Massachusetts homes for sale starting at Fifty Thousand Dollars

$5,999,000 - Edgartown, MA

135 The Boulevard & 110 Pilgrim Rd Edgartown, MA - Exceptional Waterfront Living ~ Stunning, active views of Sengekontacket Pond and Nantucket Sound set the tone for this spectacular coastal retreat. Thoughtfully designed to showcase its breathtaking surroundings, the main house captures sweeping vistas from nearly every room. With over 300 feet of frontage, you'll enjoy immediate access to the water for swimming, paddleboarding, kayaking, and a short ride to your mooring. The main level welcomes you into a light-filled living room where commanding water views instantly draw you in. The open layout creates a comfortable and connected space for gathering, with the kitchen thoughtfully positioned at the back of the home. The dining and living areas, anchored by a beautiful stone fireplace, are perfectly oriented to take in the magnificent scenery. Both rooms open to a generous wrap-around deck, ideal for effortless indoor-outdoor entertaining. A stylish half bath completes this level. The fully renovated lower level is dedicated to three inviting bedrooms. The primary suite enjoys a premier location with a private full bath, direct access to the lower deck, and stunning views-even from its private outdoor shower and hot tub. A guest bedroom also enjoys deck access and water views through sliding glass doors, while a third bedroom is located down the hall. A shared full bath and a separate laundry area complete this floor. Set apart for privacy yet with easy access to the main patio, the charming guest house offers a one-bedroom suite with a full bath, a bonus room, and a second-floor loftperfect for guests, a home office, or creative space. A second outdoor shower is located off the adjoining patio, enhancing the island-living experience. A two-bay garage provides ample room for vehicle storage and all your Vineyard essentials. With its unbeatable location, thoughtful layout, and premium amenities, including a classic boat house, this offering is the ultimate expression of Vineyard living - where comfort, nature, and coastal beauty come together in perfect harmony. First Floor: The welcoming foyer is open to the upper level and offers tremendous natural light. The primary suite enjoys premier space and views with slider doors to the fabulous deck overlooking the water. A full bath was fully renovated and boasts a private patio where you will enjoy your outdoor shower and hot tub, taking in the views. A second bedroom also has water views and sliders to the back deck, and the third bedroom is at the front of the house on this level. A shared full bath and a separate laundry complete this floor. Second Floor: The magnificent view empowers this floor. From the moment you enter this space, you are captivated by the views. The layout is designed to capture the essence of the active water views. The dining room and living room provide easy access to the expansive deck where you will spend most of your time. The kitchen is located at the front of the house and is open to the dining room. Complementing this fabulous space is the stone fireplace. What could be better?

$5,995,000 - East Sandwich, MA

46 Roos Road East Sandwich, MA - Welcome to 46 Roos Road, the largest and stunning 35-acre coastal estate on Cape Cod in Sandwich, MA, located just 60 miles from Boston. This exceptional property offers unparalleled privacy and breathtaking views, bordered by Cape Cod Bay and conservation land. Truly one of a kind with diverse landscape, including trails, wooded areas, open fields, along with 5 freshwater ponds. The beautifully appointed, eco-friendly, light filled main home features a chef's dream kitchen with Wolf range, oven and SubZero Fridge,, beautiful recycled glass countertops, and breakfast bar island. An open floor plan with fireplaced living and family rooms. vaulted ceilings, separate dining area, three bedrooms, two full and two half bathrooms, and pond views create an exceptional main residence. The nearby large barn/garage/workshop has room for seven vehicles. The charming guest house has two additional bedrooms and two full baths, ideal for visitors or extended family.Nature enthusiasts will appreciate the five tranquil self maintaining ponds that recharge naturally every week that ensure a steady supply of fresh water. Along with solar ground panels, protected agriculture and water rights, the environmental design enhances the property's beauty and sustainability. There is development potential for an additional home and agricultural buildings/opportunities. Recreational amenities include trails that are ideal for hiking, running, biking, and even horseback riding. A dock and two floats on the ponds add to water-based activities along with 80 feet of private ocean beach along Cape Cod Bay which offers amazing sunrise and sunset views.

