40495 Main Road

Coming SoonOpen: 8/15 02:00PM - 03:00PM
Coming SoonOpen: 8/15 02:00PM - 03:00PM
Classic architecture from a home that was centered in the agricultural history of potato farms and this was all open views back in the 1800's to the water, beaches and the iconic Orient Point Inn that opened to summer retreats from the 1600's from Connecticut and surrounding areas.
Orient Beach State Park has well marked beaches.
Stunning windows and views from the wide front porch.
Super wide front porch was added in the 1920's by the King family and you can see why. Cool breeze and wide spaces to hang out and take in Orient Point living.
You can see the Craftsmanship with this wood burning fireplace and classic white mantel when you walk in the front door.
LOOK at the authentic wood work and details as well as the updated finishes and air conditioning to bring the character of the home and combine that with the amazing features we want in a country home today.
New kitchen layout with timeless finishes makes this a bright kitchen that catches the afternoon light over the kitchen sink.
Fully updated with new tile floors, kitchen cabinets with quartz countertops and stainless steel appliances makes this a kitchen you want to spend time in. With a laundry room off to the side with a back mudroom and full bathroom, it is a perfect layout when they come back from fishing off of Plum Gut and need to clean up after a day fishing on the coast or the boats.
Beautiful front and rear staircases brings the charm and character of this historic Craftsman home together. The back stairs come from the bedrooms to the country kitchen.
Expansive dining room between the front living room and large farmhouse kitchen behind. Floors are amazing and the updates keep the original wood details showing the charm and character of this classic architecture.
Amazing perspective of the Craftsman home and barns with amazing fishing opportunities off of Plum Gut less than a mile away.
Orient Beach State Park staff are always keeping the grounds clean and organized.
Orient Beach State Park has wide beaches with lifeguards for amazing days on the water.
Entrance to Orient Beach State Park with a water view is directly across the street.
Duryea's outdoor dining with stunning views of the boats and beach lined shores across the street.
Cross Sound Ferry with access to New London CT and the Foxwoods and Mohegan Sun casinos 15 minutes from the Ct ferry landing. Amazing to hear the fog horns and boat horns tying in the maritime feeling of this part of Orient Point.
Gallery Image 17
Views of the Duryea's Marina and water views across the street to the east.
The amazing wide front porch was added with the second floor dormers by Edwin King in the 1920's. He also purchased and moved the barn from the Orient Point Inn resort to the backyard.
Large backyard in front of the barn.
This is that Men's rooms and cooks building from the Orient Point Inn and moved here as the Orient Point Inn started to decline after the late 1800's heyday.
Inside view of the garage and workshop on the historic barn that came from the Orient Point Inn property decades ago.
Orient Point County Park is a few doors away with walking trails, beach along the coastline and views of Orient Point Lighthouse located on the former property of the Orient Point Inn which started in the late 1600's and was ending in the 1970's.
Duryea's Restaurant, Cross Island Ferry and Orient Beach State Park and bike and walking trail is across the street from this Classic Orient Craftsman style home from the Latham-King families dating back to the potato farming from the 1800's/
Duryrea's Restaurant and Marina shown across the street as well as the entrance to Orient Beach State Park.
Front view of the Craftsman home renovation in 1920 with historic barn and garage in the backyard. The land to the left is preserved and will not be built upon and the house to the right has a pool and historic barn
$1,699,999
4 beds2,081 sqft$817/sqft
40495 Main Rd, Orient, NY 11957
Est: $9,382/moGet pre-approved

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...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
LISTING UPDATED: 08/11/2026 05:01 AM

  1. Listed by Gerald J. Cibulski CBR E-PRO CRS G • Century 21 Albertson Realty
    P: (631) 765-3800 C: (631) 404-2507 jcibulski@albertsonrealty.com

