Middleboro Homes with Walk/Jog Trails Community Features

Welcome to Middleboro, Massachusetts—a charming town nestled in the heart of Plymouth County, where history meets modern living. Known for its rich heritage and stunning natural landscapes, Middleboro offers a unique blend of small-town charm and convenient access to urban amenities. With its picturesque streets, vibrant community, and a plethora of recreational opportunities, it’s no surprise that Middleboro is a sought-after destination for families and outdoor enthusiasts alike.

One of the standout features of Middleboro is its extensive network of walk and jog trails that wind through the town’s scenic parks and natural areas. These trails provide residents with the perfect opportunity to embrace an active lifestyle while enjoying the beauty of the great outdoors. Imagine starting your day with a refreshing jog along the serene paths or taking a leisurely stroll with your family on a sunny afternoon. The community's commitment to maintaining these trails ensures that they are well-kept and accessible for all.

In addition to its beautiful trails, Middleboro boasts a variety of homes designed to cater to different lifestyles and preferences. Whether you’re looking for a cozy single-family home or a spacious property with room to grow, you’ll find a welcoming community that values both comfort and connection. With local parks, schools, and shops just a stone's throw away, Middleboro truly embodies the ideal balance of tranquility and convenience.

Discover the charm of Middleboro, where your dream home awaits amidst a community dedicated to outdoor living and a vibrant lifestyle. Come and explore all that this delightful town has to offer!

Newest Middleboro Homes with Walk/Jog Trails Community Features

$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.

$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.

$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.

$425,900

2 Beds ⋅ 2 Baths ⋅ 73571507 MLS

Welcome to Oak Point and this beautifully renovated home! Ideally situated with a peaceful, tree-lined yard, this residence was completely updated from top to bottom in 2019. Features include an updated roof, furnace, central A/C, water heater, solid hardwood flooring throughout, and a stunning kitchen with stainless steel appliances. The spacious primary suite offers a beautifully appointed full bath with twin vanities, marble countertops, walk-in shower, and two walk-in closets. Brushed nickel hardware and lighting add a fresh, modern touch throughout. A large deck provides the perfect spot for relaxing or entertaining, while the generous laundry/mudroom connects directly to the two-car garage for added convenience. Enjoy all that Oak Point has to offer, including three heated pools—one indoor and two outdoor—two spas, fitness center, billiards room, library, craft room, and a ballroom seating up to 500. Stay active with tennis, bocce, pickleball, and more, while an activities director coordinates approximately 75 activities each month. The park fee includes the lease, lawn maintenance, snow removal, and sewer. Best of all, there are no property taxes! This exceptional, move-in-ready home offers the lifestyle, amenities, and peace of mind you've been waiting for!

7012 Oak Point Dr., Middleboro

Listing courtesy of Listing Agent: Alysandra Nemeth from Listing Office: Redfin Corp..

$350,000

2 Beds ⋅ 2 Baths ⋅ 73569910 MLS

Welcome to Edgeway Estates, a pet-friendly, resident-owned 55+ community offering comfortable, single-level living in a desirable Middleboro location close to shopping, the train & major highways. Step inside to a bright, open floor plan featuring new luxury plank laminate flooring throughout. The spacious living room is highlighted by a gas fireplace & flows seamlessly into an additional living area, offering flexible space for a formal dining room, den or gathering area. The fully applianced kitchen features a new stainless-steel refrigerator & a convenient breakfast nook. An enclosed 3-season sunroom extends the living space & offers double sliders plus front-door access, creating a separate entryway. The second bedroom offers a built-in desk area & double closets. A separate mudroom provides exterior access & houses the furnace, water heater, laundry & trash compactor. Outside, enjoy a level lot, double driveway, brand-new 11x12 composite deck & brand-new 8x16 shed for additional storage. Roof replaced in 2025 with new skylights. Water heater 2023. The low monthly fee of $440 includes property taxes, water, sewer, trash removal & street snow removal. Cash or mobile home financing only; this home will not qualify for conventional financing. Photos with furniture are virtually staged to give inspiration.

29 Lyn Ln., Middleboro

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

$350,000

2 Beds ⋅ 2 Baths ⋅ 73569909 MLS

29 Lyn Ln., Middleboro

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

$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

Listing courtesy of Listing Agent: Ashley Trapp from Listing Office: The Simply Sold Realty Co..

$437,500

2 Beds ⋅ 2 Baths ⋅ 73568487 MLS ⋅ ['The Groves'] BLDG.

Welcome to easy townhouse living at The Groves in Middleboro! This inviting home offers a bright, open layout with laminate flooring and comfortable living spaces designed for everyday living and entertaining. The spacious kitchen features abundant cabinetry, stainless steel appliances, gas cooking, and a breakfast bar overlooking the living area. Upstairs, generously sized bedrooms offer plenty of flexibility, including a spacious primary bedroom. Enjoy the convenience of gas heat, central air, an attached garage, and a full basement providing excellent storage and additional possibilities. Step outside to a private deck overlooking a nicely maintained green space—perfect for relaxing or dining outdoors. With a welcoming front porch, attractive landscaping, and a convenient location close to shopping, dining, commuter routes, and area amenities, this well-kept townhouse is ready to welcome you home.

7 Sycamore Dr Unit 7, Middleboro

Listing courtesy of Listing Agent: James OBrien from Listing Office: Keller Williams Realty.

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