Middleboro MA Single Family Real Estate, Homes for Sale

Offer deadline 7/26, Sunday 10 AM. Make offers good until 6pm. Oak Point ~ one of the South Shore's premier 55+ communities, where resort-style amenities and an active, social lifestyle come together. This well-maintained Princeton-style home offers 3 bedrooms, 2 full baths, and 1,456 square feet of thoughtfully designed living space. Step inside to a bright, open floor plan featuring updated flooring and a seamless flow between the living, dining, and kitchen areas—perfect for everyday living and entertaining. The spacious primary suite includes a private bath, while two additional bedrooms provide flexibility for guests, a home office, or hobbies. Enjoy the outdoors from the expansive back deck overlooking a peaceful setting, plus the convenience of a one-car garage and large storage shed. Tucked away from the main road, this home offers added privacy while remaining close to Route 105 and Route 44. Recent updates include a new water heater (2025) and roof and HVAC (2018). Oak Point residents enjoy exceptional amenities including heated indoor and outdoor pools, tennis, pickleball, bocce, shuffleboard, fitness center, billiards, library, and a vibrant clubhouse with year-round social events and activities. The monthly park fee includes the land lease, real estate taxes, sewer, lawn care, shrub trimming, snow removal, and trash removal, providing truly maintenance-free living so you can spend more time enjoying everything this wonderful community has to offer.

6406 Oak Point, Middleboro

$519,900

3 Beds ⋅ 2 Baths ⋅ 73553246 MLS

Newly Offered! Showings begin Sunday! OPEN HOUSE 11:00 AM–1:00 PM! 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

$649,900

3 Beds ⋅ 3 Baths ⋅ 73552853 MLS

Tucked away at the end of a long private driveway and surrounded by nature, this inviting home offers the perfect blend of privacy, comfort, and thoughtful updates. Step inside to a warm and welcoming living room featuring soaring cathedral ceilings with exposed beams and a classic wood-burning fireplace, creating a cozy gathering space year-round. Enjoy the outdoors from the spacious composite deck, an ideal spot for entertaining or simply relaxing while taking in the peaceful natural surroundings. Recent improvements provide peace of mind, including a brand-new septic system, new boiler, replacement windows and doors, Roth oil tank, updated gutters, and a well pump and pressure tank that are less than five years old. A heated garage adds year-round convenience and versatility for vehicles, hobbies, or additional workspace. If you're looking for a home that offers privacy, modern mechanical updates, and a beautiful setting, this Middleboro property is one you won't want to miss.

6 Daniel Dr, Middleboro

$539,000

2 Beds ⋅ 1 Baths ⋅ 73552234 MLS

Completely renovated and thoughtfully updated, this two-bedroom ranch offers an open, inviting layout perfect for entertaining and relaxing. Wide-plank oak flooring runs throughout the main level, where the spacious living room features a stylish electric fireplace and custom built-in shelving that creates a beautiful focal point. The updated kitchen includes modern appliances and a large center island, ideal for everyday living and entertaining. Both bedrooms are generously sized, and the remodeled full bath features a double vanity. The finished lower level adds a comfortable family room or playroom with an electric fireplace, and walk-out french doors leading to the backyard patio and room for a home gym. Outside, enjoy a cleared, fenced-in backyard with plenty of room to relax or entertain. Additional features include a one-car garage, whole-house water filtration system, updated oil tank, and convenient access to Route 44. Septic is 3 bedroom system offering options to next owner.

45 Cross St, Middleboro

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 73550874 MLS

Welcome to luxury living at its finest! Nestled on a quiet cul-de-sac in one of Middleboro's most desirable neighborhoods, this thoughtfully designed 4-bed, 2 full & 2 half bath home offers an exceptional blend of elegance, comfort, & entertainment. Every detail has been carefully curated, creating a home that's as functional as it is beautiful. The backyard is your own private retreat, featuring a stunning 5-foot semi-inground saltwater pool surrounded by space to relax, entertain, & create lasting memories. Inside, the possibilities continue with 4 complete levels of living, including a finished 4th-floor media room perfect for movie nights, gaming, or a private retreat. The finished lower level is an entertainer's dream, complete with a bar, lounge area, & the perfect setup for hosting friends or cheering on your favorite sports team. This is more than a home—it's a lifestyle where every space has been designed for gathering, celebrating, & making memories that will last a lifetime.

8 Paddock Cir, Middleboro

$450,000

3 Beds ⋅ 2 Baths ⋅ 73550717 MLS

Welcome to Oak Point, a premier 55+ community offering resort-style living and exceptional amenities. This beautifully maintained 3-bedroom, 2-bath home features a bright, open floor plan designed for comfortable everyday living and effortless entertaining. The spacious kitchen flows seamlessly into the dining and living areas, while the private primary suite offers a relaxing retreat with an en-suite bath and ample closet space. Two additional bedrooms provide flexibility for guests, hobbies, or a home office. Enjoy your morning coffee or unwind in the peaceful outdoor space. Residents of Oak Point enjoy access to a clubhouse, fitness center, swimming pools, tennis courts, walking trails, and a full calendar of social activities. Experience low-maintenance living in one of the area's most sought-after active adult communities. Land lease fee, approx $970 mo. covers taxes, lawn care, snow and trash removal and more. First showings at Open House.

307 Blueberry Circle, Middleboro

$529,900

3 Beds ⋅ 1 Baths ⋅ 73549154 MLS

Welcome to this well-maintained 3-bedroom, 1-bath home offering 1,701 square feet of comfortable living space. Situated on a desirable corner lot, this property features a fully fenced backyard with a rear deck, a dedicated fire pit area perfect for relaxing or entertaining, and a storage shed for added convenience. Enjoy peaceful views of nearby cranberry bogs and a picturesque pond, creating a serene setting right from your own property. Inside, you'll find a functional layout designed for everyday living. Ideally located with easy access to Routes 495, 44, 105, 58, and 24, this home offers both comfort and convenience for commuters. Whether you're a first-time homebuyer, downsizing, or simply looking for a move-in-ready home, this property is one you won't want to miss.

