Osterville Real Estate

Osterville is a seaside village located on Nantucket Sound in the Town of Barnstable.  The community is known for its upscale waterfront homes and exclusive private clubs.  Residents enjoy shopping and dining in the quaint business of Osterville.  Dowses Beach on East Bay Road is a popular residents-only beach and offers a sandy shoreline and the calm waters of East Bay.

Osterville Homes For Sale

Price, High to Low
100 Properties Found.
Photo of Listing #21715145
  • MLS® #: 21715145
  • 986 Sea View Avenue
  • Osterville, MA 02655
  • $11,995,000
  • 5 Bed, 6 Bath, 7773 SqFt, 2.72 Acres
  • Single Family
Add as Favorite
Photo of Listing #21607681
  • MLS® #: 21607681
  • 421 Main Street
  • Osterville, MA 02655
  • $11,500,000
  • 9 Bed, 11 Bath, 11578 SqFt, 5.46 Acres
  • Single Family
Add as Favorite
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
Add as Favorite
Photo of Listing #21801808
  • MLS® #: 21801808
  • 250 Windswept Way
  • Osterville, MA 02655
  • $9,200,000
  • 5 Bed, 5 Bath, 4235 SqFt, 4.62 Acres
  • Single Family
Add as Favorite
Photo of Listing #21807495
  • MLS® #: 21807495
  • 995 Sea View Avenue
  • Osterville, MA 02655
  • $9,199,000
  • 4 Bed, 4 Bath, 5354 SqFt, 1.06 Acres
  • Single Family
Add as Favorite
Photo of Listing #21807881
  • MLS® #: 21807881
  • 461 Main Street
  • Osterville, MA 02655
  • $8,995,000
  • 5 Bed, 9 Bath, 9780 SqFt, 1.32 Acres
  • Single Family
Add as Favorite
Photo of Listing #21609913
  • MLS® #: 21609913
  • 979 Sea View Avenue
  • Osterville, MA 02655
  • $8,500,000
  • 9 Bed, 8 Bath, 6507 SqFt, 4.15 Acres
  • Single Family
Add as Favorite
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
Add as Favorite
Photo of Listing #21801408
  • MLS® #: 21801408
  • 501 Eel River Road
  • Osterville, MA 02655
  • $7,250,000
  • 6 Bed, 9 Bath, 8200 SqFt, 2.4 Acres
  • Single Family
Add as Favorite
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
Add as Favorite
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
Add as Favorite
Photo of Listing #21806787
  • MLS® #: 21806787
  • 52 Caillouet Lane
  • Osterville, MA 02655
  • $5,795,000
  • 7 Bed, 6 Bath, 6549 SqFt, 3.09 Acres
  • Single Family
Add as Favorite

Blog Posts About Osterville

Wianno Club: Osterville Historic Landmark

With a rich history dating back to the late 1800s, the Wianno Club is a true Osterville historic landmark. Now the site of frequent gatherings, celebrations and even weddings, the club celebrates more than a century overlooking Nantucket Sound and even has a spot on the National Register of Historic Places.The Cotocheset House, now the main clubhouse of the Wianno Club, sits on land once purchased by Plymouth settlers from the Native Americans, later used as the site of a grand summer hot... Read More

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

Where to Have a Cape Cod Wedding

Planning a wedding takes a lot of work, but perhaps one of the most difficult decisions you’ll make is deciding on a location.  If you have your heart set on Cape Cod, you’ll find there’s just no competition.  There are several beautiful locations to choose from, all with their own unique attributes.   Truro Vineyards While many people may envision a beach or water setting on Cape Cod, imagine walking down an aisle surrounded by a picture-perfect vineyard.  That’s the setting for fall... 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 12/18/2018. All properties are subject to prior sale, changes or withdrawal.