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.
For sale
$4,500,000
38099 Main Road, Orient, NY 11957
3beds
2,000sqft
Single Family Residence, Residential
Built in 2003
0.69 Acres Lot
$-- Zestimate®
$2,250/sqft
$-- HOA
What's special
Gas fireplaceBathed in natural lightStone patioDetached one-car garageSecond floor bedroomExpansive great roomSecluded private one-mile road
- 2 hours
- 104
- 4
Zillow last checked:
Listing updated:
Listed by:
Douglas Elliman Real Estate 631-477-2220,
Alexander Aquino 631-477-2220,
Jill H. Dunbar,
Douglas Elliman Real Estate
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1047292
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Propane
Cooling
- Central Air
Appliances
- Included: Cooktop, Dryer, Exhaust Fan, Gas Cooktop, Gas Range, Stainless Steel Appliance(s), Washer, Water Softener Owned
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
- Flooring: Hardwood
- Basement: Finished,Full,Walk-Out Access
- Attic: None
- Number of fireplaces: 1
- Fireplace features: Wood Burning
Interior area
- Total structure area: 2,000
- Total interior livable area: 2,000 sqft
Property
Parking
- Total spaces: 15
- Parking features: Private
- Garage spaces: 15
Features
- Exterior features: Garden
- Has private pool: Yes
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Sound, Waterfront
Lot
- Size: 0.69 Acres
- Features: Front Yard, Garden, Sprinklers In Front, Sprinklers In Rear
Details
- Parcel number: 1000015000200016000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence, Residential
Materials
- Frame
Condition
- Year built: 2003
- Major remodel year: 2025
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Connected, Electricity Connected, Phone Connected, Sewer Connected, Trash Collection Private, Water Connected
Community & HOA
HOA
- Has HOA: No
Location
- Region: Orient
Financial & listing details
- Price per square foot: $2,250/sqft
- Tax assessed value: $1,781,818
- Annual tax amount: $8,206
- Date on market: 9/6/2026
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 9/6/2026 | Listed for sale | $4,500,000-10%$2,250/sqft |
Source: | ||
| 1/19/2026 | Listing removed | $4,999,000$2,500/sqft |
Source: Out East #390507 Report a problem | ||
| 10/4/2025 | Price change | $4,999,000-25.9%$2,500/sqft |
Source: Out East #390507 Report a problem | ||
| 7/31/2025 | Listed for sale | $6,750,000+68.8%$3,375/sqft |
Source: | ||
| 7/1/2024 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 2/5/2024 | Listed for rent | $35,000-65%$18/sqft |
Source: Zillow Rentals Report a problem | ||
| 2/5/2024 | Listing removed | -- |
Source: | ||
| 7/1/2023 | Listed for rent | $100,000+17.6%$50/sqft |
Source: Zillow Rentals Report a problem | ||
| 7/1/2023 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 3/24/2023 | Listed for rent | $85,000+183.3%$43/sqft |
Source: Zillow Rentals Report a problem | ||
| 7/1/2021 | Listing removed | -- |
Source: Out East Report a problem | ||
| 6/22/2021 | Listed for rent | $30,000$15/sqft |
Source: Out East #350296 Report a problem | ||
| 2/20/2021 | Listing removed | -- |
Source: Out East Report a problem | ||
| 11/21/2020 | Listing removed | $3,999,000$2,000/sqft |
Source: Douglas Elliman #3181925 Report a problem | ||
| 11/21/2020 | Listed for rent | $30,000+28.6%$15/sqft |
Source: Douglas Elliman Real Estate #350296 Report a problem | ||
| 8/11/2020 | Price change | $3,999,000+2.5%$2,000/sqft |
Source: Douglas Elliman Real Estate #348573 Report a problem | ||
| 8/7/2020 | Price change | $3,900,000-8.2%$1,950/sqft |
Source: Douglas Elliman Real Estate #348573 Report a problem | ||
| 5/7/2020 | Price change | $4,250,000-19%$2,125/sqft |
Source: Douglas Elliman Real Estate #348573 Report a problem | ||
| 11/11/2019 | Price change | $5,250,000-25%$2,625/sqft |
Source: Douglas Elliman Real Estate #348573 Report a problem | ||
| 8/1/2019 | Listed for sale | $7,000,000$3,500/sqft |
Source: Corcoran Group #44074 Report a problem | ||
| 8/1/2019 | Listing removed | $23,333$12/sqft |
Source: Shelter Island #79636 Report a problem | ||
| 5/10/2019 | Price change | $23,333+6.1%$12/sqft |
Source: Shelter Island Report a problem | ||
| 4/23/2019 | Price change | $22,000-66.7%$11/sqft |
Source: Shelter Island Report a problem | ||
| 11/14/2018 | Listed for rent | $66,000+1000%$33/sqft |
Source: Corcoran Group Shelter Island Office #79636 Report a problem | ||
| 8/8/2018 | Listing removed | $6,000$3/sqft |
Source: The Corcoran Group #79636 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $9,800 |
| 2024 | -- | $9,800 |
| 2023 | -- | $9,800 |
| 2022 | -- | $9,800 |
| 2021 | -- | $9,800 |
| 2020 | -- | $9,800 +2.1% |
| 2019 | -- | $9,600 +5.5% |
| 2018 | -- | $9,100 |
| 2017 | $6,830 | $9,100 |
| 2016 | -- | $9,100 |
| 2015 | -- | $9,100 |
| 2014 | -- | $9,100 |
| 2013 | -- | $9,100 |
| 2012 | -- | $9,100 |
| 2011 | -- | $9,100 +18.2% |
| 2010 | -- | $7,700 |
| 2009 | -- | $7,700 |
| 2008 | -- | $7,700 +8.5% |
| 2007 | $4,136 +691% | $7,100 +7.6% |
| 2005 | $523 -86.4% | $6,600 |
| 2004 | $3,847 | $6,600 |
Find assessor info on the county website
Monthly payment
Climate risks
Neighborhood: 11957
Nearby schools
Schools provided by the listing agent
- Elementary: Oysterponds Elementary School
- Middle: Greenport High School
- High: Greenport High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.





