Middleboro Homes with Shopping Community Features

Welcome to Middleboro, Massachusetts – a charming town nestled in the heart of Plymouth County. Known for its rich history and vibrant community spirit, Middleboro offers a unique blend of small-town charm and modern conveniences. With a population of just over 23,000 residents, this welcoming community is perfect for families, retirees, and everyone in between.

Middleboro is steeped in history, featuring picturesque landscapes and a variety of local attractions. From the serene shores of the picturesque Assawompset Pond to the historic sites like the Middleborough Historic District, there’s always something to explore. The town is also conveniently located just a short drive from major urban centers, making it easy to enjoy the best of both worlds – tranquil living with easy access to bustling city life.

One of the standout features of Middleboro is its vibrant shopping community. Residents enjoy a variety of shopping options, from quaint local boutiques to larger retail chains, ensuring that all your needs are met without venturing too far from home. The town’s commitment to fostering a thriving commercial scene means you’ll find everything from fresh produce at local farmers' markets to delightful dining options, making it a truly convenient place to live.

When it comes to homes, Middleboro offers a diverse selection that caters to various tastes and budgets. Whether you're looking for a cozy single-family home, a modern condo, or a spacious townhouse, you’ll find properties that fit your lifestyle. With its combination of community spirit, rich history, and shopping convenience, Middleboro is not just a place to live – it’s a place to call home. Come discover the charm of Middleboro, where your dream home awaits!

Newest Middleboro Homes with Shopping Community Features

$440,000

2 Beds ⋅ 2 Baths ⋅ 73556144 MLS ⋅ ['Ashley Place'] BLDG.

Welcome home to one-level living! This rare 2 bedroom ranch style condo offers a truly elevated living experience with absolutely no expense spared. The main level displays hardwood floors, an elegant Italian tile foyer, Hunter Douglas window treatments & designer light fixtures. The kitchen is smartly designed with custom cabinetry, granite countertops and updated appliances. The light-filled dining area flows into a spacious living room with sky lights, a fireplace and a new Anderson slider. Step out onto your private deck outfitted with custom blinds for ultimate privacy overlooking a beautifully landscaped stone patio oasis and rock garden. Two generous bedrooms reside on the main floor with a full size en-suite bathroom. There is also a 1/2 bathroom on the main level. Downstairs, the finished basement expands your living space with 2 large, versatile rooms perfect for a home office, media room or guest quarters. This turn-key showplace won't last-schedule your showing today!

151 Ashley Lane Unit 151, Middleboro

Listing courtesy of Listing Agent: Donna Crandall from Listing Office: Busch Realty Group, LLC.

$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.

$649,900

3 Beds ⋅ 3 Baths ⋅ 73552853 MLS

Tucked away at the end of a long private driveway and surrounded by nature, this inviting home offers the perfect blend of privacy, comfort, and thoughtful updates. Step inside to a warm and welcoming living room featuring soaring cathedral ceilings with exposed beams and a classic wood-burning fireplace, creating a cozy gathering space year-round. Enjoy the outdoors from the spacious composite deck, an ideal spot for entertaining or simply relaxing while taking in the peaceful natural surroundings. Recent improvements provide peace of mind, including a brand-new septic system, new boiler, replacement windows and doors, Roth oil tank, updated gutters, and a well pump and pressure tank that are less than five years old. A heated garage adds year-round convenience and versatility for vehicles, hobbies, or additional workspace. If you're looking for a home that offers privacy, modern mechanical updates, and a beautiful setting, this Middleboro property is one you won't want to miss.

6 Daniel Dr, Middleboro

Listing courtesy of Listing Agent: Robert Chestnut from Listing Office: Keller Williams Realty.

$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.

$529,900

3 Beds ⋅ 1 Baths ⋅ 73549154 MLS

Welcome to this well-maintained 3-bedroom, 1-bath home offering 1,701 square feet of comfortable living space. Situated on a desirable corner lot, this property features a fully fenced backyard with a rear deck, a dedicated fire pit area perfect for relaxing or entertaining, and a storage shed for added convenience. Enjoy peaceful views of nearby cranberry bogs and a picturesque pond, creating a serene setting right from your own property. Inside, you'll find a functional layout designed for everyday living. Ideally located with easy access to Routes 495, 44, 105, 58, and 24, this home offers both comfort and convenience for commuters. Whether you're a first-time homebuyer, downsizing, or simply looking for a move-in-ready home, this property is one you won't want to miss.

812 Plymouth St, Middleboro

Listing courtesy of Listing Agent: David Silva from Listing Office: RE/MAX River's Edge.

$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.

$249,900

2 Beds ⋅ 1 Baths ⋅ 73548212 MLS ⋅ ["Wood's Pond Condo"] BLDG.

Are you looking for a seasonal cottage/condo {4/15-10/15} to spend the rest of the summer in? This 2-bedroom condo could be yours. It's nestled in the woods on Woods Pond. It has cathedral ceiling, giving it an open feeling. There have been many updates, including central A/C, heat, plus on-demand hot water and roofing. Just unpack and move right in. Most furnishings are included and sold as is. There is extra parking for guests. This complex of homes has a private beach and a picnic area. They schedule events for the kids and adults. It's a real community of people. Middleboro has plenty of shopping and a commuter rail plus it's minutes to Route 495.

16 Kings Way Unit 22, Middleboro

Listing courtesy of Listing Agent: Arlene Hanafin 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.

$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.

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