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

Features
Heating System:
Natural Gas
Cooling System:
Ductless
Basement:
Full, Walk-out Access, Bilco Door(s)
View:
Water, Park/greenbelt
Patio:
Covered
Appliances:
Dishwasher, Refrigerator, Stainless Steel Appliance(s), Dryer, Washer, Range
Fireplace Features:
Wood Burning
Fireplaces Total:
1
Flooring:
Tile, Wood
Garage Spaces:
2
Interior Features:
Eat-in Kitchen, Open Kitchen, Kitchen Island, Original Details, Walk Through Kitchen, Formal Dining, Quartz/quartzite Counters, Built-in Features, Crown Molding
Laundry Features:
Laundry Room
Parking Features:
Driveway
Sewer:
Cesspool
Utilities:
Natural Gas Connected, Water Connected, Electricity Connected
Address Map
City:
Southold
State:
NY
Street:
Main
Street Number:
40495
Street Suffix:
Road
Postal Code:
11957
Floor Number:
0
Longitude:
W73° 45' 16.7''
Latitude:
N41° 9' 17.6''
Direction Faces:
South
Directions:
Rt 25 East. House on the left hand side just after Plum island Lane. Orient
PostalCity:
Orient
Additional Information
Architectural Style:
Craftsman
Construction Materials:
Shingle Siding, Cedar
Elementary School:
Oysterponds Elementary School
High School:
Greenport High School
Levels:
Two
Agent MlsId:
123668
MiddleOrJunior School:
Greenport High School
PhotosCount:
26
Special Listing Conditions:
No
Tax Annual Amount:
$8,896
Water Source:
Well
Office MlsId:
ALBT01

Residential - MLS# 1029031

40495 Main Road, Southold, NY

4 Bedrooms
2 Bathrooms
2,081 Sqft
$1,699,999
Listing ID #1029031
Basic Details
Property Type :
Residential
Property SubType :
Single Family Residence
Listing Type :
For Rent
Listing ID :
1029031
Price :
$1,699,999
Rooms :
12
Bedrooms :
4
Bathrooms :
2
Half Bathrooms :
1
Bathrooms Total :
3
Square Footage :
2,081 Sqft
Lot Area :
1.13 Acre
Year Built :
1838
Status :
Active
Listing Agent :
Gerald J. Cibulski CBR E-PRO CRS G
Listing Office :
Century 21 Albertson Realty
Agent info
Coldwell Banker American Homes
284 West Park Ave
Contact Agent
Walkscore