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For sale
  • $4,500,000

    38099 Main Road, Orient, NY 11957

    3beds
    2,000sqft
    Loading
    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
    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.
    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#: 1047292MLS Logo

      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

        DateEventPrice
        9/6/2026Listed for sale$4,500,000-10%$2,250/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1047292 Report a problem
        1/19/2026Listing removed$4,999,000$2,500/sqft
        Source: Out East #390507 Report a problem
        10/4/2025Price change$4,999,000-25.9%$2,500/sqft
        Source: Out East #390507 Report a problem
        7/31/2025Listed for sale$6,750,000+68.8%$3,375/sqft
        Source: OneKey® MLS as distributed by MLS GRID #895848 Report a problem
        7/1/2024Listing removed--
        Source: Zillow Rentals Report a problem
        2/5/2024Listed for rent$35,000-65%$18/sqft
        Source: Zillow Rentals Report a problem
        2/5/2024Listing removed--
        Source: Douglas Elliman Report a problem
        7/1/2023Listed for rent$100,000+17.6%$50/sqft
        Source: Zillow Rentals Report a problem
        7/1/2023Listing removed--
        Source: Zillow Rentals Report a problem
        3/24/2023Listed for rent$85,000+183.3%$43/sqft
        Source: Zillow Rentals Report a problem
        7/1/2021Listing removed--
        Source: Out East Report a problem
        6/22/2021Listed for rent$30,000$15/sqft
        Source: Out East #350296 Report a problem
        2/20/2021Listing removed--
        Source: Out East Report a problem
        11/21/2020Listing removed$3,999,000$2,000/sqft
        Source: Douglas Elliman #3181925 Report a problem
        11/21/2020Listed for rent$30,000+28.6%$15/sqft
        Source: Douglas Elliman Real Estate #350296 Report a problem
        8/11/2020Price change$3,999,000+2.5%$2,000/sqft
        Source: Douglas Elliman Real Estate #348573 Report a problem
        8/7/2020Price change$3,900,000-8.2%$1,950/sqft
        Source: Douglas Elliman Real Estate #348573 Report a problem
        5/7/2020Price change$4,250,000-19%$2,125/sqft
        Source: Douglas Elliman Real Estate #348573 Report a problem
        11/11/2019Price change$5,250,000-25%$2,625/sqft
        Source: Douglas Elliman Real Estate #348573 Report a problem
        8/1/2019Listed for sale$7,000,000$3,500/sqft
        Source: Corcoran Group #44074 Report a problem
        8/1/2019Listing removed$23,333$12/sqft
        Source: Shelter Island #79636 Report a problem
        5/10/2019Price change$23,333+6.1%$12/sqft
        Source: Shelter Island Report a problem
        4/23/2019Price change$22,000-66.7%$11/sqft
        Source: Shelter Island Report a problem
        11/14/2018Listed for rent$66,000+1000%$33/sqft
        Source: Corcoran Group Shelter Island Office #79636 Report a problem
        8/8/2018Listing removed$6,000$3/sqft
        Source: The Corcoran Group #79636 Report a problem

        Public tax history

        YearProperty taxesTax 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

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 11957

        Getting around

        2 / 100
        Car-Dependent
        32 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        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.

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