Massachusetts homes for sale starting at Fifty Thousand Dollars

$33,000,000 - Edgartown, MA

61 Butlers Cove Road Edgartown, MA - Beach Farm is a breathtaking 18.6 acre waterfront estate on Martha's Vineyard featuring unrivaled privacy, serenity, awe-inspiring views, private beaches, water sports and a rare walking path to the pristine beaches of the south shore. This truly one-of-a-kind estate borders Edgartown Great Pond, the famed South Shore, and is part of the storied Herring Creek Farm, an exclusive 200+ acre enclave of limited residences and a beautiful farm with barns, horses, sheep, cattle and meadows. All a short bike ride to Edgartown and just a 12 minute drive to Edgartown airport. The luxurious six bedroom home, completed in 2023, is designed with walls of glass that frame jaw-dropping views of the pond and ocean. Built by master craftsmen to the highest standards possible, and bespoke interiors, no expense was spared. There is a spectacular three bedroom surf house with outdoor sauna and cold plunge, a workout barn, beautiful walking paths and private beach.

$25,800,000 - Hyannis Port, MA

151 & 155 Irving Avenue Hyannis Port, MA - Situated within the prestigious coastal enclave of Hyannis Port, directly adjacent to the world renowned Kennedy Compound, 'Port View' is one of the most iconic oceanfront estates along the entire Northeastern seaboard. Behind tall privet hedge, a gated driveway leads past rolling lawns and established landscapes by the legendary Olmstead brothers to reveal an impressive and stately 7 bedroom Main House with commanding views of Hyannis Port Harbor and Nantucket Sound. For the first time ever, an additional 6 bedroom guest house is included in this rare offering, creating a one-of-one multi-generational compound. A gracious floor plan features walls of windows from which to enjoy spectacular 300 degree views, while tall ceilings and beautiful architectural details are found throughout, including the fireplaced living and dining rooms, tavern, wood paneled library, sun porches, third floor game room with mahogany inlay floors, and roof deck, all substantially renovated by current owners. Tremendous outdoor entertaining opportunities surround the large pool, hot tub, firepit and ''wedding lawn'', which overlooks gorgeous dunes and nearly 500' of private beachfront!

$25,000,000 - Edgartown, MA

25 Dock Street Edgartown, MA - UNIQUE OPPORTUNITY IN HISTORIC EDGARTOWN ON MARTHA'S VINEYARD - Seize the chance to possess a truly extraordinary, highly esteemed, and unparalleled property on the East Coast! Edgartown, known for its rich history, nautical charm, and scenic beauty is home to this remarkable property being offered for the first time in over 30 years! Edgartown's deep ties to its seafaring heritage are evident in its picturesque harbor, filled with sailboats, yachts, and fishing vessels. Strolling along the waterfront and enjoying the maritime ambiance is a favorite pastime for visitors and locals alike. Sited at the center of the harbor sits this rare offering featuring a beautifully appointed three-story residence with fabulous views, a two-story clubhouse on the harbor and more than 500 feet of deep-water dockage, capable of accommodating up to ten vessels, including superyachts. Experience the lively lifestyle of coastal living from this custom home featuring two balconies, beautiful hardwood floors, marble bath, custom stone-surround fireplace, and fabulous kitchen with high-end finishes. The waterfront clubhouse is ideal for entertaining guests at the harbor's edge. Utilize the docks for your own private fleet of boats, provide dockage for visiting friends and extended family, lease the slips, or embark on a charter business. The possibilities are endless! This landmark property in Edgartown, with its exceptional location, impressive and private deep-water docks, and refined residence with water's edge clubhouse all combine to create a special destination that captures the essence of Edgartown's vibrant cultural scene with art galleries, boutique shops and fine dining. This is truly a once in a lifetime opportunity. This property, currently known by boaters around the world as Mad Max Marina, has just celebrated their 30th season. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

$23,850,000 - Osterville, MA

17 Indian Trail Osterville, MA - A secluded treasure nestled on a private island. In the 1950s, Paul Mellon, heir to the famous banking family that established the National Gallery of Art in Washington D.C., and his wife Bunny chose this setting for a summer retreat. They created a home of elegance, comfort and great beauty, where they entertained world leaders, movie stars and industrialists. Bunny shaped the gardens and landscape, creating an exquisite blend of native plantings and trees. The 7,300-square-foot main house is integrated into the land, with its eight bedrooms offering views of either the sea or the gardens. Natural pathways wind through the property, connecting the main house to cottages—including a former art studio converted into a private suite—and lead to a beach house, where the Mellons hosted President John F. Kennedy and Jacqueline. With over five hundred feet of waterfront, a private dock, and access to a private island, now serving as a protected bird sanctuary, this is an island haven like no other.

