Whether it’s a beautiful cottage looking out upon the Atlantic Ocean from Martha’s Vineyard, a luxurious island mansion on the shores of Nantucket, or even an idyllic, historical home with bay views on Cape Cod, the shorelines of Massachusetts are appealing locations for buyers looking for a luxury, waterfront experience.

By Kristen Ordonez

Photo courtesy Maury People Sotheby’s International Realty

Gary Winn, Broker at Maury People Sotheby’s International Realty, knows all too well about the benefits of purchasing a waterfront home, specifically in Nantucket. “I can’t speak for all of Massachusetts, but buying waterfront property on Nantucket is a great opportunity and a great investment.”

Similar to other regions of New England, waterfront properties in Massachusetts aren’t limited by a small inventory, but instead face difficulties in finding room to expand. As Winn mentions, a stretch of land with water frontage is rare because “they’re not making any more” of them. However, this fact opens up the opportunity to either purchase an existing waterfront home with a long history, or start from the ground up by refurbishing or building a new construction. As featured below, many of the most expensive waterfront properties in Massachusetts are original mansions or homes that have been around for decades, as well as fully renovated estates that are new to the shore.

Nantucket and other shore towns in Massachusetts offer an array of opulent estates for the most discerning buyers, providing exclusive lifestyles that are not available elsewhere. “When you come to Nantucket, although you may not be travelling far, you really feel like you’ve gone someplace,” says Winn.

If you want to buy something for $10 million or more in Massachusetts, then here are your options:

4 Middle Valley Road and 48 Shimmo Pond Road, Nantucket
Designed by renowned Jacobsen Architecture, the Harbor Hill Estate on the Shimmo waterfront features luxurious amenities, state-of-the-art systems and exceptional execution on an elevated harborfront, 4.5-acre parcel with private beach stairs.
Listed by Donna Barnett of Maury People Sotheby’s International Realty

260 Polpis Road, Nantucket
With over 60 acres and unobstructed views over Polpis Harbor, this Swain’s Neck estate is situated on a peninsula and potentially the island’s most private family retreat.
Listed by Jonathan Radford of Coldwell Banker Residential Brokerage

$32,750,000 to $28,500,000
72, 76 and 78 Pocomo Road, Nantucket
Unique waterfront compound with 300-degree dramatic views, privacy, direct access to a gorgeous sandy beach, boat moorings and multiple dwellings, including a main house, studio, 2-bedroom cottage, 6-car garage, pavilion and guesthouse.
Listed by Gary Winn, Bernadette Meyer, and Craig Hawkins of Maury People Sotheby’s International Realty

22 & 24 Easton Street, Nantucket
Perfectly situated on the inner harbor waterfront in the heart of Brant Point, this spectacular property boasts 120-plus feet of waterfront and one of only three private deepwater docks on the island.
Listed by Edward Sanford of Great Point Properties

13 Squam Road, Nantucket
This oceanfront, private compound was designed for the discriminating buyer to enjoy the island of Nantucket with a main house, thoughtfully designed outdoor living areas and a private boardwalk that leads to Squam Beach.
Listed by Chris Kling of J. Pepper Frazier Real Estate

97 Tilippi Run Street, Cape Cod, Chatham
Boasting one of the most spectacular properties on the Cape Cod shoreline, this shingle-clad, 6-bedroom estate is poised on 1.9 acres and majestically resides over the Atlantic Ocean, Monomoy
Islands and Nantucket Sound with 10,974 square feet of living space.
Listed by Christopher Rhinesmith of Pine Acres Realty

119 and 119R Eel Point Road, Nantucket
An outstanding property consisting of 2 homes, each sitting on nearly 2 acres; offered together, the main house, studio and cottage overlook 4 acres of oceanfront real estate on the north shore of Nantucket Island.
Listed by Gary Winn of Maury People Sotheby’s International Realty

46 Easton Street, Nantucket
The most authentic, unrestored Old Nantucket homestead available on the island, “Auburn Cottage” is available for new owners for the first time in its history. This truly is a once-in-a-lifetime chance to own an iconic island landmark.
Listed by Bill McGowan of Lamacchia Realty, Inc.

