Between $500,000 - $600,000 Middleboro MA Real Estate, Homes, Condos for Sale

Newly Offered! Showings begin Sunday! OPEN HOUSE 11:00 AM–1:00 PM! Welcome home to 18 Chestnut Street in Middleboro, a charming and well-maintained 2–3 bedroom, 1.5-bath Front-to-Back Split offering the perfect blend of comfort, character, and outdoor enjoyment. The heart of the home features an eat-in kitchen with a tiled floor, ceiling fan, and pantry, while the spacious living room showcases a cozy wood-burning fireplace. Throughout the home you'll find hardwood floors and solid oak doors, adding warmth and timeless appeal. Enjoy outdoor living at its finest from the 12' x 12' screened porch with a vaulted ceiling and ceiling fan, leading to a private 20' x 12' deck overlooking a fenced inground pool complete with a pool house featuring electricity and a cold-water sink. The property also includes a barn with chicken coop, perfect for hobby farming, storage and workshop space. Additional features include: Central Air & Vacuum; Full bath with shower stall; Second-floor laundry room (washer & dryer included); Easy access attic for additional storage; Finished lower level with door opening directly to the outside, offering a family room or potential 3rd bedroom, plus a convenient half bath; Municipal Gas & Electric (MG&E). Recent updates: Heat Pump (2023); 200-Amp Electrical Panel (2023); Updated roof and replacement windows, 3-Bedroom Title V Septic System (installed 7/21/2025). This home is conveniently located with quick access to Routes 105, 495, 44, and 28. Close to downtown amenities including the post office, coffee shops, and library, and is less than four miles from the new Middleborough Commuter Rail Station. Don't miss this unique property offering indoor comfort, outdoor entertaining, and exceptional convenience!

18 Chestnut Street, Middleboro

$539,000

2 Beds ⋅ 1 Baths ⋅ 73552234 MLS

Completely renovated and thoughtfully updated, this two-bedroom ranch offers an open, inviting layout perfect for entertaining and relaxing. Wide-plank oak flooring runs throughout the main level, where the spacious living room features a stylish electric fireplace and custom built-in shelving that creates a beautiful focal point. The updated kitchen includes modern appliances and a large center island, ideal for everyday living and entertaining. Both bedrooms are generously sized, and the remodeled full bath features a double vanity. The finished lower level adds a comfortable family room or playroom with an electric fireplace, and walk-out french doors leading to the backyard patio and room for a home gym. Outside, enjoy a cleared, fenced-in backyard with plenty of room to relax or entertain. Additional features include a one-car garage, whole-house water filtration system, updated oil tank, and convenient access to Route 44. Septic is 3 bedroom system offering options to next owner.

45 Cross St, Middleboro

$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

$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

$519,000

4 Beds ⋅ 1 Baths ⋅ 73547468 MLS

Commuters Dream less then 1/2 mile from commuter rail.... Charming and beautifully updated New England Colonial conveniently located just a short distance to all the amenities of Middleboro Center—shops, restaurants, coffee, schools, library, and commuter rail. This home blends classic charm with modern style, featuring a gorgeous kitchen with granite countertops, tile backsplash, and stainless steel appliances. Freshly painted interior, refinished hardwood floors, tile in kitchen and bath, and carpeting in bedrooms and family room. Enjoy gas heat, central air, and an updated electrical panel. The flowing floor plan offers open, airy living spaces including a finished walk-out basement with Vermont Castings gas stove and plenty of storage. The attached two-car garage connects through a spacious mudroom, and the large deck overlooks a deep, private backyard perfect for relaxing or gardening. Vinyl siding completes this move-in ready gem!

53 West St, Middleboro

$569,000

3 Beds ⋅ 2 Baths ⋅ 73546007 MLS

Welcome to 45 Forest St., a comfortable Colonial offering 3 bedrooms, 10-foot ceilings, and a desirable double lot. Conveniently located near downtown Middleboro, Rte. 44, shopping, schools, and major commuter routes, this home blends classic character with functional living space. The first floor features a spacious living room, formal dining room, and an oak kitchen with hardwood floors and abundant cabinet space. A versatile bonus room provides the flexibility for a home office, playroom, guest room, or potential fourth bedroom. Upstairs, you'll find three generously sized bedrooms with large windows that fill the home with natural light. Outside, enjoy the private backyard and side deck, perfect for relaxing or entertaining. A wonderful opportunity to own a charming home with space, flexibility, and a convenient location.

