The smart way to browse the Town of Oyster Bay

This grid spans a township, so read it in bands. The central corridor — Hicksville, Syosset, Plainview, Bethpage, Jericho, Woodbury — is where most of the volume sits: postwar Capes, ranches, splits, and colonials on suburban blocks, priced community by community rather than town-wide. Massapequa carries the South Shore side. The North Shore communities — Sea Cliff, Glen Head, Locust Valley, Bayville — surface older village housing and larger parcels in smaller numbers, so a single new listing there can matter more than ten in the corridor. Two structural details do the most work when you compare listings across the town: the school district, which is drawn independently of village and hamlet lines, and whether the address answers to a village hall or to the town on permits and code.

For the full read on how the town is organized — the villages-versus-hamlets distinction, the four LIRR corridors, and the district map — start with the Town of Oyster Bay guide. To place the town inside the wider market, the Nassau County guide covers both shores. And if the North Shore is your focus, the Sea Cliff guide and Sea Cliff listings narrow this same inventory to one harbor village.

Where the homes are

The Town of Oyster Bay runs from the Long Island Sound to the South Shore bays, and the grid above follows that span. Hicksville anchors the middle — its LIRR station is the busiest east of Jamaica, Penn Station, and Grand Central Madison — with Syosset, Plainview, Jericho, Woodbury, and Bethpage around it on the Main Line and Port Jefferson corridors. Massapequa rides the electric Babylon branch near the bay. The North Shore communities sit on the slower diesel Oyster Bay branch, with Sagamore Hill — Theodore Roosevelt's home, now a National Park Service site — on Cove Neck just east of Oyster Bay hamlet. Open any point below in Google Maps to see what sits within a few minutes of a given listing.

Official Town of Oyster Bay resources

Before you tour or make an offer, it is worth checking the public record yourself. These are the primary sources for town, county, school, flood, and census information — the same ones we cross-check when we price a home here, and the reason we keep the live grid as the price answer instead of a published figure that goes stale.