Massachusetts homes for sale starting at Fifty Thousand Dollars

$8,995,000 - West Tisbury, MA

85 Reservoir Road West Tisbury, MA - Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench, offering stunning water views of Vineyard Sound and the Elizabeth Islands. Ideally located just steps from Gray's Beach and dock, this is one of the most picturesque properties in Seven Gates Farm. The Seven Gates Farm community consists of 45 homesites on 1,600 acres with 1,000 acres of protected conservation land, open fields, woodlands, ponds, and miles of trails for walking and horseback riding. Residents of Seven Gates Farm also enjoy exclusive access to 1.5 miles of private beach, two piers, and two tennis courts. This rare opportunity allows you to become part of a remarkable community, once an assembly of farms, that remains dedicated to the preservation and stewardship of the land.

$8,950,000 - Osterville, MA

255 Bayberry Way Osterville, MA - Welcome to ''Point House'' a spectacular 5.98-acre waterfront estate on a peninsula overlooking the glistening waters of West Bay. In a setting of unsurpassed beauty, the 4,896 square foot residence offers truly exceptional water vistas, beautiful gardens, an expansive private sandy beach, and a substantial deep-water dock from which you can sail into the waters of Nantucket Sound. The 6-bedroom home features generous yet comfortable living spaces, beautiful architectural detailing, custom wood flooring and 5 fireplaces. The entry foyer welcomes you to the beautiful views and impressive deck that runs the length of the home and beckons you to step outside to take in the panoramic views. Highlights include a light filled, two story great room with a beautiful floor-to-ceiling brick fireplace, a well-equipped kitchen opening into the dining area and a family room accented by a fireplace all opening to the outside living spaces making this flow ideal for quiet family enjoyment or larger scale entertaining. Two bedrooms and a sitting room with fireplace can also be found on the 1st level. The primary bedroom features beautiful water views, a spacious bath, walk in closet and a large sitting room with fireplace, and three additional bedrooms and a sitting room finish the 2nd level. A third-floor walkup to a tower provides the perfect vantage point to watch the incredible sunsets you'll experience from this property. Also offered is a detached two car garage which includes living space above for extended family and guests. This seaside estate affords the utmost privacy yet offers proximity to the village of Osterville with its boutique shops and fine dining. Experience an exceptional lifestyle from this one-of-a kind waterfront estate!

$8,500,000 - North Falmouth, MA

40 Point Road North Falmouth, MA - Ensconced on a PRIVATE Peninsula this serene and tranquil Waterfront Retreat exists.Southern facing this stunning home on 1.07 A provides waterviews of Wild Harbor sailboats sailing by and a pathway to your Private access to ocean for daily swimming and kayaking. Professionally maintained annual plantings range from ornamental grasses,hardy hydrangea bushes and sprawling lawn that highlight the gas fire pit setting for the end of one's day quiet reflection. Retaining walls /patios of New England fieldstone, bluestone and granite meander down to water's edge. Casual lounging all enhanced by the heated salt water gunite pool /jacuzzi plus a Cabana cottage /bathroom This outside Oasis accomodates relaxed togetherness of family/guests bearing sandy feet and wet bathing suits. Tailored architecture blended together with casual elegance the entry details of Mother of Pearl ceilings and coffered millwork invites one directly towards the Ocean! Pass thru glass doors into Private Business office supporting wall-sized custom built desk,bookcases, computer station and group seating for clients, Enormous shell chandelier suspends from Coffered ceiling of living rm- surrounded b pillars,gas fireplace,custom cabinetry/buffet/entertainment center with French doors leading to the Ocean! Flowing directly into the gourmet chef's kitchen for your entertainment venue.Boasting various islands for the delicious buffet-floor to ceiling cabinetry-gleaming appliances,Baker's station-wine cooler - Breakfast nook for beginning your new day ALL while enjoying gorgeous waterviews ! Enjoy a formal dining rm or the outside gazebo style porch offering Summer breezes during your El fresco dining experience. An exceptional 1st flr Master ensuite jacuzzi bathroom and private patio allowing access to the pool for the evening's last dip. Each of the three ensuite 2nd flr bedrooms are spacious furnished/decorated with European flair. There is a Common sitting area/library/relaxed game rm to be quietly enjoyed . Finally there is a charming private suite above the garage that is ideal for the au-pair or live in. Boat launch area or Fiddler's Cove Marina is nearby for your boating pleasure... OPEN HOUSE Saturday March 22 2025 and on Sunday March 23 2025. 12-3 pm OPEN HOUSE Saturday March 29 2025 and Sunday March 30 2025 12-3 pm

