38099 Main Rd

Orient, NY 11957

$4,999,000
Price
3
Beds
2,800 Sq. Ft.
$1,785 / Sq. Ft.
2,800
Sq. Ft.
$1,785
per Sq. Ft.
a view of a garden with an ocean
an aerial view of a house with a yard
a view of a lake with a city
a view of a house with a small yard plants and large tree
a living room with furniture and a large window
a living room with furniture large windows and wooden floor
a living room with furniture a fireplace and a table
a dining room with furniture window and outdoor view
a living room with furniture and large windows with wooden floor
a view of living room with furniture and a fireplace
a bedroom with a large bed and a large window
a bedroom with a bed and a window
a view of a room with gym equipment
a room with a bed and a view of living room
a bedroom with a bed a table and a window
a bedroom with a bed and a window
a bedroom with a bed and a large window with outer view
a living room with furniture and a window
a view of a bedroom with kitchen
a view of a patio with furniture and table under an umbrella
a view of a patio with a dining table and chairs under an umbrella
a view of a house with a yard and sitting area
a front view of a house with yard and green space
a view of a house with a big yard and garden
a front view of a house with a yard and garage
a view of a lake view
a view of a garden with a building in the background
a view of a lake from a balcony
a view of a yard with an empty space
a bathroom with a bathtub and a shower
a bathroom with a sink a toilet and shower
a view of entryway
a view of a lake with outdoor space
a ocean view with a outdoor space
a living room with furniture and a fireplace

Description

At the end of a secluded, private one-mile road, where the land meets the Long Island Sound, this newly renovated modern beach house offers breathtaking views, refined design, and total privacy. Set on two-thirds of an acre and surrounded by two 30 acre privately owned parcels of land, one of which is entirely vacant, the home features over 100 feet of private beachfront with a naturally sloped path leading to the shore. Every inch of this residence is bathed in natural light and designed to celebrate...At the end of a secluded, private one-mile road, where the land meets the Long Island Sound, this newly renovated modern beach house offers breathtaking views, refined design, and total privacy. Set on two-thirds of an acre and surrounded by two 30 acre privately owned parcels of land, one of which is entirely vacant, the home features over 100 feet of private beachfront with a naturally sloped path leading to the shore. Every inch of this residence is bathed in natural light and designed to celebrate its stunning surroundings—from the expansive great room with white oak flooring and gas fireplace to the vaulted dining area and sleek kitchen with a gas stove and integrated workspace. The primary suite includes a spa-inspired bath with a sauna, shower, and bidet, while the additional first floor bedroom has an en-suite bathroom with a second floor bedroom as well. There is a full fitness center in a finished basement with heat and central air conditioning with walk out stairs to the pool area. All new Pella black-framed windows perfectly frame the Sound, with nearly every room offering unobstructed water views. Outside, lush landscaping and vibrant hydrangeas surround a 50’ x 8’ heated saltwater gunite pool with an automatic cover and stone patio, creating a peaceful outdoor retreat ideal for both entertaining and everyday living. The white board and batten siding, matte black metal roof, and detached one-car garage complete the clean, modern aesthetic. With porcelain tile sunroom floors, low taxes, and deeded road rights with private gate, this is a rare opportunity to own a fully renovated waterfront home with unrivaled serenity, where the sunsets, sea breeze, and silence feel like your own private oasis.
  1. Listed by Alexander Aquino • Douglas Elliman Real Estate
    P: (631)-477-2220 C: (631)-477-2220 alexander.aquino@elliman.com

Property Details for 38099 Main Road

City/Township
Southold
View
Panoramic, Water
Architectural Style
Traditional
Garage Spaces
1.00
Waterfront
Yes
Section Area
Main Road
LISTING UPDATED: 10/06/2025 12:48 PM

Property Details for 38099 Main Road

StatusActive
MLS #895848
Days on Market146
Taxes$8,206 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built2003
Lot Size0.69 AC / 30,056 SF
CountySuffolk County

Location

Listing Courtesy of Douglas Elliman Real Estate, Alexander Aquino
Add your commute

