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$580,000
3 Beds 2 Baths 73568481 MLS
Welcome to Graywood Estates! This exceptional custom-built ranch is set on a peaceful cul-de-sac on the Sturbridge line, offering six rooms, three bedrooms, and two beautifully appointed baths on a level lot. Step inside to a bright, open-concept layout with soaring ceilings and recessed lighting throughout the kitchen and living areas. The updated gourmet kitchen features custom cabinetry, granite countertops, a center island, hardwood floors, stylish backsplash, and a convenient pot filler, flowing seamlessly into the spacious living room with a vaulted ceiling and gas fireplace. The generously sized primary bedroom offers a private retreat with a large walk-in closet and beautiful modern en-suite bath with tile flooring. Two additional bedrooms provide flexibility for guests, an office, or other needs. Additional highlights include central air, town water and sewer, and an attached two-car garage. A charming front farmer's porch welcomes you home, while sliders lead to a low-maintenance composite rear deck overlooking the expansive, flat, cleared backyard—perfect for entertaining, relaxing, or enjoying the outdoors. Located minutes from Westville Dam Recreation Area, which offers walking and biking trails, fishing, boating, and picnic areas, with convenient access to Route 20, I-90, and I-84. Quality craftsmanship, thoughtful updates, and a convenient location make this a truly special home.

17 Harwood Farm Road, Southbridge

Listing courtesy of Listing Agent: Derrick Asante from Listing Office: Century 21 XSELL REALTY.

$649,999
9 Beds 3 Baths 73568094 MLS
Rare opportunity to own a substantially renovated 3-family in Southbridge with strong in-place income and excellent rental potential. The property offers 4,134+ SF with 3 units, each featuring 3 bedrooms and 1 full bath, for a total of 9 bedrooms and 3 full baths, plus a detached 3-car garage. Recent improvements include a new roof, siding, windows, refinished/new flooring, updated electrical service with 200-amp wiring, circuit breakers, and panels, furnaces, water heaters, updated plumbing, lead paint remediation, and enclosed rear porches. Unit 1 features an in-unit washer and dryer, while Units 2 and 3 have their own washers and dryers in the basement. Conveniently located near Route 20, I-84, and I-90, with easy access to downtown Southbridge, shopping, restaurants, schools, parks, medical facilities, and public transportation. With spacious units, valuable off-street parking, and extensive recent updates, this property offers an attractive opportunity for investors seeking cash flow and portfolio growth or an owner-occupant looking to house hack while building equity. Open house will be this weekend, Sunday August 30 between 12:00pm-2:00pm.

36 Winter Street, Southbridge

Listing courtesy of Listing Agent: Skerdi Senko from Listing Office: Splice Realty.

$1,100,000
21 Beds 7 Baths 73567661 MLS
**102 Sayles, Southbridge, United States** presents a rare opportunity to acquire a distinguished multi-family residence with an astonishing current rent roll of $10,100. Encompassing an expansive 5412 square feet of living area across six units, this property offers an unparalleled scale for expanisve living and potential adaptation. With an impressive twenty-one bedrooms, this estate offers versatile unit accommodations between two bedroom one bath to five bedrooms and two baths. Rent roll will increase to $10,600 prior to closing at buyer's discretion. All units are currently rented. Seller to install commercial fire alarm system prior to closing. First group showings on Thursday September 3, 2026.

102 Sayles Street, Southbridge

Listing courtesy of Listing Agent: John Belanger from Listing Office: A-1 Realty of MA LLC.

$489,000
8 Beds 4 Baths 73567613 MLS
Welcome to this spacious and solid 3-family property in Southbridge, offering an excellent opportunity for both owner-occupants and investors. The first and second floors each feature a generously sized 3-bedroom unit with comfortable living space/washer dryer hookup. The 2nd floor has 2 FULL baths and also it's own washer/dryer hookups. First floor heated by oil. 2nd floor has a parlor heater and a very Large deck in the back for entertaining in all types of weather. All floors are carpeted throughout. Long term tenants have been on the 1st and 2nd floor. The third-floor offers 2-bedrooms.1 bath and is more "cozy". There is one garage on site and off street parking for 3 cars. All separate utilities. This building could be an exciting opportunity to renovate, add value, and increase rental income over time. Convenient location and minutes to downtown.

