Living in Head of the Harbor, New York: homes, schools and costs

The book's checklist

Lower cost of livingEveryday prices run 12.6% above the U.S. average in the New York-Newark-Jersey City metro area.
More house for the moneyThe Census survey didn't reach enough homes in Head of the Harbor to say.
A safer neighborhoodThe FBI has no 2025 figures for Head of the Harbor itself. Many small towns are patrolled by the county sheriff, so call the sheriff's office and ask what calls they get most.
Schools in town2 public schools. No public high school in town: the nearest is Smithtown High School East, about 2 miles away.
A hospital close bySuny/stony Brook University Hospital in Stony Brook, about 2 miles away, has the nearest emergency room.
Within reach of a big cityBridgeport is about 20 miles away as the crow flies. The book suggests staying within about 60 miles if you'll miss big-city sports, concerts and theater.

A check means Head of the Harbor meets the rule of thumb from Frank and Dave's book. An empty box isn't a deal breaker: it's something to weigh for your family. A question mark means there isn't enough data.

What kind of town

A suburb, not a stand-alone small town

Head of the Harbor runs into the built-up area around New York (Census Bureau, 2020 urban areas). We include suburbs under 20,000 people because some still feel like small towns, but daily life here is closer to the suburbs than to the towns Frank and Dave's book describes. Weigh it against towns farther out.

The book sorts small towns into six types. These labels come only from the numbers; take the quiz to see which type fits your family.

For a lifetime

Homes and money

Typical home value, as owners valued them in 2020-2024: $1,167,400U.S.: $332,700
Home prices since then: Up 23%Suffolk County, 2022 to 2025
Typical rent, with utilities: $2,333 a monthU.S.: $1,413
Typical household income: $250,000 or moreU.S.: $80,734
Homes owned by the people living in them: 97%U.S.: 65%
Typical property tax bill: $10,000 or more a yearNew York: $6,582
Homes built before 1940: 21%U.S.: 12%
Homes built since 2010: 2%U.S.: 11%
Vacation and seasonal homes: 6%U.S.: 3%
Everyday prices: 112.6U.S. average = 100 (the New York-Newark-Jersey City metro area)

Home values and rents are what households told the Census Bureau across 2020 to 2024, so they trail today's market: county prices have moved up 23% since 2022. Everyday prices are the government's average for the New York-Newark-Jersey City metro area, not Head of the Harbor alone. Check current listings before you budget.

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates; Federal Housing Finance Agency, House Price Index for counties (all transactions); U.S. Bureau of Economic Analysis, Regional Price Parities, 2024.

The people

Population, 2025 estimate: 1,4812020: 1,477
Median age: 44.5 yearsU.S.: 38.9
Age 65 and older: 14%U.S.: 17%
Under 18: 26%U.S.: 22%
Adults with a bachelor's degree or more: 65%U.S.: 36%
Moved here from another county or state in the past year: 3%U.S.: 6%

Sources: U.S. Census Bureau, Population Estimates (Vintage 2025); U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Work

Biggest lines of work: Schools, health care and social services (26%); professional and business services (24%); retail (14%)
Unemployment rate: 1%U.S.: 5%
Work from home: 32%U.S.: 15%
Below the poverty line: 5%U.S.: 12%

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Health care

Nearest emergency room: Suny/stony Brook University Hospital, Stony Brook, NY, about 2 miles away. It's a general hospital. Medicare gives it 5 of 5 stars.

Look up doctors, clinics and the hospitals themselves on Medicare's Care Compare. Ask where the most serious cases are sent.

Sources: Centers for Medicare & Medicaid Services, Hospital General Information.

Schools

2 public schools in Head of the Harbor, run by Smithtown Central School District and Three Village Central School District. The nearest public high school is Smithtown High School East, about 2 miles away.

See each school on the federal school search, then check test scores and graduation rates on New York's school report card.

Sources: National Center for Education Statistics, Common Core of Data, 2023-24 (via the Urban Institute Education Data Portal); National Center for Education Statistics, IPEDS institution directory, 2024.

Internet

Homes with cable, fiber or DSL internet: 91%U.S.: 76%
Homes with any internet subscription: 96%U.S.: 91%

Before you buy, look up the address on the FCC's National Broadband Map to see which providers serve it.

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Weather

January average low: 26°F
July average high: 83°F
Days 90°F or hotter: 17 a year
Nights at or below freezing: 96 a year
Rain and melted snow: 46 inches a year
Snow: 32 inches a year
Elevation: 185 feet

Weather stations: Setauket Strong (5 miles away) and Islip Li Macarthur Ap (8 miles away, rain and snow). Averages for 1991 to 2020.

Sources: NOAA National Centers for Environmental Information, U.S. Climate Normals 1991-2020; U.S. Geological Survey, 3D Elevation Program.

Getting around

Suny/stony Brook University HospitalEmergency room2

Norwalk, CTCity of 95,00019

Bridgeport, CTMetro of 1 million20

Straight-line miles. The road is always longer, and as the book says, an interstate at 70 is a different trip from a farm road at 45. Check the real drive: Suny/stony Brook University Hospital, Norwalk, Bridgeport.

Suffolk County is in a metro area of 1 million people or more (USDA rural-urban code 1, on a scale where 1 is the biggest metro areas and 9 the most rural counties).

For a day

5 places on the National Register of Historic Places, including the East Farm, Kate Annette Wetherill Estate, Shore Cottage and the Thatch Meadow Farm.

National Park Service sites within about an hour:

Fire Island National Seashore12 miles
Sagamore Hill National Historic Site17 miles
Weir Farm National Historical Park29 miles
Saint Paul's Church National Historic Site35 miles
Gateway National Recreation Area37 miles

Read about Head of the Harbor's history on Wikipedia.

Know Head of the Harbor?

Tell us what a visitor shouldn't miss, and what living there is really like. Write to Main Street at mainstreet@smalltownguide.com. The best notes from people who know the town will be added here.

Nearby

Straight-line miles.

Small towns

Nissequogue, NY1,600 people, 1 miles
St. James, NY13,200 people, 2 miles
Stony Brook, NY12,900 people, 2 miles
Village of the Branch, NY1,800 people, 3 miles
Nesconset, NY13,800 people, 4 miles
Lake Grove, NY11,200 people, 4 miles

Smaller places

Old Field, NY947 people, 5 miles
Poquott, NY932 people, 5 miles
Belle Terre, NY796 people, 7 miles
Asharoken, NY624 people, 12 miles
Great River, NY (unincorporated)1,899 people, 13 miles
Eatons Neck, NY (unincorporated)1,173 people, 13 miles
Shoreham, NY530 people, 14 miles

Sources

Census survey figures are estimates with a margin of error; we leave out any figure whose margin is too wide to be useful. Data last gathered October 5, 2026. See something wrong? Write to mainstreet@smalltownguide.com.