Massachusetts homes for sale starting at Fifty Thousand Dollars

$12,750,000 - Chilmark, MA

16 Shotnaigher Lane Chilmark, MA - New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet kitchen, adjacent butler's pantry & vast open living area with wood burning fireplace, mellow wood floors and breathtaking views out every window. Four large bedrooms, three bathrooms plus a powder room. Primary suite bathroom features an independent tub and steam shower. Fully heated, insulated and air conditioned this home is four season living. Walking paths to pond access for kayaking, swimming and boating & association tennis court. This property is protected by a Trustees of Reservation Deed of Conservation Easement.

$12,295,000 - Osterville, MA

741 Sea View Avenue Osterville, MA - Experience the epitome of coastal luxury on a sun-drenched day, where shimmering waters create an enchanting ambiance. Nestled on over 2.3 acres along prestigious Sea View Avenue, this extraordinary Osterville estate, built in 1929, is steeped in history and charm. Step inside to discover expansive windows that showcase breathtaking views of Nantucket Sound. Step outside to enjoy 170 feet of pristine, sandy beach, and a serene Gunite pool equipped with a hot tub and pool house with a full bathroom. The first floor features a spacious living area and a flexible den/dining room, both with wood-burning fireplaces. A first-floor bedroom adds convenience and versatility. The kitchen, complete with a butler's pantry and bar area, leads to a mudroom providing additional storage. The second floor offers five bedrooms, including two en-suites, and two additional full bathrooms, ensuring plenty of space for family and guests. Thoughtfully designed with multiple staircases, this home offers convenience and seamless flow between levels. Additional highlights include wide pine floors throughout, detached carriage house with a finished room, walkout basement, and 7-bedroom septic system. Located just minutes from Osterville village, this iconic home is the perfect property for anyone seeking an oceanfront sanctuary.

$12,250,000 - Osterville, MA

71 Sand Point Osterville, MA - Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coastal luxury with this magnificent Cape Cod waterfront estate, nestled in the prestigious gated community of Oyster Harbors. Boasting 450 feet of pristine water frontage with a private beach and breathtaking views over Cotuit Bay and North Bay, this property offers spectacular sunsets, an elegant coastal lifestyle, and unparalleled privacy. Stepping into the grand foyer, you are greeted by vaulted ceilings and expansive windows that showcase panoramic water views, seamlessly blending the outdoors with the refined interiors. The open-concept living spaces include a gracious living room, a fireplace-warmed dining room with custom built-ins, and a sophisticated sitting area, all designed for effortless entertaining. A private home library, accessed by a spiral staircase, overlooks both the main level and the serene waters of North Bay. The gourmet chef's kitchen is a masterpiece, featuring a granite center island, custom built-ins, and a charming breakfast nook with wraparound picture windows framing the breathtaking waterfront vistas. The sumptuous first-floor primary suite is a sanctuary of relaxation, offering private patio access, a spacious walk-in closet, and a spa-inspired en-suite with dual vanities, a luxurious soaking tub, and a glassless double-headed rain shower. The sun-drenched sunroom complete with a full wet bar and sliders on three sides opens directly to the meticulously designed outdoor living areas. The second level hosts four additional spacious bedrooms, a generous family room, and a bonus room with a private balcony, designed for both comfort and relaxation. This exceptional residence also features a partially finished lower level, thoughtfully designed to enhance both convenience and functionality with direct outdoor access perfect for accommodating small boats, golf carts and other recreational essentials. Set on 1.37 acres of pristine coastal land, this estate is an outdoor enthusiast's paradise. The meticulously landscaped grounds feature a built-in fire pit, an outdoor shower, a waterside in-ground pool, a sandy beach, and a private dock. A rare opportunity to own a world-class waterfront residence, this home delivers unparalleled elegance, modern luxuries, and the very best of Cape Cod's coastal living.

