New York metro, NY-NJ relocation guide
Moving to Southold, NY
—Median listing price
New York metro, NY-NJArea
Commuter-friendlyCommute profile
About Southold
Southold is the North Fork's anchor town, running from Laurel to Orient Point and encompassing the incorporated Village of Greenport plus the hamlets of Southold, Cutchogue, Mattituck, Peconic, New Suffolk, and Orient. It is wine country and farm country — tasting rooms, farm stands, and marinas along the Long Island Sound and Peconic Bay — with housing from waterfront estates to historic village homes and cottages.
Home prices in Southold
Home prices in Southold vary by neighborhood and property type.
Top places in Southold
- Greenport village — historic carousel, working harbor, Front Street shops, and the LIRR terminus.
- Orient Beach State Park — Sound-front beach and maritime forest at the Fork's tip.
- North Fork wineries — tasting rooms along Route 25 (Pindar Vineyards shown in the Commons photo below).
- Lavender by the Bay — seasonal lavender fields in East Marion.
- Cutchogue and Mattituck farm stands — pick-your-own fruit and produce.
- Oysterponds — historic Orient hamlet with the Webb House Museum.
- Peconic Bay and Long Island Sound marinas — sailing and sport fishing.
Commuting from Southold
- LIRR Main Line (Greenport Branch) — Greenport (terminus), Southold, and Mattituck stations; service is limited and most Penn Station trips require a transfer at Ronkonkoma (per MTA station pages, read September 25, 2026).
- Typical weekday example (researched September 25, 2026): Greenport–Penn Station approximately 2h47–3h26, usually with one Ronkonkoma transfer; Southold and Mattituck are modestly shorter.
- Approximate drive to Midtown Manhattan: ~2h15–3h depending on traffic.
Southold FAQs
- What is the housing market like in Southold, NY?
Home prices in Southold vary by neighborhood and property type. - How is the commute from Southold, NY?
LIRR Main Line (Greenport Branch) — Greenport (terminus), Southold, and Mattituck stations; service is limited and most Penn Station trips require a transfer at Ronkonkoma (per MTA station pages, read September 25, 2026).
Town links
Schools
Transit
Official town resources. School report cards via the New York State Education Department.