812 Plymouth St, Middleboro

$569,000

3 Beds ⋅ 2 Baths ⋅ 73548524 MLS

Welcome to 53 Wareham Street, a beautifully updated 3-bedroom, 2-full-bath home offering water views of the Nemasket River. A stunning 12' × 56' deck overlooks the river, creating the perfect setting for outdoor dining, entertaining, or simply unwinding while taking in the scenery. The beautifully landscaped grounds form a secluded oasis retreat with ample off-street parkin and an electrified storage shed ideal for hobbies, a workshop, or additional storage. Inside, timeless character blends seamlessly with modern comfort, featuring inviting living spaces and a well-appointed kitchen designed for both everyday living and effortless entertaining. Conveniently located just minutes from the vibrant town center and the commuter rail station, this exceptional property offers the perfect balance of privacy, comfort, accessibility, and natural beauty. Title V is sellers responsibility.

53 Wareham St, Middleboro

$519,000

4 Beds ⋅ 1 Baths ⋅ 73547468 MLS

Commuters Dream less then 1/2 mile from commuter rail.... Charming and beautifully updated New England Colonial conveniently located just a short distance to all the amenities of Middleboro Center—shops, restaurants, coffee, schools, library, and commuter rail. This home blends classic charm with modern style, featuring a gorgeous kitchen with granite countertops, tile backsplash, and stainless steel appliances. Freshly painted interior, refinished hardwood floors, tile in kitchen and bath, and carpeting in bedrooms and family room. Enjoy gas heat, central air, and an updated electrical panel. The flowing floor plan offers open, airy living spaces including a finished walk-out basement with Vermont Castings gas stove and plenty of storage. The attached two-car garage connects through a spacious mudroom, and the large deck overlooks a deep, private backyard perfect for relaxing or gardening. Vinyl siding completes this move-in ready gem!

53 West St, Middleboro

$389,900

2 Beds ⋅ 1 Baths ⋅ 73547243 MLS

Move right into this charming, well-maintained 2-bedroom ranch in the desirable Woods Pond neighborhood! This inviting home offers an open floor plan with a bright living room flowing into the eat-in kitchen, perfect for everyday living and entertaining. The spacious primary bedroom features a cathedral ceiling with skylights, while the second bedroom also offers a cathedral ceiling and charming details. Hardwood floors add warmth, and the full bath includes a classic clawfoot tub. Recent improvements include a new roof (2020) and extensive plumbing upgrades beneath the home (approximately $18,000, per owner). Enjoy the large level, fully FENCED yard, ideal for pets or gardening, plus a 10'x20' utility shed with electric for extra storage. Just a short stroll to Woods Pond for fishing, kayaking, nature, and peaceful neighborhood walks.

38 Atwood Ave., Middleboro

$709,000

3 Beds ⋅ 3 Baths ⋅ 73546901 MLS

Tucked away at the end of a quiet dead-end street, this brand-new Colonial sits on a desirable corner lot, offering privacy and a peaceful setting. This beautiful home features 3 bedrooms and 2.5 baths, including a spacious primary suite with a private bath and two walk-in closets. The main level offers a generously sized living room and a stunning kitchen with white cabinetry, black hardware, granite countertops, and a center island. The dining area opens through sliding glass doors to a private back deck overlooking the backyard. You'll also find a half bath, a walk-in laundry room, and a versatile bonus room perfect for a home office, playroom, or formal dining room. The full walkout basement offers endless possibilities for future living space, storage, or a home gym. Enjoy modern finishes, a functional layout, and all the benefits of brand-new construction in this beautiful move-in-ready home.

5 Sand Street, Middleboro

$489,000

3 Beds ⋅ 1 Baths ⋅ 73546653 MLS

Opportunity awaits with this centrally located mixed-use property in Middleborough! Whether you're looking for your first home or planning to downsize, this 3-bedroom ranch offers comfortable one-level living with plenty of potential to make it your own. The main level features three bedrooms, a full bath, and a functional floor plan ready for your personal updates and finishing touches. Step outside to enjoy the above-ground pool and private backyard providing a peaceful natural setting. Conveniently located near shopping, restaurants, schools, and major routes. Property is being sold AS IS, offering a great opportunity for buyers to add their own style and value. Title V buyers responsibility.

260 Wood Street, Middleboro

$420,000

4 Beds ⋅ 1 Baths ⋅ 73546474 MLS

Welcome Home ! Nestled on a sprawling 1.37-acre lot, this charming 4-bedroom, 1-bath home offers the perfect blend of space, opportunity, and everyday comfort. Inside, you'll find an open-concept kitchen and dining area designed for easy entertaining, along with the convenience of first-floor laundry.Step outside to enjoy the expansive backyard, featuring an above-ground pool, ideal for summer gatherings and relaxing weekends at home.With endless potential, this home is ready for its next owners to add their own style and vision. Whether you're looking for a place to make a home or a property with room to grow, this home is an exceptional opportunity you won't want to miss. *HIGHEST AND BEST 7/12, 12pm*

899 Plymouth St, Middleboro

$465,000

3 Beds ⋅ 2 Baths ⋅ 73546412 MLS

Welcome to Oak Point, a premier 55+ community offering exceptional resort-style living! This bright and airy 3-bedroom, 2-bath home features an open floor plan filled with natural light and an oversized sunroom perfect for relaxing, entertaining, or enjoying the beautifully landscaped backyard. The spacious primary suite offers a private bath, while two additional bedrooms provide space for guests or a home office. The professionally landscaped lot enhances the home's curb appeal and outdoor enjoyment. Oak Point residents enjoy outstanding amenities including multiple swimming pools, pickleball, tennis and bocce courts, a fitness center, clubhouse, walking trails, and an active social calendar with clubs and events. Experience the perfect combination of comfort, convenience, and an active lifestyle in one of the area's most desirable 55+ communities. Buyers will need to be approved by Hometown America. Land lease fee is approx $970 covers snow removal, lawn care, trash and more.

