Browse All Middleboro MA Properties with Pool for Sale

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

Listing courtesy of Listing Agent: Peter Edwards from Listing Office: Hayden Rowe Properties.

$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

Listing courtesy of Listing Agent: Selling South of Boston Team from Listing Office: Keller Williams Realty Colonial Partners.

$519,900

3 Beds ⋅ 2 Baths ⋅ 73553246 MLS

Newly Offered! 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.

$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.

$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

Listing courtesy of Listing Agent: Matt Ciullo from Listing Office: Conway - Lakeville.

$799,900

3 Beds ⋅ 3 Baths ⋅ 73545512 MLS

Come home to a setting that feels like your own private retreat. Set on nearly 2 wooded acres, this custom Cape welcomes you with a bright, inviting foyer that opens to beautifully connected living spaces designed for both everyday comfort and effortless entertaining. The stunning living room, anchored by a striking stone fireplace, flows seamlessly into a spacious kitchen featuring granite countertops, ample cabinetry, and an open dining area where family and friends naturally gather. A sunroom invites quiet mornings with coffee, while the composite deck overlooks a backyard made for summer, complete with an above-ground pool, gardens, and room to unwind. Upstairs, the expansive primary suite is a true escape with a private balcony, walk-in closet, and spa-like bath with a whirlpool tub. Hardwood floors, generous room sizes, three full baths, a 2-car garage complete a home that offers the space, warmth, and lifestyle buyers have been searching for.

49 Plain St, Middleboro

Listing courtesy of Listing Agent: Janine Wuschke from Listing Office: Keller Williams Realty.

$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.

$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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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Middleboro Homes with Pool

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