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

112 Spruce St, Middleboro

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

Listing courtesy of Listing Agent: Lawrence Costa from Listing Office: Century 21 Tassinari Gold.
$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

Listing courtesy of Listing Agent: Jennifer Soderquist from Listing Office: Conway - Mansfield.
$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.
$199,000
73521441 MLS
***Attention builders or developers*** Potential form A lot to the right side of #62 Rocky Meadow St. (to be subdivided from larger parcel), subject to perk, planning & concom approval. We are looking for builders/developers to do the engineering required to get lots approved. Price is for minimum required land/frontage to obtain a buildable lot. Price negotiable based on experience, number of lots you want to permit and your terms to close on each... Contact listing agent for further info.

64 Rocky Meadow St, Middleboro

Listing courtesy of Listing Agent: Doug Crane from Listing Office: Conway - Bridgewater.
$475,000
73517983 MLS
Beautiful 4-acre wooded parcel offering 541 feet of frontage with excellent potential. Appears to be all high and dry with no visible wetlands. Former farmland from decades ago, now a picturesque wooded setting with a nice blend of privacy and natural landscape. Strong potential for 2 Form A lots (buyer to perform own due diligence and obtain approvals). Plenty of frontage and flexibility for a private estate, or a family compound. Convenient location with easy access to highway and area amenities while still offering a country feel. Rare opportunity to own a large parcel with development potential and strong frontage.

Clay St, Middleboro

Listing courtesy of Listing Agent: Lawrence Costa from Listing Office: Century 21 Tassinari Gold.
$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

Listing courtesy of Listing Agent: Jessica Hancock from Listing Office: Coldwell Banker Realty - Westwood.
$1,200,000
3 Beds ⋅ 1 Baths ⋅ 73464405 MLS
Presenting APR 50 Acre Farmhouse w/ several barns-a unique opportunity to embrace a lifestyle steeped in history and tranquility. This Antique farmhouse offers 1515 sf of comfortable personal spaces for rest & rejuvenation. Several barns of which one was built in the 80s offering room for horses or other animals. There are hay barns, feeding stations, shelters, a barn for equipment, chicken sheds plus so much more. This Land is under Agricultural Protection. Gently set in the lake area of Middleboro/Lakeville. The home features wood floors, fireplaces which at one time was the main source of heat and cooking, now other methods of heating.This 1835 home allows one to own a piece of History and allow a family to live in a recreation area with the ponds and lakes and forest land. Currently there are horses, sheep & cows as well as chickens. This forever farm is a gem just waiting for the right forever farm family. There is a small pond & miles of trails to the lakes for riding.

295 Cherry St, Middleboro

Listing courtesy of Listing Agent: Marie Paulsen from Listing Office: Keller Williams Realty.

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