Homes for Big Families

Here are spacious homes with at least five bedrooms, making it family friendly with enough space for everyone.

$10,500,000

7 Bed

6 Bath

Oak Bluffs

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East Chop waterfront – Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 3.) Or convert to condominiums, paperwork has been completed but would be a buyers choice. Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 7-bedroom property includes a 106 ft dock with water/electric for 8 slips and a 40’ T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, all new heating/AC mini-splits, new exterior security cameras and dredged dockage. Features include high end finishing in all units, as well as beautifully landscaped grounds. The first floor consists of three 1-bedroom units, each with new kitchen, living and dining areas and private covered front porches over-looking the water. The second floor consists of two 2-bedroom units each with kitchen, living and dining areas as well as private covered front porches. A separate detached year-round cottage apt unit with Murphy bed, kitchen, full bathroom and washer/dryer can serve as a rental unit or as live in office for a property manager/caretaker and, has an additional loft area with double bed for kids. Each apartment has electric baseboard heat plus mini-split heat/AC. Generator. Furniture included depending on price. Private outdoor shower with dressing area. On town sewer.

$10,500,000

8 Bed

6 Bath

Oak Bluffs

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East Chop waterfront - Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 3.) Or convert to condominiums, paperwork has been completed but would be a buyers choice. Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 7-BR main house plus 1-BR guest cottage, includes a 106 ft dock with water/electric for 8 slips and a 40' T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, all new heating/AC mini-splits, and new exterior security cameras.

$2,999,000

7 Bed

6 Bath

West Tisbury

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Picturesquely sited on a spacious 4.6-acre parcel, this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach, hiking trails, Up-Island Cronig's, and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels, each area provides spacious yet private surroundings. The main living area features a dramatic great room with a vaulted ceiling. The chef's kitchen with an adjoining pantry opens to the spacious dining room with access to a side deck. An ensuite bedroom, half bath, and laundry/mudroom complete this floor. The upper level is dedicated to the primary ensuite with a walk-in closet and a three-bedroom guest wing with a private den and full bath. You will be pleasantly surprised with the additional 2100 sf lower level, designed for fun and recreation. The spacious game room is perfect for entertaining, watching sports on TV, playing billiards or ping pong, or simply relaxing at the delightfully designed bar with oak barrel barstools. Two additional bedrooms on the lower level provide a more private space for guests and visitors with two exquisitely appointed bathrooms. The library is truly one-of-a-kind with built-in floor-to-ceiling bookshelves and boasts an 81" TV that can be hidden away behind custom cabinets when entertainment calls for a more formal ambiance. A Sonos Sound System was installed throughout the house, ensuring you can always listen to your favorite tunes. There is so much to enjoy here, indoors and out, and creating this stunning Vineyard Farmhouse Estate has truly been a passion of love. The two-story guest house with a new deck overlooks the Egyptian Lotus Pond and awaits your vision. Completing this offering is a large two-story post and beam barn built in 2014. OTHER STRUCTURES: The 1146 sf guest house with a full basement is an unfinished space awaiting your vision. The septic system is for 8 bedrooms, allowing room for expansion. Magnificent barn with a high beamed ceiling, built in 2014. Electrical and water service to the Barn. Open to large corral areas occupied today by alpacas, goats, and donkeys, but could be converted to a yoga barn or other fun studio space with special permitting. Separate private roadway to the barn easily accessed from the main house. There is another smaller barn/shed in the upper corral near the entrance to the property. Sellers have a pool application with plans previously approved. A buyer would need to resubmit for permitting.

$16,950,000

6 Bed

9 Bath

Edgartown

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This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown's finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon entering, you'll be greeted by a sophisticated interior with open-plan living spaces designed for easy entertaining. The main level features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscaped outdoor patio, ideal for al fresco dining and relaxation. Beyond the patio, a lush lawn and manicured gardens surround an impressive 42' x 18' swimming pool, creating a true outdoor oasis. The second level houses four spacious bedrooms, including a luxurious primary suite with an office, ensuite bath, and a private deck overlooking the pool. The third floor offers a large sleeping area with six twin beds, a full bath, a game area, and French doors leading to a sun-drenched deck.

