Question: Bear Island is one of the five islands of this town with a population of about 150 as of 2010 located in which county?

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Five Islands Nature Reserve: The Five Islands Nature Reserve is a protected nature reserve located in the Tasman Sea, off the Illawarra east coast of the state of New South Wales, Australia.  The 26 ha reserve comprises five continental islands that are situated between 0.5 and east of Port Kembla .  The Five Islands are Flinders Islet (Toothbrush Island), Bass Islet, Martin Islet, Big Island (also called Rabbit or Perkins Island) and Rocky Islet.

Bear Island (Wisconsin): Bear Island is one of the Apostle Islands of northern Wisconsin in Lake Superior, and is part of the Apostle Islands National Lakeshore.  Unlike nearby Madeline Island, it is not open to commercial development.  There is another Bear Island in Balsam Lake.

Five Islands, Nova Scotia: Five Islands is a rural community in Colchester County Nova Scotia with a population of 300 located on the north shore of Minas Basin, home of the highest tides in the world.  It is named after five small islands – Moose, Diamond, Long, Egg, and Pinnacle – located just off the coast.  The islands are an exposed part of the North Mountain Basalt.  Moose Island is in Colchester County.  The remaining islands are in Cumberland County.  Beyond Pinnacle Island is a seastack called Pinnacle Rock.

Bear Island (Maine): Bear Island is an island located in Maine.  It is one of the five islands of the Town of Cranberry Isles, Maine.  The island is located just off Northeast Harbor, Maine and south of Mount Desert Island.

Bear Island (Lake Winnipesaukee): Bear Island is the second largest of the 262 islands in Lake Winnipesaukee in New Hampshire, United States.  In the summer it is accessible only by boat because it is not connected to the mainland via a bridge.  In the winter it can be reached by crossing the frozen lake, including by snowmobile.  According to the Lake Winnipesaukee Historical Society, the island got its name when a few hunters along with a few members of the Pennacook tribe were sent to survey the island.  However, they encountered a few bears, which they decided to hunt.  Originally the island was named "Big Bear Island", which was later shortened to "Bear Island" when the island was annexed by the town of Meredith in 1799.

Rock Island (Trinidad and Tobago): Rock Island is a small island in Trinidad and Tobago, part of the "Five Islands" group of islands.  It is located in the Gulf of Paria, approximately 2 kilometres off the main island of Trinidad from Point Gourde.  Of the "Five Islands", which are actually made up of six different islands, Rock is the second smallest (after Craig Island) and the most western of the group.

Bear Island (Maryland): Bear Island is an island located in Potomac, Montgomery County, Maryland between the Potomac River and the Chesapeake and Ohio Canal near the Great Falls.  It is managed by the National Park Service as part of the Chesapeake and Ohio Canal National Historical Park and is co-owned by The Nature Conservancy.  One of its most popular attractions is the Billy Goat Trail.  Pets are not allowed on Bear Island, nor is smoking.

Lefferts Island: Lefferts Island (also known as: Lefert Island, Leferts Island, Leffert Island, or Lefters Island) is a Baffin Island offshore island located in the Canadian Arctic Archipelago in the territory of Nunavut.  The island lies in Frobisher Bay between Beare Sound and Lupton Channel.  Other islands also in the immediate vicinity of the tip of Hall Peninsula include the Harper Islands, Bear Island, Little Hall Island, and Hudson Island.

Cranberry Isles, Maine: Cranberry Isles is a town in Hancock County, Maine, United States.  The population was 141 at the 2010 census.

Black Bear Island: Black Bear Island (2006–2010) was a Thoroughbred racehorse from Ireland.  Sired by Sadler's Wells from the dam Kasora, Black Bear Island was a full brother to six time Group One winner High Chaparral.

Supporting paragraphs: Bear Island (Maine) Cranberry Isles, Maine
Answer: Hancock County