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$849,000
3 Beds 2 Baths 73562337 MLS
OPEN HOUSES CANCELLED, SELLER ACCEPTED OFFER. This exceptional one-owner home offering nearly 3,000 sq ft of thoughtfully designed living space on 1.4 meticulously maintained & landscaped acres. Set on approx 200 ft of street frontage in an established Middleboro neighborhood, this property offers a private setting while remaining convenient to Rtes 44, 3 & 495. Step inside to a home created for both comfortable everyday living & memorable entertaining. The showpiece is the expansive, open-concept Great Room featuring soaring ceilings, a dramatic 16-ft stone FP & stunning curved balcony overlooking the space below. Beautiful 3/4” hardwood floors flow throughout, adding warmth & timeless character. Unique floating bedroom balconies add architectural interest, while the upscale billiard room provides another inviting space to gather. The finished lower level continues the entertainment theme w/a custom pub—the perfect setting for game days, celebrations or relaxing w/friends. Outside, the property transforms into your own family resort. Spend summer days around the impressive 20x40 inground pool framed by a beautiful stone apron, gather under the 18-ft pavilion or enjoy evenings around the stone fire pit. A 30x40 basketball/sport court adds even more opportunity for recreation right at home. Extensive stone walls & brick pavers surround the property, complementing the mature landscaping & showcasing the attention to detail throughout the grounds. A Hunter irrigation system helps maintain the lush landscape. A 3-car garage offers generous space for vehicles, storage, hobbies & recreational equipment. From the dramatic interior architecture to the resort-style backyard, this home has been carefully designed, maintained & enjoyed by its original owner.

35 Margaret Rd, Middleboro

Listing courtesy of Listing Agent: Selling South of Boston Team from Listing Office: Keller Williams Realty Colonial Partners.

$749,900
5 Beds 3 Baths 73561338 MLS
Presenting an exceptional & extremely UNIQUE opportunity at "35 Peirce Street", Middleboro. This majestic & distinguished single-family residence encompassing over 3,000 square feet of living space; stands as an attractive property in great condition(with MANY updates)in an area of similar homes offering a unique blend of historical grandeur and contemporary comfort. Classic side entry(off wrap around porch-slate & wood Flooring)into a separate entry room and then into a stunning grand foyer w/wood flooring, rich crown molding & tucked away sunken 1/2 bath. The kitchen is thoughtfully appointed with stainless steel appliances and features practical counter space & charming butler's pantry designed for both culinary exploration and casual gatherings. The spacious living room provides a welcoming ambiance centered around a fireplace that offers a focal point for relaxation and social interaction complementing the interior's refined spaces. Two staircases(one leading into the kitchen). Potential 3rd floor in-law consisting of two rooms, a full bath & unfinished attic area. The property's exterior, characterized by its American Foursquare and traditional architectural style, includes a private(.67 acre)in-town yard, several patios(slate), screened outbuilding(cabana)and a porch extending the living experience outdoors. With five bedrooms, two full bathrooms, one half bathroom and a two-car detached garage this residence is meticulously prepared for sophisticated living. town water, town sewer, town gas & municipal electric(Middleboro Gas & Electric). Many recent updates: harvey replacement windows, vinyl siding, roof, gutters-downspouts, driveway, garage doors, bulkhead, 200 amp. electric(generator hook-up),(5) mini splits, backyard patio, sprinkler system, gas boiler, kitchen appliances, cabana & fencing. Super convenient commuting location-Close to highways(105, 44, 495 & 24), walking distance to library, bakery, post, coffee shops, playground(pool),other downtown amenities & UNDER 2 miles to the NEW Middleboro commuter rail! To truly appreciate the meticulous craftsmanship and lifestyle potential of this residence we encourage a private showing.

35 Peirce Street, Middleboro

Listing courtesy of Listing Agent: Kyle Belken from Listing Office: Realty One Group, LLC.

$1,195,000
4 Beds 4 Baths 73560669 MLS
Custom Built Three Year Young Colonial ~ Thoughtfully designed with over 3,000 sq. ft. of living space that gives a feeling of home instantly as you step inside! Boasting sun-drenched living with an open floor plan perfect for entertaining family & friends. Spacious living room with gas fireplace and added built-ins flows beautifully into the heart of the home, the kitchen. Gather around the 9’ center island while the chef of the home prepares a favorite meal. Jenn-Air appliances, quartz counters, and double wall ovens are just a few of the features that make meal times and special occasions a breeze. First-floor primary suite w/walk-in closet, tiled shower, heated floor, and a soaking tub to relax and unwind. Step outside to the expansive deck and take in the natural landscape, with ample room for outdoor entertaining, gardening, and recreation. The second level offers an additional 3 bedrooms and 2 full baths. An extensive list of bonuses includes a 3-car garage, Kohler generator, well water filtration system, 2 heating systems, one for each floor, office/den, first-floor laundry room, plus a walk-up attic and a full walk-out lower level, providing abundant storage and endless possibilities for future expansion. Schedule your private tour to see all this home has to offer.