$1,695,000

5 Bed

5 Bath

Chilmark

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Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard. The property feels quintessentially Chilmark with ancient stone walls and mature plantings. The detached guest quarters features a spacious bedroom, full bath, kitchenette eating area, and a garage. Menemsha Hills Reservation is your backyard - 211 acres described by its Trustees as follows: ''Menemsha Hills was shaped by thousands of years of glacial advance and retreat. Today an array of mini-environments comprise a rugged, pleasant landscape: low wetlands, woodland groves leading to a hilltop, wind-blasted coastal plains, a rocky ocean edge, and 308-foot Prospect Hill.'' Not to mention - Menemsha sunsets are a short distance away!

$2,495,000

5 Bed

5 Bath

Vineyard Haven

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Welcome to your dream home! The perfect blend of comfort and luxury awaits you in this custom-designed 5-bedroom, 4.5-bathroom residence. With over 3200 square feet of spacious living, upscale furnishings, finished basement with entertainment bar, and all the right touches to make every day feel like a retreat. Conveniently located under a half mile from downtown Vineyard Haven, where you will find restaurants, shops, and the Ferry to the mainland. Equal distance to Owen Park and Tashmoo beaches. Step inside to find an open-concept floor plan filled with natural light, soaring ceilings, and elegant hardwood flooring throughout the first and second n levels. This home contains two primary bedrooms on the first and second levels. The kitchen features a Wolf stove, stainless steel Kitchen-Aid appliances, granite countertops, and walk-in pantry. An island and custom glass front cabinetry separate the kitchen from the dining room. The screened porch has a comfortable sitting area with exterior flat screen TV. Off the deck another set of French doors opening into the inviting living room with a cozy marble Heat Glow fireplace with circulating blower fan providing atmosphere and warmth. A beautiful first floor en suite bedroom features dual closets and a marble floor bathroom. A powder room off the hall has a full size Samsung stackable washer and dryer. Upstairs you will find the primary bedroom suite with cathedral ceiling, large windows with a half-round window above, walk in closet, another closet, a spa-like tiled bathroom with jetted soaking tub and separate glass shower. Another large bedroom with a cathedral ceiling and a palladium window. The fourth bedroom is just as nice. Off the hall is a tiled bathroom with a quartz vanity and glass walk-in shower. Downstairs, the fully finished basement is a true showstopper. Whether you're entertaining guests or enjoying a quiet night in, you'll love the custom-built bar, cabinetry, wine cooler and full refrigerator in the lounge area. There's a bedroom with walk-in closet providing privacy for family or guests., A tiled bathroom with tub shower and a second full size washer and dryer. Additional features include two storage closets, a utility room with on demand tankless water heater, Rudd furnace with air filtration. Retaining walls allow natural light to flow into the basement. A private entrance walks out to stairs leading to the front yard. Additional highlights include a breezeway connecting the home to an oversized 1 car garage with attic. A beautifully landscaped yard with irrigation system, enclosed outside shower, a Generac generator protecting you from any unexpected outages. Invisible Fence installed and ready for your pet along with a home security system. This property has it all space, style, and endless possibilities. All furnishings and Island-themed artwork are negotiable.

$3,300,000

5 Bed

5 Bath

Edgartown

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Here is the Edgartown compound you've been waiting for - a 5-bedroom main house, 2-bedroom guest house, and elevated swimming pool area located on 1.5 acres. Next door there is 25 acres of conservation land. The property is barely 2/10s of a mile to Morning Glory Farm, and just a mile and a half to the village on the bike path. The house combines island country charm with modern amenities - honey pine floors, Douglas fir beams, and shiplap pine ceilings are among the custom details. The spacious kitchen has just undergone a renovation that includes new appliances and countertops. The guest house is in classic beach cottage style with open floor plan and cathedral ceilings. Get ready to make memories here. Sitting out and enjoying dinner beneath the stars on a balmy summer evening will be a highlight. The backyard is its own oasis with its centerpiece being an elevated pool with mahogany decking. With an acre and a half of land there is plenty of space to install other amenities your family might desire - Bocce court, firepit, the list is long. This property could be your family's Martha's Vineyard escape, and it can also be a healthy source of rental income to offset your expenses Right now the property generates over $100,000 in rental income annually - close soon and the money is yours! Showings will begin on April 20, 2025 - more photos to come.

