Middleboro Real Estate

Middleboro Real Estate

Welcome to Middleboro, Massachusetts – a charming town nestled in the heart of Plymouth County. With a rich history dating back to 1669, Middleboro offers a unique blend of small-town charm and modern conveniences, making it an ideal place to call home.

Known for its picturesque landscapes and friendly community, Middleboro boasts a variety of outdoor activities. Residents can explore the stunning natural beauty of the nearby Myles Standish State Forest, which features miles of hiking and biking trails, serene lakes, and abundant wildlife. The town's historic downtown area is filled with delightful shops, cozy cafes, and local eateries, perfect for enjoying a leisurely afternoon.

Middleboro is also conveniently located, providing easy access to major highways and the commuter rail, making it a prime spot for those who work in nearby cities like Boston or Providence. Families will appreciate the highly-rated schools and a strong sense of community, with numerous events and activities throughout the year that bring neighbors together.

For those who appreciate history, Middleboro offers a wealth of historical sites, including the Middleborough Historical Museum and the iconic Oliver Mill Park, where you can learn about the town's rich past. With its vibrant community spirit, beautiful surroundings, and convenient location, Middleboro is not just a place to live; it’s a place to thrive. Come discover your new home in this delightful town where history meets modern living!

Newest Listings in Middleboro

$399,000
3 Beds ⋅ 2 Baths ⋅ 73554455 MLS
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

Listing courtesy of Listing Agent: Jessica Fernald from Listing Office: Coldwell Banker Realty - Plymouth.
$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

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

Listing courtesy of Listing Agent: Robert Chestnut from Listing Office: Keller Williams Realty.
$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

Listing courtesy of Listing Agent: Emmie Flaherty from Listing Office: Keller Williams Realty Colonial Partners.
$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

Listing courtesy of Listing Agent: Tiffany Weigold from Listing Office: Keller Williams Elite.
$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

Listing courtesy of Listing Agent: Jennifer Soderquist from Listing Office: Conway - Mansfield.
$439,000
2 Beds ⋅ 2 Baths ⋅ 73550121 MLS ⋅ ['The Groves At Middleboro Village'] BLDG.
Welcome to 21 Sycamore Dr, an immaculate end-unit condo at The Groves in Middleboro offering 1,556 sq. ft. with 2 bedrooms and 1.5 baths. The main level features hardwood floors, great natural light, and an easy flow into the dining area and kitchen. The kitchen includes brand-new appliances and direct access to deck for added outdoor space. Upstairs offers two spacious bedrooms with strong closet space, including a second bedroom with a walk-in closet. The full bath features a double vanity with laundry located within the bathroom. The full basement provides storage with the opportunity to create a space that fits your needs, while the attached garage adds convenience. Features include central air, central vacuum, 200 amp electrical service, newer high-efficiency tankless boiler, plus more. Located in a desirable area near Route 44, highways, shopping, dining, and amenities, this condo offers low-maintenance living. First showings begin July 19th from 11 AM–1 PM.

21 Sycamore Dr Unit 21, Middleboro

Listing courtesy of Listing Agent: Miguel Camara from Listing Office: RE/MAX Real Estate Center.
$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

Listing courtesy of Listing Agent: David Silva from Listing Office: RE/MAX River's Edge.
$495,000
73548811 MLS
The subject is currently a vacant land parcel that contains approximately 1.59 acres and is located in the GU (General Use) Zone according to the town of Middleboro and is designated as Map: 79 Lot: 798. The subject is located in an industrial park/cul-de-sac

Abbey Lane, Middleboro

Listing courtesy of Listing Agent: Michael Lefrancois from Listing Office: Regal Commercial Real Estate.
$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

Listing courtesy of Listing Agent: Blake Starratt from Listing Office: RE/MAX Legacy.
$249,900
2 Beds ⋅ 1 Baths ⋅ 73548212 MLS ⋅ ["Wood's Pond Condo"] BLDG.
Are you looking for a seasonal cottage/condo {4/15-10/15} to spend the rest of the summer in? This 2-bedroom condo could be yours. It's nestled in the woods on Woods Pond. It has cathedral ceiling, giving it an open feeling. There have been many updates, including central A/C, heat, plus on-demand hot water and roofing. Just unpack and move right in. Most furnishings are included and sold as is. There is extra parking for guests. This complex of homes has a private beach and a picnic area. They schedule events for the kids and adults. It's a real community of people. Middleboro has plenty of shopping and a commuter rail plus it's minutes to Route 495.

16 Kings Way Unit 22, Middleboro

Listing courtesy of Listing Agent: Arlene Hanafin from Listing Office: RE/MAX Real Estate Center.
$1,650,000
73547995 MLS
Newly Offered-Location, Location, Location/Sought After & Central 2.14 Acre Rare Commercial SITE(GENERAL USE Lot With 342.85' of Frontage on Busy Route 28-Wareham Street)/Off Exit 8 Route 495 South Middleborough)/High Traffic Count & Great Visibility/Many Possibilities Available: Motor Vehicle Sales, Hotel, Retail, Restaurant, Business or Professional Office(Including Medical), Bank, Warehouse, Manufacturing, Funeral Home, Medical Clinic, Movie Theatre....Much More/Former Location of Landmark "Ben Howes Chicken House Restaurant"/Cleared-Flat Parcel/Conveniently Located off 495(Superb Access to Cape Cod and Only 5 Miles and 1 Exit to NEW Middleborough Commuter Rail!

450 Wareham Street, Middleboro

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