$5,995,000 - West Yarmouth, MA

31 Moss Road West Yarmouth, MA - Stunning Cape Cod contemporary on Great Island with a private sandy beach. The perfect seaside retreat for entertaining or relaxing, this exquisite residence enjoys an unprecedented combination of luxury and natural beauty within an exclusive gated community. Upon entering, sweeping views of Nantucket Sound can be seen through oversized windows and glass doors that lead to a spacious wooden deck and infinity-edge pool, where summer days can be spent basking in a resort-like setting. Unsurpassed quality and craftsmanship are found throughout the interiors, with a thoughtful layout that effortlessly flows from an open concept living and dining space to a gourmet kitchen with top-of-the-line appliances and a breakfast bar. A home office showcasing magnificent millwork and a brilliant mural of constellations on the ceiling is located just off the main living area, while a sitting room and secluded en suite guest bedroom complete the main level. The primary suite boasts an entire wing on the second floor, with breathtaking views, a luxurious bathroom, and large walk-in closet. A well-appointed bedroom suite on the far side of the home provides elegant accommodations for family or guests. At the center of the second level, an elevated and awe-inspiring observation room currently configured as a home office benefits from panoramic ocean vistas with access to a large balcony and a rooftop deck above. The ground level features a fourth bedroom, a den, and a mudroom leading to an attached two-car garage. Association amenities include a private beach, dock, and security. Meticulously designed to the highest standards, this one-of-a-kind beach home is ready to be enjoyed.

$5,995,000 - New Marlborough, MA

390 Tamaridge Rd New Marlborough, MA - Rare 330 acre parcel with stunning long views, abutting conservation land. Total seclusion and privacy, bucolic countryside with open meadows. Once a grand Berkshire estate, the property consists of the main Tudor style residence with indoor pool, shingled barn, Dutch colonial multi family dwelling, a guest house & several smaller sheds and workshop. All buildings in need of extensive work. Divided into distinct areas, the sunken gardens feature different design elements. A unique and wonderful opportunity, within close proximity to Gedney Farm, Old Inn on the Green, Southfield Store, and just minutes to ski Butternut and Great Barrington Mullany helen_mullany@yahoo.com 413-429-7733 HELEN MULLANY REAL ESTATE, LLC

$5,900,000 - Chatham, MA

25 Wikis Way Chatham, MA - Prepare to be embraced by one of the most breathtaking panoramas in all of Cape Cod. This exceptional property offers sweeping and unobstructed views that stretch from Stage Harbor and the iconic Chatham Lighthouse, to the natural beauty of Monomoy Island and the sparkling expanse of the Atlantic Ocean. From first light until sunset, this coastal retreat is surrounded by nature's stage of everchanging tides and migratory birds. The property itself is a private oasis of hydrangeas, native oak trees, and pollinator gardens. Set on nearly two acres, the grounds offer resort style living with amenities including a heated gunite pool overlooking the ocean, a tennis court, and sandy beach access to the private association beach. Renovated throughout the years, this classic Cape Cod shingle-style estate exudes both warmth and luxury. As you step into the formal foyer, your eye is immediately drawn to the stunning views beyond.Expansive windows capture the breathtaking scenery throughout. The dining room seamlessly connects to the kitchen, guiding you to the dramatic living room with its cathedral beamed ceilings and a large central hearthan ideal setting for family gatherings and entertaining. This wing also offers abundant storage, including pantry space, a project room, laundry facilities, and a half bath, ensuring both convenience and functionality.The home is thoughtfully designed layout offers the perfect blend of private spaces and convivial family living. The private primary suite is a sanctuary all its own, occupying the entire second floor and accessed by a private stairway. It includes a view-filled office and features two expansive his-and-hers closets. On the main level, the unique "grandchildren suite" provides separate living quarters with three en-suite bedrooms, direct access to the pool, a kitchenette with an inviting sitting area and a cozy central hearth. Beneath this wing and adjacent to the outdoor shower is a separate bunk room with a full bath and laundry accessed from the outdoors offering the perfect hideaway for kids to play and relax while still being close to the main living areas. This magnificent Morris Island estate offers endless possibilities and is a once-in-a-lifetime opportunity.