303 Blueberry Circle, Middleboro

$649,900

4 Beds ⋅ 3 Baths ⋅ 73546235 MLS

Renovated Colonial in great condition offering 4 bedrooms, 3 full baths, and 2,693 sq ft of living space on a corner lot near downtown Middleboro. The main level features hardwood and tile flooring, a spacious living room with fireplace, dining area, first-floor laundry, and an impressive remodeled kitchen with granite countertops, kitchen island, pantry, gas range, and recessed lighting. The first-floor primary suite includes a full bath with double vanity and exterior balcony access. Upstairs offers three additional bedrooms and two full baths. Major updates include a roof approximately 1 year old, vinyl siding, town water, 200 amp electric, PVC plumbing, furnace and tankless water heater both under 5 years old, and a septic system approximately 5–6 years old that was pumped last year. Recently paved driveway, detached garage, central air, vinyl deck, and backyard space complete the package. A move-in ready home with modern updates, generous space, and New England character.

73 Wareham St, Middleboro

$569,000

3 Beds ⋅ 2 Baths ⋅ 73546007 MLS

Welcome to 45 Forest St., a comfortable Colonial offering 3 bedrooms, 10-foot ceilings, and a desirable double lot. Conveniently located near downtown Middleboro, Rte. 44, shopping, schools, and major commuter routes, this home blends classic character with functional living space. The first floor features a spacious living room, formal dining room, and an oak kitchen with hardwood floors and abundant cabinet space. A versatile bonus room provides the flexibility for a home office, playroom, guest room, or potential fourth bedroom. Upstairs, you'll find three generously sized bedrooms with large windows that fill the home with natural light. Outside, enjoy the private backyard and side deck, perfect for relaxing or entertaining. A wonderful opportunity to own a charming home with space, flexibility, and a convenient location.

45 Forest St, Middleboro

$799,900

3 Beds ⋅ 3 Baths ⋅ 73545512 MLS

Come home to a setting that feels like your own private retreat. Set on nearly 2 wooded acres, this custom Cape welcomes you with a bright, inviting foyer that opens to beautifully connected living spaces designed for both everyday comfort and effortless entertaining. The stunning living room, anchored by a striking stone fireplace, flows seamlessly into a spacious kitchen featuring granite countertops, ample cabinetry, and an open dining area where family and friends naturally gather. A sunroom invites quiet mornings with coffee, while the composite deck overlooks a backyard made for summer, complete with an above-ground pool, gardens, and room to unwind. Upstairs, the expansive primary suite is a true escape with a private balcony, walk-in closet, and spa-like bath with a whirlpool tub. Hardwood floors, generous room sizes, three full baths, a 2-car garage complete a home that offers the space, warmth, and lifestyle buyers have been searching for.

49 Plain St, Middleboro

$450,000

2 Beds ⋅ 1 Baths ⋅ 73544349 MLS

Have you been searching for a move-in ready starter home in Middleboro? This adorable 2-bedroom home could be the perfect place to begin your homeownership journey! Featuring a spacious backyard, a detached garage, and an extra-large storage shed, there's plenty of room for hobbies, storage, and outdoor enjoyment. Located just minutes from highways, the commuter rail, shopping, restaurants, and everything Middleboro has to offer, this home combines comfort, convenience, and value. Plus, you'll have peace of mind knowing the roof and water heater are both only about 2 years old. Great Price. Great Location and Great Condition. Sounds like a win! All parties to verify information contained herein.

47 Anderson Ave, Middleboro

$365,000

2 Beds ⋅ 2 Baths ⋅ 73545248 MLS

Beautiful Sudbury-style home in the desirable 55+ Oak Point community. The open floor plan is perfect for entertaining, featuring bright sunlit rooms and a spacious family room with a gas fireplace open to the living and dining areas. Sliders lead to a private deck for relaxing or gatherings. The cheerful kitchen includes a windowed breakfast nook. The large main bedroom offers a walk-in closet, ceiling fan, and private bath with a walk-in shower. The second bedroom also has a walk-in closet and ceiling fan. 2nd bath with tub/shower. NEW FLOORS, newer heating/AC and hot water heater. A two-car garage provides ample storage and workspace. Enjoy resort-style living with Oak Point’s exceptional amenities; Two pools, bocce court, fitness center, clubhouse, and a wide variety of social programs and activities.

2602 Green St, Middleboro

$479,000

4 Beds ⋅ 2 Baths ⋅ 73541190 MLS

Welcome to this classic New England Colonial, offering a rare opportunity with exceptional versatility, generous living space & endless potential. Utilized previously as a 2 family residence & more recently as a single-family home, this property offers a flexible floor plan to accommodate a variety of living arrangements. The updated kitchen features raised-panel oak cabinetry, Silestone countertops, a stainless-steel sink, a 5 burner gas range with griddle & a charming walkout bay. The 1st floor offers both a spacious front living room & a rear family room overlooking the backyard. A 1st floor bedroom, full bath & laundry area provide the convenience of single-level living, while the 2nd floor offers the flexibility of an additional 3 or 4 bedrooms. The 2nd floor bath was fully remodeled 5 years ago & includes a modern vanity, updated fixture & a tiled shower w/a glass enclosure. Cosmetics & updating is needed so bring your ideas & expertise to revamp & revitalize this property.

