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Hidden Gems: The Most Unique & Unusual Homes on Long Island

The Enchanting World of Bay Houses (Long Island)

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Tucked away amid the tidal marshes and quiet bays of Long Island’s south shore lies a row of uniquely fascinating homes — the legendary Bay Houses. These aren’t your typical suburban colonials or beach-front mansions; they occupy a world of their own: perched above the water, accessible often only by boat or narrow walkway, built for living at the edge of land and water. Let’s plunge into their history, lifestyle and why they remain one of Long Island’s most evocative architectural oddities — and then we’ll explore other quirky homes that keep the local real-estate scene delightfully unconventional.


A Brief History

The story of the Bay Houses begins in the 1700s when marshland leases were granted to fishermen, salt-hay collectors and baymen who built humble shacks on the water. One municipal site notes:

“Beginning in the 1700’s, individuals leased plots of marshland in the bay from the Town of Hempstead. Lessees built small cottages that afforded them shelter during periods of activity on the bay.” Hempstead Town

By the 1920s these houses had grown into informal seasonal communities — by the time records were clearer there were about 300 Bay Houses in Hempstead Bay. Hempstead Town+1
Today only about 20-30 remain, due to storms, erosion, changing regulations and the sheer fragility of their environment. Hempstead Town+1


What Makes Them So Unique

1. Location & Access

  • Many Bay Houses sit south of the mainland, literally out on the marsh or bay, often on stilts or piers. Hempstead Town+1

  • Some have no road access; you arrive by boat or by walking a narrow boardwalk. One commenter described them as:

    “small houses built right on top of marshes and wetlands - no road access, power, sewer, or running water.” Reddit

  • The landscape itself is dynamic: salt marshes, tidal flows, and changing baylines mean these homes live in a constantly shifting environment.

2. Built for Lifestyle, Not Permanence

  • The original occupants were fishermen, salt-hay harvesters, hunters: people whose work was on the water. The houses reflect that heritage. Hempstead Town

  • Many were seasonal retreats rather than full-time homes.

  • Utilities, road infrastructure, sewer and power were limited or added much later — living in a Bay House means accepting some nature-led unpredictability.

3. Architectural Charm & Fragility

  • These homes often have rustic wood frames, weathered siding, simple forms — less “design statement”, more “functional get-away”.

  • Because they’re built on the edge of marsh and sea, they face storms, flooding, erosion and maintenance-challenges. The documentary A World Within a World: The Bay Houses of Long Island explores exactly that. Apple TV+1

  • Their rarity and unique setting give them a kind of mythic status on Long Island.


Why They Still Exist — And Thrive

Despite all their challenges, Bay Houses survive and still have communities around them. Several reasons:

  • So many are family-owned for generations, giving them continuity and care.

  • They appeal to folks who want off-grid-ish living, closer to nature and less conventional.

  • Their rarity means they have niche cultural value — as local landmarks, photographic curiosities, conversation pieces.

  • Events like the “Bay House Tours” celebrate them, bringing awareness & preservation energy. longislandtraditions.org


Other Peculiar Homes Around Long Island

While Bay Houses are a special case, Long Island’s real-estate landscape has other notable oddities that capture imagination. Here are a few:

1. X‑Shaped Manor — Lloyd Harbor, North Shore

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This home, located at 20 Plover Ln., Lloyd Harbor, was listed for over US$12 million. It earns its name from the distinctive X-shape layout, making it unusual in form and presence. Forbes
Its geometry, luxury finishes and waterfront plot give it the kind of architectural daring we associate with estate homes — but the shape makes it stand out as “odd” in the context of Long Island’s more typical houses.

2. Inisfada (Demolished) — North Hills

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Although it no longer stands, Inisfada was once a sprawling 87-room Tudor-Revival estate on Long Island — among the largest in the area. Wikipedia
Its scale, room count and history make it a standout in any list of unusual Long Island homes.

3. The Modern Elevated Cottage — North Fork

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A less conventional home type: a 1920s fisherman’s cottage on the North Fork was redesigned by architect Toshiko Mori into a 1,200 sq ft modern beach house, elevated eight feet above flood level and blending traditional materials with modern detail. Architectural Digest
It’s a great example of how Long Island isn’t just about mansions or bay house relics: there are inventive, quirky homes adapting to the future.