Building Information for 38099 Main Road

Stories-Year Built2003Building Size-Lot Size0.69 AC / 30,056 SF

Payment Calculator

$25,386 per month

30 year fixed, 6.28% Interest

Principal and Interest

$24,702

Property Taxes

$684

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 38099 Main Road

Summary
Location and General Information
  • Senior Community YN: No
  • Year Built Effective: 2025
  • Property Attached: No
  • Structure Type: false
  • Property Condition: Updated/Remodeled
  • Frontage Length: 100
  • State Or Province: NY
  • Water Access YN: Yes
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: 1000-015-00-02-00-016-000
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Beach Access, Beach Front, Beamed Ceilings, Bidet, Built-in Features, Cathedral/Vaulted/High Ceiling, Ceiling Fan(s), Crown Molding, ENERGY STAR Qualified Door(s), Entrance Foyer, First Floor Full Bath, Formal Dining, Garage(s), Garden, Gas, Gas Grill, Granite Counters, Hardwood Floors As Seen, High Ceilings, High Speed Internet, In Ground, Natural Woodwork, New Windows, Open Floorplan, Open Kitchen, Outdoor Pool, Panoramic, Pool Cover, Primary Bathroom, Salt Water, Sauna, Security System, Soaking Tub, Sound, Sound System, Traditional, Water Access, Water View, Waterfront, Well
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Bidet, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, ENERGY STAR Qualified Door(s), Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, High Speed Internet, Natural Woodwork, Open Floorplan, Open Kitchen, Primary Bathroom, 1st Fl Master Bedroom, Sauna, Soaking Tub, Sound System
  • Appliances: Dryer, Electric Water Heater, Freezer, Gas Cooktop, Gas Oven, Gas Range, Humidifier, Refrigerator, Stainless Steel Appliance(s), Washer, Water Purifier Owned, Water Softener Owned
  • Number Of Kitchens: 1.0
  • Total Rooms: 7
  • Primary on Main: Yes
  • Basement: Finished, Storage Space, Walk-Out Access
  • Attic Description: None
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Gas
  • Location Amenities: Stainless Steel Appliances, Walk Out Basement, Exposure North, Hardwood Floors As Seen, 1st Fl Master Bedroom, Bidet, Cathedral/Vaulted/High Ceiling, Entry Foyer, Foyer, Formal Dining Room, Granit Countertops, High Ceilings, High Speed Internet, Open Kitchen, Soacking Tub, Garden, Privacy, Waterfront, In Ground Pool, Pool Outdoor, Security System, Open View, Water View, Water Access, New Windows
  • Security Features: Security System
  • Window Features: New Windows
  • Flooring: Hardwood
  • Living Area: 2,800.00
  • Basement: Yes
Exterior Features
  • Exterior Features: Garden, Gas Grill
  • Exterior Property Features: Garden, Gas Grill, In Ground, Outdoor Pool, Pool Cover, Salt Water, New Windows, Back Yard, Fill Needed, Front Yard, Landscaped, Level, Private, Secluded, Sprinklers In Front, Sprinklers In Rear, Waterfront
  • Elevation Certificate: No
  • Construction Materials: Frame
  • Other Structures: Garage(s)
  • Waterfront Features: Beach Access, Beach Front, Sound, Water Access, Waterfront
  • Horse: No
  • Pool Private: Yes
  • Pool Features: In Ground,Outdoor Pool,Pool Cover,Salt Water
  • Pool Details: In Ground,Outdoor Pool,Pool Cover,Salt Water
  • Direction Faces: North
Lot Information
  • Lot Features: Back Yard, Fill Needed, Front Yard, Garden, Landscaped, Level, Private, Secluded, Sprinklers In Front, Sprinklers In Rear, Waterfront
  • Additional Parcel: No
  • Site Features: Back Yard, Fill Needed, Front Yard, Garden, Landscaped, Level, Private, Secluded, Sprinklers In Front, Sprinklers In Rear, Waterfront
  • Building Area Units: Square Feet
Parking
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Electric, Propane
  • Heat Fuel Type: Electric, Propane
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Cable Connected, Electricity Connected, Phone Connected, Propane, Sewer Connected, Water Connected
Green Features
  • Green Features: New Windows, Dryer, Electric Water Heater, Freezer, Gas Cooktop, Gas Oven, Gas Range, Humidifier, Refrigerator, Stainless Steel Appliance(s), Washer, Water Purifier Owned, Water Softener Owned, Electric, Propane, Garden, Gas Grill, In Ground, Outdoor Pool, Pool Cover, Salt Water
Agent
Payment and Rate
  • Down Payment Resource: No

Public Records for 38099 Main Road

Taxable ValueLand$3,200Additions$6,600Total$9,800
Home Facts
Beds0Lot Size30,056 SqFtStyleSingle Family ResidenceZoningR-80CountySUFFOLKAPN1000-015.00-02.00-016.000

Schools near 38099 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.

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More information about 38099 Main Road, Orient, NY 11957

38099 Main Road is a single family home for sale in Orient, NY 11957. This property was listed for sale on July 31, 2025 by Douglas Elliman Real Estate, it's currently listed at $4,999,000. This listing's school district is Oysterponds Union Free School District. Nearby schools include Oysterponds Elementary School. 38099 Main Road is a 3-bed, 2-bath, 2,800 sqft single family home built in 2003.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Douglas Elliman Real Estate, Alexander Aquino

Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/24/2025 02:14 PM. All data is obtained from various sources and may not have been verified by broker orMLS GRID. Supplied Open House Information is subject to change without notice. All informationshould be independently reviewed and verified for accuracy. Properties may or may not be listed bythe office/agent presenting the information.