62 Coombs Street, Southbridge

Listing courtesy of Listing Agent: Karen Lowe from Listing Office: New England Home Realty.

$450,000
3 Beds 2 Baths 73567556 MLS
Discover a contemporary single-family residence, meticulously constructed in 2020, offering 1605 square feet of refined living space within the 55+ adult community at Pleasant Hill Estates. This property presents an exceptional opportunity for discerning buyers seeking modern comfort and design. The residence encompasses three well-proportioned bedrooms, providing ample private accommodations. Two full bathrooms are thoughtfully appointed to serve both residents and guests with convenience and style. Further enhancing the property's appeal is the open concept design with hard wood flooring, recessed lighting and propane fireplace for setting a relaxing and tranquil environment. The cabinet packed chef's kitchen is enhanced by the granite counter tops and black stainless steel appliances. Additional amenities include an integrated two-car garage, offering secure parking and additional storage solutions. The whole house generator and solar panels offer you a peaceful mindset. The expansive 13,504 square foot lot provides generous outdoor space, presenting opportunities for landscaping and personal enjoyment. This distinguished property invites you to experience a lifestyle of sophisticated ease.

42 Highfield Drive, Southbridge

Listing courtesy of Listing Agent: Keith Hollett from Listing Office: Coldwell Banker Realty - Worcester.

$1,100,000
4 Baths 73567544 MLS
GREAT BUILDING! PLUS A TWO FAMILY FOR INCOME! GREAT LOCATION! GREAT SPACE! BUILDING FOR SALE! 52' x 114'. HUGE 6000sf building plus 6000sf full basement with garage door. Vinyl Sided. First floor has flooring business. Lower Level storage for cars, boats, materials. Parking area out front. Two garage doors, one for main level and one for lower level. Easy delivery of materials. Concrete block construction. Four electrical panels so building can be split up into separate units. Gas heat-blowers. Basement not heated but could be. Office room SF aprox. 1st floor has several rooms. Downstairs wide open with one large separate room in rear. Modern lovely two family has 4 rooms 2 bedrooms each, great rental history! Renovated in 2018. Turn key property.See Listing # 73493616 for all 4 properties listed together.

16-18 Park St, Southbridge

Listing courtesy of Listing Agent: Brenda Ryan from Listing Office: Aucoin Ryan Realty.

$465,000
3 Beds 3 Baths 73566252 MLS
First showing at OPEN HOUSE 8/30, 12-1:30, Country living at its finest! This home boasts of land and space! Sitting on 2.78 acres of land, having privacy will NOT be an issue. Long extended driveway. This home offers Hardwood floors, cathedral ceilings, and more! updates in 2020 by previous owner include a NEW oil Tank and NEW water heater both.First floor boasts of large country kithcen, 1/2 bath and laundry area along with large bedroom with full bath, an office space suitable for a 4th bedroom. 2 additional bedrooms located on the second floor along with a full bath. Large deck off the kitchen and above ground pool. Located near Cohasse Country Club/Golf Course & CT State line. located near all major routes.Approx. 60 miles to Boston, Providence and Hartford.

1235 Eastford Rd, Southbridge

Listing courtesy of Listing Agent: Beth Ann Dion from Listing Office: eXp Realty LLC.

