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

Osterville Homes For Sale June 8, 2023
17
Listed
78
Avg. DOM
N/A
Avg. $ / Sq.Ft.
$3,995,000
Med. List Price
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17 Properties
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835 Sea View Avenue Osterville, MA 02655
$30,000,000
 
835 Sea View Avenue
Osterville, MA 02655
7
Beds
9F51/2
Baths
3.66
Acres
2012
Year Built
190
Days on Site
22200155
MLS
Set on Osterville's exclusive Sea View Avenue with commanding views over Nantucket Sound and an unprecedented 280 feet of private sandy beach, a once-in-a-lifetime coastal oasis awaits. Magnificent...
Berkshire Hathaway Homeservices Robert Paul Properties
132 South Bay Road Osterville, MA 02655
$21,500,000
 
132 South Bay Road
Osterville, MA 02655
8
Beds
10F21/2
Baths
2.02
Acres
2019
Year Built
87
Days on Site
22300830
MLS
Sophisticated interiors and sweeping ocean views define this extraordinary waterfront estate. Newly finished and set on two acres with a swimming pool and private dock, unsurpassed quality and...
Berkshire Hathaway Homeservices Robert Paul Properties
255 Bayberry Way Osterville, MA 02655
$13,000,000
 
255 Bayberry Way
Osterville, MA 02655
7
Beds
6
Baths
5.98
Acres
1988
Year Built
322
Days on Site
22203874
MLS
Welcome to ''Point House'' a spectacular 5.98-acre waterfront estate on a peninsula overlooking the glistening waters of West Bay. In a setting of unsurpassed beauty, the 4,896 square foot residence...
Berkshire Hathaway Homeservices Robert Paul Properties
227 Bridge Street Osterville, MA 02655
$12,500,000
 
227 Bridge Street
Osterville, MA 02655
8
Beds
4F11/2
Baths
2.45
Acres
1900
Year Built
83
Days on Site
22300899
MLS
From its unparalleled location on Little Island in Osterville, this special waterfront estate overlooks the sparkling waters of West Bay and offers breathtaking water vistas from its private and...
Berkshire Hathaway Homeservices Robert Paul Properties
468 Wianno Avenue Osterville, MA 02655
$10,000,000
 
468 Wianno Avenue
Osterville, MA 02655
6
Beds
6F21/2
Baths
1.33
Acres
1884
Year Built
100
Days on Site
22300596
MLS
The Grand Dame of Wianno is available....this signature property has been lovingly restored to even better than in its Glory Days. The perfect home for entertaining with 6 plus bedrooms, a grand...
Compass Massachusetts, Llc
150 Sea View Avenue Osterville, MA 02655
$6,475,000
 
150 Sea View Avenue
Osterville, MA 02655
7
Beds
5F11/2
Baths
0.82
Acres
1910
Year Built
100
Days on Site
22300677
MLS
In the heart of Wianno, this premier Sea View Avenue residence, is steps to the Wianno Club. Designed by Philadelphia architect, Wilson Eyre in his deliberately informal, prairie shingle style, this...
Kinlin Grover Compass
149 East Bay Road Osterville, MA 02655
$5,495,000
 
149 East Bay Road
Osterville, MA 02655
4
Beds
3F11/2
Baths
0.96
Acres
1958
Year Built
106
Days on Site
22300514
MLS
In the heart of Osterville Village, this masterfully restored classic shingle-style home blends timeless charm with sophisticated design. An estate-like entranceway with Belgian block stonework and...
Sotheby's International Realty
320 Seapuit River Road Osterville, MA 02655
$5,250,000
 
320 Seapuit River Road
Osterville, MA 02655
6
Beds
5F21/2
Baths
1.1
Acres
1985
Year Built
63
Days on Site
22301219
MLS
New Price! Move in by summer! Experience resort-style living in your very own Royal Barry Wills Cape Colonial in Osterville's prestigious Oyster Harbors. Nestled in a tranquil corner of the island,...
Sotheby's International Realty
878 Sea View Avenue Osterville, MA 02655
$3,995,000
 
878 Sea View Avenue
Osterville, MA 02655
6
Beds
6
Baths
1.76
Acres
1929
Year Built
52
Days on Site
22301406
MLS
Looking for an opportunity to make a stunning Cape Cod estate your own? Look no further than 878 Sea View Ave. in Osterville, MA! This classic property is an incredible opportunity to create the home...
Berkshire Hathaway Homeservices Robert Paul Properties
321 Wianno Avenue Osterville, MA 02655
$2,950,000
 
321 Wianno Avenue
Osterville, MA 02655
5
Beds
4
Baths
0.75
Acres
1937
Year Built
1
Day on Site
22302308
MLS
Wonderful Home within a half mile to Dowses beach & the quaint village of Osterville! Built in 1937, this home has had many transformations over the years including a complete rehab, kitchen, and...
William Raveis Real Estate & Home Services
219 Wianno Avenue Osterville, MA 02655
$2,850,000
 
219 Wianno Avenue
Osterville, MA 02655
3
Beds
2F11/2
Baths
1.29
Acres
1938
Year Built
3
Days on Site
22302266
MLS
Wianno Avenue perfection, this elegant and timeless residence sits on an oversized lot in the heart of Osterville, within walking distance to Dowses Beach and Main Street. The sprawling grounds...
Berkshire Hathaway Homeservices Robert Paul Properties
Open 6/10
321 Tower Hill Road Osterville, MA 02655
$1,899,000
 
321 Tower Hill Road
Osterville, MA 02655
4
Beds
3
Baths
0.37
Acres
1960
Year Built
29
Days on Site
22301726
MLS
Introducing the epitome of easy living in Osterville Village: a meticulous NEW CONSTRUCTION pond-front property that offers a harmonious blend of luxury and serenity. This exceptional property has...
Compass Massachusetts, Llc
From Our Blog - Osterville
Osterville Boasts One of the Clearest Ponds in MA

Photo: Massachusetts Office of Travel & Tourism There are plenty of fantastic locations on Cape Cod to cool off and enjoy the natural scenery, but if you’re looking for one of the clearest ... Read more about Osterville Boasts One of the Clearest Ponds in MA

The Cachet of Oyster Harbors

As one of Cape Cod’s most exclusive neighborhoods, Oyster Harbors is a gated, resort community of exceptional homes and amenities on Grand Island. The extremely private gated community only ... Read more about The Cachet of Oyster Harbors

Osterville Landmark Evokes Memories

While one spot in Osterville is now technically the site of luxury townhomes, many still have memories of a true Cape Cod landmark. Originally constructed in the late 1800s, the old East Bay Lodge ... Read more about Osterville Landmark Evokes Memories

The Most Exclusive Areas on the Cape

With dozens of beaches, hundreds of charming shops and some beautiful homes, it’s hard to point out just one great location on the Cape. However, some of the most exclusive areas of Cape Cod ... Read more about The Most Exclusive Areas on the Cape

Osterville-- Mid Cape Upscale Living

Described by some as an upscale Mid Cape village, Osterville is a fantastic place to live and visit. Ocean views, waterfront homes and a quaint downtown all come together to make this such a ... Read more about Osterville-- Mid Cape Upscale Living