Middleboro Homes with Highway Access Community Features

Welcome to Middleboro, Massachusetts – a charming town steeped in history and surrounded by natural beauty. Nestled in Plymouth County, Middleboro serves as a gateway to both urban excitement and serene countryside living. With its rich heritage dating back to the 17th century, this vibrant community offers a unique blend of small-town charm and modern conveniences.

One of the standout features of Middleboro is its exceptional highway access, making it an ideal location for commuters and families alike. With easy access to Route 495 and the Massachusetts Turnpike, residents can enjoy seamless travel to nearby cities like Boston, Providence, and Cape Cod. This connectivity not only enhances daily commutes but also opens up a world of recreational opportunities, from beach days to cultural excursions.

The homes in Middleboro reflect the town’s diverse character, ranging from classic New England colonials to contemporary designs, all set against a backdrop of picturesque landscapes. Many properties are situated within vibrant neighborhoods that boast community features such as parks, walking trails, and family-friendly amenities. Whether you’re enjoying a sunny afternoon at a local playground or exploring the scenic trails, Middleboro embraces a lifestyle that fosters connection and community.

In addition to its easy highway access, Middleboro is known for its friendly atmosphere and a strong sense of community. With annual events, farmers' markets, and local shops, the town offers a welcoming environment that makes it easy to feel at home. Discover the charm of Middleboro and explore the possibilities of finding your dream home in this delightful Massachusetts town!

Newest Middleboro Homes with Highway Access Community Features

$750,000

3 Beds ⋅ 3 Baths ⋅ 73556157 MLS

Welcome home to the sought-after Whispering Pines community! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect combination of comfort, privacy, and functionality. Relax on the charming farmer's porch and enjoy the peaceful wooded setting that provides exceptional privacy in both the front and back of the property. Inside, the sun-filled first floor is filled with natural light and features a spacious, open flow between the living room, kitchen, and dining area, making it ideal for everyday living and entertaining. A convenient first-floor laundry room and half bath add to the home's thoughtful layout. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite, along with two full bathrooms. Step outside to a fully fenced backyard complete with an above-ground pool, perfect for summer gatherings or quiet evenings at home. Additional highlights include a new boiler and hot water heater (both approximately one year old), attic storage above the attached garage, and a private well and water conditioning system. Conveniently located near local amenities while offering the tranquility of a desirable neighborhood, this home is ready for its next owners!

31 Pine Street, Middleboro

Listing courtesy of Listing Agent: Beatrice Murphy from Listing Office: Lamacchia Realty, Inc..

$440,000

2 Beds ⋅ 2 Baths ⋅ 73556144 MLS ⋅ ['Ashley Place'] BLDG.

Welcome home to one-level living! This rare 2 bedroom ranch style condo offers a truly elevated living experience with absolutely no expense spared. The main level displays hardwood floors, an elegant Italian tile foyer, Hunter Douglas window treatments & designer light fixtures. The kitchen is smartly designed with custom cabinetry, granite countertops and updated appliances. The light-filled dining area flows into a spacious living room with sky lights, a fireplace and a new Anderson slider. Step out onto your private deck outfitted with custom blinds for ultimate privacy overlooking a beautifully landscaped stone patio oasis and rock garden. Two generous bedrooms reside on the main floor with a full size en-suite bathroom. There is also a 1/2 bathroom on the main level. Downstairs, the finished basement expands your living space with 2 large, versatile rooms perfect for a home office, media room or guest quarters. This turn-key showplace won't last-schedule your showing today!

151 Ashley Lane Unit 151, Middleboro

Listing courtesy of Listing Agent: Donna Crandall from Listing Office: Busch Realty Group, LLC.

$389,000

3 Beds ⋅ 2 Baths ⋅ 73556084 MLS

Showings begin on Thursday 9/30, commuter open house, 5:00 - 7:00. Welcome to 408 Green Street in the desirable Oak Point 55+ Community! This attractive Princeton-style home is bright, open, and inviting, creating a great first impression from the moment you step inside. The thoughtfully designed split-bedroom floor plan offers both privacy and comfort. The primary suite features two closets and a private bath with a step-in shower. A nice sized living room flows seamlessly into the dining room, creating an ideal setting for everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, updated stainless steel appliances, vinyl flooring, and a morning room for casual dining (virtually staged with a table). A sliding glass door opens to the spacious screened porch with wood flooring—the perfect place to enjoy your morning coffee, unwind with a good book, or entertain family and friends. Located on the other side of the home are two additional bedrooms. These 2 rooms have been virtually staged to showcase their flexibility as a comfortable guest bedroom a craft room or home office, a full hall bath with a tub/shower combination. Built in 2003, this manufactured home on leased land offers 1,344 square feet of living space on a nicely situated lot. Additional features include attractive Pergo flooring in the main living areas and vinyl flooring in the kitchen and baths (no wall-to-wall carpeting), and a one-car garage. Updates: Refrigerator & stove April 2026, furnace and central air conditioning system replaced in 2022, gutter guards installed, and a roof replacement in 2016. Enjoy the exceptional Oak Point lifestyle with resort-style amenities, including three swimming pools (two outdoor), tennis and pickleball courts, bocce, a fitness center, gym, a 300-seat ballroom, billiards room, a library, and an extensive selection of clubs, classes, and social activities. Fee includes; lawn mowing, snow removal, trash pickup, sewer treatment and amenities.

408 Green Street, Middleboro

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

$485,000

2 Beds ⋅ 1 Baths ⋅ 73555583 MLS

If you have been searching for affordability, look no further! Offered below $500,000 and on Middleboro gas and electric, the carrying costs are sure to be the best deal on the South Shore. You can also enjoy peace of mind as a homeowner because many of the big-ticket items have been taken care of recently! The bathroom was redone in 2023, new windows in 2024, kitchen renovation in 2021, central air in 2023, switched from oil to gas in 2018 and installed a new furnace, siding and roof in 2024, replaced and upgraded electric panel in 2018 w/ 200 amp service, and septic was replaced in 2016. You can start packing, call the movers, and settle in to your new home! Enjoy one-level living with the option to expand in the large walkout basement. Set on a 1/2 acre, it is the perfect-sized yard for entertaining and enjoying a summer afternoon! Conveniently located near Rte. 44, this is an ideal location for commuters and anyone looking to enjoy all the South Shore has to offer in a short drive! The minute you enter this adorable ranch-style home, you will see the thoughtful upgrades and renovations made by the seller, as this home showcases pride of ownership throughout!

688 Plymouth St, Middleboro

Listing courtesy of Listing Agent: Moriah Wicker from Listing Office: Keller Williams Realty Colonial Partners.

$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.

$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.

$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.

$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.

$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.

$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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