$579,900
5 Beds 3 Baths 73566124 MLS
From the moment you set foot onto the quaint brick walkway, you'll be drawn in by this warm, inviting home. With quintessential New England design throughout, each room has its own special appeal. The living room has a stunning fireplace that can be enjoyed from the kitchen as well, and entertaining is easy with the kitchen serving (buffet) counter and eat-in area. For larger gatherings, there's a spacious formal dining room with chair rails and large windows overlooking the beautiful grounds. Gleaming, warm wood beams, wainscoting, doors & trim just add to the ambiance. Four bedrooms on the main floor give you choices for a home office or den. You'll love the mudroom/laundry area with a full pantry and loads of storage. From here, you'll step into a cheerful sunroom where you can sip your coffee and listen to birdsong while overlooking the professionally landscaped yard and sparkling Inground pool area. (All pool equipment and furniture remains for your enjoyment!). The Cabana doubles as a storage shed and changing room, making pool parties such fun! This home makes multi-generational living possible with a full in-law apartment that is accessed directly from the garage and also has an electric chair lift that leads upstairs to the mudroom. For the car enthusiast or crafter, the oversized garage has an incredible workbench/cabinet area that runs the length of the garage. There’s something for everyone here! Located on an upscale street with nice wooded areas, this charming home has been loved and has given love back to all who have entered. With the peace of mind of a 1 year warranty, It's time to make this haven of rest your own!

310 Briarwood Avenue, Southbridge

Listing courtesy of Listing Agent: Brenda Flower from Listing Office: HB Real Estate, LLC.

$399,000
3 Beds 2 Baths 73566070 MLS
Welcome home to this charming 3-bedroom, 1.5-bath home, set on a spacious double lot in a quiet neighborhood just a short walk from Westville Dam/Recreation Area. Lovingly maintained by the same family for over 60 years, this home is ready for its next chapter! The traditional floor plan features a spacious living room with hardwood floors and a fireplace, an updated kitchen with newer cabinets and countertops, and a large dining room with built-ins and plenty of space for holiday gatherings! A half bath and enclosed three-season porch complete the main level. Upstairs, you’ll find three generously sized bedrooms and a beautifully renovated full bath. Outside, enjoy a private backyard with plenty of space to relax or entertain, along with the convenience of a one-car garage. Full of warmth, character, and pride of ownership, this well-cared-for home is ready to welcome its next owners!

25 Westwood Pkwy, Southbridge

Listing courtesy of Listing Agent: Dawn Truax from Listing Office: Red Door Realty.

$255,000
73565878 MLS
Incredible opportunity to purchase beautiful 33.76 acres located on Lebanon Hill Road in Southbridge Ma. A unique lot set back from the road with access that leads into a cleared area with a small field. Situated on a tranquil road in an established neighborhood. Conveniently located with easy access to major highways and shopping. The property features a natural setting, secluded and privacy. Mature forest, abundant wildlife with Great Blue Heron nests. 4 miles of trails, large beaver pond on lower part of the property that stretches beyond the boundaries. Small area of wetlands. 32.76 acres in Chapter 61A, Agricultural & Horticultural leaving 1 acre out of chapter 61A. Perc test in hand.

Lot 12 Lebanon Hill Rd, Southbridge

Listing courtesy of Listing Agent: Lisa Berry from Listing Office: Simply Sell Realty.

$449,000
1 Baths 73565735 MLS
Own a well-established automotive repair and Massachusetts State Inspection business with a legacy dating back to 1919. This turnkey operation has successfully served the community for more than a century and is now available as the owner prepares for retirement. The sale includes the real estate, equipment, and a front office, providing everything needed for a seamless transition. The approximately 3,700-square-foot facility is ideally located in the central business district on Hamilton Street, offering outstanding visibility, strong traffic counts, and excellent exposure. Exciting things are happening in the town, with new programs and initiatives that may offer opportunities for eligible property owners and businesses to potentially take advantage of as the community continues to invest in its future. Buyers are encouraged to explore available local programs and incentives to determine eligibility and potential benefits. This is a rare opportunity to acquire a long-standing, fully operational automotive repair and inspection center with an established reputation, loyal customer base, real estate, and the potential to benefit from continued investment and positive momentum within the community.

93 Hamilton St, Southbridge

Listing courtesy of Listing Agent: The Prosperity Group from Listing Office: eXp Realty LLC - Corporate Office.

