106 Chestnut St Southbridge, MA ^$ 459,000

106 Chestnut St

^$ 459,000

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Open House 10/16 5:30pm - 7pm

106 Chestnut St

Southbridge, MA, 01550

^$ 459,000

Bedrooms6 Baths2.1 Sq 2,872

Monthly Estimate*

^$ 3,170

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Multi-Family Home for sale in Southbridge, MA

for $459,000 with 6 bedrooms and 2 full baths, 1 half bath. This 2,872 square foot home was built in 1925 on a lot size of 0.21.

Rich in architectural character and timeless appeal, this spacious two-family residence offers a rare combination of historic charm, generous living space, and versatility. Maintained within the same ownership for decades, the property reflects years of history and offers an opportunity to preserve its original character while introducing modern updates. Beautiful wide-plank pine flooring and traditional details add warmth and distinction throughout. The first unit features multiple bedrooms, a full bath, and additional upper-level space with two rooms and a half bath. The second unit offers two bedrooms, an exceptionally spacious living room, a generously sized kitchen with pantry, and a full bath. Additional features include a substantial, well-maintained basement, attic designated for storage only, a garage, off-street parking, a manageable yard, and an inviting porch. While the property would benefit from updating, its spacious layout, distinctive craftsmanship, and two-unit configuration present a variety of possibilities, including owner occupancy, rental income, or multigenerational use. A property with a meaningful past and exceptional potential for its next chapter.

Open House

10/16/2026 5:30 PM - 7:00 PM

10/17/2026 11:00 AM - 12:30 PM

106 Chestnut St Southbridge, 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

^$ 459,000

Bedrooms

Full Bath

Half Bath

Property Type

Multi-Family

Taxes

^$ 5,481

Style

Multi Family

Lot Size

0.21

Year Built

1925

Town/City

Southbridge

County/Region

Worcester

MLS | Web ID

73590382

List By

Mandy Fontanez

Listing Agent

Coldwell Banker Realty - Worcester

Broker

Affordability Calculator

$3,627

Per Month

Monthly Principal & Interest: $3,170
Monthly Property Taxes: $457
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 7.375% 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 Southbridge, MA

Average List Price ^$620,622

Percent of Sale Price 35%

About Southbridge, MA

16,273 Population

-5% Since 2002

^$48,238 Median Income

40.1 Median Age

27% 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
10/14/2026	$459,000		Listed Price

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106 Chestnut St, Southbridge, MA, 01550 is a Multi-Family Home for sale at $459,000 with 2,872 sqft and a lot size of 0.21. 106 Chestnut St has 6 bedrooms, 2.1 baths, and was built in 1925. The property's zip code is 01550 which is in Southbridge, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 7.375% 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 10/15/2026.

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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106 Chestnut St

Multi-Family Home for sale in Southbridge, MA

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