What They Say About Long Island’s Real Estate Character

  • Diversity of typologies. From marsh-perched Bay Houses to elevated modern cottages to gold-coast mansions, Long Island’s home types vary widely.

  • Interaction with water & nature. Many unusual homes share one trait: living at the edge of environment — marshes, bays, ocean, storms. The Bay Houses especially highlight this.

  • Heritage + novelty. The odd homes often carry stories: fisherman shacks turned retreats, modern architectural statements, estates of eras past. They blend history with oddity.

  • Challenges & rewards. Unusual homes often mean unusual maintenance, zoning, access. But the reward is uniqueness, character, something memorable.


If You’re Curious

  • Take a boat or kayak along Hempstead Bay and look for the Bay Houses built out on the water.

  • Attend a Bay House tour if you can: events like the 2025 End-of-Season Bay House Tours give a rare inside look. longislandtraditions.org

  • Keep an eye out for listings of unusual homes. News outlets sometimes call them out: e.g., “5 unusual Long Island homes for sale”. Newsday

  • If you’re a homeowner: consider the unique story your home tells. Building character is part of what makes real estate memorable.

🔹 10 Other Hidden & Unusual Homes on Long Island

  1. X-Shaped Manor – Lloyd Harbor
    A striking waterfront home designed in an X-formation, blending symmetry with coastal luxury. Its bold architecture earned national attention for breaking away from the traditional Long Island estate style.

  2. Fair Field Estate – Sagaponack
    One of the largest private residences in the U.S., this 64,000-sq-ft mansion redefined opulence in the Hamptons — a hidden world of theaters, pools, and underground amenities few will ever see.

  3. Windmill House – Amagansett
    Once a working windmill, now a private home, this 1800s structure embodies the essence of Hamptons charm with a twist of whimsy — rustic blades replaced by balconies and coastal breezes.

  4. Inisfada Mansion – North Hills (Lost Icon)
    Once an 87-room Tudor Revival masterpiece, Inisfada was a spiritual retreat before its demolition in 2013. It remains legendary among Long Island’s lost architectural marvels.

  5. Mulford Farmhouse – East Hampton
    Built around 1680, this is one of the best-preserved English colonial farmsteads in America. A true time capsule of Long Island’s agrarian past, it’s open for tours through the East Hampton Historical Society.

  6. Suydam House – Centerport
    A 1730s saltbox-style home with charming asymmetry, antique glass panes, and an aura of history — one of the oldest standing homes in the Town of Huntington.

  7. Rynwood Estate – Old Brookville
    A Tudor and Cotswold hybrid built in the 1920s, Rynwood’s formal gardens, steep gables, and storybook design make it one of the most romantic estates on the North Shore.

  8. Odd Fellows Windmill Home – Hollis
    A converted windmill tower that once served as part of the Odd Fellows complex — its structure now a rare residential curiosity blending Gothic revival and turn-of-the-century craftsmanship.

  9. McKinley Bungalow – Montauk
    A beach retreat that doubles as a shoppable showroom — everything inside is for sale. This design experiment blurs the line between art installation and home.

  10. Modern Elevated Cottage – North Fork
    A minimalist, flood-resistant beach house elevated above the landscape by architect Toshiko Mori, showing how modern design meets Long Island’s environmental challenges.


🌊 Why These Hidden Homes Matter

Long Island’s most fascinating homes aren’t always behind gated drives or on MLS. They’re tucked into coves, preserved on marshlands, or quietly reinventing old forms. Together, they reflect:

  • Adaptation: Living in rhythm with water, wind, and history.

  • Innovation: Turning necessity — like elevation or repurposing — into creativity.

  • Heritage: Every structure tells a story, from colonial farms to eccentric estates.


✨ Closing Thought

The next time you drive along the North Shore or cross a causeway to the South Shore, remember — some of Long Island’s most remarkable homes aren’t the ones you see. They’re the hidden homes — built from imagination, endurance, and a little island magic.

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