleasant St

Winchendon, MA, 01475

^$ 445,000

Bedrooms5 Baths2.1 Sq 2,763

Monthly Estimate*

^$ 2,810

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Multi-Family Home for sale in Winchendon, MA

for $445,000 with 5 bedrooms and 2 full baths, 1 half bath. This 2,763 square foot home was built in 1870 on a lot size of 0.25.

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.

Open House

8/15/2026 11:00 AM - 12:30 PM

8/16/2026 11:00 AM - 12:30 PM

142 Pleasant St Winchendon, MA

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Multi-Family Active

Price

^$ 445,000

Bedrooms

Full Bath

Half Bath

Property Type

Multi-Family

Taxes

^$ 3,996

Style

Multi Family

Lot Size

0.25

Year Built

1870

Town/City

Winchendon

County/Region

Worcester

MLS | Web ID

73563079

List By

Noelle Medugno

Listing Agent

Lamacchia Realty, Inc.

Broker

Affordability Calculator

$3,143

Per Month

Monthly Principal & Interest: $2,810
Monthly Property Taxes: $333
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Multi-family listings in Winchendon, MA

Average List Price ^$454,200

Percent of Sale Price 2%

About Winchendon, MA

10,666 Population

11% Since 2002

^$63,271 Median Income

40.44 Median Age

31% Households with Children

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Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
8/13/2026	$445,000		Listed Price

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142 Pleasant St, Winchendon, MA, 01475 is a Multi-Family Home for sale at $445,000 with 2,763 sqft and a lot size of 0.25. 142 Pleasant St has 5 bedrooms, 2.1 baths, and was built in 1870. The property's zip code is 01475 which is in Winchendon, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 8/13/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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142 Pleasant St

Multi-Family Home for sale in Winchendon, MA

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