Middleboro Real Estate

Welcome to Middleboro, Massachusetts – a charming town nestled in the heart of Plymouth County. With a rich history dating back to 1669, Middleboro offers a unique blend of small-town charm and modern conveniences, making it an ideal place to call home.

Known for its picturesque landscapes and friendly community, Middleboro boasts a variety of outdoor activities. Residents can explore the stunning natural beauty of the nearby Myles Standish State Forest, which features miles of hiking and biking trails, serene lakes, and abundant wildlife. The town's historic downtown area is filled with delightful shops, cozy cafes, and local eateries, perfect for enjoying a leisurely afternoon.

Middleboro is also conveniently located, providing easy access to major highways and the commuter rail, making it a prime spot for those who work in nearby cities like Boston or Providence. Families will appreciate the highly-rated schools and a strong sense of community, with numerous events and activities throughout the year that bring neighbors together.

For those who appreciate history, Middleboro offers a wealth of historical sites, including the Middleborough Historical Museum and the iconic Oliver Mill Park, where you can learn about the town's rich past. With its vibrant community spirit, beautiful surroundings, and convenient location, Middleboro is not just a place to live; it’s a place to thrive. Come discover your new home in this delightful town where history meets modern living!

Newest Listings in Middleboro

$459,000

3 Beds ⋅ 2 Baths ⋅ 73576033 MLS ⋅ ['Plymouth Street Condominiums'] BLDG.

NO CONDO FEES! Title V passed. Welcome to this well cared for duplex offering three levels, including walk out basement to gorgeous fenced back yard.The first floor includes updated kitchen ( granite, stainless steel appliances and beautiful cabinetry), eat-in dining area, spacious family room and 1/2 bath. Second level has three bedrooms (main bedroom with walk in closet) and full bath. Your walk out basement ( you may finish) leads to great yard for relaxation and entertainment. Off street parking and front porch. Convenient to amenities including short distance to Public T Station. Call to view this special home.

581 Plymouth St Unit 581, Middleboro

Listing courtesy of Listing Agent: Joanne Mecke from Listing Office: Conway - Mattapoisett.

$879,000

4 Beds ⋅ 4 Baths ⋅ 73575935 MLS

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

Listing courtesy of Listing Agent: Sherry Costello from Listing Office: Waterfront Realty Group.

$550,000

3 Beds ⋅ 2 Baths ⋅ 73575720 MLS

Charming 1847 Farmhouse with Character, Privacy & Modern Comfort. Step into a piece of history with this renovated home with the craftsmanship of its era. Set on an expansive lot that comes to a point between Plymouth Street and Everett Street, the property offers a rare combination of privacy and natural beauty. The original architectural details complement the home's modern conveniences, including wide pine floors, high ceilings, exposed wood beams, (original to the house), decorative moldings, and built-in cabinetry. A double-sided fireplace between the living and dining room creates a warm and inviting atmosphere perfect for relaxing or entertaining. Just beyond, the large kitchen serves as the heart of the home. Exposed original beams, a generous center island, and a comfortable eat-in area blend old-world farmhouse charm with modern functionality. The adjacent laundry room adds convenience and practicality. A thoughtfully designed family room addition expands the home's living space and is filled with natural light, providing the perfect setting for everyday living, gatherings, or quiet relaxation. The main level offers two bedrooms and a bathroom, while the second-floor bedroom suite includes a private bath and kitchenette, creating a wonderful opportunity for guests or those seeking additional privacy and independence. Tall ceilings and skylights bring an abundance of natural light to the upper level. Additional highlights include a newer roof, newer furnace and water heater. This home has been lovingly cared for by the current owners for nearly 20 years; this special property is ready to begin its next chapter. Middleboro is an agricultural town surrounded by horse farms, and plenty of peace and tranquility!

294 Plymouth St, Middleboro

Listing courtesy of Listing Agent: Landry & Co. Realty Group from Listing Office: REMAX Executive Realty.

$674,900

3 Beds ⋅ 3 Baths ⋅ 73575453 MLS

Brand-new construction in Middleboro! Step inside this beautifully designed home featuring a bright, open-concept floor plan perfect for everyday living and entertaining. The spacious living room flows seamlessly into the dining area and stylish kitchen, all accented by attractive laminate hardwood flooring. The kitchen shines with a center island, quartz countertops, stainless steel appliances, and pendant lighting. Three generously sized bedrooms include a primary suite with a private bath. The unfinished basement offers plenty of storage and exciting potential for future expansion. Outside, relax or entertain on the stamped concrete patio overlooking the newly fenced backyard. Conveniently located just off Route 28 with easy access to schools, playing fields, shopping, dining, and more. Move right in and enjoy everything this brand-new home has to offer!

