Browse All Middleboro MA Properties with Pool for Sale

Ideally located less than a half mile from route 495 and the new commuter rail station! This multigenerational home is rich with character and reminiscent of a bygone era with beautiful architectural details such as a curved staircase, multiple built-ins, wide pine wood floors, decorative moldings, 3 wood burning fireplaces, 2 gas fireplaces, and a pantry with a wet bar. Set on a one-acre level lot, the flexible floor plan includes a main house with 3-4 bedrooms, 2 ½ baths, and an attached accessory apartment offering 1 bedroom, 1 bath, a custom designed kitchen, and a large garage that offers additional space. Enjoy beautiful views of the inground saltwater pool, pergola and private backyard surrounded by many beautiful perennial plantings. There is plenty of room inside to host holidays and gatherings, along with great outdoor space for summer entertaining! Many improvements during current ownership include a new asphalt shingle roof on the entire house and garage, new luxury vinyl plank flooring in kitchen and den, replacement of 5 skylight windows, pool converted to salt water, new liner, pump and tank, four composite decks, composite outdoor shower, and new electric garage door and remote! Multiple new breaker panels and rough plumbing were installed by previous owner for potential transformation into a multiple dwelling. Easy access to major roadways, and just minutes to downtown Middleboro with its many restaurants, shops, art and cultural centers and an elementary school that abuts the property!

100 S. Main St., Middleboro

$599,900

3 Beds ⋅ 1 Baths ⋅ 73573809 MLS

Set back off Old Center St on 2.72 wooded acres, this raised ranch offers exceptional outdoor living. A deck and patio combination is ideal for hosting, and the in-ground pool makes every summer feel like a staycation. Inside, hardwood floors run through the entire first floor. The living room features a vaulted ceiling that adds an open, airy feel, The kitchen offers granite counters with stainless appliances. A standout feature is the bonus room just off the kitchen, a flexible space perfect as a formal dining room or sitting room, complete with a pellet stove for added warmth and charm. Three bedrooms complete the main floor, including a primary room with its own vaulted ceiling. Downstairs, a fully finished family room provides additional living space for any lifestyle. The paved driveway accommodates 8+ vehicles Built in 2002, the major systems still have plenty of life remaining. Schedule a showing and experience everything this home has to offer!

15 Old Center St, Middleboro

$549,900

3 Beds ⋅ 1 Baths ⋅ 73570150 MLS

Welcome to 38 Frank Street! This inviting 3-bedroom Ranch offers comfortable one-level living with plenty of space inside and out. Beautiful hardwood floors run throughout much of the home, and the freshly painted interior and exterior give it a clean, move-in-ready feel. The kitchen features white cabinetry, granite countertops, stainless steel appliances, a center island and tile flooring. Relax in the family room featuring a wood stove with a charming brick hearth. The primary bedroom offers double closets, and the full bath features an update tiled shower. Enjoy the comfort of forced-air gas heat and central air, with the heating system installed in November 2021. The roof is approximately 8 years old. Outside, the fully fenced backyard is made for entertaining, complete with an above-ground pool installed in 2020 with its own deck, fire pit, large storage shed and a separate entertaining/storage area with a wet bar. A full basement offers additional possibilities with a partially finished room, laundry area and plenty of storage. Conveniently located in Middleboro and ready for its next owner!

38 Frank St, Middleboro

$995,000

5 Beds ⋅ 5 Baths ⋅ 73568734 MLS

Own a rare piece of local 19th Century history with this iconic historical home custom built for P.T. Barnum entertainer, General Tom Thumb. Sitting in front of 114 acres of conservation land, with its distinctive Mansard roof, this nearly 4761 square foot Victorian is full of architectural character throughout, where 10 foot ceilings, exquisite original plasterwork, oversized hardwood doors, ornate hand turned railings and balusters, built ins, crown moldings, ceiling medallions and custom wall alcoves showcase craftsmanship rarely found today. A striking main staircase anchors the home, while a separate original servant staircase connects its four finished levels and offers a fascinating glimpse into the home's history. Thoughtfully updated over the years, the home blends historic character with modern comfort. The renovated chef's kitchen features custom cabinetry, high end appliances including a Viking gas stove and oven, and dramatic brick archways opening to the family room. A working dumbwaiter connects to the dining room and butler's pantry, while the original lower height stove is another unique reminder of the home's past. With 5 bedrooms, 4.5 bedrooms including a spacious primary suite, multiple gathering spaces, gas heating and central air, this property is as functional as it is nostalgic. Outside, the nearly 1.5 acre property was designed for entertaining. The fenced grounds feature an oversized in-ground pool, expansive patio, and a pool house with kitchenette and bath offering exciting potential for future ADU use, subject to buyer due diligence and required approvals. A separate cabana with built-in grill and Italian brick oven creates another destination for outdoor gatherings, while an awesome garden shed adds charm and useful storage. A heated and insulated three car garage provides abundant parking and storage. Rich in history, architectural detail and scale, the Tom Thumb House offers the rare opportunity to own a home with a story unlike any other, while still enjoying the space, amenities and comfort today's lifestyle demands.