45 Forest St, Middleboro

$565,000

3 Beds ⋅ 2 Baths ⋅ 73540421 MLS

*OFFER DEADLINE Tuesday 6/30 6p.m.*Don't miss your opportunity to call 16 Marie Drive home! Freshly painted and ready for its next owner, this well-maintained home features a new roof installed in 2020 and a new septic system completed in 2019, offering peace of mind for years to come. Inside, you'll find 3 bedrooms and 1.5 bathrooms, gleaming stainless steel appliances in the kitchen and a bright open living room, providing comfortable living space for a variety of lifestyles. Enjoy your morning coffee on the inviting front porch or entertain family and friends on the wraparound back deck overlooking the generous backyard. With plenty of outdoor space for gatherings, gardening, recreation, or pets, this property offers the perfect blend of indoor and outdoor living. Conveniently located with easy access to major highways and just minutes from the commuter rail, this home makes commuting throughout Massachusetts a breeze while still offering the comfort of a residential neighborhood.

16 Marie Dr, Middleboro

$550,000

3 Beds ⋅ 1 Baths ⋅ 73539976 MLS

Conveniently located near shopping, restaurants, and major highways, this charming 3-bedroom, 1-bath home offers comfort, character, and practical amenities. The spacious first-floor primary bedroom features a vaulted ceiling, creating a bright and airy retreat. Inside, you'll find an updated kitchen with granite countertops and a layout that flows seamlessly into the living area highlighted by a cozy fireplace. Outside, enjoy the convenience of covered carport parking during New England winters, new windows in 2025, and a large backyard workshop/shed equipped with electricity and propane heat—perfect for hobbyists, contractors, craftsmen, or additional storage. A brand-new septic system will be installed prior to closing, providing added peace of mind for the next owner. Whether you're looking for your first home, downsizing, or simply seeking a property with functional workspace and easy commuter access, this home is a must-see!

156 Bedford Street, Middleboro

$599,800

4 Beds ⋅ 2 Baths ⋅ 73537865 MLS

WOW! Incredible new low price for this cant miss property. Open House Sunday, 7/26 12-1:30. Opportunity, functionality, and charm come together in a move-in ready package. This versatile home offers flexible living spaces to fit a variety of lifestyles. A home office with its own separate entrances presents exciting possibilities for a home business, guest space, or potential ADU conversion. Inside, you'll find stunning wide-plank wood floors, a formal living room, formal dining room, family room/playroom, first-floor laundry, and a spacious kitchen with room for an eat-in nook. Upstairs are 4 bedrooms, one of which has been transformed into an impressive walk-in closet. The primary has vaulted ceilings and skylight, plus a separate stairwell from the first floor for added privacy. Comfort and efficiency are a focus with a gas stove, three-zone Energy Star Instinct heating system, and two ductless mini-splits. The oversized garage has a wood-stove and offers the perfect space for hobbies or storage. Easy access to commuter rail, shopping, dining, parks, library + more!

4 Star Ave, Middleboro

$599,000

3 Beds ⋅ 2 Baths ⋅ 73533529 MLS

Step back in time where 18th-century grace meets modern day living in this 1740 antique Cape. Nestled on nearly 2 acres, this home showcases historical craftsmanship and a versatile layout. The main level offers a kitchen where sourdough bread deserves to be made by hand, a magnificent original fireplace & walk-in pantry. Off of the kitchen is a quaint library, a sun-filled front living room, a large den (once used as a first floor bedroom), a private home office & a bathroom. Relax in the serene sitting room or enjoy the breeze from the screened-in porch overlooking the tranquil koi pond. Easy interior access to a one car garage & workshop. Upstairs, you will find 3 bedrooms & a full bathroom. The crown jewel of this property is the spectacular custom-built treehouse, artisan-crafted from timber harvested directly from the property, a one-of-a-kind retreat for relaxation or creative inspiration. This rare estate offers the perfect blend of historic character and expanded living space.

65 Summer St, Middleboro

$509,000

3 Beds ⋅ 3 Baths ⋅ 73531856 MLS ⋅ ['Elisha Place Condominiums'] BLDG.

Beautiful 2015-built condo that lives like a single-family home! Attached only on the garage side, this desirable unit offers its own private driveway, attached 1-car garage, and a peaceful wooded setting. Enjoy outdoor living on the covered composite deck overlooking the backyard. Inside, the open-concept floor plan features hardwood flooring throughout the living room, dining area, and all 3 bedrooms. The kitchen boasts beautiful countertops, stainless steel appliances, upgraded cabinetry, and a peninsula breakfast bar. Convenient first-floor primary suite includes two closets, one being a walk-in. Also on the main level are a half bath and laundry closet. Upstairs you’ll find two additional bedrooms, a full bath, and a bonus craft room/home office. Full unfinished basement offers excellent storage or future expansion potential. Natural gas heat and central air. Condo fee includes master insurance, trash, sewer, landscaping, and snow removal.