14 Frank St, Middleboro

$789,000

3 Beds ⋅ 2 Baths ⋅ 73541081 MLS

EASY TO SHOW and will include a NEW Septic! This 7.7-acre private retreat, offers privacy, nature, and convenience in the middle of the South Shore. The flexible floor plan hosts a first floor large living room with fireplace, bonus room with patio access, laundry room, and a bright sunroom/office with garage and patio access. Upstairs offers 3 bedrooms and 2 full baths, including a primary suite, eat-in kitchen with stainless appliances and deck access, and a dining/living room option. This well-maintained home features updates, including the roof, water heater, well pump, water filtration, stone wall, granite countertops, finished walls/ceiling in garage, 3.25" hardwood floors upstairs and engineered wood & tile downstairs. Enjoy 3 mini-splits with heat pumps, propane heat and gas stove. Additional features oversized garage door with pull-down loft storage with 2 windows, added carport, shed, French drains, generator hookup, ADU potential on first floor or separately on the property and many outdoor areas. Check out the video!

233 Tispaquin St, Middleboro

$565,000

3 Beds ⋅ 2 Baths ⋅ 73540421 MLS

*OFFER DEADLINE Tuesday 6/30 6p.m.*Don't miss your opportunity to call 16 Marie Drive home! Freshly painted and ready for its next owner, this well-maintained home features a new roof installed in 2020 and a new septic system completed in 2019, offering peace of mind for years to come. Inside, you'll find 3 bedrooms and 1.5 bathrooms, gleaming stainless steel appliances in the kitchen and a bright open living room, providing comfortable living space for a variety of lifestyles. Enjoy your morning coffee on the inviting front porch or entertain family and friends on the wraparound back deck overlooking the generous backyard. With plenty of outdoor space for gatherings, gardening, recreation, or pets, this property offers the perfect blend of indoor and outdoor living. Conveniently located with easy access to major highways and just minutes from the commuter rail, this home makes commuting throughout Massachusetts a breeze while still offering the comfort of a residential neighborhood.

16 Marie Dr, Middleboro

$550,000

3 Beds ⋅ 1 Baths ⋅ 73539976 MLS

Conveniently located near shopping, restaurants, and major highways, this charming 3-bedroom, 1-bath home offers comfort, character, and practical amenities. The spacious first-floor primary bedroom features a vaulted ceiling, creating a bright and airy retreat. Inside, you'll find an updated kitchen with granite countertops and a layout that flows seamlessly into the living area highlighted by a cozy fireplace. Outside, enjoy the convenience of covered carport parking during New England winters, new windows in 2025, and a large backyard workshop/shed equipped with electricity and propane heat—perfect for hobbyists, contractors, craftsmen, or additional storage. A brand-new septic system will be installed prior to closing, providing added peace of mind for the next owner. Whether you're looking for your first home, downsizing, or simply seeking a property with functional workspace and easy commuter access, this home is a must-see!

156 Bedford Street, Middleboro

$499,000

2 Beds ⋅ 2 Baths ⋅ 73539882 MLS

Welcome home to this beautifully renovated and move-in-ready gem, where classic charm meets modern convenience. From the moment you step into the inviting mudroom, you'll appreciate the thoughtful updates and attention to detail throughout. The stunning kitchen features granite countertops, stainless steel appliances, and ample cabinet space, making it perfect for both everyday living and entertaining. Just off the kitchen is a full bathroom with convenient first-floor laundry. The dining area opens to the backyard and deck, creating a seamless indoor-outdoor living experience including a new 400 sq ft patio. A cozy living room with an electric fireplace and a charming front porch complete the main level. Upstairs, you'll find two spacious bedrooms with generous closet space and a beautifully appointed full bathroom. Extensive renovations provide peace of mind, including roof, vinyl fencing, and all major mechanics are less than 5 years young!

89 West St, Middleboro

$799,900

3 Beds ⋅ 2 Baths ⋅ 73537380 MLS

Have you been looking for a home where you can expand your living space w/a 1 bedroom ADU? This home has been verbally ADU verified w/building dept w/no changes to size of septic; just a tie into current system per BOH. Woodshop in the front garage would be perfect for this. This beautiful home offers this kind of versatility w/unique amenities. There are 3-bedroom w/the primary bedroom fitting a king sized bed, 2 baths, kitchen w/SS appl, quartz countertops, custom cabinetry, center island & cedar closet, comfortable living room, formal dining room w/its own fireplace, while the sunroom w/gas fireplace & minisplit will allow you to enjoy this space year-round. Main-level laundry adds to the home. The finished lower level expands your living space w/an office area & bonus room. Step outside to enjoy a large deck w/gazebo along w/an above-ground pool & deck. Car enthusiasts or those in need of extra workspace will love the 3 garages; 3 w/heat & 2 w/ built in a/c. Also has an RV plug w/water source & 2 generator hookups.

536 Plymouth St, Middleboro

$599,800

4 Beds ⋅ 2 Baths ⋅ 73537865 MLS

WOW! Incredible new low price for this cant miss property. Open House Sunday, 7/26 12-1:30. Opportunity, functionality, and charm come together in a move-in ready package. This versatile home offers flexible living spaces to fit a variety of lifestyles. A home office with its own separate entrances presents exciting possibilities for a home business, guest space, or potential ADU conversion. Inside, you'll find stunning wide-plank wood floors, a formal living room, formal dining room, family room/playroom, first-floor laundry, and a spacious kitchen with room for an eat-in nook. Upstairs are 4 bedrooms, one of which has been transformed into an impressive walk-in closet. The primary has vaulted ceilings and skylight, plus a separate stairwell from the first floor for added privacy. Comfort and efficiency are a focus with a gas stove, three-zone Energy Star Instinct heating system, and two ductless mini-splits. The oversized garage has a wood-stove and offers the perfect space for hobbies or storage. Easy access to commuter rail, shopping, dining, parks, library + more!

