Middleboro Homes with Wooded Lot Features

Welcome to Middleboro, Massachusetts – a charming town nestled in the heart of Plymouth County, where rich history meets the tranquility of nature. With its picturesque landscapes and vibrant community spirit, Middleboro is an ideal destination for families, retirees, and anyone seeking a serene lifestyle while remaining conveniently close to urban amenities.

Middleboro boasts a variety of homes that cater to diverse tastes and preferences, particularly those featuring wooded lot characteristics. Imagine waking up to the gentle rustle of leaves and the melodious chirping of birds, all from the comfort of your own home. These properties provide not only a peaceful retreat but also a unique opportunity to immerse yourself in nature. The wooded lots offer ample space for outdoor activities, gardening, or simply enjoying the beauty of the changing seasons.

With its rich historical roots, Middleboro is home to numerous parks and recreational areas, making it perfect for outdoor enthusiasts. You can explore the nearby Myles Standish State Forest, which spans over 12,000 acres of lush woodlands, or take a leisurely stroll along the picturesque shores of one of the many local lakes. The town's friendly atmosphere and community events foster a strong sense of belonging, where neighbors become friends and memories are made.

Whether you’re looking to settle down in a cozy cottage surrounded by towering trees or a modern home with a rustic touch, Middleboro’s wooded lot homes provide the perfect blend of comfort and natural beauty. Discover your dream home in this enchanting town today!

Newest Middleboro Homes with Wooded Lot Features

$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.

$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.

$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..

$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..

$745,000

4 Beds ⋅ 4 Baths ⋅ 73568396 MLS

Reduced and Move in ready. Realocating Owners recognize some work is needed and have reduced to refelct. Offers are encouraged. Peaceful and Private, this charming home is nestled on a wooded cul-de-sac lot bordered by beautiful stone walls, offering nature at its best. The spacious interior features hardwood floors, a center-island kitchen, and a versatile formal dining room that can also serve as a home office. Built-in bookshelves and crown molding add warmth and character throughout. IN-LAW / SEPARATE LIVING QUARTERS offering a full bath, bedroom, living room and office or possible 2nd Kitchen. Step outside to your own backyard oasis, complete with a lagoon-style inground pool surrounded by lovely perennial gardens—perfect for relaxing, entertaining, and enjoying the beauty of every season. Convenient 3/4 bath for those outdoor activities and entertaining. Additional highlights include TOWN WATER AND TOWN GAS ! See Floor Plan in Pics.

10 Brenrae Dr, Middleboro

Listing courtesy of Listing Agent: Madelyn Maksy from Listing Office: Uptown REALTORS®, LLC.

$1,090,000

4 Beds ⋅ 3 Baths ⋅ 73565999 MLS

Stunning 3-year-young Modern Colonial set on 5 acres! This "better than new" home offers 2,594 sq ft of luxury living space, a perfect blend of modern comfort with vast outdoor potential. Step through the welcoming front entry into a sun-drenched floor plan designed for both sophisticated entertaining and effortless daily living. The focal point of the expansive main living area is a grand, light-filled living room featuring a fireplace that anchors the open layout, providing a warm and inviting setting. The space seamlessly flows into a well equipped kitchen with premium fixtures, ample cabinetry, and sleek quartz surfaces. The half bath & laundry room, pantry and mud-room leads you to the oversized 2-car garage. A dedicated in-home office and formal dining area complete the first floor level. Upstairs you will be greeted by 3 generous bedrooms that share a large hall bathroom, and the expansive primary suite offering two spacious walk-in closets and an en-suite bathroom featuring modern design elements, tiled shower and a jacuzzi soaking tub. In the basement you will find an in-home sauna, whole-home water filtration system with reverse osmosis and UV purification, ample storage and potential to be finished for even more living space. Built with contemporary design and lifestyle in mind with high-end finishes throughout, this home offers zero worry and maximum efficiency. Complete with a large storage shed, and potential for a retreat like pool area, ADU and more!