9 Elisha Dr Unit 9, Middleboro

$575,000

4 Beds ⋅ 2 Baths ⋅ 73525836 MLS

Charming and move-in ready Cape-style home offering 4 bedrooms, 2 updated baths, and a spacious 2-car garage! This beautifully maintained home features an updated galley-style kitchen with stainless steel appliances, a large fireplaced living room perfect for cozy nights, and a wonderful blend of wood and LVP flooring throughout. The flexible floor plan includes a desirable first-floor primary bedroom, good-sized additional bedrooms, one full bath on each level, and the convenience of first-floor laundry. Filled with warmth and character, this home combines classic charm with modern updates. Step outside to a backyard designed for relaxing or entertaining, complete with mature trees, a beautiful stone wall, and plenty of outdoor space to enjoy. A wonderful opportunity to own a turnkey home with comfort, style, timeless appeal, and located in a desirable Middleboro neighborhood!

89 School St, Middleboro

$599,000

5 Beds ⋅ 4 Baths ⋅ 73514428 MLS

Steeped in local history, the Nathaniel Eddy House in scenic Eddyville, East Middleborough, is offered for the first time since 1965. Ideally located just down the street from the Eddy Homestead and the Joshua Eddy House, it sits at the heart of this storied enclave. Built in 1806, this rare property features 5 bedrooms, 7 fireplaces (including 2 in bedrooms), wide pine floors, exposed beams, and a hidden staircase. A long ell connects the home to the barn and offers potential for a first-floor primary suite. Oversized stone pillars frame the driveway, reflecting its historic charm. The property includes multiple barns, including a separate barn with stall and hayloft. Set on 1.66 acres with an additional .64-acre parcel included (over 2 acres total). Brand New Roth Tank installed April 2026. If you’ve ever dreamed of preserving a piece of local history, this is your chance. Sold as-is; buyer responsible for new septic.

155 Plympton Street, Middleboro

$525,000

3 Beds ⋅ 1 Baths ⋅ 73470953 MLS

JUST MOVE RIGHT IN! If your New Year’s resolution is to buy a home you won’t find a better buy in 2026 than this 3 bedroom Raised Ranch! All the big ticket items have been done for you within the past 5 years so you can rest easy knowing that your future home comes with a new asphalt shingle roof in 2023, a new heating system in 2021, new oil tank in 2021, new hot water heater in 2022, fresh paint throughout the whole first floor in 2025, and a newly finished basement in 2025 with new recessed lighting, new laminate flooring, new walls, and new ceilings which adds square footage and floor plan flexibility. Situated on three quarters of an acre of level ground, you’ll have all the outdoor space you need, but it’s not just the lot size that makes this home special. You’ll fall in love with the beautiful hardwood floors throughout the first floor, enjoy the updated full bath, and get cozy with the working fireplace in the living room. First showings at the open house!

70 Wall Street, Middleboro

$595,000

4 Beds ⋅ 1 Baths ⋅ 73440183 MLS

Nestled at 246 Everett St in Middleboro, MA was once a duplex then a farm. Now waiting for those with a vision. This property is a great option for investors & handy homeowners alike. Within this residence are 4 bedrooms & 1 full bath, providing ample space to fashion personalized sanctuaries for rest & rejuvenation. Mature plantings, lots of open spaces for gardens ...so many options with this Rehab property. Large foundation size of 55x25. Fruit trees, active hay field, lots of barns & sheds for animals which need attention. The 12+ ACRES (2 separate lots) represents 9.87 acres of nature study (taxes only $117.51) & 2.64 acres for single family home (taxes are $5,297). Great access to major routes to Boston, Providence & Cape Cod. Constructed in 1832, this property holds a unique place in time. This residence represents a rare chance to reshape a piece of history. Cash Sale. Do not enter the property without an appointment.

246 Everett Street, Middleboro

Browse All Middleboro MA Between $500K - $600K Properties for Sale

Between $500K - $600K Middleboro Real Estate