4 Star Ave, Middleboro

$430,000

2 Beds ⋅ 1 Baths ⋅ 73535267 MLS

This home has had many updates within the last three years including new kitchen cabinets, countertops and flooring. Bathroom has also been updated with a new tub, vanity and flooring. The hardwood floors were refinished, and a laundry room/ office has been added in one side of the garage. This two-bedroom home with attached two car garage has Town water and sewer and FHW by oil. Vinyl siding for easy maintenance and the potential for additional living space by converting the two-car garage. Close to schools and highway access. Easy to show.

31 Acorn St, Middleboro

$425,000

2 Beds ⋅ 2 Baths ⋅ 73534416 MLS

Welcome to the highly desirable Oak Point Community. This beautifully maintained home features an open concept floor plan that is ideal for entertaining, with gorgeous hardwood floors and a gas fireplace. The spacious kitchen has all new appliances and has plenty of storage with a cozy dining area complete with a built in bench seat. The dining room opens to a front sitting area and larger family room which provides access to a 3 season room with a pellet stove. The primary bedroom features a large private bathroom with all new fixtures and a walk in closet. The other bedroom is bright and spacious with a full bathroom nearby. The home offers a 1 car garage with a large storage area attached. It has a newer heating system, newer roof and a new hot water heater, and. a NEW whole house GENERATOR. The front entrance is new with vinyl and Trex decking. There are many amenities, such as bocce, pickleball, tennis, billiards, workout gym, an indoor pool and 2 outdoor pools, and much more.

4402 Pheasant Ln, Middleboro

$635,000

3 Beds ⋅ 2 Baths ⋅ 73533589 MLS

NEW PRICE & OPEN HOUSE SAT 6/27! Welcome home to this sun-drenched Colonial offering 1,756 sq ft of pristine main-level living space, plus a massive, professionally finished 23x23 lower-level bonus room—bringing your total functional living area to 2,248 sq ft! Set on a private 1.11-acre lot surrounded by mature trees, the main level features a seamless flow between the kitchen, family room, spacious living room, formal dining room, and a half bath. Upstairs, you’ll find three generous bedrooms with excellent closet storage, while the pristine lower level serves as the ultimate recreation space or home office. Outside, a long driveway provides ample off-street parking. Situated in a fantastic neighborhood with quick, unbeatable access to Route 495, this beautifully maintained property is a private commuter's dream!

27 N Grove St, Middleboro

$599,000

3 Beds ⋅ 2 Baths ⋅ 73533529 MLS

Step back in time where 18th-century grace meets modern day living in this 1740 antique Cape. Nestled on nearly 2 acres, this home showcases historical craftsmanship and a versatile layout. The main level offers a kitchen where sourdough bread deserves to be made by hand, a magnificent original fireplace & walk-in pantry. Off of the kitchen is a quaint library, a sun-filled front living room, a large den (once used as a first floor bedroom), a private home office & a bathroom. Relax in the serene sitting room or enjoy the breeze from the screened-in porch overlooking the tranquil koi pond. Easy interior access to a one car garage & workshop. Upstairs, you will find 3 bedrooms & a full bathroom. The crown jewel of this property is the spectacular custom-built treehouse, artisan-crafted from timber harvested directly from the property, a one-of-a-kind retreat for relaxation or creative inspiration. This rare estate offers the perfect blend of historic character and expanded living space.

65 Summer St, Middleboro

$724,900

4 Beds ⋅ 2 Baths ⋅ 73533391 MLS

Set far back from the road on 2.3 acres, this beautifully maintained 3–4 bedroom Cape offers a peaceful, retreat-like setting with privacy, comfort, and a flexible floor plan. All bedrooms are generously sized, including two conveniently located on the first floor, one currently being used as a home office. Hardwood floors run throughout, and the inviting dining room features a fireplace with a wood insert, adding warmth and character. This move-in ready home includes two full baths and numerous updates, including a heating system just 1.5 years old and central air only 6 years old. Outside, enjoy mature plantings that create a private backyard oasis, along with a shed equipped with electricity—ideal for hobbies, storage, or workspace. The attached 2-car garage offers walk-up storage above for added convenience. Abutting Pratt Farm with over 160 acres of walking and riding trails, this property provides a rare opportunity to enjoy nature right from your own property.

71 E Main St, Middleboro

$1,100,000

4 Beds ⋅ 3 Baths ⋅ 73532821 MLS

This Saltbox style home is just so impressive from top to bottom, stem to stern! Impressively landscaped. Enter into a pristinely maintained home and become absorbed with the attention to details in every room. Polished solid oak flooring leads you through to the LR with expanded windows, crown moldings and french doors. Or, the floor plan draws you beyond a spacious DR into a magnificent solid Cherry cabinet Kitchen with granite countertops, an oversized central island, a breakfast nook area and with spotless, top end appliances! De-stress and collect yourself daily in the fireplace Family Room with cathedral ceiling and exterior access to the inground pool and patio. The Primary Bedroom is generously sized with a full bathroom, 2 walkin closets and Hdwd floors. Completeing the 2nd level are three additional Bedrooms equally oversized. There are multiple outer buildings, attached 2 car garage, expandable walkup 3rd floor, fruit bearing plants, mature landscaping.

