38099 Main Rd, Orient, NY 11957
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Property image
OFF MARKET

38099 Main Rd
Orient, NY 11957

  • 3 Beds
  • 2 Baths
  • 2,800 sqft (on 0.69 acres)

$1,876,300

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $12,269/mo*
Refinance Your Home

$1,876,300

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $12,269/mo*
Refinance Your Home
3 Beds
2 Baths
2,800 sqft
(on 0.69 acres)

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1999
Lot Size
0.69 acres
Living Area
2,800 sqft
Price/Sqft
$670
Parking
Garage

Description

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.
38099 Main Rd, Orient, NY 11957 is a 3 bedroom, 2 bathroom, 2,800 sqft single-family home built in 1999. More recently, it was listed as a rental in February 2024 with an asking price of $35,000 per month. That rental listing was removed on July 1, 2024. It is currently off market. The Trulia Estimate is $1,876,300, with a rent estimate of $6,275/month.
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Home Details for 38099 Main Rd

Interior Features

Interior Details
Basement: Yes
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2800 Square Feet
Heating & Cooling
Has CoolingAir Conditioning: Central AirNo Heating
Fireplace & Spa
Has a FireplaceNo Spa
Levels, Entrance, & Accessibility
Stories: 2
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Has a Private Pool
Parking & Garage
No CarportHas a GarageNo Attached GarageParking: GarageDetached
Pool
Pool: HeatedPool
Frontage
WaterfrontWaterfront: WaterfrontFrontage Type: WaterfrontOn Waterfront

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Is a New Construction
Property Information
Condition: New Construction

Price & Status

Price
List Price: $4,999,000

Active Status

MLS Status: Active

Location

Direction & Address
City: Orient

Building

Building Area
Building Area: 2800 Square Feet

Community

Community Features: Room for a Tennis Court

Lot Information

Lot Area: 0.69 acres

Miscellaneous

BasementMls Number: 390507Listing UrlWater ViewWater View: Water

Additional Information

Room for a Tennis Court
Source: Out East, MLS#390507

Price History for 38099 Main Rd

DatePriceEventSource
01/19/2026$4,999,000ListingRemovedOut East #390507
10/04/2025$4,999,000PriceChange
Out East #390507
07/31/2025$6,750,000Listed For SaleOneKey® MLS as distributed by MLS GRID #895848
07/01/2024ListingRemovedZillow Rentals
02/05/2024$35,000Listed For RentZillow Rentals
02/05/2024ListingRemovedDouglas Elliman
07/01/2023$100,000Listed For RentZillow Rentals
07/01/2023ListingRemovedZillow Rentals
03/24/2023$85,000Listed For RentZillow Rentals
07/01/2021ListingRemovedOut East
06/22/2021$30,000Listed For RentOut East #350296
02/20/2021ListingRemovedOut East
11/21/2020$3,999,000ListingRemovedAgent Provided
11/21/2020$30,000Listed For RentAgent Provided
08/11/2020$3,999,000PriceChange
Agent Provided
08/07/2020$3,900,000PriceChange
Agent Provided
05/07/2020$4,250,000PriceChange
Agent Provided
11/11/2019$5,250,000PriceChange
Agent Provided
08/01/2019$7,000,000Listed For SaleAgent Provided
08/01/2019$23,333ListingRemovedAgent Provided
05/10/2019$23,333PriceChange
Agent Provided
04/23/2019$22,000PriceChange
Agent Provided
11/14/2018$66,000Listed For RentAgent Provided
08/08/2018$6,000ListingRemovedAgent Provided
08/07/2018$6,000Listed For RentAgent Provided

Market trends in Orient

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

Year2025
Tax
Assessment$1,781,818
Home facts updated by county records

Comparable Sales for 38099 Main Rd

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
815 Uhl Lane, Orient, NY
0.34
Single-Family Home
$1,450,000
06/10/26
4
3.5
2,700
685 Greenway W, Orient, NY
0.31
Single-Family Home
$825,000
04/23/26
2
2
1,264
655 N Sea Drive, Orient, NY
0.34
Single-Family Home
$2,100,000
10/30/25
4
4.5
4,028
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
1855 Greenway East, Orient, NY
0.23
Single-Family Home
$1,775,000
09/09/25
5
4.5
2,950
2670 Grandview Drive, Orient, NY
1.23
Single-Family Home
$4,000,000
07/02/26
6
6.5
6,800

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Assigned Schools

These are the assigned schools for 38099 Main Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Apartments for Rent

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Explore by feature - Air Conditioning

12 rentals with air conditioning in Orient, NY

Explore by feature - Pool

10 rentals with a pool in Orient, NY

Homes for sale near 38099 Main Rd

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Off Market Homes Near 38099 Main Rd

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