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40495 Main Road

Orient, NY 11957
  • $1,699,999
  • STATUS: Active
  • ON SITE: 65 Days
  • MLS #: 1029031
UPDATED: 47 min ago
$1,699,999
  • 4
    BEDS
  • 1.13
    ACRES
  • 2
    BATHS
  • 1
    1/2 BATHS
  • 2,081
    SQFT
  • $817
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1838
County:
Area:

School Information

Elementary School:
Middle School:
High School:
School District:

Description

Steeped in the history of Orient, this exceptional Craftsman-style residence occupies a remarkable setting along historic Main Road, once known as King’s Highway, directly across from the entrance to Orient Beach State Park. Originally purchased by a member of the pioneering Latham farming family, the home was thoughtfully expanded in the 1920s with the addition of its signature wide front porch and interior improvements. In 1938, the family donated the land across the street that would become the entrance to today’s Orient Beach State Park, forever connecting this property to one of the North Fork’s most treasured destinations. Architecturally, the home showcases timeless Craftsman character with distinctive three part windows across the front facade, each crowned with elegant lozenge paned transoms. The welcoming front entrance, framed by classic sidelights, opens to interiors where original woodwork, period doors, and handcrafted details remain beautifully intact. Modern updates to the large country kitchen, bathrooms, natural gas heating, and central air provide today’s comforts while preserving the home’s historic integrity. The property’s story extends beyond the main residence. A historic building from the famed Orient Point Inn, a resort established in 1672, was relocated to the backyard in the early twentieth century. Once serving as the inn’s men’s rooms and kitchen building, it now anchors the grounds as a fascinating reminder of Orient’s maritime heritage. Life here is defined by both history and location. Relax on the expansive front porch where seasonal water views, cool coastal breezes, and the distant sound of ferry horns create an unmistakable North Fork atmosphere. The original wood-burning fireplace, gracious front and rear staircases, and oversized country kitchen invite gatherings both large and small. Protected open space bordering one side of the property, paired with a classic neighboring farmhouse and historic barn on the other, preserves the peaceful character that has defined Orient for generations. Just moments away are Orient Beach State Park, Duryea’s Marina and Restaurant, the Cross Sound Ferry, and Orient Point County Park with its iconic lighthouse. Whether exploring by bicycle, spending the day on the beach, or simply enjoying the quiet rhythm of this waterfront community with some of the best fishing off of Plum Gut, every day feels connected to the rich history and natural beauty that make Orient one of Long Island’s most treasured destinations. This is more than a historic home. It is an opportunity to become the next steward of a property that has helped shape the story of Orient for generations

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© 2026 OneKey MLS. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Mark Seiden Real Estate Team. Data last updated: 2026-10-15T18:22:59.51.
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40495 Main Road Orient, NY 11957

  • Price: $1,699,999
  • Status: Active
  • On Site: 65 Days
  • Updated: 47 min ago
  • MLS #: 1029031
4
Beds
2
Baths
1
½ Baths
1.13
Acres
2,081
SQFT
$817
$/SQFT
1838
Built
Neighborhood:
Southold
County:
Suffolk
Area:
Southold
Elementary School:
Oysterponds Elementary School
Middle School:
Greenport High School
High School:
Greenport High School
School District:
Greenport
Property Description
Steeped in the history of Orient, this exceptional Craftsman-style residence occupies a remarkable setting along historic Main Road, once known as King’s Highway, directly across from the entrance to Orient Beach State Park. Originally purchased by a member of the pioneering Latham farming family, the home was thoughtfully expanded in the 1920s with the addition of its signature wide front porch and interior improvements. In 1938, the family donated the land across the street that would become the entrance to today’s Orient Beach State Park, forever connecting this property to one of the North Fork’s most treasured destinations. Architecturally, the home showcases timeless Craftsman character with distinctive three part windows across the front facade, each crowned with elegant lozenge paned transoms. The welcoming front entrance, framed by classic sidelights, opens to interiors where original woodwork, period doors, and handcrafted details remain beautifully intact. Modern updates to the large country kitchen, bathrooms, natural gas heating, and central air provide today’s comforts while preserving the home’s historic integrity. The property’s story extends beyond the main residence. A historic building from the famed Orient Point Inn, a resort established in 1672, was relocated to the backyard in the early twentieth century. Once serving as the inn’s men’s rooms and kitchen building, it now anchors the grounds as a fascinating reminder of Orient’s maritime heritage. Life here is defined by both history and location. Relax on the expansive front porch where seasonal water views, cool coastal breezes, and the distant sound of ferry horns create an unmistakable North Fork atmosphere. The original wood-burning fireplace, gracious front and rear staircases, and oversized country kitchen invite gatherings both large and small. Protected open space bordering one side of the property, paired with a classic neighboring farmhouse and historic barn on the other, preserves the peaceful character that has defined Orient for generations. Just moments away are Orient Beach State Park, Duryea’s Marina and Restaurant, the Cross Sound Ferry, and Orient Point County Park with its iconic lighthouse. Whether exploring by bicycle, spending the day on the beach, or simply enjoying the quiet rhythm of this waterfront community with some of the best fishing off of Plum Gut, every day feels connected to the rich history and natural beauty that make Orient one of Long Island’s most treasured destinations. This is more than a historic home. It is an opportunity to become the next steward of a property that has helped shape the story of Orient for generations
Exterior Features

Architectural Style Craftsman Carport YN No Construction Materials CedarShingle Siding Cross Street Plum Island Lane Direction Faces South Foundation Details Concrete Perimeter Garage YN Yes Levels Two Parking Features Driveway Patio And Porch Features Covered Pool Private YN No Property Attached YN Yes View Park/GreenbeltWater Waterfront YN No

Interior Features

Appliances DishwasherDryerRangeRefrigeratorStainless Steel Appliance(s)Washer Attic Unfinished Basement Details Bilco Door(s)FullWalk-Out Access Basement YN Yes Cooling Ductless Fireplace Features Wood Burning Fireplace YN Yes Fireplaces Total 1 Flooring TileWood Interior Features Built-in FeaturesCrown MoldingEat-in KitchenFormal DiningKitchen IslandOpen KitchenOriginal DetailsQuartz/Quartzite CountersWalk Through Kitchen Laundry Features Laundry Room Number Of Kitchens 1 Rooms Total 12

Property Features

Association YN No Community Features Park Down Payment Resource YN No Electric Company PSEG Heating Natural Gas Lease Considered YN No Other Structures Barn(s) Property Condition Actual Property Sub Type Single Family Residence Senior Community YN No Sewer Cesspool Special Listing Conditions None Tax Annual Amount 8896 Tax Source Municipality Utilities Electricity ConnectedNatural Gas ConnectedWater Connected Water Source Well

Listing courtesy of Gerald J. Cibulski Cbr E-Pro Crs G of Century 21 Albertson Realty: 631-765-3800
© 2026 OneKey MLS. All rights reserved.


© 2026 OneKey MLS. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Mark Seiden Real Estate Team. Data last updated: 2026-10-15T18:22:59.51.
 
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