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

$750,000

3 Beds ⋅ 3 Baths ⋅ 73556157 MLS

Welcome home to the sought-after Whispering Pines community! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect combination of comfort, privacy, and functionality. Relax on the charming farmer's porch and enjoy the peaceful wooded setting that provides exceptional privacy in both the front and back of the property. Inside, the sun-filled first floor is filled with natural light and features a spacious, open flow between the living room, kitchen, and dining area, making it ideal for everyday living and entertaining. A convenient first-floor laundry room and half bath add to the home's thoughtful layout. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite, along with two full bathrooms. Step outside to a fully fenced backyard complete with an above-ground pool, perfect for summer gatherings or quiet evenings at home. Additional highlights include a new boiler and hot water heater (both approximately one year old), attic storage above the attached garage, and a private well and water conditioning system. Conveniently located near local amenities while offering the tranquility of a desirable neighborhood, this home is ready for its next owners!

31 Pine Street, Middleboro

Listing courtesy of Listing Agent: Beatrice Murphy from Listing Office: Lamacchia Realty, Inc..

$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.

$799,000

3 Beds ⋅ 2 Baths ⋅ 73555359 MLS

Welcome to 229 Tispaquin! This charming 3-bedroom, 2-bathroom home sits on a beautiful 2.8-acre lot and offers the perfect blend of comfort, space, and versatility. A true highlight of the property is the impressive 40' x 30' detached garage, complete with electricity, vehicle lift, wood stove, and a spacious loft area above, perfect for hobbies, projects, storage, or recreational use.Inside, the spacious kitchen features an oversized center island, gas range, and plenty of cabinet and counter space, making it the perfect gathering spot. Just off the kitchen, the mudroom includes a pellet stove for added warmth and convenience. Enjoy the bright sunroom overlooking the property, or relax in the inviting living room with a fireplace and pellet stove insert.The flexible first-floor bonus room is currently used as an additional bedroom but could also serve as a home office, guest room, playroom, or den. Central air keeps the home comfortable year-round. The partially finished basement offers additional living space, laundry, and plenty of storage.Outside, enjoy the brand-new deck, perfect for relaxing or entertaining, along with an oversized shed for tools, lawn equipment, and outdoor gear. With its expansive lot, incredible garage setup, and thoughtful features throughout, 229 Tispaquin offers space and versatility that are hard to find. Conveniently located near local amenities, shopping, dining, and commuter routes, this is one you won't want to miss!

229 Tispaquin St, Middleboro

Listing courtesy of Listing Agent: Elizabeth Moses from Listing Office: LPT Realty - Home & Key Group.

$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.

$495,000

73548811 MLS

The subject is currently a vacant land parcel that contains approximately 1.59 acres and is located in the GU (General Use) Zone according to the town of Middleboro and is designated as Map: 79 Lot: 798. The subject is located in an industrial park/cul-de-sac

Abbey Lane, Middleboro

Listing courtesy of Listing Agent: Michael Lefrancois from Listing Office: Regal Commercial Real Estate.

$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.

$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.

$489,000

3 Beds ⋅ 1 Baths ⋅ 73546653 MLS

Opportunity awaits with this centrally located mixed-use property in Middleborough! Whether you're looking for your first home or planning to downsize, this 3-bedroom ranch offers comfortable one-level living with plenty of potential to make it your own. The main level features three bedrooms, a full bath, and a functional floor plan ready for your personal updates and finishing touches. Step outside to enjoy the above-ground pool and private backyard providing a peaceful natural setting. Conveniently located near shopping, restaurants, schools, and major routes. Property is being sold AS IS, offering a great opportunity for buyers to add their own style and value. Title V buyers responsibility.

260 Wood Street, Middleboro

Listing courtesy of Listing Agent: Matt Ciullo from Listing Office: Conway - Lakeville.