40, 41 & 43 Ocean Avenue, Nantucket
Located just a short distance from the center of Main Street, “The Sheiling” is an elegant home with many custom details throughout and panoramic ocean views from almost every room.
Listed by Jeanne Hicks of Lee Real Estate

7 Starbuck Neck Road, Edgartown
A rare offering in one of Edgartown’s most coveted neighborhoods, this exclusive, 1.2-acre estate has spectacular water views of Edgartown Harbor, Edgartown lighthouse and Nantucket Sound from three sides of the house.
Listed by Thomas Wallace of Wallace and Co. Sotheby’s International Realty

79 Turkeyland Cove Road, Edgartown
Custom-designed by Bradenburger Taylor Lombardo Architects from San Francisco, and built by reputable island builder John Early, this unique and lavish home is in a league by itself.
Listed by Thomas Leclair of LandVest

192 and 187 Mishaum Point Road, Dartmouth
At the tip of Mishaum Point, Robert A.M. Stern created a Shingle-style masterpiece that is perfectly sited to embrace the full scope of its 270-degree ocean views and features handcrafted details throughout.
Listed by Robert Kinlin of Robert Paul Properties

The Oaks, 49 Margin Street, Cohasset
The Oaks, a private 9.41-acre peninsula with 1,800 feet of ocean frontage and a protected 112-foot deepwater dock, is a magnificent 20,000-square-foot Georgian Revival mansion that has been renovated to the highest standards.
Listed by Jonathan Radford of Coldwell Banker Residential Brokerage

45 Hulbert Avenue, Nantucket
The iconic Brant Point property is complemented by native Rosa Rugosa, a lush side and front lawn for entertaining and a 6-bedroom home, which boasts a balanced blend of yesteryear and today’s modern amenities.
Listed by Laura Fletcher of Great Point Properties

50 Oyster Watcha Road, Edgartown
Ideally and prominently positioned on the southernmost peninsula of Oyster Pond, this idyllic compound offers over 1,200 feet of private waterfront on Oyster Pond and access to over 2,200 feet of Atlantic beach.
Listed by Peyton Wallace of Wallace and Co. Sotheby’s International Realty

Kragsyde, 27 Smiths Point Road, Manchester
Finished in 2015, this modern stone and glass estate is a spectacular waterfront property that combines uncompromised ocean views with breathtaking modern architecture, contemporary convenience and unsurpassed luxury.
Listed by Darin Thompson of Stuart St. James, Inc.

2 and 4 Morse Street, Edgartown
Multi-lot waterfront family compound consisting of two primary homes of equal quality and a separate studio/office, all with dramatic views of Edgartown Harbor, the Lighthouse, and Katama Bay.
Listed by Twanette Tharp of The Tharp Group

96 Beach Road, Edgartown
This dramatic compound is set amidst 150 acres of conservation land. Completed in 2010, and offering almost 10,000 square feet of living space, this 5-bedroom, 7-bath custom home affords every amenity with exceptional finishes.
Listed by LandVest

33 Proctor Street, Manchester
A rare opportunity to own a waterfront family compound consisting of 2± acres on Manchester Harbor. With 325± feet of water frontage, the property offers direct boating access to Manchester Bay and beyond.
Listed by Lanse Robb of LandVest

8 Lavendar Lane, Nantucket
Stunning 280-degree panoramic and unobstructed water views can be enjoyed from this Eel Point location. The house and cottage sit on 5.5 acres and have direct beach paths to some of the island’s most ideal beaches.
Listed by Chris Kling of J. Pepper Frazier Real Estate

421 Main Street, Osterville
Overlooking the beautiful waters of East Bay and Nantucket Sound sits this sophisticated yet intimate waterfront estate that has been completely upgraded from stem to stern with the highest-grade
materials and exceptional craftsmanship.
Listed by Robert Kinlin of Robert Paul Properties

19 East Tristram Avenue, Nantucket
The quintessential Dionis waterfront property featuring an
attractive 4-bedroom, 4-bath home, high elevations allowing for expansive views of Nantucket Sound, and a wonderful bath and beach house.
Listed by Edward Sanford of Great Point Properties