158 Wood Street, Middleboro

Listing courtesy of Listing Agent: Tom Dixon from Listing Office: Keller Williams Realty.

$399,900

2 Beds ⋅ 2 Baths ⋅ 73575395 MLS

NEW PRICE on this rare 2 bedroom single level condo! 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 gas 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 2nd 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.

151 Ashley Lane Unit 151, Middleboro

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

$1,299,900

4 Beds ⋅ 4 Baths ⋅ 73574032 MLS

Custom Colonial on 12 Private Acres – ADU/In-Law Potential. This 13-room custom Colonial offers over 5,900 sq ft of living space on a private 12-acre lot. The first floor features a Thomasville kitchen with double wall oven and walk-in pantry, media room with surround sound, formal dining room, living room, sitting room, office, mudroom, and half bath. Upstairs offers 4 bedrooms, including a primary suite with two walk-in closets (bath to be finished) and a second en-suite bedroom, plus two additional bedrooms and a main bath with garden tub. Laundry room completes the second floor. Oversized 3-car garage with industrial-sized doors offers potential for a 35x36+ ADU/in-law suite above. Additional features include Hardie board siding, underground electric, whole-house water filtration, and 400-amp Weil-McLain system. Flexible living at every turn — a must-see! Showings Start Now! Some pictures are virtually staged.

60 Precinct, Middleboro

Listing courtesy of Listing Agent: Kelly Crowley from Listing Office: Keller Williams Elite.

$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

Listing courtesy of Listing Agent: Cassandra Wadden from Listing Office: Keller Williams Realty Colonial Partners.

$749,900

3 Beds ⋅ 3 Baths ⋅ 73573236 MLS

Welcome Home To 32 Pocksha Dr! Set at the end of a cul-de-sac in a desirable neighborhood, this beautifully maintained Colonial was newly built in 2019 and offers the perfect combination of privacy, space & modern finishes. Featuring 3 bedrooms, 2.5 baths & an attached 2-car garage, this home sits on 1.39 acres with a professionally landscaped yard & irrigation system. Step inside to an inviting floor plan featuring formal dining & living rooms and an impressive eat-in kitchen complete W/ Farmer's Sink, Center Island, Quartz Countertops, SS Appliances, Soft-Close Cabinetry, Gas Stove, Herringbone Tile Backsplash & Recessed Lighting. A slider leads to the PVC back deck overlooking the woods, creating a peaceful setting to relax or entertain. Convenient first-floor laundry completes the main level. Upstairs, retreat to the spacious Primary Suite W/ Walk-In Closet & Private Full Bath featuring Double Vanity, Quartz Countertops & Walk-In Shower. Additional features include Custom Vinyl Blinds, Central Air, Propane Gas Heating W/ Hydro Air, Electric Hot Water Tank, Private Water W/ Filtration & Softener System & affordable Middleboro Municipal Electric. The full basement W/ Regular-Sized Windows offers plenty of storage & great potential for future expansion. Move right in & enjoy everything this beautiful home has to offer!

32 Pocksha Dr, Middleboro

Listing courtesy of Listing Agent: Dan Gouveia Team from Listing Office: Keller Williams Realty.

$399,900

2 Beds ⋅ 2 Baths ⋅ 73573193 MLS ⋅ ['ashley Place'] BLDG.

Newly Offered/Showings Begin @ Saturday Open House 11-12:30pm/SOUGHT After "Ashley Place" Condominium/Stylish "Barrington" Townhouse Style w/Superb Architectural Features(Cathedral Ceiling, Moldings, Skylight, Sunken Livingroom)Situated on a Beautiful 35 Acre "Park Like" Setting/Front-Covered Farmer's Porch/Gleaming WOOD Flooring Thru Out(Downstairs(Livingroom & Dining Room)& Upstairs(Stairs, Hall & Bedroom(s)/Tiled Foyer(Skylight, Plant Shelf, 16'2" CATHEDRAL Ceiling)/BRIGHT & OPEN Floor Plan w/SUNKEN Living Room(Wood Burning Fireplace)& Dining Area Leading to 14'x12' Deck That Overlooks PRIVATE Wooded Area/Kitchen(Eat-In)w/Tiled Flooring/SPACIOUS Master w/Closeted Dressing Area/FULL Basement w/Finished Room-Separate Laundry Room/Town Water, GAS(Gas Heat) & Municipal Electric(Middleborough Gas & Electric)/CENTRAL AIR/Superb Commuting Location-Convenient & Close to Highways(28, 105, 495 & 24), Schools, Downtown Amenities(Post, Library, Cafe)& Under 4 Miles to the New Middleborough Commuter Rail!