128 Thomas St, Middleboro

Listing courtesy of Listing Agent: Derouen Levinson Group from Listing Office: Keller Williams Realty.

$649,900

4 Beds ⋅ 2 Baths ⋅ 73565598 MLS

CANCEL OPEN HOUSE......OFFER ACCEPTED..... A true Farmhouse Cape w/ all the Charm, Comfort & Style to the MAX....WARM & COZY Throughout this 8 room, 4 bedroom, 2 full bath home. Designer kitchen w/ Energy Efficient stainless steel appliances, Quartz counter tops, Shaker style cabinets. Updated or new MARVIN INTEGRITY Windows, 1st fl. heated with Natural Gas w/Electric Hot water. 2nd fl. heated by Electric (supplier Middleboro Gas & Electric ) Renovated hardwood fls, Luxury vinyl and all new wall to wall carpet 2nd floor. Bonus a well tucked away Pvt. Home Office designed for work & privacy. In the rear is a 1 car under, full basement with insulation & studding ready for your own expansion ideas (walkout) HIGHLIGHT 3 Season Porch ( 14x24) ... Backyard offers storage shed & lg. dog kennel & so much more to see. This almost acre lot is a short ride to # 495 and all roads in between provides great access for commuters !! .... Zoning States Commercial / Residential is allowed/Buyer & Buyer Agent please confirm w/Town possibilities NEW SEPTIC CURRENTLY BEING INSTALLED

618 Wareham St., Middleboro

Listing courtesy of Listing Agent: Mary Butler from Listing Office: Realty One Group Dream Makers.

$674,900

3 Beds ⋅ 2 Baths ⋅ 73558587 MLS

Turnkey & Completely Updated! This beautifully renovated home features a brand-new roof, all-new energy-efficient windows, and a freshly painted interior throughout. Enjoy total peace of mind with top-tier mechanics, including a new Weil-McLain indirect hot water heater and a whole-house generator to keep you powered during outages. Outdoors, sitting on 3.32 acres you’ll find mature, lush landscaping offering great curb appeal and privacy on a Cul-de-sac. The septic system is fully compliant and Title V/septic certified—ready for a smooth, hassle-free closing. Conveniently located with quick access to Route 24. 30 minutes from Boston, 45 minutes from Providence RI. Truly move-in ready with zero work required!

3 Kelly Drive, Middleboro

Listing courtesy of Listing Agent: Gary Pisa from Listing Office: Pisa Real Estate Center.

$215,000

73563384 MLS

Excellent opportunity to own 0.70 acres of General Use-zoned land in a prime Middleboro location. With Middleboro continuing to grow and benefit from major investment and improved commuter access, including the new MBTA station, this property offers exciting potential for investors, developers, or end users. Conveniently located near major routes, local amenities, shopping, dining, and transportation, this versatile parcel is positioned in an area experiencing continued growth. Bring your vision and explore the possibilities at 50 Cambridge Street! Buyer and buyer’s agent to perform all due diligence regarding zoning, permitting, utilities, and potential uses.

50 Cambridge St, Middleboro

Listing courtesy of Listing Agent: Kade Phillips from Listing Office: RE/MAX Legacy.

$425,000

2 Beds ⋅ 1 Baths ⋅ 73559110 MLS

Welcome to peaceful one-level living at 40 Lake Shore Dr! This charming 2-bedroom, 1-bath home is privately situated on nearly half an acre with picturesque views of Savery Pond. Whether you’re a first-time buyer, looking to downsize, or searching for a quiet retreat, this property offers the perfect blend of privacy, tranquility and convenience. A 2-car detached garage provides plenty of space for vehicles, storage, hobbies or a workshop. Additional highlights include a brand-new hot water tank, forced hot air heating system, and a 3-bedroom septic design offering future potential. With forced hot air already in place, simply add an A/C condenser for central air. Enjoy beautiful water views and a peaceful setting while still being close to all that Middleboro has to offer. Don’t miss this opportunity!

40 Lake Shore Dr, Middleboro

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

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