$650,000
8 Beds 4 Baths 73565585 MLS
Excellent investment opportunity! Spacious four-family property featuring 8 bedrooms and 4 full bathrooms across 3,276 square feet. All four units offer desirable townhouse-style layouts with living space on the first floor and bedrooms upstairs. Two units have been renovated with updated kitchens, bathrooms, flooring, lighting and appliances. Current gross rental income is $6,675 per month. Tenants pay their own separately metered electricity and electric heat; owner pays water, sewer, trash and recycling. Property includes three designated off-street parking spaces, a full fieldstone basement and a convenient corner-lot location. Fully occupied and ideal for investors seeking strong existing income. Advance notice required for showings. Buyers and buyer agents to perform their own due diligence and verify all information.

74-82 North St, Southbridge

Listing courtesy of Listing Agent: Darin Thompson from Listing Office: Stuart St James, Inc..

$335,000
6 Beds 2 Baths 73564726 MLS
Welcome to this duplex, owner-occupied for approximately 40 years. The property offers a great opportunity for an owner-occupant or investor, with the first-floor unit to be delivered vacant and a long-term second-floor tenant of 9 years currently in place at will. The first floor features hardwood floors throughout, an updated pantry, and a tiled bathroom. The second floor has a new natural gas furnace. Additional highlights include off-street parking, natural gas utilities and a neighborhood setting conveniently located near a hospital and a conservation area complete with walking and biking trails.Home is being sold As-Is. Information on property is limited. Seller makes no implied representations or warranties.

48 Litchfield Ave, Southbridge

Listing courtesy of Listing Agent: Denise Blais from Listing Office: RE/MAX Prof Associates.

$415,000
3 Beds 2 Baths 73564370 MLS
Welcome home to this spacious 3-bedroom, 2-bath raised ranch offering versatility, space, and incredible potential! The partially finished walkout basement provides additional living space, a great opportunity for a home office, recreation room, or whatever suits your needs. Outside, the .53-acre lot offers plenty of room to relax, entertain, or enjoy the outdoors. The detached 2-car garage is a standout feature, complete with a huge heated bonus room above—perfect for a workshop, studio, gym, home office, or additional gathering space. There’s even a third garage bay underneath, providing exceptional storage and workspace. With multiple levels of usable space and a property designed for both everyday living and hobbies, this is one you won’t want to miss! Seller may need additional time to secure suitable housing.

595 Lebanon Hill Rd, Southbridge

Listing courtesy of Listing Agent: The Jackson & Nale Team from Listing Office: REMAX Connections - Belchertown.

$225,000
2 Beds 2 Baths 73563672 MLS
Discover a thoughtfully designed living experience at 44 Maria Ave U:105, a condominium in Southbridge, MA, built in 1987. This 1082 square foot residence offers a harmonious blend of comfort and practicality, presenting an opportunity for a refined lifestyle. This inviting condominium features two comfortable bedrooms, providing ample personal space for residents. Complementing these are two full bathrooms, ensuring convenience and privacy for all. Situated on the second floor, this single-story unit offers effortless living. Imagine the ease of navigating a home designed for comfort and accessibility. This condominium presents a compelling opportunity to embrace a balanced and convenient lifestyle.

44 Maria Ave Unit 105, Southbridge

Listing courtesy of Listing Agent: Nana Yaa Frimpongmaah from Listing Office: Century 21 XSELL REALTY.

$535,000
6 Beds 3 Baths 73563453 MLS
Turnkey 3-unit investment opportunity in Southbridge! This well-maintained multifamily offers a mix of unit sizes: a 2-bed/1-bath basement unit (current tenant, lease through 11/30/2026, $1,499/mo), a vacant 1-bed/1-bath unit ready for immediate occupancy or owner-use ($1,600/mo market rent), and a 2-bed/1-bath unit (current tenant, lease through 5/31/2027, $1,550/mo). Total gross rent potential of approximately $4,649/month. Low operating expenses with 2025 actuals including taxes ($2,915), R&M ($665), and utilities. Ideal for an investor seeking immediate cash flow with upside from the vacant unit. Don't miss this opportunity to add a solid asset to your portfolio! Buyer to do due diligence.

165 Pleasant St., Southbridge

Listing courtesy of Listing Agent: Jason Saphire from Listing Office: www.HomeZu.com.

