$459,000
106 Chestnut St
Southbridge, MA, 01550
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.
Property Details
Price:
$459,000
MLS #:
73590382
Status:
Active
Beds:
6
Baths:
2.5
Type:
Multi Family
Listed Date:
Oct 14, 2026
Finished Sq Ft:
2,872
Total Sq Ft:
2,872
Lot Size:
9,148 sqft / 0.21 acres (approx)
Year Built:
1925
Units:
2
Schools
Interior
Above Grade Finished Area
2872
Appliances
Range, Microwave, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
None
Flooring
Wood, Tile, Laminate, Hardwood
Heating
Natural Gas
Interior Features
Cedar Closet(s), Bathroom With Tub, Pantry, Living Room, Dining Room, Kitchen, Family Room, Office/Den
Levels
3
Exterior
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, House of Worship, Public School
Construction Materials
Frame
Covered Spaces
1
Garage Spaces
1
Open Parking Spaces
5
Open Parking YN
1
Parking Features
Paved Drive, Off Street, Paved
Parking Spots
6
Parking Total
6
Patio And Porch Features
Porch
Roof
Shingle
Stories
3
Financial
Tax Year
2026
Taxes
$5,481
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Multi Family in Southbridge as of Oct 20, 2026
27
Multi Family Listed
88
Avg DOM
161
Avg $ / SqFt
$605,959
Avg List Price
Community
- Address106 Chestnut St Southbridge MA
- CitySouthbridge
- CountyWorcester
- Zip Code01550
Subdivisions in Southbridge
Similar Listings Nearby
Property Summary
- 106 Chestnut St Southbridge MA is a Multi Family for sale in Southbridge, MA, 01550. It is listed for $459,000 To schedule a showing of MLS#73590382 at 106 Chestnut St in Southbridge, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of eXp Realty. The property listing data and information 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 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 set forth herein.
106 Chestnut St
Southbridge, MA












