Property Details for 40495 Main Road

Status
Coming Soon
MLS #
1029031
Days on Market
-
Taxes
$8,896 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Single Family
Year Built
1838
Lot Size
1.13 AC / 49,223 SF
County
Suffolk County
City/Township
Southold
View
Park/Greenbelt, Water
Architectural Style
Craftsman
Community Features
Park
Garage Spaces
2
Waterfront
No
Section Area
Plum Island Lane

Open Houses

Saturday, Aug 15th2:00 PM - 3:00 PM
PublicView contact

Location

Listing Courtesy of Century 21 Albertson Realty, Gerald J. Cibulski CBR E-PRO CRS G
Add your commute

Building Information for 40495 Main Road

Stories-Year Built1838Building Size-Lot Size1.13 AC / 49,223 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$9,382 per month

30 year fixed, 6.55% Interest

Principal and Interest

$8,641

Property Taxes

$741

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 40495 Main Road

Summary
Location and General Information
  • Senior Community YN: No
  • Directions: Rt 25 East. House on the left hand side just after Plum island Lane. Orient
  • Year Built Effective: 1920
  • Property Attached: Yes
  • Structure Type: Attached
  • Levels: Two
  • Property Condition: Actual
  • State Or Province: NY
School Information
  • School District: Oysterponds, Greenport
  • Elementary School District: Oysterponds
  • Elementary School: Oysterponds Elementary School
  • Middle Or Junior School District: Greenport
  • Middle Or Junior School: Greenport High School
  • High School District: Greenport
  • High School: Greenport High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 1000-015-00-08-00-014-002
  • Tax Assessed Value: $9,000.00
  • Tax Source: Municipality
  • Tax Year: 2025
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: Barn(s), Built-in Features, Covered, Craftsman, Crown Molding, Eat in Kitchen, Formal Dining, Kitchen Island, Laundry Room, Open Kitchen, Original Details, Park, Park/Greenbelt, Quartz/Quartzite Counters, Tile, Walk Through Kitchen, Water View, Well, Wood, Wood Burning
  • Interior Features: Built-in Features, Crown Molding, Eat-in Kitchen, Formal Dining, Kitchen Island, Open Kitchen, Original Details, Quartz/Quartzite Counters, Walk Through Kitchen
  • Appliances: Dishwasher, Dryer, Range, Refrigerator, Stainless Steel Appliance(s), Washer
  • Number Of Kitchens: 1
  • Total Rooms: 12
  • Basement: Bilco Door(s), Full, Walk-Out Access
  • Attic Description: Unfinished
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Wood Burning
  • Location Amenities: Stainless Steel Appliances, Walk Out Basement, Exposure South, Eat in Kitchen, Formal Dining Room, Island Kitchen, Open Kitchen, Original Details, Walk Through Kitchen, Barn(s), Park View, Water View
  • Laundry Features: Laundry Room
  • Flooring: Tile, Wood
  • Living Area: 2081
  • Foundation Details: Concrete Perimeter
  • Basement: Yes
Exterior Features
  • Exterior Property Features: Covered, Driveway, Park
  • Elevation Certificate: No
  • Patio And Porch Features: Covered
  • Construction Materials: Cedar, Shingle Siding
  • Other Structures: Barn(s)
  • Pool Private: No
  • Direction Faces: South
Lot Information
  • Site Features: Park
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Ductless
  • Heating: Natural Gas
  • Heat Fuel Type: Natural Gas
  • Sewer: Cesspool
  • Water Source: Well
  • Utilities: Electricity Connected, Natural Gas Connected, Water Connected
Green Features
  • Green Features: Dishwasher, Dryer, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Natural Gas
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 40495 Main Road

DateEvent & SourcePriceAppreciation
Nov 3, 2024

Expired

ONEKEY #3549163

$1,795,000—
May 3, 2024

Listed (Active)

ONEKEY #3549163

$1,795,000—
DateEvent & SourcePrice
11/03/2024

Expired

ONEKEY #3549163

$1,795,000
05/03/2024

Listed (Active)