$11,995,000 - Provincetown, MA

337 Commercial Street Provincetown, MA - Available for purchase following 70 years of ownership, this exceptional waterfront property presents a rare investment opportunity. This historic commercial parcel, once home of the Hillard Wharf now Lands End Marine Supply & Hardware store, is one of the largest parcels in the TCC Zoning District with 141.87+/- feet of frontage. This multi-use property consists of over 15,000+/- sq.ft. of retail space on the first floor and over 7,000+/- sq.ft. of combined office, retail and residential spaces on the second and third floors. The residential space consist of two units, each over 2,400sq.ft. One penthouse unit features 2 bedrooms, 1 & 1/2 baths, 2 fireplaces, an office and panoramic views of the bay on one side and Commercial St. on the other. The second penthouse, a spacious waterfront deed-restricted 2 bedroom 2 bath with an oversized deck boasts spectacular panoramic views, as well. The basement storage extends throughout the entire footprint of the building. 18+ parking spaces available. Seller welcomes offers with requests for buyer concessions.

$11,000,000 - Nantucket, MA

3 Lyford Road Nantucket, MA - First time offered ! Tom Nevers property with unobstructed ocean views! Presenting a custom-built 2-bedroom cottage just a short distance from the private steps leading to the expansive beach below. This 2.45 ac property boasts an additional 2600 sf ft of allowable ground cover that becomes your blank canvas to create the ultimate beachfront retreat. You have the chance to live comfortably in the existing cottage while your vision for the main house takes shape. And that's not all! Consider the prospect of lounging by your future pool, fire pit or even inviting guests over for friendly matches on your private tennis court. With the many possibilities abound, this property offers an unparalleled chance to craft the coastal oasis you've always desired. Make your vision a reality, this property is available to view by appointment only.

$10,995,000 - Osterville, MA

168 Garrison Lane Osterville, MA - Set on highly sought-after Garrison Lane, this extraordinary residence boasts one of the most desirable locations in Osterville with panoramic views of West Bay and Eel River. The property is a boater's paradise with a protected deep-water dock offering easy access to Nantucket Sound. Beautifully constructed with exquisite finishes, the five-bedroom home is positioned to provide stunning water views from nearly every room with multiple outdoor living areas. A large great room with double-height ceilings sits at the center of the home, with an adjacent eat-in kitchen that opens to a waterside terrace. Comfort and convenience are afforded with expansive primary suites on both the first and second floors. Three additional guest bedrooms are located on the second floor, while the finished walkout basement provides flexible bonus space with a kitchenette and wet bar. Set amidst rolling lawns and manicured gardens, this magnificent estate is minutes from everything Osterville has to offer.

$10,950,000 - Cotuit, MA

122 Pinquickset Cove Circle Cotuit, MA - Presenting one of Cape Cod's most extraordinary waterfront estates, set on 7.6 acres of park-like grounds. Manicured gardens and specimen trees set the stage as one approaches this inimitable property designed by renowned architect Andrew Franz, featuring a main residence, guest cottage, and carriage house. Reminiscent of a private resort, the waterside of the home boasts an expansive terrace and infinity pool, ideal for relaxing or entertaining on any scale. Inside, an unprecedented combination of Old World elegance and modern luxury are found throughout, from the Savant Smart Home system to 200-year-old columns and hand-painted tiles imported from Europe. A chef's dream, the kitchen boasts two La Cornue ranges, soapstone counters, whitewashed brick walls and breathtaking water views. The primary suite is luxury redefined, complete with a sumptuous bathroom, dressing rooms, a private balcony, and a sitting room. Located minutes from Oregon Beach and everything else the area has to offer, this one-of-a-kind estate delivers a rare and extraordinary lifestyle.

