440 Windward Rd, Orient, NY 11957
OFF MARKET

440 Windward Rd
Orient, NY 11957

  • 4 Beds
  • 4.5 Baths
  • 3,700 sqft (on 1.16 acres)

$2,919,500

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $14,875/mo*
Refinance Your Home

$2,919,500

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $14,875/mo*
Refinance Your Home
4 Beds
4.5 Baths
3,700 sqft
(on 1.16 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

"Clear Day Cottage". This Nantucket Style Residence Has 114 Feet Of Private Beachfront, Spectacular Sunsets And Lush Perennial Gardens. Situated Up A Private Road, The Custom Millwork, Family Room With Barrel Vaulted Ceiling And Two Story W/B Fireplace Add To This Fabulous Respite On The L I Sound. A Rare And Resort-Like Experience In Orient.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 440 Windward Rd

Interior Features

Heating & Cooling
Heating: Other, Stove, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Interior Details
Number of Rooms: 8Types of Rooms: Dining Room
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: OtherDeckGardenPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Lot Information

Lot Area: 1.16 acres

Price History for 440 Windward Rd

DatePriceEventSource
04/26/2016$2,650,000Sold
N/A
01/28/2016$2,650,000Sold
N/A
07/24/2015$2,750,000ListingRemovedAgent Provided
06/25/2015$2,750,000PriceChange
Agent Provided
04/10/2015$2,850,000Listed For SaleAgent Provided
02/18/2015$2,850,000ListingRemovedAgent Provided
11/25/2014$2,850,000Listed For SaleAgent Provided
01/14/2003$850,000Sold
N/A
04/26/2000$295,500Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$3,254,545
Home facts updated by county records

Comparable Sales for 440 Windward Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
655 N Sea Drive, Orient, NY
1.11
Single-Family Home
$2,100,000
10/30/25
4
4.5
4,028
1855 Greenway East, Orient, NY
0.64
Single-Family Home
$1,775,000
09/09/25
5
4.5
2,950
215 Hillcrest Drive N, Orient, NY
1.16
Single-Family Home
$3,625,000
03/31/26
3
3
5,837
32260 Main Rd, Orient, NY
0.21
Single-Family Home
$700,000
07/21/25
2
1
1,200
900 N View Drive, Orient, NY
1.33
Single-Family Home
$3,150,000
02/05/26
3
2.5
2,127
2000 Greenway East E, Orient, NY
0.67
Single-Family Home
$875,000
10/27/25
3
2
1,621
685 Greenway W, Orient, NY
0.59
Single-Family Home
$825,000
04/23/26
2
2
1,264
555 Three Waters Lane, Orient, NY
1.22
Single-Family Home
$1,010,000
10/29/25
3
3
2,400
110 Soundview Rd, Orient, NY
0.96
Single-Family Home
$1,850,000
06/23/25
5
7.5
-
1075 Narrow River Road, Orient, NY
1.86
Single-Family Home
$1,800,000
12/09/25
4
2.5
2,264

Assigned Schools

These are the assigned schools for 440 Windward 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

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 440 Windward Rd

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Homes for rent near 440 Windward Rd

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Off Market Homes Near 440 Windward Rd

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Explore by feature

440 Windward Rd, Orient, NY 11957 is a 4 bedroom, 5 bathroom, 3,700 sqft single-family home built in 2005. This property is not currently available for sale. 440 Windward Rd was last sold on Apr 26, 2016 for $2,650,000. The current Trulia Estimate for 440 Windward Rd is $2,919,500.