$20,000,000 - Nantucket, MA

258 Polpis Road Nantucket, MA - “Harbor Creek’ is one of the finest Polpis estates that exists. This private and stunning property on just over 4 acres and across the way from acres of protected conservation land includes a five bedroom main house and a two bedroom guest house, room for a pool, direct harbor access as well as outstanding panoramic views and beyond. Renovated by Cross Rip Builders and decorated to perfection, this custom built home includes an outstanding ‘chef’s kitchen’, two separate bright and open living rooms each with a fireplace, antique details and a large primary bedroom with a private deck looking out towards the harbor. There are three sets of French doors leading to the rear deck making for easy access to the lush and flowing expansive yard; perfect for sunset cocktails, entertaining and family gatherings as well as direct access to your own boat! There is a separate two bedroom guest house and mature, beautiful landscaping surrounding the entire property providing much privacy. Whether you are looking for the ideal summer retreat or want to enjoy all of the island seasons, look no further than this exquisite and sophisticated one of a kind property. This is an opportunity to own one of the most iconic properties on Nantucket, also known as the house with the white dory in the front yard; a true island landmark!

$19,500,000 - Provincetown, MA

105 Bradford Street Extension Provincetown, MA - Nestled high on a hill in the coveted west end of Provincetown, Seaglass Inn & Spa presents an exceptional opportunity for those seeking a remarkable investment with breathtaking views and limitless potential. With 4.2 acres of prime Provincetown real estate, this expansive 57-room property combines recent upgrades with a versatile range of uses, making it a choice candidate for creative visionaries. The inn features 57 well-appointed guestrooms, some with water views, and has benefited from significant recent enhancements, including a new roof and numerous upgraded rooms. The property's allure is further heightened by its breathtaking sunrises and sunsets. Guests can indulge in a serene retreat by the sparkling pool. There is a 2-bedroom apartment on the property. And, a bonus is 109R Bradford Street Ext., a 1.16 acre lot (included in the 4.2 acre total) with unimpeded water views and approved building plans. The possibilities for Seaglass Inn & Spa are as vast as the views it offers. Continue operating the beloved inn and spa to enhance guest experiences and attract high-end clientele. Alternatively, elevate the property into a luxurious destination with state-of-the-art amenities and exclusive services. For those looking to create a residential community, the ample land is ideal for a distinguished single-family home development, offering modern homes that capitalize on the unique location and spectacular views. Additionally, the property holds potential as a vibrant non-profit arts center, fostering creativity and community engagement in a stunning, scenic setting. Seaglass Inn & Spa boasts a prime location, providing both privacy and exclusivity while remaining close to the vibrant heart of Provincetown. With endless possibilities and unparalleled scenic beauty, this property is a rare gem that invites visionary projects and offers boundless potential for its next chapter. Seller welcomes offers with requests for buyer concessions.