55 Eel Point Road, Nantucket
One of Nantucket’s most beautiful homes in one of Nantucket’s most valuable locations! Immaculate 5-bedroom, 5-bath residence on 2 acres with a rare backyard beach path.
Listed by Steve DiFrancesco of Hunter, Reed and Company

27 Ocean Bluff Drive, New Seabury, Mashpee
This truly exquisite home has easy access to the flawless white sandy beach and is situated close to all the activities of Popponesset, New Seabury country club and golf club.
Listed by Paul Grover of Robert Paul Properties

10-54 Sipson Island, Orleans
Sipson Island, a 25-acre landmark on the eastern coast of Cape Cod, is presented for sale in its entirety for the first time in generations and features several year-round dwellings and an extensive private beach.
Listed by Paul Grover of Robert Paul Properties

17 Squam Road, Nantucket
With 180 degrees of spectacular ground-floor ocean views, few opportunities arise to find another rare 5-acre waterfront parcel like this one.
Listed by Susan Chambers and Juliet Hunter of Maury People Sotheby’s International Realty

13 Kingsbury Lane, Orleans
This secluded 4.4-acre waterfront estate overlooking Pleasant Bay features a new 8,500-square-foot residence with magnificent views of a bay studded with islands.
Listed by Robert Kinlin of Robert Paul Properties

260 North Bay Road, Osterville
Capturing the luxurious spirit of Oyster Harbors, a private gated community, this stunning Royal Barry Wills waterfront residence features elegant interiors with rich details, extraordinary views and 275 feet of water frontage.
Listed by Robert Kinlin of Robert Paul Properties

4 Gosnold’s Way, Chillmark
A rare opportunity to own one of Chillmark’s premier waterfront
locations. Enjoy over 22.75 acres of scenic, natural landscape from this unique parcel.
Listed by Gerret Conover of LandVest

520 Shore Road, Chatham
Sand Bars is the largest waterfront parcel on Shore Road and offers stunning, elevated views of Chatham Harbor and the Atlantic.
Listed by Christopher Rhinesmith of Pine Acres Realty

“The Whale,” 849 Main Street, Vineyard Haven
Affectionately known as “The Whale” and owned by the same Vineyard family for more than 60 years, this West Chop waterfront home on 1.62 acres in Vineyard Haven is a true Martha’s Vineyard classic.
Listed by Carol Shore of Coldwell Banker Landmarks Real Estate

46 Shimmo Pond Road, Nantucket
“High Shimmo” is ideally situated at the end of Shimmo Pond Road, creating a private oasis accented with private beach and sweeping views of the harbor, the channel, and out to Nantucket Sound.
Listed by Edward Sanford of Great Point Properties

$10,750,000 or $20,000 a week
53 South Water Street, Edgartown
Harborfront on South Water Street, this 4-bedroom home is impeccably landscaped right down to the water’s edge. A quaint boathouse for kayak and fishing pole storage, plus a deepwater dock complete this special village home.
Listed by Gerret Conover of LandVest

32 Ocean View Avenue, Edgartown
Located on exclusive Ocean View Avenue, this custom contemporary home offers panoramic views of Edgartown Harbor and Chappaquiddick Island.
Listed by Thomas Leclair of LandVest

205 Eel Point Road, Nantucket
This waterfront wonder represents an opportunity to own 2.9 acres on the well-protected Madaket Harbor in Dionis. Enjoy beautiful sunsets, over 130 feet of beach, and water sports right out your back door.
Listed by John McGarr and Kristen Gaughan of William Raveis

“Cliff Cottage,” 22 Quitsa Lane, Chillmark
Originally built in 1850 and remodeled by the current owners, “Cliff Cottage” enjoys one of the most picturesque settings and water views on Martha’s Vineyard and reflects today’s lifestyle and amenities.
Listed by Thomas Wallace of Wallace and Co. Sotheby’s International Realty

32 Boldwater Road, Edgartown
This amazing property offers open living areas, countless unique features and an abundance of glass windows and doors facing the water and the beautiful landscaped grounds.
Listed by Gerret Conover of LandVest

This story originally appeared in Unique Homes Summer 2017.