$469,500
4 Beds 3 Baths 73562614 MLS
At 757 South St, Southbridge, an inviting single-family residence, offers 2634 square feet of living space. This property stands as a testament to comfortable living, ready for immediate occupancy. The heart of the home resides in its open-plan kitchen, featuring a practical peninsula that seamlessly connects to the living room. A half bath, large dining room with custom built-ins, and an office space complete the first floor. The layout fosters an environment conducive to both everyday living and entertaining. With four bedrooms and two full bathrooms on the second floor, the residence provides ample private accommodations. The spacious primary suite has 2 walk-in closets and offers the additional privacy of having a separate staircase. A dedicated single-car garage offers convenience and secure parking. Beyond the interior, a private yard provides a tranquil retreat, enhanced by the presence of solar panels contributing to energy efficiency. A patio extends the living space outdoors, leading to a private pool, ideal for relaxation and recreation. Just 1.4 miles from Harrington Hospital and just a few miles from shopping, dining, and Sturbridge with highway access. This property represents an exceptional opportunity to acquire a distinguished residence that harmonizes comfort with practical amenities in a convenient location!

757 South St, Southbridge

Listing courtesy of Listing Agent: Michelle Terry Team from Listing Office: eXp Realty LLC.

$332,900
2 Beds 1 Baths 73561734 MLS
Welcome to this beautiful, ready-to-move-in ranch offering the convenience of single-level living! This home features 2 bedrooms, 1 full bathroom, and a functional, inviting layout. The property offers several updated features, including the siding, roof, fuel tank, and kitchen cabinets, adding value and functionality to the home.Enjoy the convenience of an attached garage and ample off-street parking. Step outside to a spacious, level backyard—perfect for summer gatherings, entertaining, gardening, or simply relaxing outdoors. A great opportunity to enjoy easy one-level living with generous outdoor space and plenty of parking. Join us for the open house this Saturday August 15th from 12:00-2:00pm and Sunday August 16th from 12:00-2:00pm.

10 Union St, Southbridge

Listing courtesy of Listing Agent: Marcia Velis from Listing Office: Five Stars Realty LLC.

$475,000
3 Beds 3 Baths 73560553 MLS
Welcome Home to Easy Living Near the Sturbridge Line. Discover comfort, convenience, and room to grow in this inviting 3-bedroom, 2.5-bath home set on a half-acre lot in one of Southbridge’s most accessible locations. The main level offers a bright open floor plan perfect for everyday living and entertaining, with modern finishes and plenty of natural light throughout. Downstairs, a versatile bonus room with its own half bath creates the ideal space for a home office, playroom, guest suite, or media room—whatever fits your lifestyle. Situated near the Sturbridge line, you’ll enjoy quick access to popular restaurants, shopping, and several major routes, making commuting a breeze. This is the kind of home that checks all the boxes for today’s buyers: space, convenience, and a location that keeps life simple. Come see why this one stands out. Homes like this don’t stay available long.

Lot 14 Cournoyer Blvd, Southbridge

Listing courtesy of Listing Agent: Christi Smith from Listing Office: eXp Realty LLC.

$620,000
9 Beds 4 Baths 73559403 MLS
Welcome to this rare four unit with four garages bays for additional monthly income, with plenty of yard space perfect for an owner occupied or investment opportunity. Two units are going to be vacant and have been renovated. The other two units have been occupied by the current tenants for over 20 years. Walk up attic areas perfect for possible additional living space or storage (not included in the total living area). Tenants pay own heat, hot water and electric. Landlord pays trash, water and sewer. Reasonable water/sewer fees. Newer Oil Tanks for three of the units and hot water heater, all replaced within the last two years, and furnace also replaced in the last year, adding additional peace and mind, don't miss your chance to occupy this well taken care of house!

48 Union St, Southbridge

Listing courtesy of Listing Agent: John Monterroso from Listing Office: The Neighborhood Realty Group.