137 Cedar St, Middleboro

$899,000

3 Beds ⋅ 1 Baths ⋅ 73532671 MLS

Equestrian's dream! Step back in time while enjoying the comfort and convenience of modern living at this charming renovated 1800's farmhouse set on a meticulously maintained 1.8-acre lot. Extensive updates completed within the past year have thoughtfully preserved the home's timeless character while incorporating today's most desired features and improvements. (full list of recent updates available) A 30x36 Horizon Structures 5-stall barn, completed just six months ago and designed with both horse and owner in mind. Each 10x12 stall offers individual in-and-out access to private paddocks and is equipped with chew guards, fans, lighting, and camera monitoring. The professionally designed facility features premium drainage systems, quality footing, and outstanding attention to detail throughout. Custom tack room with built-in cabinetry/ample storage. A turn-key equestrian retreat where luxury, functionality,and timeless New England charm come together, Simply unpack, settle in and ride!

60 Benson St, Middleboro

$739,900

4 Beds ⋅ 3 Baths ⋅ 73531874 MLS

An exceptional opportunity awaits to own this amazing property located just a short stroll from the picturesque town center. Have you ever envisioned owning a residence that encompasses a Beautiful Main home, showcasing the epitome of modern living with an amazing updated kitchen,3 bedrooms, a garage, an expansive workshop (originally a milk bottling plant), an inviting entertainment area, a charming tiny house with heat, a spacious shed, a horseshoe driveway, and an extensive parcel of land? This remarkable property fulfills those dreams. Positioned on a acre of beautifully landscaped level lot with fruit trees, perennial gardens, The main home emanates character and allure, Maple hardwood floors grace the entire of home, adding a touch of timeless elegance. Newer Gas heating systems and Water Heater. The rear structure encompasses a 2 car garage, oversized workshop, above huge bonus room with bedroom and a 1/2 bath, endless possibilities for it, In-law's ,Au Pair suite & much more

19 Montello St, Middleboro

$410,000

3 Beds ⋅ 2 Baths ⋅ 73531008 MLS

"Oak Point"/ 2003 3 Bedroom & 2 Full Bath Handicap Accessible "Oak Point Unit"/One Level Living, Handicap Accessible Shower(s) & Garage Chair Lift-Can Stay/SUPER Private Location Within "Oak Point"-Off the Beaten Path-NO Units Behind Property/Charming Covered Entry/Cathedral Ceiling in Livingroom & Dining Room/Carpets Shampooed(June 2026)/HEATED 14/x12' Sun Room Addition w/Wood Laminate Flooring Overlooking Serene PRIVATE 21'x12' Deck/10'x12' Storage Shed/Eat-In Kitchen w/Dining Area(Refrigerator, Gas Stove, Dishwasher & Microwave Stay)/Laundry Off Kitchen(Staying)/Primary Bedroom w/Full Bath(Walk-In Shower)/Two Additional Bedrooms/Main Bath w/Step-In Shower, Safety Bars & Skylight/One Car Garage w/Opener, Additional Storage & Wheel Chair Lift/Famous "Oak Point" Amenities: Club House, Pools-Hot Tub, Tennis-Pickleball, Fitness Center & MORE!/Town Water & Municipal Electric/Convenient Commuting Locations-Close to Highways(44, 105, 495 & 24)& Less Than 5 Miles to NEW Middleborough Rail!

507 Crystal Way, Middleboro

$899,900

4 Beds ⋅ 3 Baths ⋅ 73530799 MLS

Set on a cul-de-sac lot in Middleboro, this spacious Colonial offers over 3,000 sq ft of above-grade living with 4 bedrooms, 2.5 baths, and a flexible 12-room layout. A dramatic two-story foyer opens to warm hardwood floors, generous living and dining areas, and a fireplaced living room filled with natural light. The granite kitchen features abundant cabinetry, tile flooring, dining area, and sliders to the deck, creating an easy flow for everyday living and entertaining. Upstairs, the oversized primary bedroom offers great space, while three additional bedrooms provide room for everyone. The finished lower level adds exceptional versatility with hardwood flooring and space ideal for a media room, gym, game room, or home office. Outside, enjoy a large deck, above-ground pool, professional landscaping, storage shed, and wooded backyard setting. Additional highlights include central air, tankless hot water, heated 2-car garage, and 12 off-street parking spaces.

10 Amanda Street, Middleboro

$465,000

3 Beds ⋅ 2 Baths ⋅ 73530629 MLS

Welcome to 5604 Oak Point Drive, Middleboro MA 02346 - This 55+ community has so much to offer such as multiple pools, putting green, tennis, huge club house with something for everyone. I was so very impressed by all the activities that are offered. Pool Tables, Bingo, Ballroom, Fitness center, basketball and I could go on!!! I have spoken with many owners there and they love it here. It's time to kick off your shoes and relax in a low maintenance way of living. This 3 bed, 2 bath, 2 car garage with a newer add on addition perfect for reading, relaxing, or enjoying your morning coffee or for entertaining. If you have been looking for something just like this, 5604 Oak Point Drive is the one for you...

5604 Oak Point Drive, Middleboro

$724,900

5 Beds ⋅ 3 Baths ⋅ 73530129 MLS

Beautifully remodeled home in Middleboro retains its old charm with modern updates .This 2 level main residence with attached 2 bedroom Accessory dwelling Unit is perfect for an In-Law set up or to bring in extra rental income. Both units showcase all newly remodeled kitchen with new stainless steel appliances and new hardwood floors as well as newly remodeled tiled bathrooms. Large barn on property can be used as storage or a bonus workshop area on a beautiful spacious lot with parking for 8 cars. Conveniently located near shopping, dining, schools and highway access. located 8 miles from Middleboro center.