ONEKEY #3549163

$1,795,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 40495 Main Road

Taxable ValueLand$2,100Additions$6,900Total$9,000
Tax Record2024$7,892 ($658 / month)
Home Facts
Beds0Lot Size49,223 SqFtStyleSingle Family ResidenceZoningR-40CountySUFFOLKAPN1000-015.00-08.00-014.002

Schools near 40495 Main Road

This home is within Oysterponds Union Free School District.
Rating
School
Type
Grades
Distance
Oysterponds Elementary School
Public - PK to 6
Rating
School
Distance
Oysterponds Elementary School
PublicPK to 6

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 11957

a front view of a house with a garden
1/21

Listing Courtesy of Daniel Gale Sothebys Intl Rlty, Janet J. Markarian

Open: 8/15 11:00AM - 01:00PM

$949,000

2
Bedrooms
1,235
Square Feet
0.43
Acres

700 Plum Island Lane, Orient, NY 11957

$950,000 | 395 Uhl Lane, Orient, NY 11957
1/25

Listing Courtesy of Daniel Gale Sothebys Intl Rlty, Nancy J. Cervelli; Daniel Gale Sothebys Intl Rlty, Barry B. Novick

Open: 8/15 12:00PM - 02:00PM

$950,000

2
Bedrooms
1,688
Square Feet
0.92
Acres

395 Uhl Lane, Orient, NY 11957

$8,400,000 | 1600 King Street, Orient, NY 11957
1/34

Listing Courtesy of Daniel Gale Sothebys Intl Rlty, Janet J. Markarian

$8,400,000

6
Bedrooms
5,700
Square Feet
7.49
Acres

1600 King Street, Orient, NY 11957

an aerial view of a house with a garden
1/47
Listed By Compass

$6,000,000

3
Bedrooms
2,500
Square Feet
9.1
Acres

4725 Orchard Street, Orient, NY 11957

$4,250,000 | 1640 Grandview Drive, Orient, NY 11957
1/50

Listing Courtesy of William Raveis New York LLC, Nicholas J. Planamento

$4,250,000

4
Bedrooms
5,200
Square Feet
0.93
Acres

1640 Grandview Drive, Orient, NY 11957

$1,625,000 | 1060 Navy Street, Orient, NY 11957
1/25

Listing Courtesy of Daniel Gale Sothebys Intl Rlty, Nancy J. Cervelli; Daniel Gale Sothebys Intl Rlty, Barry B. Novick

$1,625,000

4
Bedrooms
2,534
Square Feet
0.3
Acres

1060 Navy Street, Orient, NY 11957

$1,395,000 | 295 Willow Terrace Lane, Orient, NY 11957
1/49

Listing Courtesy of Century 21 Albertson Realty, Krystal Kohles

$1,395,000

4
Bedrooms
1,700
Square Feet
0.58
Acres

295 Willow Terrace Lane, Orient, NY 11957

$2,850,000 | 35335 Main Road, Orient, NY 11957
1/25
Listed By Compass

$2,850,000

3
Bedrooms
2,800
Square Feet
1.33
Acres

35335 Main Road, Orient, NY 11957

an aerial view of residential house with outdoor space and trees
1/31
Listed By Compass

$2,499,999

5
Bedrooms
4,200
Square Feet
1.02
Acres

290 Windward Road, Orient, NY 11957

Explore Nearby Homes

More information about 40495 Main Road, Orient, NY 11957

40495 Main Road is a single family home Coming Soon in Orient, NY 11957. This property is currently priced at $1,699,999. This listing's school district is Oysterponds Union Free School District. Nearby schools include Oysterponds Elementary School. 40495 Main Road is a 4-bed, 3-bath, 2,081 sqft single family home built in 1838.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Century 21 Albertson Realty, Gerald J. Cibulski CBR E-PRO CRS G

Based on information submitted to the MLS GRID as of 08/11/2026 05:01 AM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. 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. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.