163 Ashley Lane Unit 163, Middleboro

Listing courtesy of Listing Agent: Kyle Belken from Listing Office: Realty One Group, LLC.

$269,900

1 Beds ⋅ 1 Baths ⋅ 73573114 MLS ⋅ ['38-40 School Street Condominium'] BLDG.

Welcome to Downtown Living offering a beautiful blend of Historic Charm and Modern conveniences of nearby Restaurants, Shopping, Repair shops, Clubs, Churches, Salons etc. This 7 Unit condo complex is Owner Occupied and Renovated just 3 Years ago. The interior is Bright with Tasteful Updates to all rooms, The Extra Laundry/ Pantry Space is a real Plus to the Kitchen area. The Kitchen offers stainless appliances and Granite tops for a modern culinary Look. The Full Bath is Clean, Bright w/ a Granite top Vanity. A smaller area just off Kitchen can be used as Walk-in Closet/ or Office area w/ outside egress.. This 1st Floor- Garden Style Unit has a Beautiful Covered Welcome Porch to Enjoy Peace and Relaxation. The Condo has assigned Parking. Easy access to Rts 44 & 105,and18/28 and Near by T Station . A Great Starter Home OR Just a wonderful opportunity for the Downsizer! Don't Pay Rent, when you can Own this lovely Gem!

38-40 School St Unit 40-2, Middleboro

Listing courtesy of Listing Agent: Karen M. Pettenati from Listing Office: Fathom Realty MA.

$569,900

3 Beds ⋅ 1 Baths ⋅ 73572436 MLS

Step into something truly special at Woods Pond...a charming A-frame retreat with storybook character, chalet-inspired details and a rare waterfront setting. Even the name on the front of the home has a story: “Asnemscussett,” the historic Native American name for Woods Pond, believed to reference the brook flowing over small stones. Surrounded by mature trees on a double lot, this distinctive year-round home offers water views from all three levels and direct access to the lake, with 125 feet of waterfront. The main level welcomes you with open-concept living, dining & kitchen area, featuring gas cooking and a floor-to-ceiling fieldstone wood-burning fireplace that anchors the space. A first-floor bedroom adds flexibility for guests or one-level living. Upstairs, two additional rooms each enjoy their own private balcony, creating peaceful spots to take in the wooded surroundings & water views. The finished lower level adds even more living space with a comfortable family room featuring custom built-in cabinetry & a cozy wood stove. A spacious laundry & storage area provides excellent functionality, while walk-out access leads to a stone patio overlooking the water. From there, outdoor stairs lead down to the lake, making it easy to launch a kayak or canoe to enjoy life on the water. A large shed & carport provide valuable storage, while the convenient location offers easy access to major highways and the commuter rail. Whether you're looking for a year-round home, weekend escape or possible rental income, this one-of-a-kind Woods Pond property invites you to slow down, settle in & enjoy the view. (photos with furniture are virtually staged to provide inspiration)

9 Lakeview Ter., Middleboro

Listing courtesy of Listing Agent: David Michael from Listing Office: Conway - Lakeville.

$599,900

3 Beds ⋅ 2 Baths ⋅ 73572145 MLS

Discover a home where comfort meets classic charm. This attractive single-family residence spans 1421 square feet and is presented in great condition, offering an immediate sense of welcome. The heart of this home is its kitchen, designed for both culinary exploration and everyday living. It features sleek stainless steel appliances, providing a modern touch to a timeless space. With three well-proportioned bedrooms and one full bathroom, alongside a convenient half bathroom, this residence accommodates a variety of lifestyles. The exterior, a harmonious blend of Cape Cod and bungalow architectural styles, exudes curb appeal and promises a relaxed living experience. Further enhancing the property's functionality is a full basement, offering additional space for storage or future customization. This is an exceptional opportunity to embrace a lifestyle of ease and comfort in a thoughtfully designed home. Close to shopping and highway. Come take a peak on September 12th for a first viewing

22 Starrett Ave, Middleboro

Listing courtesy of Listing Agent: MaryAnn Dempsey from Listing Office: Lamacchia Realty, Inc..

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