$18,875,000 - Nantucket, MA

35 Shell Street Nantucket, MA - For the first time in nearly 100 years, the iconic Wade Cottages—a cherished cornerstone of ’Sconset history—are being offered for sale. Originally acquired in 1929 as a family estate, this storied property has since served as both an inn and a beloved single-family home. Rich in character, steeped in history, and unrivaled in location, this is truly a once-in-a-lifetime opportunity. Perched high on the bluff with sweeping views of the Atlantic Ocean, the estate features a stately main house complemented by a classic three-bay garage. A gracious covered porch welcomes you, leading into a stunning living room adorned with a fireplace, multiple seating areas, and a wall of windows that frame breathtaking ocean views. The residence is as functional as it is elegant, with a grand living room at the heart of the home separating two thoughtfully designed wings. The house offers over 11 bedrooms—nine of which are ocean-facing—and six bathrooms, including two en suite rooms and two bedrooms connected by a Jack-and-Jill bath. The north wing includes an office/mudroom, a kitchen, pantry, and a formal dining room. The south wing features a den with a fireplace and a two-room suite complete with an en suite bath and private sitting room. The dining room, main living area, and den all have direct access to a wide ocean-view deck, ideal for al fresco dining or shaded relaxation. Dual staircases—one in each wing—enhance privacy and circulation for residents and guests alike. Upstairs, the second level offers nine bedrooms, including a spacious primary suite that spans the depth of the house, connects the north and south wings, and features a dressing area and private bath. The north wing contains three bedrooms that share a spacious full bathroom. The south wing includes five bedrooms: three share a hall bath, while two twin bedrooms share a Jack-and-Jill bath. The beautifully landscaped grounds boast an expansive lawn stretching to the bluff’s edge, a private hedged patio with water views, and a second hedged patio featuring a firepit, seating area, and space for lawn games. Additional amenities include two outdoor showers and direct access to the ’Sconset Bluff Walk and the beach via a Land Bank staircase. More than a home, the Wade Cottages represent a legacy—an irreplaceable piece of Nantucket’s heritage. This is a rare chance to own one of ’Sconset’s most treasured bluff properties, where generations have gathered and enduring memories have been made.

$16,950,000 - Edgartown, MA

68 N Water Street Edgartown, MA - 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.

$14,995,000 - Dartmouth, MA

1 Mattarest Lane Dartmouth, MA - 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.

$13,995,000 - Edgartown, MA

5 Briggs Road Edgartown, MA - NEW CONSTRUCTION - COMPLETED. POND FRONT on WINTUCKET COVE. The epitome of Luxury Living, yet understated. 6,343 sq.ft., 7 Bed, 9 Bath home, w/16ft x 42ft saltwater heated pool, 2 car garage & a dramatic over sized screened porch w/11ft high ceilings. Discover a beautiful Vineyard oasis on 9.2 acres of land on the South Shore w/376ft of frontage on Wintucket Cove. An expansive property, merging traditional & contemporary design, creating a warm, streamlined, elegant home. Huge living room w/fireplace flanked by two inviting alcoves for lounging/reading. Wall of glass doors leads to patio, yard, pool & down to a boardwalk on the Cove. Gourmet Kitchen w/large island, Quartz Counters, Thermador stainless appliances w/professional stove. Scullery w/additional fridge, dishwasher & sink. Quartz island w/contrasting cabinets which seats 6 comfortably. Adjacent dining room, with views towards the water, complete w/custom serving hutch. Hallway to oversized screened porch w/wood burning fireplace, or to a very bright Bonus Room w/multiple windows & doors leading to mahogany deck that directs you to the Gunite POOL & SPA. At the opposite end of the house, Ground Floor Primary Bedroom w/ensuite including soaking tub, shower, private outdoor shower enclosure & private deck. Upstairs you'll find another large suite w/private deck facing the water, WIC, writing area & huge bathroom w/double vanities. Two more guest suites nearby each w/private bathroom. Wonderful media room w/sumptuous seating & views over Wintucket Cove. Special reading nook on the way to super mahogany deck overlooking the pool, yard & Wintucket Cove. A 5th Private Suite finishes off this wing w/its own WIC & full private bathroom. Heading towards the 'East Wing', two guest bedrooms w/shared bathroom & a second laundry. A second staircase brings you down to a wonderful built-in mudroom, storage area & powder room. Mudroom leads to a huge very bright two car garage w/Tesla Charger & numerous windows. Expansion Possibilities included adding a Guest House, an accessory dwelling unit. Enjoy Swimming, Boating, Kayaking, Paddle boarding on Edgartown Great Pond, continue to Land Bank Beach, Atlantic Ocean & South Beach. Drive to Morning Glory Farm, Airport, Vineyard Golf & Downtown Edgartown. Potential Family Compound! Beautifully Furnished, contents may be purchased separately. Additional photos will be added!

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