$5,900,000 - Provincetown, MA

336 Commercial Street Provincetown, MA - Showpiece Hospitality Complex branded as The Pilgrim House and Landing Restaurant is now available for sale. The fabulous location is just steps away from the beach and all of downtown. The current configuration includes 18 well appointed hotel rooms situated across three levels and serviced by a fully functional elevator and multiple stairways. The first floor space includes a reception area flanked by a full service restaurant and additional dining and theatrical room for the presentation of artistic productions. There is also a private bar / lounge on the second floor, private office for management and a workforce housing unit in the rear. The business is loaded with amenities including bikes, high speed wi-fi, private outside space and much more! There is exclusive dedicated parking for guests with electric fueling stations as a green amenity. Countless recent upgrades compliment this thriving diversified business! Revenue streams include rooms, shows, events, bar, restaurant, ticket and much more. Signage, frontage, location and condition make this an absolute must see for any hotelier or entrepreneur!

$5,900,000 - Provincetown, MA

580 Commercial Street Provincetown, MA - Imagine a time before antique homes were ''rehabilitated'' or ''renovated.'' Imagine discovering an untouched jewel, sparkling quietly in Provincetown's coveted east end Commercial Street neighborhood of Captain's homes, boathouses, beach cottages and sandy lanes. There is still one of those hard to find gems remaining, an untouched sprawling home, once several residences in one, on a large parcel of land with a private, enclosed rear garden, home to a two storey Carriage House and a broad front yard, with the expanded antique Cape set comfortably back from Commercial Street with a view to the bay. The main house offers 11 rooms, period correct with pantry, closets, nooks, crannies, double doors, wood flooring, original staircases and details at every turn, a surprise of antiquity with every glance paid. The bonus Carriage House in the back garden is ripe for conversion to a spacious artist's studio, home office, writing studio or gracious guest quarters. You won't be disappointed if you are a connoisseur of old Cape Cod style and New England architecture. Secure this untouched masterpiece today to preserve it for generations to come. You'll be proud to call this legacy property home and you'll be the envy of your neighbors and a respected contributor to the very limited inventory of preserved antique Provincetown historic homes.

$5,900,000 - Orleans, MA

40 Toms Hollow Lane Orleans, MA - A rare offering on the shores of Little Pleasant Bay, 40 Tom's Hollow is a generational waterfront estate encompassing nearly four acres of bucolic landscape with an expansive shoreline, private sandy beach, and iconic boathouse. A winding drive leads through a serene coastal setting to a timeless center-entrance Colonial, where soaring ceilings and panoramic bay views set the tone. The cathedral-ceilinged great room, with pass-through hearth, forms the heart of the home—flanked by a custom kitchen and gracious dining area, perfectly positioned to capture the beauty beyond. A first-floor primary suite offers privacy and comfort, while separate guest quarters provide flexibility for extended stays. The finished walkout lower level adds space for recreation, gatherings, or overflow guests—all opening to a lawn that invites entertaining and the potential for a pool. Outside, a wide stretch of shoreline allows for private beach access, and mooring rights open the door to water-sport adventures. The historic boathouse, brimming with potential, anchors the property in authentic Cape Cod tradition. This is a rare legacy estate where nature and coastal elegance live in quiet harmony.

$5,900,000 - Osterville, MA

804 Main Street Osterville, MA - Welcome to Osterville, Massachusetts! One of the most affluent communities on Cape Cod. Osterville has much to offer! Now you can own a piece of Osterville center. 804 Main is THE gathering spot of the village. Boasting a Speedway gas station/convenience store and the only Dunkin' Donuts within several miles, 804 Main draws from several neighboring communities. The site is the heart of Osterville and ideally located in the center of the village, the one-acre parcel is improved by a 12,000 square foot well-appointed office building with four long-term tenants. The smaller building on the property, a 6,000 square foot charming structure, occupied by Speedway convenience store and Dunkin Donuts. There is also a large office upstairs with a separate side entrance, home to the seventh tenant of the property. 50 parking spaces surround the property. 804 Main offers exceptional investment potential, with a history of stable rental income and a prime location that continues to attract new businesses and customers. Property values on Cape Cod, and especially Osterville, have increased tremendously over the past several years. Get in now before this opportunity slips through your fingers!

$5,900,000 - Egremont, MA

25 Sheffield Road Egremont, MA - Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of the future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+-year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by.

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