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)

$2,903,600

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $19,172/mo*
Refinance Your Home

$2,903,600

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $19,172/mo*
Refinance Your Home
4 Beds
4.5 Baths
3,700 sqft
(on 1.16 acres)

Home Value

Trulia Estimate
$2.9M
Since last month
Decreased$21K (-0.7%)
Since last year
Increased$423K (+17%)
Since last sale
Increased$254K (+9.6%)
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 +10% in the last 10 years
MonthEstimated value
2026
August 2026$2.9M
July 2026$2.9M
June 2026$2.92M
May 2026$2.89M
April 2026$2.84M
March 2026$2.77M
February 2026$2.8M
January 2026$2.75M
2025
2024
2023
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
2670 Grandview Drive, Orient, NY
0.60
Single-Family Home
$4,000,000
07/02/26
6
6.5
6,800
815 Uhl Lane, Orient, NY
1.07
Single-Family Home
$1,450,000
06/10/26
4
3.5
2,700
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
175 Uhl Lane, Orient, NY
0.96
Single-Family Home
$770,000
05/29/26
4
2.5
2,100
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
65 Greenway W, Orient, NY
0.63
Single-Family Home
$968,000
06/10/26
2
1
962

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
290 Windward Road, Orient, NY 11957
0.16
$2,499,999
5
4
4,200
For Sale
735 Bight Rd, Orient, NY 11957
0.20
-
-
-
-
Off Market
695 E Pettys Drive, Orient, NY 11957
0.18
-
-
-
-
Off Market
75 Pettys Drive, Orient, NY 11957
0.30
$2,100,000
-
-
-
For Sale
555 Grandview Drive, Orient, NY 11957
0.33
$2,407,600
4
4.5
4,300
Off Market
1405 Terry Lane, Orient, NY 11957
0.37
$3,039,800
3
2.5
2,200
Off Market
1640 Grandview Dr, Orient, NY 11957
0.39
$4,250,000
5
4.5
5,200
For Sale
34600 Main Rd, Orient, NY 11957
0.46
-
6
5.5
5,500
Off Market
1790 Grandview Dr, Orient, NY 11957
0.42
$3,523,700
4
3.5
3,900
Off Market
35335 Main Rd, Orient, NY 11957
0.53
$2,850,000
3
3
2,800
For Sale
420 Willow Terrace, Orient, NY 11957
0.56
-
-
-
-
Off Market
2205 Grandview Drive, Orient, NY 11957
0.51
$3,413,400
5
4.5
4,785
Off Market

Local Information

  • Map ViewExplore the area around 440 Windward 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
2005
Lot Size
1.16 acres
Living Area
3,700 sqft
Price/Sqft
$785
Parking
Garage

About this House

"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.
440 Windward Rd, Orient, NY 11957 is a 4 bedroom, 5 bathroom, 3,700 sqft single-family home built in 2005. It last sold for $2,650,000 on Apr 26, 2016. It is currently off market. The Trulia Estimate is $2,903,600, with a rent estimate of $7,745/month.

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 and Tax history

DateEventPrice
Apr 26, 2016
Source: N/A
Sold
$2,650,000
Jan 28, 2016
Source: N/A
Sold
$2,650,000
Jul 24, 2015
Source: Agent Provided
ListingRemoved
$2,750,000
Jun 25, 2015
Source: Agent Provided
PriceChange
$2,750,000
Price decreased by 4%
Apr 10, 2015
Source: Agent Provided
Listed For Sale
$2,850,000

Market trends in Orient

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
13
1MoM
Skip to last item
  • Results are loading
Skip to first item

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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Explore by feature - Air Conditioning

12 rentals with air conditioning in Orient, NY

Explore by feature - Pool

9 rentals with a pool in Orient, NY

Homes for sale near 440 Windward Rd

Skip to last item
Skip to first item

Off Market Homes Near 440 Windward Rd

Skip to last item
Skip to first item

Frequently asked questions about 440 Windward Rd

  • What is 440 Windward Rd estimated to be worth?
    Trulia's estimated value for 440 Windward Rd in Orient, NY is $2,903,600.
  • What is the price history for 440 Windward Rd?
    440 Windward Rd in Orient, NY last sold for $2,650,000 in April 2016.
  • Is Orient a buyer's or seller's market?
    Orient is currently a seller's market, based on recent for-sale activity.
  • 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 recently sold homes in Orient, NY.
  • Does 440 Windward Rd have air conditioning?
    Yes, 440 Windward Rd in Orient, NY has air conditioning.
  • Does 440 Windward Rd have a pool?
    Yes, 440 Windward Rd in Orient, NY has a pool.