38099 Main Road

New
New
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Active
$4,500,000
3 beds2,000 sqft$2,250/sqft
38099 Main Rd, Orient, NY 11957
Est: $23,557/moGet pre-approved
Single FamilyProperty Type
0.69 acresLot Size
2003Year Built
$2,250/sq ftPrice per sq ft
15 carsParking Spaces

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.
Days on Market Listed Today
  • Listed by: Alexander Aquino 631.477.2220 alexander.aquino@elliman.com • Douglas Elliman Real Estate
  • Listed by: Jill H. Dunbar 631.477.2220 jill.dunbar@elliman.com • Douglas Elliman Real Estate
Last updated: 09/06/2026 01:54 PM • Source: ONEKEY as distributed by MLS GRID, MLS#: 1047292

Location

Listing Courtesy of Douglas Elliman Real Estate, Alexander Aquino; Douglas Elliman Real Estate, Jill H. Dunbar
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$23,557 per month

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Principal and Interest

$22,873

Property Taxes

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Property Information for 38099 Main Road

Property Details
  • Taxes: $8,206 / year
  • MLS Type: Single Family
  • County: Suffolk County
  • City/Township: Southold
  • View: Water
  • Architectural Style: Traditional
  • Garage Spaces: 15
  • Waterfront: Yes
  • Section Area: Main Road
Building Information
  • Year Built: 2003
  • Lot Size: 0.69 AC / 30,056 SF
Summary
Location and General Information
  • Senior Community YN: No
  • Year Built Effective: 2025
  • Property Attached: No
  • Structure Type: Detached
  • 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
  • Tax Source: Municipality
  • Tax Year: 2025
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Beamed Ceilings, Breakfast Bar, Built-in Features, Cathedral/Vaulted/High Ceiling, Ceiling Fan(s), First Floor Full Bath, Formal Dining, Garden, Hardwood Floors As Seen, High Ceilings, High Speed Internet, Kitchen Island, Quartz/Quartzite Counters, Recessed Lighting, Soaking Tub, Sound, Sound System, Speakers, Traditional, Water View, Well, Wood Burning
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Breakfast Bar, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Formal Dining, High Ceilings, High Speed Internet, Kitchen Island, Quartz/Quartzite Counters, Recessed Lighting, Soaking Tub, Sound System, Speakers
  • Appliances: Cooktop, Dryer, Exhaust Fan, Gas Cooktop, Gas Range, Stainless Steel Appliance(s), Washer, Water Softener Owned
  • Total Rooms: 7
  • Basement: Finished, Full, Walk-Out Access
  • Attic Description: None
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Wood Burning
  • Location Amenities: Stainless Steel Appliances, Walk Out Basement, Hardwood Floors As Seen, 1st Fl Master Bedroom, Cathedral/Vaulted/High Ceiling, Formal Dining Room, High Ceilings, High Speed Internet, Island Kitchen, Soacking Tub, Garden, Waterfront, Water View
  • Flooring: Hardwood
  • Living Area: 2000
  • Basement: Yes
Exterior Features
  • Exterior Features: Garden
  • Exterior Property Features: Garden, Private, Front Yard, Sprinklers In Front, Sprinklers In Rear, Waterfront
  • Elevation Certificate: No
  • Construction Materials: Frame
  • Waterfront Features: Sound
  • Pool Private: Yes
Lot Information
  • Lot Features: Front Yard, Garden, Sprinklers In Front, Sprinklers In Rear, Waterfront
  • Site Features: Front Yard, Garden, Sprinklers In Front, Sprinklers In Rear, Waterfront
  • Building Area Units: Square Feet
Parking
  • Parking Features: Private
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Propane
  • Heat Fuel Type: Propane
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Cable Connected, Electricity Connected, Phone Connected, Sewer Connected, Trash Collection Private, Water Connected
Green Features
  • Green Features: Cooktop, Dryer, Exhaust Fan, Gas Cooktop, Gas Range, Stainless Steel Appliance(s), Washer, Water Softener Owned, Propane, Garden

Property History for 38099 Main Road

DateEvent & SourcePriceAppreciation
Sep 6, 2026

Listed (Active)

ONEKEY #1047292

$4,500,000—
Jan 13, 2026

Expired

ONEKEY #895848

$4,999,000—
Jul 31, 2025

Listed (Active)

ONEKEY #895848

$6,750,000—
DateEvent & SourcePrice
09/06/2026

Listed (Active)

ONEKEY #1047292

$4,500,000
01/13/2026

Expired

ONEKEY #895848

$4,999,000
07/31/2025

Listed (Active)

ONEKEY #895848

$6,750,000

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

Public Records for 38099 Main Road

Taxable ValueLand$3,200Additions$6,600Total$9,800
Tax Record2024$7,487 ($624 / month)
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 September 6, 2026 by Douglas Elliman Real Estate, it's currently listed at $4,500,000. 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, 2,000 sqft single family home built in 2003.

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. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make 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; Douglas Elliman Real Estate, Jill H. Dunbar

Based on information submitted to the MLS GRID as of 09/06/2026 01:54 PM. 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.