63 Whitetail Lane, Middleboro

Listing courtesy of Listing Agent: Cesidia Brousseau from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$899,000
4 Beds 3 Baths 73556945 MLS
Experience a perfect balance of modern luxury and energy independence on 4.67 private acres in South Middleborough featuring walking trails and recently cleared grounds. This updated 4-bedroom, 3-bath Colonial is engineered for complete self-reliance with owned Tesla solar panels, a whole-house backup generator, private well water, and city water available at the simple turn of a lever. Enjoy incredible seasonal efficiency with a high-efficiency wood boiler that heats the entire home all winter long, supplemented by a wood cooking stove and pellet stove. Step inside to rich cherry hardwood floors and a bright, open floor plan connecting the island kitchen and cozy living room. The main level conveniently offers a full bath and a bedroom with a walk-in closet—ideal for guests or a home office. Upstairs features two additional bedrooms with walk-in closets, a full bath, a sitting area reading nook, and direct access to flexible unfinished third-floor space ready for future expansion. The primary suite serves as a peaceful retreat featuring soaring vaulted ceilings, a custom-tiled shower, and a private balcony overlooking the lush yard, paver patio, and fire pit. Out back, contractors and hobbyists will love the massive 30x40 detached 2-stall garage with 13-foot ceilings and expansive unfinished space above. Complete with established gardens, producing fruit trees, a greenhouse, and zoned for horses and livestock—this property has it all! Buyer and buyer's agent to verify all listing information.

112 Spruce St, Middleboro

Listing courtesy of Listing Agent: Philip Rebello from Listing Office: Keller Williams South Watuppa.

$379,000
3 Beds 2 Baths 73556084 MLS
Lowest-Priced Home in the Desirable Oak Point 55+ Community! Move right into this bright and inviting Princeton-style home featuring a popular split-bedroom floor plan for added privacy. The spacious primary suite offers two closets and a private bath with a step-in shower. The open living and dining rooms provide an ideal space for everyday living and entertaining, while the kitchen features abundant cabinetry, updated stainless steel appliances, and a sunny morning room. Relax in the screened porch with wood flooring, perfect for morning coffee or evening gatherings. Two additional bedrooms and a full bath offer flexibility for guests, a home office, or hobby space (virtually staged). Built in 2003 and nicely situated on the lot, this home has been thoughtfully updated with a new refrigerator and stove (2026), furnace and central air (2022), roof (2016), and LeafGuard gutters. Additional features include Pergo flooring in the main living areas, vinyl flooring in the kitchen and baths, no wall-to-wall carpeting, and a one-car garage. Enjoy Oak Point’s exceptional resort-style amenities, including three swimming pools, tennis, pickleball, bocce, fitness center, ballroom, library, clubs, and countless social activities. The monthly fee includes lawn care, snow removal, trash pickup, sewer treatment, and access to all community amenities.

408 Green Street, Middleboro

Listing courtesy of Listing Agent: Toni Manning from Listing Office: Conway - Hanover.

$799,000
3 Beds 2 Baths 73555359 MLS
Welcome to 229 Tispaquin! This charming 3-bedroom, 2-bathroom home sits on a beautiful 2.8-acre lot and offers the perfect blend of comfort, space, and versatility. A true highlight of the property is the impressive 40' x 30' detached garage, complete with electricity, vehicle lift, wood stove, and a spacious loft area above, perfect for hobbies, projects, storage, or recreational use.Inside, the spacious kitchen features an oversized center island, gas range, and plenty of cabinet and counter space, making it the perfect gathering spot. Just off the kitchen, the mudroom includes a pellet stove for added warmth and convenience. Enjoy the bright sunroom overlooking the property, or relax in the inviting living room with a fireplace and pellet stove insert.The flexible first-floor bonus room is currently used as an additional bedroom but could also serve as a home office, guest room, playroom, or den. Central air keeps the home comfortable year-round. The partially finished basement offers additional living space, laundry, and plenty of storage.Outside, enjoy the brand-new deck, perfect for relaxing or entertaining, along with an oversized shed for tools, lawn equipment, and outdoor gear. With its expansive lot, incredible garage setup, and thoughtful features throughout, 229 Tispaquin offers space and versatility that are hard to find. Conveniently located near local amenities, shopping, dining, and commuter routes, this is one you won't want to miss!

229 Tispaquin St, Middleboro

Listing courtesy of Listing Agent: Elizabeth Moses from Listing Office: LPT Realty - Home & Key Group.

$519,900
3 Beds 2 Baths 73553246 MLS
Newly Offered! Welcome home to 18 Chestnut Street in Middleboro, a charming and well-maintained 2–3 bedroom, 1.5-bath Front-to-Back Split offering the perfect blend of comfort, character, and outdoor enjoyment. The heart of the home features an eat-in kitchen with a tiled floor, ceiling fan, and pantry, while the spacious living room showcases a cozy wood-burning fireplace. Throughout the home you'll find hardwood floors and solid oak doors, adding warmth and timeless appeal. Enjoy outdoor living at its finest from the 12' x 12' screened porch with a vaulted ceiling and ceiling fan, leading to a private 20' x 12' deck overlooking a fenced inground pool complete with a pool house featuring electricity and a cold-water sink. The property also includes a barn with chicken coop, perfect for hobby farming, storage and workshop space. Additional features include: Central Air & Vacuum; Full bath with shower stall; Second-floor laundry room (washer & dryer included); Easy access attic for additional storage; Finished lower level with door opening directly to the outside, offering a family room or potential 3rd bedroom, plus a convenient half bath; Municipal Gas & Electric (MG&E). Recent updates: Heat Pump (2023); 200-Amp Electrical Panel (2023); Updated roof and replacement windows, 3-Bedroom Title V Septic System (installed 7/21/2025). This home is conveniently located with quick access to Routes 105, 495, 44, and 28. Close to downtown amenities including the post office, coffee shops, and library, and is less than four miles from the new Middleborough Commuter Rail Station. Don't miss this unique property offering indoor comfort, outdoor entertaining, and exceptional convenience!

18 Chestnut Street, Middleboro

Listing courtesy of Listing Agent: Kyle Belken from Listing Office: Realty One Group, LLC.

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