Middleboro Homes with Pool Community Features

Middleboro Homes with Pool Community Features

Welcome to Middleboro, Massachusetts – a hidden gem nestled in the heart of Plymouth County. This charming town is steeped in rich history and offers a perfect blend of small-town charm and modern amenities. With its picturesque landscapes, vibrant community, and convenient access to major highways, Middleboro is an ideal place to call home.

One of the standout features of Middleboro is its welcoming atmosphere, where neighbors become friends and community events bring everyone together. Whether you’re strolling through the quaint downtown area, enjoying the local parks, or exploring the beautiful natural surroundings, you’ll quickly fall in love with the warmth and friendliness of this community.

For those seeking a home that offers both comfort and leisure, Middleboro boasts a selection of stunning properties with pool community features. Imagine coming home to a beautifully designed residence complete with a sparkling pool, perfect for cooling off during those warm summer days or hosting unforgettable gatherings with family and friends. These homes not only provide a private oasis but also foster a sense of community, as residents can enjoy shared amenities and socialize with neighbors in a relaxed setting.

In addition to the luxurious poolside lifestyle, Middleboro offers a wealth of recreational opportunities. From hiking and biking trails to nearby lakes and beaches, outdoor enthusiasts will find endless ways to enjoy nature. Plus, with top-rated schools and a variety of shopping and dining options, Middleboro has everything you need for a fulfilling lifestyle.

Explore the enchanting homes with pool community features in Middleboro, and discover why this charming town is the perfect place to create lasting memories. Your dream home awaits!

Newest Middleboro Homes with Pool Community Features

$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.
$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.
$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.
$450,000
3 Beds ⋅ 2 Baths ⋅ 73550717 MLS
Welcome to Oak Point, a premier 55+ community offering resort-style living and exceptional amenities. This beautifully maintained 3-bedroom, 2-bath home features a bright, open floor plan designed for comfortable everyday living and effortless entertaining. The spacious kitchen flows seamlessly into the dining and living areas, while the private primary suite offers a relaxing retreat with an en-suite bath and ample closet space. Two additional bedrooms provide flexibility for guests, hobbies, or a home office. Enjoy your morning coffee or unwind in the peaceful outdoor space. Residents of Oak Point enjoy access to a clubhouse, fitness center, swimming pools, tennis courts, walking trails, and a full calendar of social activities. Experience low-maintenance living in one of the area's most sought-after active adult communities. Land lease fee, approx $970 mo. covers taxes, lawn care, snow and trash removal and more. First showings at Open House.

307 Blueberry Circle, Middleboro

Listing courtesy of Listing Agent: Jennifer Soderquist from Listing Office: Conway - Mansfield.
$429,000
2 Beds ⋅ 2 Baths ⋅ 73550121 MLS ⋅ ['The Groves At Middleboro Village'] BLDG.
Welcome to 21 Sycamore Dr, an immaculate end-unit condo at The Groves in Middleboro offering 1,556 sq. ft. with 2 bedrooms and 1.5 baths. The main level features hardwood floors, great natural light, and an easy flow into the dining area and kitchen. The kitchen includes brand-new appliances and direct access to deck for added outdoor space. Upstairs offers two spacious bedrooms with strong closet space, including a second bedroom with a walk-in closet. The full bath features a double vanity with laundry located within the bathroom. The full basement provides storage with the opportunity to create a space that fits your needs, while the attached garage adds convenience. Features include central air, central vacuum, 200 amp electrical service, newer high-efficiency tankless boiler, plus more. Located in a desirable area near Route 44, highways, shopping, dining, and amenities, this condo offers low-maintenance living. First showings begin July 19th from 11 AM–1 PM.

21 Sycamore Dr Unit 21, Middleboro

Listing courtesy of Listing Agent: Miguel Camara 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.
$709,000
3 Beds ⋅ 3 Baths ⋅ 73546901 MLS
Tucked away at the end of a quiet dead-end street, this brand-new Colonial sits on a desirable corner lot, offering privacy and a peaceful setting. This beautiful home features 3 bedrooms and 2.5 baths, including a spacious primary suite with a private bath and two walk-in closets. The main level offers a generously sized living room and a stunning kitchen with white cabinetry, black hardware, granite countertops, and a center island. The dining area opens through sliding glass doors to a private back deck overlooking the backyard. You'll also find a half bath, a walk-in laundry room, and a versatile bonus room perfect for a home office, playroom, or formal dining room. The full walkout basement offers endless possibilities for future living space, storage, or a home gym. Enjoy modern finishes, a functional layout, and all the benefits of brand-new construction in this beautiful move-in-ready home.

5 Sand Street, Middleboro

Listing courtesy of Listing Agent: Kaylee Emerson from Listing Office: JLK Realty.
$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.
$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.
$639,900
7 Beds ⋅ 2 Baths ⋅ 73514466 MLS
Well-maintained two-family in the heart of Middleboro offering strong rental income and major updates throughout. Second floor will be delivered vacant, first floor TAW. Each unit features 3 bedrooms, 1 full bath, an eat-in kitchen, and spacious living room. Many big-ticket improvements completed in 2022 including new electrical, all new plumbing, new roof, new siding, rebuilt exterior porches, new gutters, motion-detection lighting in common areas, new furnace for Unit 1, and new exterior doors. Full basement includes coin-op washer & dryer or separate washer/dryer hookups for each unit. Great opportunity for investors or owner-occupants seeking income potential in a convenient in-town location.

65 Oak Street, Middleboro

Listing courtesy of Listing Agent: Chelsea McLaughlin from Listing Office: RE/MAX Legacy.
$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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