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

Price, High to Low
12 Properties Found.
Photo of Listing #21609028
  • MLS® #: 21609028
  • 260 North Bay Road
  • Osterville, MA 02655
  • $10,250,000
  • 5 Bed, 8 Bath, 7828 SqFt, 1.52 Acres
  • Single Family
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Photo of Listing #21801808
  • MLS® #: 21801808
  • 250 Windswept Way
  • Osterville, MA 02655
  • $8,695,000
  • 5 Bed, 5 Bath, 4235 SqFt, 4.62 Acres
  • Single Family
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Photo of Listing #21610144
  • MLS® #: 21610144
  • 81 & 73 Oyster Way
  • Osterville, MA 02655
  • $7,900,000
  • 5 Bed, 8 Bath, 7205 SqFt, 2.78 Acres
  • Single Family
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Photo of Listing #21805370
  • MLS® #: 21805370
  • 150 Carriage Road
  • Osterville, MA 02655
  • $6,695,000
  • 8 Bed, 7 Bath, 5134 SqFt, 2.13 Acres
  • Single Family
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Photo of Listing #21712514
  • MLS® #: 21712514
  • 248 North Bay Road
  • Osterville, MA 02655
  • $6,390,000
  • 7 Bed, 10 Bath, 9103 SqFt, 1.4 Acres
  • Single Family
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Photo of Listing #21808208
  • MLS® #: 21808208
  • 72 North Bay Road
  • Osterville, MA 02655
  • $5,400,000
  • 3 Bed, 3 Bath, 2082 SqFt, 1.12 Acres
  • Single Family
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Photo of Listing #21808625
  • MLS® #: 21808625
  • 230 Seapuit River Road
  • Osterville, MA 02655
  • $3,650,000
  • 6 Bed, 5 Bath, 5220 SqFt, 2.12 Acres
  • Single Family
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Photo of Listing #21807340
  • MLS® #: 21807340
  • 30 Oakdale Path
  • Osterville, MA 02655
  • $2,950,000
  • 5 Bed, 7 Bath, 5213 SqFt, 1.36 Acres
  • Single Family
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Photo of Listing #21807036
  • MLS® #: 21807036
  • 123 Pineleigh Path
  • Osterville, MA 02655
  • $2,675,000
  • 4 Bed, 6 Bath, 5287 SqFt, 1 Acre
  • Single Family
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Photo of Listing #21804232
  • MLS® #: 21804232
  • 140 Pineleigh Path
  • Osterville, MA 02655
  • $1,750,000
  • 4 Bed, 5 Bath, 3909 SqFt, 1 Acre
  • Single Family
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Photo of Listing #21607269
  • MLS® #: 21607269
  • 266 Indian Trail
  • Osterville, MA 02655
  • $1,345,000
  • 5 Bed, 6 Bath, 3100 SqFt, 1.02 Acres
  • Single Family
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Photo of Listing #21710819
  • MLS® #: 21710819
  • 578 Grand Island Drive
  • Osterville, MA 02655
  • $1,195,000
  • 1.21 Acres
  • Single Family
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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

The 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 02/22/2019. All properties are subject to prior sale, changes or withdrawal.