38099 Main Road, Orient, NY 11957
Property image
Property image
FOR SALE
0.69 ACRES

$4,500,000

  • 3 Beds
  • 2 Baths
  • 2,000 sqft (on 0.69 acres)

38099 Main Road, Orient, NY 11957

Est. Mortgage $30,434/mo*
Get Pre-Qualified

Home Highlights

Single-Family Home
Built in 2003
0.69 acre lot
$2,250/sqft
Garage

Local Information

  • Map ViewExplore the area around 38099 Main Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 3 hours ago
Listing by: Douglas Elliman Real Estate, (631) 477-2220
Alexander Aquino, (631) 477-2220
Douglas Elliman Real Estate, (631) 477-2220
Jill H. Dunbar
Source: OneKey® MLS as distributed by MLS GRID, MLS#1047292
Also Listed on OneKey® MLS as distributed by MLS GRID, Douglas Elliman.

Home Details for 38099 Main Road

Interior Features

Interior Details
Basement: Finished,Full,Walk-Out AccessNumber of Rooms: 7
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2000 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Phone Connected, Sewer Connected, Trash Collection Private, Water ConnectedAppliances: Cooktop, Dryer, Exhaust Fan, Gas Cooktop, Gas Range, Stainless Steel Appliance(s), Washer, Water Softener OwnedDryerWasher
Heating & Cooling
Heating: PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Propane
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood BurningHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Floors: Hardwood
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Exterior: GardenGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 15Number of Covered Spaces: 15No CarportHas a GarageParking Spaces: 15Parking: Private
Pool
Pool
Frontage
WaterfrontWaterfront: Sound, WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 1Days on Market: 8

Property Information

Year Built
Year Built: 2003Year Renovated: 2025
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Traditional
Building
Construction Materials: FrameNot Attached Property

Price & Status

Price
List Price: $4,500,000Price Per Sqft: $2,250

Active Status

MLS Status: Active

Location

Direction & Address
City: Orient
School Information
Elementary School: Oysterponds Elementary SchoolJr High / Middle School: Greenport High SchoolHigh School: Greenport High SchoolHigh School District: Greenport

Agent Information

Listing Agent
Listing ID: 1047292

Building

Building Area
Building Area: 2000 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.69 acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 1047292Attic: NoneWater ViewWater View: WaterAttribution Contact: 631-477-2220Showing Requirements: Call Listing Agent, Call Listing Office

Around this home

What Locals Say about Orient

At least 7 Trulia users voted on each feature.

  • 100 % Say car is needed

  • 100 % Say it's dog friendly

  • 100 % Say yards are well-kept

  • 100 % Say kids play outside

  • 100 % Say people would walk alone at night

  • 92 % Say parking is easy

  • 89 % Say there's wildlife

  • 86 % Say there's holiday spirit

  • 78 % Say there are community events

  • 74 % Say neighbors are friendly

  • 73 % Say they plan to stay for at least 5 years

  • 60 % Say there are sidewalks

  • 55 % Say it's quiet

  • 38 % Say it's walkable to grocery stores

  • 31 % Say streets are well-lit

  • 25 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Cornelljohn
    "Amazing place to raise a family. It feels like a forgotten time in America where people are really friendly and take time to get to know each other"
    0
    Flag
  • Jyahalom5344
    "I love this neighborhood People are caring and friendly, they look out for each other. It is very safe and clean "
    1
    Flag
  • Afophis
    "I just move here , ppl are friendly and respectful to the nature . I love being here . I would like to having house around here 😀"
    0
    Flag
  • Jerry C.
    "Orient State Park is part of the New York State park system. The park offers kayak rentals, wide beaches, hiking trails, bike trails and plenty of picnic tables and charcoal grills. The facilities are clean and the park offers rental equipment for the volley ball courts. "
    1
    Flag

