Artboard 1? alert-icon? Artboard 1? ? ? delete-icon? edit-icon? email-icon hide-hover-icon? Artboard 1? login-icon-white Artboard 1? next-icon-left next-icon-right-left next-icon-left-ochre next-icon next-icon-right-grey next-icon-right-ochre plus-with-circle-iconP search-fw-icon? search-icon-ochre search-icon-white

106 Chestnut St

Southbridge, MA 01550
$459,000
6 Beds
2/1 Baths
2,872 Living Area
  • Property Description
    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.
  • Highlights
    • Heating: Natural Gas
    • Parking Spots: 6
    • Property Type: Multi Family
    • Total Rooms: 14
    • Status: Active
    • Levels: 3
    • Property Class: Residential Income
    • Stories: 3
    • Year Built: 1925
  • Additional Details
    • Appliances: Range, Microwave, Refrigerator, Washer, Dryer
    • Construction: Frame
    • Foundation: Stone
    • Road Frontage Type: Public
    • SqFt Source: Public Record
    • Year Built Details: Actual
    • Zoning: R2
    • Basement: Full
    • Flooring: Wood, Tile, Laminate, Hardwood
    • Interior Features: Cedar Closet(s), Bathroom With Tub, Pantry, Living Room, Dining Room, Kitchen, Family Room, Office/Den
    • Roof: Shingle
    • Total Number of Units: 2
    • Year Built Source: Public Records
  • Amenities
    • Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, House of Worship, Public School
    • Parking Features: Paved Drive, Off Street, Paved
    • Covered Parking Spaces: 1
  • Utilities
    • Sewer: Public Sewer
    • Water Source: Public
  • Fees / Taxes
    • Assessed Value: $368,100
    • Taxes: $5,481
    • Tax Year: 2026

Location

106 Chestnut St, Southbridge, MA 01550

Loading Map...

Similar Listings

92 Dresser St 1
36 Photos
92 Dresser St Southbridge, MA 01550
$509,900
6 Beds 2 Baths 2,434 Sqft
View Details
7 Pearl Street 1
41 Photos
7 Pearl Street Southbridge, MA 01550
$474,999
6 Beds 2 Baths 1,850 Sqft
View Details
17-19 Coolidge Ave 1
8 Photos
17-19 Coolidge Ave Southbridge, MA 01550
$429,900
6 Beds 2 Baths 2,576 Sqft
View Details
42 Fox Run 1
13 Photos
42 Fox Run Southbridge, MA 01550
$379,900
4 Beds 2 Baths 1,800 Sqft
View Details
Sold
16 Main St 1
39 Photos
16 Main St Sturbridge, MA 01566
$550,000
6 Beds 2/1 Baths 3,331 Sqft
View Details
Sold
85 Everett St 1
42 Photos
85 Everett St Southbridge, MA 01550
$529,900
7 Beds 3 Baths 3,744 Sqft
View Details
Sold
723 Main St 1
41 Photos
723 Main St Southbridge, MA 01550
$520,000
4 Beds 3/1 Baths 3,014 Sqft
View Details
Sold
89-91 Hartwell St 1
39 Photos
89-91 Hartwell St Southbridge, MA 01550
$520,000
4 Beds 2 Baths 3,060 Sqft
View Details
Content © 2026 MLS Property Information Network, Inc. The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Coldwell Banker Realty - Worcester. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.
  • Request More Information:

    617.262.2500
    When you are ready, please contact us and we will put our unrivaled knowledge of the Boston real estate market to work for you. Whether you are buying a luxury condo or renting a luxury apartment, we pledge to make your experience as stress free and enjoyable as possible.

    Please call, email, or send us a message through the web form below. An LRG Real Estate agent will contact you promptly.

    For More Info Please Call:

    617.262.2500

    or

    Email Us
  • Hidden
  • This field is for validation purposes and should be left unchanged.

By joining you agree to our Terms of Use and Privacy Policy