Oyster Harbors - Osterville

oyster harbors - osterville ma

Oyster Harbors is a waterfront gated community situated on Grand Island in Osterville.  This neighborhood of luxury homes is known for its extraordinary privacy, security and ambiance.  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.

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.

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.

Oyster Harbors Homes For Sale

New
51 Sunset Point, Osterville
  • Single Family
  • 5 Beds
  • 7 Baths
  • 6,460 SqFt

51 Sunset Point, Osterville

$16,500,000
260 North Bay Road, Osterville
  • Single Family
  • 5 Beds
  • 8 Baths
  • 7,828 SqFt

260 North Bay Road, Osterville

$10,250,000 ↑ $1,000,000
250 Windswept Way, Osterville
  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,235 SqFt

250 Windswept Way, Osterville

$8,695,000 ↑ $505,000
81 & 73 Oyster Way, Osterville
  • Single Family
  • 5 Beds
  • 8 Baths
  • 7,205 SqFt

81 & 73 Oyster Way, Osterville

$7,900,000 ↑ $350,000
150 Carriage Road, Osterville
  • Single Family
  • 8 Beds
  • 7 Baths
  • 5,134 SqFt

150 Carriage Road, Osterville

$6,695,000
248 North Bay Road, Osterville
  • Single Family
  • 7 Beds
  • 10 Baths
  • 9,103 SqFt

248 North Bay Road, Osterville

$6,390,000 ↑ $510,000
72 North Bay Road, Osterville
  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,082 SqFt

72 North Bay Road, Osterville

$5,400,000
230 Seapuit River Road, Osterville
  • Single Family
  • 6 Beds
  • 5 Baths
  • 5,220 SqFt

230 Seapuit River Road, Osterville

$3,650,000 ↓ $150,000
123 Pineleigh Path, Osterville
  • Single Family
  • 4 Beds
  • 6 Baths
  • 5,287 SqFt

123 Pineleigh Path, Osterville

$2,675,000
New
163 Pineleigh Path, Osterville
  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,750 SqFt

163 Pineleigh Path, Osterville

$1,950,000
140 Pineleigh Path, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,909 SqFt

140 Pineleigh Path, Osterville

$1,750,000
266 Indian Trail, Osterville
  • Single Family
  • 5 Beds
  • 6 Baths
  • 3,100 SqFt

266 Indian Trail, Osterville

$1,345,000 ↑ $5,000

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 04/22/2019. All properties are subject to prior sale, changes or withdrawal.