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 September 29, 2023
19
Listed
99
Avg. DOM
N/A
Avg. $ / Sq.Ft.
$2,595,000
Med. List Price
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19 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
303
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
1825 S County Road Osterville, MA 02655
$13,500,000
 
1825 S County Road
Osterville, MA 02655
5
Beds
5F11/2
Baths
12.28
Acres
2001
Year Built
114
Days on Site
22302314
MLS
Unveiling 1825 S County Road, a masterpiece of privacy nestled in Osterville. This unique 5-bed, 6-bath sanctuary on a sprawling 12-acre property with a private island is a testament to unparalleled...
Griffin Realty Group
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
435
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
196
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
200 N North Bay Road Osterville, MA 02655
$8,850,000
Neighborhood: Oyster Harbors
200 N North Bay Road
Osterville, MA 02655
4
Beds
3F21/2
Baths
1.31
Acres
1981
Year Built
23
Days on Site
22303812
MLS
Iconic Royal Barry Will's designed waterfront home on Oyster Harbors. Spectacular sunset views await the new stewards of this home which affords water views from almost every room. One of a handful...
Landvest, Inc.
150 Sea View Avenue Osterville, MA 02655
$5,150,000
 
150 Sea View Avenue
Osterville, MA 02655
7
Beds
5F11/2
Baths
0.82
Acres
1910
Year Built
213
Days on Site
22300677
MLS
Wianno, Osterville on Sea View Avenue! Discover this unique and stunning property, offering resort style living, perfect for your summer pleasure. Featuring 7 bedrooms, 5.5 baths, a grand living...
Kinlin Grover Compass
101 Warren Street Osterville, MA 02655
$4,290,000
 
101 Warren Street
Osterville, MA 02655
6
Beds
5F11/2
Baths
0.46
Acres
2021
Year Built
70
Days on Site
22302979
MLS
Welcome to this magnificent 2021-built real estate gem located in the sought-after Wianno neighborhood. With its beautiful open spaces, this home is perfectly designed for accommodating large...
Compass Massachusetts, Llc
97 Old Mill Road Osterville, MA 02655
$3,300,000
 
97 Old Mill Road
Osterville, MA 02655
5
Beds
3F11/2
Baths
1.15
Acres
1890
Year Built
49
Days on Site
22303190
MLS
Amazingly private acre + Custom home within walking distance to everything Osterville ! Entertain your friends & family at the heated pool area with pool house or make pizza in the outdoor...
Barnstable Harbor Realty
98 Bunker Hill Road Osterville, MA 02655
$3,200,000
Neighborhood: Seapuit
98 Bunker Hill Road
Osterville, MA 02655
5
Beds
4F11/2
Baths
2.03
Acres
1978
Year Built
51
Days on Site
22303312
MLS
A drive through lighted stone pillars alongside the sweeping lawn sets the stage. Sited on a two-acre parcel within the exclusive neighborhood of Seapuit, Osterville, is this stunning 4715 square...
Sotheby's International Realty
Open 10/1
18 Parker Road Osterville, MA 02655
$2,595,000
 
18 Parker Road
Osterville, MA 02655
3
Beds
3F11/2
Baths
0.21
Acres
1848
Year Built
66
Days on Site
22303035
MLS
Experience the ultimate in coastal living with your dream home in Osterville Village! This Cape Cod gem has undergone meticulous renovations and boasts an ideal location, steps away from the shops,...
Compass Massachusetts, Llc
1676 South County Road Osterville, MA 02655
$2,395,000
 
1676 South County Road
Osterville, MA 02655
3
Beds
3
Baths
1.06
Acres
2001
Year Built
106
Days on Site
22302455
MLS
Pristine Federal Colonial Revival has open floor plan with private areas for today's lifestyle. High-end original and updated quality materials, appliances and mechanics throughout. Cedar roofing,...
Sotheby's International Realty
24 Farm Valley Road Osterville, MA 02655
$2,200,000
Neighborhood: Farm Valley
24 Farm Valley Road
Osterville, MA 02655
4
Beds
3F11/2
Baths
1.11
Acres
2002
Year Built
19
Days on Site
22303881
MLS
Nestled in the heart of picturesque Osterville,this charming Cape Cod home offers the quintessential New England coastal living experience. As you approach this property in what we call ''Hidden...
Kinlin Grover Compass
From Our Blog - Osterville
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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