440 Windward Road
- Listed by: McCloskey, Thomas E • Douglas Elliman Real Estate
Recent comparable sales
Median sold price
$1,900,000
Avg days on market
132
Sale-to-list ratio
87.7%
Orient, NY
9 comparable properties found
$2,410,000
Sold 11/22/24
- 4
- Bedrooms
- 5
- Bathrooms
- 5,000
- Square Feet
- 2.98
- Acres
$2,100,000
Sold 10/30/25
- 4
- Bedrooms
- 5
- Bathrooms
- 4,028
- Square Feet
- 0.57
- Acres
$2,899,000
Sold 10/01/24
- 4
- Bedrooms
- 4
- Bathrooms
- 2,950
- Square Feet
- 0.58
- Acres
$1,900,000
Sold 09/02/26
- 4
- Bedrooms
- 4
- Bathrooms
- 3,359
- Square Feet
- 0.93
- Acres
$1,800,000
Sold 06/10/25
- 4
- Bedrooms
- 4
- Bathrooms
- 4,000
- Square Feet
- 0.12
- Acres
$1,775,000
Sold 09/09/25
- 5
- Bedrooms
- 5
- Bathrooms
- 2,950
- Square Feet
- Unavailable
- Acres
$2,350,000
Sold 11/07/25
- 3
- Bedrooms
- 4
- Bathrooms
- 2,870
- Square Feet
- 0.25
- Acres
$1,800,000
Sold 12/09/25
- 4
- Bedrooms
- 3
- Bathrooms
- 2,264
- Square Feet
- 0.26
- Acres
Location
Payment Calculator
$14,678 per month
30 year fixed, 6.55% Interest
$13,470
$1,208
$0
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1Property Information for 440 Windward Road
- Taxes: $14,500 / year
- MLS Type: Residential / Detached
- County: Suffolk County
- Garage Spaces: 1.5
- Basement: Full
- Cross Street: Main Road
- Year Built: 2004
- Lot Size: 1.16 AC / 50,530 SF
- Directions: Main Road To Windward Road
- School District Name: Oyster Ponds
- School District Num: 1
- District: 1000
- Total Taxes: $14,500.00
- Zone: 30
- Lot Size: 0X0
- Block: 200
- Section: 1400
- Wall To Wall Carpet: Y
- Fuel: Oil
- Air Conditioning: Cac
- Heating Zones: 3
- Rooms: 10
- CAC Zones: 3
- Construction: Frame
- Green Features: N
- Driveway: Pvt
- Dining Room: Other
- Primary bedroom 1st Floor: Y
- Fireplaces Num: 1
- Refigerator: Y
- Dishwasher: Y
- Floor Plan Level 1: Eik, Mbr Ensuite, Mud Room, Lr, Den, Half Bath
- Washer: Y
- Dryer: Y
- Den Family Room: Y
- Eat In Kitchen: Y
- Families Num: 1
- Kitchens Num: 1
- Wood Floors: Y
Property History for 440 Windward Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Apr 6, 2016 | Sold (Public Record) Public Record #571516176 | $2,650,000 | +9.0% / yr |
| Jan 28, 2016 | Sold MLSLI #P1245022 | $2,650,000 | — |
| Jan 28, 2016 | Listed (Active) MLSLI #P1245022 | $2,750,000 | — |
| Sep 30, 2015 | Expired ONEKEY #2752470 | $2,750,000 | — |
| Jul 23, 2015 | Withdrawn ONEKEY #L2752470 | $2,750,000 | — |
| May 31, 2015 | Expired ONEKEY #2723087 | $2,850,000 | — |
| Apr 10, 2015 | Listed (Active) ONEKEY #2752470 | $2,850,000 | — |
| Feb 18, 2015 | Withdrawn ONEKEY #L2723087 | $2,850,000 | — |
| Nov 24, 2014 | Listed (Active) ONEKEY #2723087 | $2,850,000 | — |
| Jan 14, 2003 | Sold (Public Record) Public Record #107482316 | $850,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 04/06/2016 | Sold (Public Record) Public Record #571516176 | $2,650,000 +9.0% / yr |
| 01/28/2016 | Sold MLSLI #P1245022 | $2,650,000 |
| 01/28/2016 | Listed (Active) MLSLI #P1245022 | $2,750,000 |
| 09/30/2015 | Expired ONEKEY #2752470 | $2,750,000 |
| 07/23/2015 | Withdrawn ONEKEY #L2752470 | $2,750,000 |
| 05/31/2015 | Expired ONEKEY #2723087 | $2,850,000 |
| 04/10/2015 | Listed (Active) ONEKEY #2752470 | $2,850,000 |
| 02/18/2015 | Withdrawn ONEKEY #L2723087 | $2,850,000 |
| 11/24/2014 | Listed (Active) ONEKEY #2723087 | $2,850,000 |
| 01/14/2003 | Sold (Public Record) Public Record #107482316 | $850,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 440 Windward Road
Schools near 440 Windward Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 6 |
Rating | School | Distance |
|---|---|---|
Oysterponds Elementary School PublicPK to 6 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 440 Windward Road, Orient, NY 11957 | $2,650,000 | 4 | 5 | – | 50,530 |
– | – | – | – | 46,609 | |
– | – | – | – | 68,389 | |
– | – | – | – | 40,511 | |
– | – | – | – | 71,874 | |
– | – | – | – | 422,968 | |
$130,000 | – | – | – | 40,075 | |
– | – | – | – | 366,775 | |
– | – | – | – | 198,198 | |
$999,000 | 4 | 3 | 2,300 | 41,382 | |
$3,037,500 | 5 | 5 | 4,935 | 41,382 | |
$75,000 | – | – | – | 41,382 | |
– | – | – | – | 40,075 | |
– | – | – | – | 40,075 | |
$213,000 | – | – | – | 29,185 | |
– | – | – | – | 40,075 |
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of Douglas Elliman Real Estate, McCloskey, Thomas E
The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS. Information Copyright 2026, OneKey® MLS. All Rights Reserved.