Oyster Harbors - Osterville

oyster harbors - osterville ma

Oyster Harbors is an waterfront, gated community situated on Grand Island in Osterville.  This neighborhood of luxury homes encompasses the entirety of Grand Island and is known for its extraordinary privacy, security and ambiance.  Oyster Harbors is often cited as the finest and most exclusive community on Cape Cod.  With world-class deep-water boating, an exclusive country club and private beaches, Oyster Harbors offers something for everyone.    Read more about Oyster Harbors.  

Oyster Harbors Homes For Sale

274 Carriage Road, Osterville
  • Single Family
  • 5 Beds
  • 4 Baths
  • 5,000 SqFt

274 Carriage Road, Osterville

$8,500,000
250 Windswept Way, Osterville
  • Single Family
  • 6 Beds
  • 5 Baths
  • 4,235 SqFt

250 Windswept Way, Osterville

$7,495,000
360 Bay Road, Osterville
  • Single Family
  • 6 Beds
  • 6 Baths
  • 3,719 SqFt

360 Bay Road, Osterville

$6,950,000 ↓ $300,000
New
71 Sand Point, Osterville
  • Single Family
  • 5 Beds
  • 6 Baths
  • 4,938 SqFt

71 Sand Point, Osterville

$6,495,000
92 Bay Road, Osterville
  • Single Family
  • 6 Beds
  • 7 Baths
  • 6,482 SqFt

92 Bay Road, Osterville

$5,500,000
320 Seapuit River Road, Osterville
  • Single Family
  • 6 Beds
  • 7 Baths
  • 4,958 SqFt

320 Seapuit River Road, Osterville

$4,300,000
285 Windswept Way, Osterville
  • Single Family
  • 5 Beds
  • 6 Baths
  • 4,727 SqFt

285 Windswept Way, Osterville

$3,400,000
292 Grand Island Drive, Osterville
  • Single Family
  • 6 Beds
  • 6 Baths
  • 4,707 SqFt

292 Grand Island Drive, Osterville

$2,995,000
New
473 Grand Island Drive, Osterville
  • Single Family
  • 6 Beds
  • 6 Baths
  • 7,126 SqFt

473 Grand Island Drive, Osterville

$2,895,000
20 Grand Island Drive, Osterville
  • Single Family
  • 8 Beds
  • 5 Baths
  • 2,811 SqFt

20 Grand Island Drive, Osterville

$1,495,000

More About Oyster Harbors

Oyster Harbors Club

The community is anchored by the private Oyster Harbors Club which features a challenging 18-hole golf course designed by Donald Ross and legendary landscape architects John and Frederick Olmstead.  The course was updated in 2009 by Tom Doak of Renaissance Golf Design with a restoration of all the bunkers and removal of trees to open up the course to its original design. The Oyster Harbors Course plays 6,807 yards, par 72 from the longest black tees with a course rating of 73.2. Three holes on the course are particularly noteworthy including the 147-yard 3rd which plays over an oddly shaped bunker, the 434-yard 11th which features a challenging water hazard short and left of the green and the 410-yard 18th with a dogleg to the right before the home green.  

The Oyster Harbors Clubhouse is a 41,000 building sited on hill overlooking Tim's Cove and beyond to Cotuit Bay.  It was was completely rebuilt in 2006 in a contemporary Cape Cod architectural design with weathered cedar shingles.  The clubhouse features a lounge, casual and fine dining and offers stunning views of Cotuit Bay.  The Oyster Harbors Club also offers five tennis courts and a beach.

The Oyster Harbors Club is capped at 440 members and about 30% are from the Oyster Harbors community.  

Oyster Harbors Real Estate

Homes in the Oyster Harbors community include waterfront gems on Cotuit Bay, West Bay, North Bay and Nantucket Sound with private docks as well as homes with views of the golf course.  Architectural designs in Oyster Harbors are predominantly traditional Cape Cod homes, many of which feature custom enhancements and coastal elegance.  Architecturally significant homes are found throughout Oyster Harbors designed by renown architects including Royal Barry Willis, Don Hisaka, Tom Catalano, Reed Morrison, Hutker Architects, Fine Line Design, Polhemus Savery DaSilva and Patrick Ahern.  Select homes at Oyster Harbors have deeded rights to a beach and dock on Cotuit Bay.