36 Spruce, Middleboro

$749,900

3 Beds ⋅ 2 Baths ⋅ 73527479 MLS

Nestled on a beautifully landscaped lot surrounded by mature trees, this inviting home offers the perfect blend of privacy, comfort, and outdoor living. The fully applianced kitchen features granite countertops, tile backsplash, abundant cabinetry, center island seating, and opens seamlessly to the dining area with gleaming hardwood floors and an open layout ideal for entertaining. A bright family room with sliders overlooks the backyard and provides easy access to the patio. A separate living room offers additional space for gatherings and everyday living. Offering 3 spacious bedrooms, a second-floor skylite bonus room perfect for a teen or guest suite, and a second-floor office. Enjoy the deck, patio, expansive yard, and peaceful wooded setting. Additional highlights include hardwood floors, great natural light, a two-car garage, and excellent basement storage. Conveniently located near shopping, schools, and major routes. New septic to be installed!

5 Brook St, Middleboro

$575,000

4 Beds ⋅ 2 Baths ⋅ 73525836 MLS

Charming and move-in ready Cape-style home offering 4 bedrooms, 2 updated baths, and a spacious 2-car garage! This beautifully maintained home features an updated galley-style kitchen with stainless steel appliances, a large fireplaced living room perfect for cozy nights, and a wonderful blend of wood and LVP flooring throughout. The flexible floor plan includes a desirable first-floor primary bedroom, good-sized additional bedrooms, one full bath on each level, and the convenience of first-floor laundry. Filled with warmth and character, this home combines classic charm with modern updates. Step outside to a backyard designed for relaxing or entertaining, complete with mature trees, a beautiful stone wall, and plenty of outdoor space to enjoy. A wonderful opportunity to own a turnkey home with comfort, style, timeless appeal, and located in a desirable Middleboro neighborhood!

89 School St, Middleboro

$489,000

4 Beds ⋅ 2 Baths ⋅ 73521805 MLS

Great opportunity to own this charming Antique Colonial just moments from the heart of town! Rich with character and timeless appeal, this well-maintained home offers an abundance of living space with an inviting open floor plan, soaring 9-foot ceilings, and beautiful original trim work that showcases its historic charm. The spacious modern kitchen features ample cabinetry and flows seamlessly into the living room with hardwood flooring—perfect for everyday living and entertaining alike. The main level also offers a generous first-floor bedroom, oversized full bath, and a fantastic bonus entertainment room, a charming three-season porch, and access to the large deck—perfect for relaxing or hosting guests. Upstairs, you’ll find three comfortable bedrooms and a convenient half bath. Step outside to your private fenced-in backyard retreat featuring an above-ground pool, storage shed, and off-street parking for 2-3 vehicles. Commuters will love the close proximity to the train station, whi

166 Center Avenue, Middleboro

$780,000

4 Beds ⋅ 3 Baths ⋅ 73511717 MLS

This 2024 NEW Build, 4 Bed, 3 Bath Colonial offers Quality construction on 1.38-acres among new homes. Bright with a modern color palette and 3.25” Oak Hardwood floors BOTH floors. The main-level features a living area Open to eat-in kitchen with granite counters, large island, white cabinets, stainless appliances and modern fixtures. Sliders lead to a composite deck, manicured lawn and wooded views. First floor hosts a 4TH Bedroom OR use as office/formal dining/playroom, laundry/pantry, garage entry and Bathroom w/shower. Upstairs find 2-Bedrooms, 2nd Bathroom and 3rd Bed/Primary Suite with 3rd Bath and 2 walk-in closets. More Highlights: shaker vanities/granite in Bathrooms, insulated basement w/2 full-sized windows and interior/exterior access stairways, pull-down attic, attached ~600SF 2-car garage with finished ceiling/walls, vinyl siding, 2-zone heat/AC, 200-AMP, 4-Bed septic, irrigation, & on-demand hot water. Minutes to downtown Middleboro, I-495, Rte.44 and New Train Station.

287 Wareham, Middleboro

$599,000

5 Beds ⋅ 4 Baths ⋅ 73514428 MLS

Steeped in local history, the Nathaniel Eddy House in scenic Eddyville, East Middleborough, is offered for the first time since 1965. Ideally located just down the street from the Eddy Homestead and the Joshua Eddy House, it sits at the heart of this storied enclave. Built in 1806, this rare property features 5 bedrooms, 7 fireplaces (including 2 in bedrooms), wide pine floors, exposed beams, and a hidden staircase. A long ell connects the home to the barn and offers potential for a first-floor primary suite. Oversized stone pillars frame the driveway, reflecting its historic charm. The property includes multiple barns, including a separate barn with stall and hayloft. Set on 1.66 acres with an additional .64-acre parcel included (over 2 acres total). Brand New Roth Tank installed April 2026. If you’ve ever dreamed of preserving a piece of local history, this is your chance. Sold as-is; buyer responsible for new septic.

155 Plympton Street, Middleboro

$749,900

3 Beds ⋅ 2 Baths ⋅ 73510731 MLS

Welcome to 77 Thomas Street Middleboro! A spacious 2,550 sq ft Contemporary Cape set back on a private 2.77-acre lot. This 3 bed, 2 bath home features an open layout with a stunning living room showcasing cathedral ceilings, hardwood floors, and a floor-to-ceiling stone fireplace. The eat-in kitchen offers stainless steel appliances and access to the rear deck—perfect for entertaining. Two bedrooms and full bathroom are located on the main level, while the private primary suite upstairs features vaulted ceilings, skylights, and a full bath with whirlpool tub. Additional highlights include a second-floor family room with fireplace overlooking down to the living room & dining room, Laundry in the first floor, 2-car garage, irrigation, generator hook-up, and a newer heating & septic system. Conveniently located near major highways and under 4 miles to the commuter rail.