$8,000,000 - Osterville, MA

440 Grand Island Drive Osterville, MA - Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. 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.

$7,950,000 - Chilmark, MA

308 South Road Chilmark, MA - Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers a rare blend of privacy, elegance, and modern comfort. Originally built by Tom Tate and renovated in 2018, it exudes contemporary sophistication while embracing its natural surroundings. A private dock on Chilmark Pond provides direct water access and stunning South Shore sunsets. Follow a beautifully manicured path—an iconic Vineyard feature—to your dock and cross the pond to your private beach lot. Surrounded by over 7 acres of abutting conservation land, the setting is peaceful and secluded. Meticulously designed gardens enhance the home's timeless charm. The expansive first floor is perfect for entertaining, with open living spaces and a private office. The ground level offers a relaxed lounge with wet bar and backyard access. Upstairs, a luxurious primary suite spans the entire second floor, featuring two private bathrooms and panoramic water views. More than a home—this is an elegant, serene lifestyle. Separate guest house available; please inquire.

$7,500,000 - Nantucket, MA

45 Brewster Road Nantucket, MA - A RARE and SPECIAL Nantucket Experience awaits you in Monomoy! Tucked behind a tall privet hedge graced with a garden gate lies a serene private oasis. The stunning gardens, mature trees and plantings, thoughtfully manicured lawn and sparkling in-ground pool provide a setting that invites one to experience tranquility, calm and the desire to breathe deeply. With over 1.2 acres (which abut the State Forest), there is space for family, friends and guests to enjoy a game of croquet or volleyball, an outdoor bbq on the bluestone patio, smore's around the large firepit or a garden party on the sprawling back lawn. Although it's tempting to linger outside indefinitely, there are additional reasons to be "wowed" once you step inside. The main house was newly renovated in 2023 in a chic sophisticated style. It boasts 4 bedrooms, 3 bathrooms and an impressive gourmet kitchen complete with large island, high end appliances and a conversation nook in front of a wood burning fireplace. The separate guest/pool house (also fully renovated in 2023) boasts 3 bedrooms, 2 bathrooms, a living room with kitchenette and wood burning fireplace and a separate den overlooking the back lawn. Interior Design work in both dwellings was artfully curated by acclaimed Boston designer Eric Roseff and showcases stunning fabrics, awe inspiring paint techniques, elegant wall and floor coverings, and stylish marble and tile. Both dwellings feature quarter sawn oak floors throughout, central AC, new roofs and shingles and new domestic hot water tanks. There is ample parking for multiple cars AND there is available ground cover for expansion! It's a short distance to Monomoy harbor for your walking, boating and fishing pleasure. The property has been loved and meticulously maintained by the same owner for 22 years, never rented and ready for immediate Summer occupancy. This gem is a MUST SEE!