Oyster Harbors Location

Oyster Harbors is located 2.5 miles from the quaint village of Osterville which boasts upscale shops, unique restaurants and more.  Other nearby attractions include Dowses Beach, Oyster Harbor Marina and the Crosby Boat Yard.  To reach Oyster Harbors from Osterville Village, head south on Parker Road, then turn right on West Bay Road, then take the second left onto Bridge Street and follow one mile to the Oyster Harbor Gate House.

Boston and Providence are both conveniently located just 75 mile from Oyster Harbors in Osterville.  The Barnstable Municipal Airport in Hyannis is located nine miles from Oyster Harbors and offers commercial flights to Boston and New York and can also accommodate private aviation.   

Oyster Harbors Boating

Boaters are drawn to Oyster Harbors and a number of homes in this exclusive community feature private deep-water docks that can accommodate significant yachts. Boating enthusiasts without private docks enjoy convenient access three marinas located just outside the Oyster Harbor gates on Crosby Basin. 

The community is surrounded by water on all four sides with Cotuit Bay to the west, North Bay to the north, West Bay to the east and the Seapuit River to the south. Access to the open waters of Nantucket Sound is unrestricted and just minutes away.  A cruise to Martha's Vineyard, Cuttyhunk or Nantucket is a breeze from Oyster Harbors.

Oyster Harbors History

A look back at the history of Grand Island offers a fascinating view into the origins of Oyster Harbors. Before European settlers arrived, the island was inhabited by the Wampanoag who lived in the area that is now Southeast Massachusetts, Cape Cod and the Islands.

Legend has it that in the 1680's pirate Captain Kidd visited the area buried his treasure at Noisy Point on Cotuit Bay. Allegedly the treasure was guarded by a witch named Hannah Screecham who lived alone on Grand Island. It is thought that Hannah's ghost still haunts the island and that her loud shrieks can still be heard on the Grand Island Dunes. To this day, the pirates treasure has never been found at Noisy Point.

In the 1706 the Wampanoags sued the Lovells for grazing cattle on Grand Island and won the case, but ultimately had to sell this land to the Lovells in 1737 to cover their legal fees. For much of the the 18th and early 19th centuries, Grand Island was uninhabited and used for grazing and saltworks along the Sepuit River. After the Civil War parcels of Grand Island were sold to prominent Cotuit residents who likely used the land for hunting.

The first home was built on Grand Island in 1904 at Noisy Point by Pulitzer Prize winning Harvard Professor Edward Channing. By the time of the first world war, Grand Island was developed with seven houses. Boston developer Forris Norris purchased Grand Island in 1925 and started developing it as a summer resort. Prominent golf course designer Donald Ross and landscape architects the Olmstead Brothers were hired to design the resort. Much of the original vision of these top minds still exists today nearly 100 years later at Oyster Harbors.

oyster harbors original plan

Photo: Courtesy of the National Park Service, Frederick Law Olmsted National Historic Site

Blog Posts About Oyster Harbors

Oyster Harbors: Luxury on Nantucket Sound

 Home to some of the most expensive properties on Cape Cod, Oyster Harbors offers pure luxury for those searching for an estate on Nantucket Sound. The home of billionaires and philanthropists, the gated, waterfront community features its own golf course and extreme privacy. Formerly known as Grand Island, the location became the setting for the summer homes of prominent Boston families around the turn-of-the-century. The 1920s ushered in a new offering, with construction of the stylish ... Read More

Cape Cod img src Islands Association of Realtors LogoThe data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than ROBERT PAUL PROPERTIES are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor ROBERT PAUL PROPERTIES shall be responsible for any typographical errors, misinformation or misprints and shall be held totally harmless. This site was last updated 09/24/2020. All properties are subject to prior sale, changes or withdrawal.

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