38099 Main Road Orient, NY $ 4,999,000
38099 Main Road
$ 4,999,000
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38099 Main Road

Orient, NY, 11957
$ 4,999,000
Bedrooms3 Baths2.0 Sq 2,800

Monthly Estimate*

$ 31,187

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Single Family Home for sale in Orient, NY

for $4,999,000 with 3 bedrooms and 2 full baths. This 2,800 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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Single Family Active

Price

$ 4,999,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 8,205

Style

Traditional

Lot Size

0.69

Year Built

2003

Town/City

Orient

County/Region

Suffolk

MLS | Web ID

895848

Features
Interior
Interior Amenities 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
Basement Finished Storage Space Walk-Out Access
Flooring Hardwood
Total Fireplaces 1
Fireplace Features Gas
Basement Features Finished Storage Space Walk-Out Access
Basement (Y/N) Y
Window Features New Windows
Fireplace Y/N Y
Half Baths 0
Total Bedrooms 3
Total Baths 2
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General
Sewer Septic Tank
Heating Electric Propane
Cooling Central Air
Utilities Cable Connected Electricity Connected Phone Connected Propane Sewer Connected Water Connected
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
Garage Spaces 1
Architectural Style Traditional
Pool Features In Ground Outdoor Pool Pool Cover Salt Water
Security Features Security System
Construction Materials Frame
Year Built 2003
View Panoramic Water
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 1000-015-00-02-00-016-000
Waterfront Features Beach Access Beach Front Sound Water Access Waterfront
County Suffolk County
Property Type Residential
HOA N
Facing Direction North
Garage Y/N Y
Other Structures Garage(s)
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 8205.56
Showing Instructions Please call text or email Alexander Aquino at 631.902.7351 or Alexander.Aquino@Elliman.com
Middle/Junior High School Greenport High School
Property Condition Updated/Remodeled
Additional Parcels Y/N N
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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Exterior
Exterior Amenities Garden Gas Grill
Water Source Well
Frontage Length 100
Waterfront Y/N Y
Horse Y/N N
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Internal Only
Street Number 1 38099
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* Excluded Features
List By
Alexander Aquino

Listing Agent

Douglas Elliman Real Estate

Broker

631-477-2220

Contact

Affordability Calculator

$31,871
Per Month
98%
2%
0%
Monthly Principal & Interest
$31,187
Monthly Property Taxes
$684
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% 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.
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Nearby
5166483 Elementary School
4100514 Middle School
Greenport High School High School
Pricing History
DatePricePrice ChangeDescription
10/6/2025$4,999,000 -25.94% Price Down
7/31/2025$6,750,000 Listed Price

Map


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38099 Main Road, Orient, NY, 11957 is a Single Family Home for sale at $4,999,000 with 2,800 sqft and a lot size of 0.69. 38099 Main Road has 3 bedrooms, 2.0 baths, and was built in 2003. The property's zip code is 11957 which is in Orient, NY