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$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..
$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, Leaf Guard, gutter system 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.
$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.
$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.
$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

Listing courtesy of Listing Agent: Shauna Fanning from Listing Office: William Raveis R.E. & Home Services.
$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

Listing courtesy of Listing Agent: Brenda Busch from Listing Office: Busch Realty Group, LLC.
$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

Listing courtesy of Listing Agent: Fern Langella from Listing Office: The Firm.
$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

Listing courtesy of Listing Agent: Pamela Coletti from Listing Office: Keller Williams Realty Colonial Partners.
$775,900
3 Beds ⋅ 3 Baths ⋅ 73421533 MLS
Welcome to this beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Tanglewood neighborhood. Move-in ready and featuring a brand-new roof, this home offers comfort, functionality, and year-round comfort with central air conditioning. The spacious floor plan includes inviting living areas, a main-floor office or den, and a finished basement ideal for a recreation room, media room, gym, or additional living space. The primary suite features a remodeled en-suite bath and a custom walk-in closet. Two additional bedrooms and a full bath provide plenty of space, while a convenient half bath serves the main level. Enjoy your private backyard oasis with an in-ground swimming pool, perfect for relaxing or entertaining. The attached 2-car garage includes loft storage and an electric bike lift.

52 Saddleworth Way, Middleboro

Listing courtesy of Listing Agent: Kris Lippi from Listing Office: Get Listed Realty, LLC.

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