Market trends in Orient

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
14
1MoM

Home Value

Trulia Estimate
$4.38M
Since last month
Increased$2M (+131.2%)
Since last year
Decreased$2M (-33.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +323% in the last 10 years
MonthEstimated value
2026
September 2026$4.38M
August 2026$1.91M
July 2026$1.9M
June 2026$4.56M
May 2026$4.56M
April 2026$4.62M
March 2026$4.62M
February 2026$4.6M
January 2026$4.58M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2000 Greenway East E, Orient, NY
0.19
Single-Family Home
$875,000
10/27/25
3
2
1,621
350 Soundview Road, Orient, NY
0.23
Single-Family Home
$1,095,000
07/06/26
3
1.5
1,245
175 Uhl Lane, Orient, NY
0.26
Single-Family Home
$770,000
05/29/26
4
2.5
2,100
685 Greenway W, Orient, NY
0.31
Single-Family Home
$825,000
04/23/26
2
2
1,264
815 Uhl Lane, Orient, NY
0.34
Single-Family Home
$1,450,000
06/10/26
4
3.5
2,700
555 Three Waters Lane, Orient, NY
0.48
Single-Family Home
$1,010,000
10/29/25
3
3
2,400
65 Greenway W, Orient, NY
0.38
Single-Family Home
$968,000
06/10/26
2
1
962
655 N Sea Drive, Orient, NY
0.34
Single-Family Home
$2,100,000
10/30/25
4
4.5
4,028
1680 Lands End Road, Orient, NY
0.57
Single-Family Home
$1,900,000
09/02/26
4
4
3,359
255 S View Drive, Orient, NY
1.87
Single-Family Home
$2,100,000
09/14/26
3
3
2,538

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
65 Ryder Farm Ln, Orient, NY 11957
0.15
$1,350,200
3
2
1,900
Off Market
2000 Greenway East E, Orient, NY 11957
0.19
$889,300
3
2
1,621
Off Market
125 Soundview Road, Orient, NY 11957
0.17
$3,071,100
4
3.5
2,950
Off Market
110 Soundview Rd, Orient, NY 11957
0.18
$1,989,000
5
7.5
-
Off Market
1855 Greenway East, Orient, NY 11957
0.23
$1,872,600
5
4.5
2,950
Off Market
130 Soundview Road, Orient, NY 11957
0.20
$1,525,700
3
3
2,504
Off Market
350 Soundview Road, Orient, NY 11957
0.23
$1,095,000
3
1.5
1,245
Recently Sold
1250 N Sea Drive, Orient, NY 11957
0.24
$1,265,300
3
3.5
1,800
Off Market
175 Uhl Lane, Orient, NY 11957
0.26
$770,000
4
2.5
2,100
Recently Sold
685 Greenway W, Orient, NY 11957
0.31
$825,000
2
2
1,264
Recently Sold
395 Uhl Lane, Orient, NY 11957
0.29
$950,000
2
2
1,688
For Sale

Price and Tax history

DateEventPrice
Sep 6, 2026
Source: OneKey® MLS as distributed by MLS GRID #1047292
Listed For Sale
$4,500,000
Jan 19, 2026
Source: Out East #390507
ListingRemoved
$4,999,000
Oct 4, 2025
Source: Out East #390507
PriceChange
$4,999,000
Price decreased by 26%
Jul 31, 2025
Source: OneKey® MLS as distributed by MLS GRID #895848
Listed For Sale
$6,750,000
Jul 1, 2024
Source: Zillow Rentals
ListingRemoved

LGBTQ Local Legal Protections

Alexander Aquino, Douglas Elliman Real Estate, (631) 477-2220
Agent Phone: (631) 477-2220
Based on information submitted to the MLS GRID as of 2026-09-14 14:38:24 PDT 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. Some IDX listings have been excluded from this website. Click here for more information

Similar Homes You May Like

Skip to last item
Skip to first item

New Listings near 38099 Main Road

Skip to last item
Skip to first item

Frequently asked questions about 38099 Main Road

  • What is the estimated monthly payment for 38099 Main Road?
    Based on a $4,500,000 list price with 20% down at today's rates, the estimated monthly payment for 38099 Main Road in Orient, NY is approximately $31,058 (about $24,045 principal & interest, $6,938 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Orient?
    Residents describe Orient, NY as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See homes for sale in Orient, NY.
  • What are the closest schools to 38099 Main Road?
    The closest schools to 38099 Main Road in Orient, NY are Greenport High School (Middle, rated 5/10), Oysterponds Elementary School (Pre-K, rated 4/10).
  • What is 38099 Main Road estimated to be worth?
    Trulia's estimated value for 38099 Main Road in Orient, NY is $4,384,500.
  • Does 38099 Main Road have air conditioning?
    Yes, 38099 Main Road in Orient, NY has air conditioning.
  • Does 38099 Main Road have a pool?
    Yes, 38099 Main Road in Orient, NY has a pool.
38099 Main Road, Orient, NY 11957 is a 3 bedroom, 2 bathroom, 2,000 sqft single-family home built in 2003. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on Sep 6, 2026. The MLS # for this home is MLS# 1047292.