$3,500,000

6 Bed

4 Bath

Oak Bluffs

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Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to shops, restaurants, beaches, and ferries. . The commercial zoned land has been approved for several different situations from housing to store fronts. Come take a look at all this property has to offer.

$3,500,000

6 Bed

4 Bath

Oak Bluffs

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Circuit Ave. Commercial Property Build your own commercial building of your dreams on the last B1 undeveloped commercial property on Circuit Avenue's main strip. The commercial land had previously approved development plans including mixed use with commercial store front and apartments or condos above. Located on the corner of Circuit Ave and Massasoit Ave. this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms. With a large warp around porch the spacious home has a lot to offer from Employee housing to a bed and breakfast. The commercial zoned land has been approved for several different situations from housing to store fronts. Easy to show.

$999,000

5 Bed

5 Bath

East Wareham

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Built in 2011 and first time on the market. This spacious, well loved and thoughtfully designed 5 bedroom, 4.5 bath home offers exceptional comfort, space and flexibility. Complete with a first floor primary with ensuite and pool view. The additional four bedrooms on the second level conveniently have 2 shared baths between each. Laundry room is located on second level with additional laundry in the basement. The bright open kitchen living room space with dining room creates a great space for gathering. The finished bonus space over the garage is perfect for movie night or entertaining. Complete with a beautiful home office with custom built ins and french doors. Additional permitted finished basement has a full bath. This home was designed with storage in mind with a third level walk up attic. The quiet setting and spacious yard with pool makes this a perfect get a way or year round retreat.

$1,900,000

5 Bed

4 Bath

Barnstable

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COTUIT -Come and enjoy one of CAPE COD'S nicest villages. Situated in close proximity to Cotuit Bay and several boat ramps. This builder's home boasts an impressive layout of 5 Bedrooms, eat-in Kitchen, formal Living and Dining Rooms for entertaining, Family room and Office. The large Kitchen has Granite counters and a six burner Gas stove for those who enjoy cooking. The Primary bedroom is on the 2nd floor with a private bath and a whirlpool tub. 3 Additional bedrooms share a bath with a tub shower and a large Linen Closet. The 5th Bedroom (over the garage) has a sitting area and a private bath with a private entrance into the garage. Possibility of an In-law apartment. Hardwood flooring on the first floor and carpeting on the second. Roof was replaced in October of 2024, Hot Water Tank in 2017. 5 Zone Gas Furnace. Cedar closet in the basement. Agent is the Owner of this property.

$565,000

6 Bed

3 Bath

New Bedford

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Fantastic investment opportunity awaits with this beautifully updated three-family home, ideally located on a quiet dead-end street! Each unit has been thoughtfully refreshed, featuring modern touches. Offering spacious living areas, and a quaint yard, this property offers hassle-free ownership and steady income potential. Convenient to local amenities and commuter routes this home is a perfect investment opportunity! Don’t miss out on this turnkey multi-family gem!

$2,299,999

7 Bed

9 Bath

Fairhaven

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Discover your dream coastal estate on a stunning peninsula, offering breathtaking sunrise and sunset views. This rare estate includes four buildings, perfect for creating a family compound, boutique bed-and-breakfast, or vacation rentals. The main home features 4 bedrooms, 3 baths, and potential for additional space in the attic. The updated pool/guest house and barn-style building with an apartment and workshop add to the charm. Recent improvements include new roofs on all buildings, fresh exterior paint, two new heating systems, and a new pool liner for the in-ground pool. New septic system for the back house to be installed prior to closing, passing Title V for front septic. This is your chance to own a breathtaking coastal retreat with endless opportunities!