$845,900
3 Beds 3 Baths 73558272 MLS
Architecturally striking Deck House overlooking Morse Pond, privately set on 5.93 acres.This unique contemporary features dramatic exposed beams, soaring cedar vaulted ceilings, walls of windows capturing the stunning water & woodland views. At the heart of the home a floor-to-ceiling solid granite chimney w/ 3 fireplaces anchors the home from the fully finished walk-out LL to the 2nd FL loft.The kitchen boasts abundant cabinetry, stainless steel appliances & granite countertops, opening effortlessly into the inviting family room~creating a warm welcoming homey feel atmosphere. An expansive deck overlooking the Pond.The fully finished LL offers exceptional flexibility, ideal for multi-generational living or private retreat. Complete w/ a full kitchen, full bath, 2 bed, spacious living area, built-in bar, wine closet, & walk out to the pond.A rare opportunity to own a true architectural gem offering private trails, acreage, & waterfront lifestyle!

1023 North Woodstock Rd, Southbridge

Listing courtesy of Listing Agent: Lora Savage from Listing Office: Century 21 XSELL REALTY.

$849,900
12 Beds 6 Baths 73556982 MLS
Turnkey SIX-UNIT multifamily in Southbridge, MA, featuring a 2-family and a 4-family on one lot with a 5-bay garage and ample parking. The property's proforma will generate north of $10,000/month and offers significant value-add potential. The 2-family has two units (up & down) each with 2 bedrooms, 1 bathroom, full kitchen, living room, and dining room. The 4-family includes four units each with two stacked side-by-side units- three 2-bedroom, 1-bath with eat-in kitchens and living rooms, and one 3-bedroom, 1-bath with an eat-in kitchen, living room, and sunroom. Four units are on tenant-at-will leases for flexibility, and two have annual leases. Recent updates include electrical panels and porches completed in 2025, and the property also offers generous outdoor space. A well-maintained, cash-flowing asset with upside, this is a rare investment opportunity.

90 Sayles St, Southbridge

Listing courtesy of Listing Agent: We Close Deals Team from Listing Office: Lamacchia Realty, Inc..

$499,900
7 Beds 2 Baths 73553152 MLS
Seller Says Sell! 37 Oakes Ave in Southbridge is a fully renovated, vacant two-family offering a rare turnkey opportunity for both owner-occupants and investors. Thoughtfully updated from top to bottom, this property features a new roof, new windows, updated electrical and plumbing, a brand-new boiler and hot water heater for one unit, and beautifully renovated interiors throughout. The first-floor unit offers 3 bedrooms and 1 full bathroom, while the second unit features 4 bedrooms and 1 full bathroom. Both units include in-unit laundry hookups, separate utilities, and are delivered completely vacant, offering immediate flexibility for owner occupancy or rental income. Lead compliance certificates for both units are already in hand for added peace of mind. Ideally located directly across from UMass Memorial Health – Harrington Hospital and just minutes from downtown shops, restaurants, parks, schools, and major commuter routes. With extensive updates already completed and both units ready for occupancy, this is a true turnkey property with excellent income potential in a convenient, high-demand location. Don't miss this opportunity!

37 Oakes Ave, Southbridge

Listing courtesy of Listing Agent: The Equity Group from Listing Office: Lock and Key Realty Inc..

$499,000
73553038 MLS
Rare opportunity to own approximately 38 acres of income-producing land in Southbridge with an established solar energy facility operated by AES Renewable Holdings. The property currently generates approximately $24,750 in annual lease income with approximately 18 years remaining on the existing ground lease, providing stable passive cash flow for investors.In addition to the current income stream, the property offers long-term ownership of the underlying land with future potential following the expiration of the lease. Conveniently located with excellent accessibility, this unique offering combines dependable income with long-term land value, making it an attractive addition to an investment portfolio.The solar facility is currently operational, and the lease transfers to the new owner at closing. Buyer to perform all due diligence regarding the lease, future use, zoning, environmental matters, and all property characteristics.

80 Dresser Hill Rd, Southbridge

Listing courtesy of Listing Agent: JS & The City Team from Listing Office: Serhant.

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