$7,495,000 - Provincetown, MA

54 Commercial Street Provincetown, MA - The iconic ''1807 House,'' believed to have been built in the late 1700's, is one of the oldest homes in Provincetown. Throughout its history, from Captain Stephen Nickerson, who built the house, many have called it home and many, during the years it was a guest house, shared its timeless beauty and Cape Cod Bay views. While many original details remain, this home has been thoughtfully brought up to date and styled impeccably. Today, there are four condominium units in the main house, including a grand four bedroom residence that occupies most of the original building. Gorgeous wide pine wood flooring, fireplaces, inviting spacious rooms, a broad, water view front porch and a private patio are just a few of the highlights of this impressive home. Enhancing the flexibility of your enjoyment of the property, there are three additional separate residential condominiums included. Immediately adjacent to the main unit at the western front corner of the building is a recently updated two room water view studio condo, ideal for an in-law, au pair or guest accommodation. To the rear of the building, surrounded by beautifully green grounds, there are two additional, spacious condominiums. There is a comfortable first floor one bedroom apartment with private entrance and a spacious second floor open plan studio unit with fireplace and vaulted ceiling. Arrange to visit this highly coveted west end Provincetown property and imagine how you can enjoy the stewardship of this venerable home into the future.

$7,200,000 - North Chatham, MA

238 Cranberry Lane North Chatham, MA - This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and the Atlantic Ocean beyond. Over 114 feet of private beach protected by a beautiful rock revetment. Quick salt water access to anywhere by boat from your own beach. A perfect spot for relaxing, entertaining under the sun or stars and creating lasting memories .This coastal property features panoramic water views, five bedrooms, three baths, and 1850+ square feet of living space to leave as you will or make it your own... A 69,000 plus square foot lot in R 40 zone would allow a guest house and a pool with town approvals in addition to the main house. A short jaunt to Main Street, Chatham Bars Inn and Wequassett, and all that Chatham has to offer....Buyers and agents should verify all information herein.

$6,999,999 - Harwich Port, MA

27 Saquatucket Bluffs Road Harwich Port, MA - Saquatucket Bluffs, Harwich Port: Discover the epitome of coastal luxury in this upscale waterfront retreat! Boasting 200' of pristine shoreline, this property is a haven for maritime enthusiasts. A grand 120-foot deep water dock, offering 240 usable feet with a 9' channel out to Nantucket Sound and the Atlantic. A majestic family owned estate, designed by renowned architect Royal Barry Wills, the property boasts extensive views with panoramic scenes of the sparkling harbor waters and serene landscapes of the salt water inlets. This fabulous design offers five generous bedrooms, five and a half baths, including two living rooms, spacious kitchen, private primary bedroom with ensuite bath, guest bedrooms on the second floor with private bathrooms, and a secluded spacious waterview office. Indulge in the expansive outdoor space, with in-ground pool, perfect for al fresco dining and entertaining, or simply savoring the breathtaking sunset views over the water. An idyllic retreat for those seeking the perfect blend of luxury and coastal living this property offers unrivaled access to a deeded private beach. Seize this rare opportunity to own a piece of Coastal Cape Cod!

$6,999,990 - Orleans, MA

64 Pershing Lane Orleans, MA - Mayflower Point, Orleans. This extraordinary waterfront estate on Little Pleasant Bay is now complete for Summer 2025. Eastward Companies, synonymous with Lower Cape luxury homebuilding, has exquisitely designed this 5800 sq ft shingle-style masterpiece to showcase their coastal aesthetic in a fantastic saltwater setting. The covered entry porch beckons to the main floor which is entirely dedicated to gathering and enjoyment. The coffered-ceiling great room features walls of windows and access to the classic porch w/retractable screens. The hand-crafted luxury kitchen is replete with features including a butler's pantry and a custom island that seats eight. Extensive fenestration ushers in light and captures deep views. Ornate millwork and finishes adorn every room. The 2nd floor, accessible by stairs or an elevator, offers three guest suites plus an elegant primary bedroom wing and a fireplaced family room, both with dramatic views. The lower level provides media, exercise and additional sleeping space. The waterside outdoor area includes a saltwater gunite pool, gas firepit, expansive granite patio and stairs to water's edge for swimming, kayaking and mooring access

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