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106 Chestnut St, 
Southbridge, MA 01550

$459,000


6

Beds


3

Baths


2,872

Sq Ft


Multi-Family

Active

508-795-7500

Last updated:

October 22, 2026, 11:17 AM

MLS#

73590382

Source:

MLSPIN

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About This Home

106 Chestnut St

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.

Home Facts

Multi-Family

3 Baths

6 Bedrooms

Built in 1925

Price Summary

459,000

$159 per Sq. Ft.

MLS #:

73590382

Last Updated:

October 22, 2026, 11:17 AM


Rooms & Interior

Bedrooms

Total Bedrooms:

6

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

2,872 Sq. Ft.


Structure

Structure

Building Area:

2,872 Sq. Ft.

Year Built:

1925


Lot

Lot Size (Sq. Ft):

9,148


Finances & Disclosures

Finances

Price:

$459,000

Price per Sq. Ft:

$159 per Sq. Ft.

106 Chestnut St
Source:MLSPIN
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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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.