$14,995,000

7 Bed

11 Bath

Dartmouth

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This sensational oceanfront estate is located in the coveted, gated beachfront community of Nonquitt. The 7+ bed Main House boasts breathtaking water views through expansive walls of glass, while the guest and pool houses are seamlessly integrated to create a one-of-a-kind coastal retreat. Light-filled living and dining spaces are designed for effortless indoor-outdoor living and entertaining, flowing beautifully onto patios and poolside areas. The detached garage includes the fully equipped guest suite with a bedroom, sitting room, full bath, washer and dryer. Set behind a tall privet hedge and surrounded by natural beauty, this custom home was recently built by Parker Construction with top finishes throughout. Resort-style grounds include level lawns, elegant hardscapes, and a stunning infinity-edge pool and spa overlooking a private beach and the shimmering sea beyond. Nonquitt blends laid-back coastal charm with exclusive amenities including golf, tennis, and sailing.

$2,249,999

7 Bed

9 Bath

Fairhaven

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$549,900

6 Bed

2 Bath

New Bedford

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Spacious 2 family on corner lot with lots of street parking. Open floor plan with dining room/living room. Updated baths. Good size kitchens. Partially finished basement with family room and full bath. Fenced in yard. Short distance to the train station. First showing at open house per seller

$599,900

6 Bed

3 Bath

Fairhaven

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Overflowing with character and modern updates, this beautifully maintained 2-family home is a true gem. The first-floor unit offers 2 spacious bedrooms, a full bath, a sunlit living area, and a warm, eat-in kitchen. Upstairs, the townhouse-style second unit impresses with two full levels of living—featuring a main floor with a bedroom, full bath, living room, and eat-in kitchen, plus a third floor with 3 additional bedrooms, a cozy lounge space, and a half bath. Step outside to your private, fully fenced yard—complete with a deck, above-ground pool, and space to relax or entertain. With separate utilities, vacant delivery, and parking for 4 in a paved driveway, this property offers both comfort and opportunity. Ideally located minutes from highways, shopping, dining, and more—this is one you won’t want to miss!

$599,000

5 Bed

2 Bath

Dartmouth

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Back on the market due to buyer financing! Here's your chance!!! Welcome to 99 Bryant St, a charming home nestled in the serene Smith Mills neighborhood of Dartmouth, MA. This stunning 5-bedroom, 2-bathroom residence exudes character and timeless appeal, offering the perfect blend of modern comfort and classic charm.Set on a spacious 1-acre lot, this property is ideal for pets, children and entertaining, providing endless possibilities for outdoor living. Enjoy peaceful mornings surrounded by mature trees, with the tranquility of the area just steps away from local amenities.Don’t miss your chance to own this hidden gem — a slice of paradise that’s ready to become your forever home. Schedule a tour today and start envisioning the lifestyle that awaits you!

$560,000

6 Bed

3 Bath

Fall River

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All units vacant and ready for immediate occupancy—a rare find! This three-family property features separate utilities, off-street parking, and tons of potential. Priced below market value, it’s ideal for owner-occupants looking to offset their mortgage or savvy investors ready to add a serious performer to their portfolio. Whether you're building wealth or seeking a multi-generational home, this is the one. Let this property be your cash-flow queen!

$599,000

5 Bed

3 Bath

Freetown

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Welcome home to the quaint historic community of Assonet Village in Freetown. This eye catching white raised ranch with stately pillars offers 5 bedrooms, 2.5 baths, and spacious living. Ideally located near Rte 24 and the new commuter rail—making your daily commute effortless. A perfect blend of style, comfort, and convenience. Featuring central air, wood burning stove, cherry cabinets, stainless appliances and granite countertops. Lower level features family room, mudroom and sliders to back yard. Major updates include a 3-year-old roof, 3-year-old pellet stove on the lower level, and composite deck. Additional improvements feature new laminate flooring, a refreshed lower-level bathroom, updated kitchen backsplash, modern light fixtures, recessed lighting, upgraded doors, and fresh paint throughout. This well-maintained, lovingly cared-for home is move-in ready and waiting for you to make it your own. Brand new 5 bedroom septic to be installed by sellers prior to closing