$799,900

3 Beds ⋅ 3 Baths ⋅ 73545512 MLS

Come home to a setting that feels like your own private retreat. Set on nearly 2 wooded acres, this custom Cape welcomes you with a bright, inviting foyer that opens to beautifully connected living spaces designed for both everyday comfort and effortless entertaining. The stunning living room, anchored by a striking stone fireplace, flows seamlessly into a spacious kitchen featuring granite countertops, ample cabinetry, and an open dining area where family and friends naturally gather. A sunroom invites quiet mornings with coffee, while the composite deck overlooks a backyard made for summer, complete with an above-ground pool, gardens, and room to unwind. Upstairs, the expansive primary suite is a true escape with a private balcony, walk-in closet, and spa-like bath with a whirlpool tub. Hardwood floors, generous room sizes, three full baths, a 2-car garage complete a home that offers the space, warmth, and lifestyle buyers have been searching for.

49 Plain St, Middleboro

Listing courtesy of Listing Agent: Janine Wuschke from Listing Office: Keller Williams Realty.

$450,000

2 Beds ⋅ 1 Baths ⋅ 73544349 MLS

Have you been searching for a move-in ready starter home in Middleboro? This adorable 2-bedroom home could be the perfect place to begin your homeownership journey! Featuring a spacious backyard, a detached garage, and an extra-large storage shed, there's plenty of room for hobbies, storage, and outdoor enjoyment. Located just minutes from highways, the commuter rail, shopping, restaurants, and everything Middleboro has to offer, this home combines comfort, convenience, and value. Plus, you'll have peace of mind knowing the roof and water heater are both only about 2 years old. Great Price. Great Location and Great Condition. Sounds like a win! All parties to verify information contained herein.

47 Anderson Ave, Middleboro

Listing courtesy of Listing Agent: Mishelle Joy from Listing Office: Keller Williams Realty.

$789,000

3 Beds ⋅ 2 Baths ⋅ 73541081 MLS

EASY TO SHOW and will include a NEW Septic! This 7.7-acre private retreat, offers privacy, nature, and convenience in the middle of the South Shore. The flexible floor plan hosts a first floor large living room with fireplace, bonus room with patio access, laundry room, and a bright sunroom/office with garage and patio access. Upstairs offers 3 bedrooms and 2 full baths, including a primary suite, eat-in kitchen with stainless appliances and deck access, and a dining/living room option. This well-maintained home features updates, including the roof, water heater, well pump, water filtration, stone wall, granite countertops, finished walls/ceiling in garage, 3.25" hardwood floors upstairs and engineered wood & tile downstairs. Enjoy 3 mini-splits with heat pumps, propane heat and gas stove. Additional features oversized garage door with pull-down loft storage with 2 windows, added carport, shed, French drains, generator hookup, ADU potential on first floor or separately on the property and many outdoor areas. Check out the video!

233 Tispaquin St, Middleboro

Listing courtesy of Listing Agent: Nicole DeBenedictis from Listing Office: Homistic Real Estate Inc..

$799,900

3 Beds ⋅ 2 Baths ⋅ 73537380 MLS

Have you been looking for a home where you can expand your living space w/a 1 bedroom ADU? This home has been verbally ADU verified w/building dept w/no changes to size of septic; just a tie into current system per BOH. Woodshop in the front garage would be perfect for this. This beautiful home offers this kind of versatility w/unique amenities. There are 3-bedroom w/the primary bedroom fitting a king sized bed, 2 baths, kitchen w/SS appl, quartz countertops, custom cabinetry, center island & cedar closet, comfortable living room, formal dining room w/its own fireplace, while the sunroom w/gas fireplace & minisplit will allow you to enjoy this space year-round. Main-level laundry adds to the home. The finished lower level expands your living space w/an office area & bonus room. Step outside to enjoy a large deck w/gazebo along w/an above-ground pool & deck. Car enthusiasts or those in need of extra workspace will love the 3 garages; 3 w/heat & 2 w/ built in a/c. Also has an RV plug w/water source & 2 generator hookups.

536 Plymouth St, Middleboro

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

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.