38099 Main Road
Orient, NY, 11957 $ 4,500,000
Bedrooms3 Baths2.0 Sq 2,000 Monthly Estimate*
$ 28,413
for $4,500,000 with 3 bedrooms and 2 full baths. This 2,000 square foot home was built in 2003 on a lot size of 0.69.
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.
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FeaturesInteriorInterior Amenities 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/Qua
Basement Finished Full Walk-Out Access
Flooring Hardwood
Total Fireplaces 1
Fireplace Features Wood Burning
Basement Features Finished Full Walk-Out Access
Basement (Y/N) Y
Fireplace Y/N Y
Half Baths 0
Total Bedrooms 3
Total Baths 2
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GeneralSewer Septic Tank
Heating Propane
Cooling Central Air
Utilities Cable Connected Electricity Connected Phone Connected Sewer Connected Trash Collection Private Water Connected
Appliances Cooktop Dryer Exhaust Fan Gas Cooktop Gas Range Stainless Steel Appliance(s) Washer Water Softener Owned
Garage Spaces 15
Architectural Style Traditional
Construction Materials Frame
Year Built 2003
View Water
Property Subtype Single Family Residence
Tax Year 2025
Waterfront Features Sound
County Suffolk County
Property Type Residential
HOA N
Garage Y/N Y
Total Rooms 7
Full Baths 2
High School Greenport High School
City Southold
Senior Community Y/N N
High School District Greenport
Carport Y/N N
Elementary School Oysterponds Elementary School
Property Attached Y/N N
Tax Annual Amount 8206
Middle/Junior High School Greenport High School
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Greenport
Elementary School District Oysterponds
Year Built Effective 2025
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ExteriorExterior Amenities Garden
Parking Features Private Private
Water Source Well
Waterfront Y/N Y
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* Excluded FeaturesList ByAlexander AquinoListing Agent
Douglas Elliman Real EstateBroker
Affordability Calculator
- Monthly Principal & Interest
- $28,413
- Monthly Property Taxes
- $684
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Orient, NY
Average List Price $2,956,846
Percent of Sale Price 34%
About Orient, NY 776 Population
9% Since 2002
$ 74,886 Median Income
60.22 Median Age
10% Households with Children
Trends Information provided by ATTOM Data Solutions.
5166483 Elementary School
4100514 Middle School
Greenport High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 9/6/2026 | $4,500,000 | | Listed Price |