10 Pine Path, Port Jefferson, NY 11777 — A Historic Opportunity

A significant shift has hit the Belle Terre luxury market. “The Cottage” at 10 Pine Path—a historic waterfront estate that commanded an $8 million asking price in 2023—is now available for $4,490,000.

For luxury buyers watching the North Shore, this is the moment where “aspirational” becomes “attainable.” This post breaks down why this property is now one of the most compelling values on the entire Long Island Sound.

🌳 About the Neighborhood

Town: Village of Belle Terre (Port Jefferson PO) School District: Port Jefferson Union Free School District The Vibe: Belle Terre remains one of the few truly private enclaves on Long Island. With its staffed gatehouse and winding wooded roads, it feels worlds away from the rest of the Island. It is a community of estates, privacy, and quiet wealth, all while being just minutes from the deep-water harbor and restaurants of Port Jefferson Village.

🏡 About the Property (“The Cottage”)

Then vs. Now: In 2023, this estate hit the market at $7,995,000, pricing it as one of the most expensive homes in the area. Today, at $4,490,000, the home itself hasn’t changed—the opportunity has.

This is a 5,800-square-foot piece of history sitting on nearly 4 acres of waterfront. It was built in 1906 for the President of the Long Island Rail Road, and the quality reflects that era. We are talking about 530 feet of private beach, a cobblestone driveway, and an interior that functions like a living gallery.

The centerpiece is the two-story atrium and mezzanine. It’s a dramatic architectural feature that you simply don’t see in modern construction. With 8 bedrooms, a resort-style primary suite, and that massive wrap-around enclosed porch overlooking the Sound, this is a “legacy property”—the kind of home that stays in a family for generations.

At the new price point, you are effectively buying a landmark waterfront estate for the price of a standard new-construction luxury home in other parts of the Island.

🔗 View the Full MLS Listing

See the full details, taxes, and current status here:

View the full MLS listing here

📈 Local Market Insight

The Story of the Numbers: The drop from ~$8M to ~$4.5M signals a motivated alignment with the current market. In 2023, the luxury market was testing new highs. Now, we are seeing a consolidation where buyers are demanding undeniable value. At $4.49M, this property is no longer competing with the ultra-high-end Hamptons alternatives; it is now aggressively positioned against local high-end inventory that lacks this level of acreage and history. For buyers: This is a rare chance to acquire equity instantly by buying a property that was valued significantly higher just 24 months ago.

🧭 Why People Love Living in Belle Terre

• Unmatched Privacy: The gatehouse is a major draw for high-profile residents.
• The Waterfront: Access to private beaches and unblocked sunsets.
• The History: Living in a community designed by the Olmsted Brothers (who designed Central Park).
• The Value: You typically get more land and square footage here than in comparable Gold Coast villages further west.

📝 Disclaimer

This post is for informational purposes only. For full listing details, please refer to the official MLS listing.