$10,800,000 - Osterville, MA

545 Sea View Avenue Osterville, MA - Set on Osterville's prestigious Sea View Avenue, this exquisite waterfront estate boasts an unparalleled combination of privacy, presence, and natural beauty. Sweeping views of Nantucket Sound and a pristine private sandy beach highlight this one-of-a-kind offering, located just minutes from everything Osterville has to offer. Accessed via a long, tree-lined driveway, coastal gardens and rolling lawns set the stage as one approaches the classic Cape Cod residence. Immediately upon entering, breathtaking views are on full display and continue throughout, with large windows and glass doors that seamlessly connect to multiple outdoor living spaces. At the heart of the home, a generously proportioned living room with three exposures is flooded with natural light, opening to a den on one side and a dining room on the other. Fit for any occasion, the dining room connects to the adjacent kitchen featuring an eat-in breakfast bar and water views. A guest bedroom completes the first level, offering convenience and flexibility. On the second floor, five additional bedrooms - including a spacious primary suite with mesmerizing vistas over Nantucket Sound - ensure ample accommodations for family and friends. Outside, the expansive lawn and terraces are ideal for embracing the outdoor lifestyle, while a staircase at the edge of the yard leads to one of Cape Cod's finest private sandy beaches. Just moments from The Wianno Club, Oyster Harbors, and the shops and restaurants of Osterville's Main Street, this rare and extraordinary property is ready to be enjoyed.

$10,750,000 - Orleans, MA

71 Towhee Lane Orleans, MA - Extraordinary new construction on sought-after Pleasant Bay. This rare opportunity features a stunning five-bedroom residence with a swimming pool, boathouse, deeded beach access, and rights to a private mooring. Showcasing unsurpassed quality and craftsmanship, the open concept floor plan caters to modern living with a spacious living and dining area with coffered ceilings, a gas fireplace, and sweeping water views through sliding glass doors that line the waterside of the home. The adjacent gourmet kitchen is a chef's dream with a Wolf range, Sub-Zero refrigerator, granite countertops, and a butler's pantry. Just outside, the pool and spa area provides a resort-like setting, complete with a cabana featuring a kitchenette, bathroom, and outdoor shower. A secluded first-floor primary suite offers total comfort and convenience, boasting a large walk-in closet and luxurious bathroom. On the second level, three well-appointed bedroom suites all enjoy bay views. The walkout lower level is perfect for relaxing after a day on the water, finished with an entertainment area, kitchenette, and full bathroom. Ideal for boating and fishing enthusiasts, the newly renovated boathouse on Pleasant Bay includes a kitchenette, living room, bathroom, and large deck with stairs to the water. Additional highlights include a three-car garage with a guest apartment above. Ready to be enjoyed, this one-of-a-kind estate delivers Cape Cod living at its finest, located minutes from Wequassett Resort, Eastward Ho!, and everything else the area has to offer. 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.

$10,500,000 - Osterville, MA

501 Eel River Road Osterville, MA - Discover the epitome of luxury living in this custom-designed waterfront estate, featuring breathtaking views of Eel River and Nantucket Sound. Located in the village of Osterville and set on an expansive and beautifully landscaped 2.4-acre lot, this stunning residence features over 8,000 square feet of meticulously crafted living space with rich details, modern comforts and extraordinary views. The grand interiors seamlessly blend with the exquisitely landscaped outdoor spaces, featuring an inground pool, hot tub, spacious pool house, and a substantial private deep-water dock. Upon entering the home, the grand foyer leads you into the magnificent great room with a two-story custom fireplace, where panoramic vistas of the water and breathtaking sunsets set the scene for unforgettable family gatherings as well as effortless entertaining. The generous floor plan also features a refined library, formal dining room, a gourmet kitchen with center island, custom cabinetry and top-of-the-line appliances and a state-of-the-art home theatre. The six ensuite bedrooms include a first-floor suite with French doors leading to the back yard and a lavish primary suite with a luxurious bathroom, two walk-in closets and a private deck overlooking the water. Enhanced with modern conveniences such as a Sonos whole-house sound system and a 9-zone Hydro air system, every detail has been carefully planned and implemented. Additional highlights include a private guest suite above the attached 3-car garage and a sprawling entertainment room with a balcony on the third level highlighted by western exposure to experience breathtaking sunsets. Located just minutes from the upscale boutiques and renowned dining of Osterville village, this extraordinary property offers a lifestyle of unparalleled elegance and tranquility by the sea. 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.

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