77 Thomas St, Middleboro

$425,000

2 Beds ⋅ 2 Baths ⋅ 73510435 MLS

Welcome to easy living at Oak Point.This bright and sunny 2-bedroom home at 6802 Oak Point Drive has been freshly painted and is ready for its next chapter. The interior offers a clean, inviting feel with natural light pouring in, creating a warm and comfortable space you’ll actually want to spend time in. Located in the sought-after Oak Point 55+ community, this home is all about lifestyle. Residents enjoy a relaxed, low-maintenance way of living with access to exceptional amenities, including multiple pools, tennis courts, a clubhouse, fitness center, and a full calendar of social activities. Whether you’re looking to stay active or just kick back and enjoy the surroundings, it’s all right here.If you’ve been waiting for a simple, turnkey home in a vibrant community where everything is taken care of, this is it.

6802 Oak Point Drive, Middleboro

$825,000

3 Beds ⋅ 3 Baths ⋅ 73510247 MLS

Opportunity knocks with this stunning 2,072 sq. ft. new construction home, perfectly positioned for commuters with quick access to Routes 44 and 495. Designed for effortless modern living, the first floor features a spacious layout including a living room, formal dining area, and a kitchen that flows into a comfortable family room. From the family room, a slider leads to a rear wood deck with stairs to the backyard—perfect for outdoor entertaining—while the front of the home boasts a durable, low-maintenance composite porch. The main level also conveniently hosts a half-bath with integrated laundry. Upstairs, you’ll find three generous bedrooms, including two with large walk-in closets. A walkout basement offers a great footprint for future expansion, and with construction still underway, there is still time to pick your colors and select upgrades to truly make this home your own!

49 Thompson St, Middleboro

$949,000

4 Beds ⋅ 4 Baths ⋅ 73505593 MLS

The "Investor’s Dream" -Rare Development Opportunity or Live/Work Estate in Middleboro! Unlock the massive potential of 357 Wareham St... Situated on a sprawling 2.62-acre level lot, this property is a goldmine for developers, entrepreneurs, or those seeking a multi-generational compound! The site features a beautifully updated 4-bedroom, 3.5-bathroom Colonial (full interior remodel by the amazing re:fab!) boasting over 2,500 sq. ft. of living space. Inside, you’ll find a beautiful kitchen, both a first-floor and second-floor primary suite, both complete with a gorgeous 3/4 bath with huge walk-in showers (YES, TWO PRIMARY BEDROOM SUITES!!)! The Real Value: Development Potential: Conceptual plans are attached for THREE HOMES and THREE TWO CAR GARAGES! Seller is providing a conceptual plan for you to complete this project. See attached conceptual plan. Commercial Use: Zoning allows for unique "live-where-you-work" opportunities. Run your business right from home with so many options!

357 Wareham St, Middleboro

$369,900

3 Beds ⋅ 2 Baths ⋅ 73502190 MLS

Welcome to the 55+ Oak Point Community! This home is set on a private wooded lot for added peace and privacy. Living room features an open floor plan highlighted by a vaulted ceiling, creating a bright and airy feel. The eat-in kitchen offers gas cooking, two-toned cabinetry, and ample prep space, while the formal dining area is perfect for entertaining. The main bedroom includes double closets and a private bath with a skylight. Two additional generously sized bedrooms, central air, and a newer roof (2016) add to the home’s appeal. The attached One-car garage is ideal for New England winters. Enjoy resort-style living with HOA amenities including three swimming pools, tennis, pickleball, bocce courts, a library, billiards room, and fitness center. HOA covers sewer, trash, lawn care, and snow removal—plus no real estate taxes! Settled near Rt 105, the Sportmans Club and more.

1307 Blueberry Circle, Middleboro

$399,999

3 Beds ⋅ 1 Baths ⋅ 73485743 MLS

PRICE REDUCED-Don't miss this opportunity!Charming 3-bedroom Colonial featuring a welcoming covered front porch and a private, spacious back patio—perfect for relaxing or entertaining. Town water, sewer, gas, and municipal electric. Off-street parking with shared driveway easement. “Cedar Impression” siding and recently updated roof. Handicap accessible: back ramp, under-counter wheelchair access, wide doorways, and a luxurious walk-in first-floor shower. Freshly painted interiors, cozy master bedroom, and a bright eat-in kitchen with new appliances. The living room is airy and inviting, complete with, central air, plastered walls with full insulation, upgraded electric, new vinyl windows, and updated bath and kitchen. First-floor laundry and bath provide ultimate convenience.Ideally located near schools, library, restaurants, shops, playgrounds, and commuter-friendly paths.SOLD AS IS

17 School St, Middleboro

$469,000

3 Beds ⋅ 2 Baths ⋅ 73480769 MLS

Located in Middleborough’s desirable West End, just steps from ball fields, playgrounds, and neighborhood amenities, this updated 4-bedroom, 2-bath Antique Colonial combines classic charm with extensive recent improvements. Many updates completed between 2021–2024 including electrical and plumbing, a second-floor full bath, and renovated first-floor bath. The kitchen has been fully updated with new cabinetry and appliances, while additional upgrades include blown-in insulation and newer water heater (2021) offering low-maintenance ownership for years to come. Additional features include an enclosed heated porch, washer/dryer hookups, a fenced yard, town water and sewer, and a large garage with electricity, offering potential for a future in-law or ADU-style conversion on the second floor (buyer to perform due diligence; repairs needed). Assurant Premium 1 year Home Warranty included.

958 Centre St., Middleboro

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