351 Plymouth Street, Middleboro

$745,000

4 Beds ⋅ 4 Baths ⋅ 73568396 MLS

Reduced and Move in ready. Realocating Owners recognize some work is needed and have reduced to refelct. Offers are encouraged. Peaceful and Private, this charming home is nestled on a wooded cul-de-sac lot bordered by beautiful stone walls, offering nature at its best. The spacious interior features hardwood floors, a center-island kitchen, and a versatile formal dining room that can also serve as a home office. Built-in bookshelves and crown molding add warmth and character throughout. IN-LAW / SEPARATE LIVING QUARTERS offering a full bath, bedroom, living room and office or possible 2nd Kitchen. Step outside to your own backyard oasis, complete with a lagoon-style inground pool surrounded by lovely perennial gardens—perfect for relaxing, entertaining, and enjoying the beauty of every season. Convenient 3/4 bath for those outdoor activities and entertaining. Additional highlights include TOWN WATER AND TOWN GAS ! See Floor Plan in Pics.

10 Brenrae Dr, Middleboro

$399,777

3 Beds ⋅ 1 Baths ⋅ 73567710 MLS

Great opportunity in Middleboro! This charming 3-bedroom, 1-bath home offers a functional layout, plenty of character, and tons of potential for a homeowner looking to add their own personal touch. The property needs some TLC, but the bones and layout provide a great starting point to create a home that truly feels like your own. The home features a comfortable and practical floor plan with spacious living areas and three bedrooms. Outside, enjoy the beautiful backyard pool, perfect for relaxing and entertaining during the warmer months. With some updates and vision, this property could shine. Whether you're looking for a project to build equity or a home you can customize to your own taste, this is an opportunity worth seeing. A great value and one of the best opportunities currently available in Middleboro! Property is sold strictly AS IS. Schedule a showing today!

15 Hillside Ave, Middleboro

$815,000

3 Beds ⋅ 3 Baths ⋅ 73562520 MLS

Custom home built in 2020 and packed with upgrades! From the moment you arrive, the inviting farmer’s porch sets the tone for a home that blends modern style, comfort, and functionality. Inside, thoughtful design includes an open concept living room and chefs kitchen with large island. The first floor also offers a large dinning room, laundry room, massive mudroom and half bath. The 2nd floor features 3 bedrooms and 2 full bathrooms including a large primary suite with 2 walk-in closets and full bath. The basement provides great storage or a blank canvas for additional living space. Step outside and discover even more potential—a pool is already in place and ready for you to add your finishing touches and create the ultimate backyard oasis. With newer construction, custom details and a wonderful neighborhood setting, this is a home you won’t want to miss!

25 Cobblestone Ln, Middleboro

$849,000

3 Beds ⋅ 2 Baths ⋅ 73562337 MLS

OPEN HOUSES CANCELLED, SELLER ACCEPTED OFFER. This exceptional one-owner home offering nearly 3,000 sq ft of thoughtfully designed living space on 1.4 meticulously maintained & landscaped acres. Set on approx 200 ft of street frontage in an established Middleboro neighborhood, this property offers a private setting while remaining convenient to Rtes 44, 3 & 495. Step inside to a home created for both comfortable everyday living & memorable entertaining. The showpiece is the expansive, open-concept Great Room featuring soaring ceilings, a dramatic 16-ft stone FP & stunning curved balcony overlooking the space below. Beautiful 3/4” hardwood floors flow throughout, adding warmth & timeless character. Unique floating bedroom balconies add architectural interest, while the upscale billiard room provides another inviting space to gather. The finished lower level continues the entertainment theme w/a custom pub—the perfect setting for game days, celebrations or relaxing w/friends. Outside, the property transforms into your own family resort. Spend summer days around the impressive 20x40 inground pool framed by a beautiful stone apron, gather under the 18-ft pavilion or enjoy evenings around the stone fire pit. A 30x40 basketball/sport court adds even more opportunity for recreation right at home. Extensive stone walls & brick pavers surround the property, complementing the mature landscaping & showcasing the attention to detail throughout the grounds. A Hunter irrigation system helps maintain the lush landscape. A 3-car garage offers generous space for vehicles, storage, hobbies & recreational equipment. From the dramatic interior architecture to the resort-style backyard, this home has been carefully designed, maintained & enjoyed by its original owner.

35 Margaret Rd, Middleboro

$1,050,000

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

$482,000

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

$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

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