For sale

$2,499,999

Est. $14,568/mo —

•

4,200

sq ft

290 Windward Rd, Orient, NY 11957

About this home

This modern custom-built home, spanning 4200 square feet, is a masterpiece of architectural design, meticulously crafted with thoughtful details at every turn. Situated in the serene landscape of the North Fork, this property boasts breathtaking views that will captivate and inspire. Upon entering, you're greeted by an open pavilion like great room maximizing natural light and panoramic vistas. The interior features sleek lines, high ceilings, and premium finishes, creating a contemporary yet inviting atmosphere. The kitchen is a chef's dream, equipped with state-of-the-art, energy-efficient appliances that make cooking a joy. With ample counter space, custom cabinetry, and a spacious island, it's perfect for both intimate dinners and entertaining guests. The tranquility of the North Fork surrounds this home, offering a peaceful retreat from the hustle and bustle of everyday life. Whether you're lounging on the expansive patio, taking a dip in the pool, or strolling down to the Long Island Sound, you'll find serenity and relaxation at every turn. Beyond the property's boundaries, the North Fork offers an array of attractions to explore. From stunning beaches and charming farms to world-renowned vineyards, fine dining establishments, and boutique shopping, there's something for everyone to enjoy. This architectural gem combines luxury, functionality, and natural beauty to create an unparalleled living experience. Whether you're seeking a tranquil retreat or a sophisticated entertainer's paradise, this custom-built home is sure to exceed your expectations.

Single-familyProperty Type

2023Year Built

1.02 acresLot Size

$595Price/Sq.Ft.

2 car garageParking

Listing by Maureen Orientale • Compass Greater NY LLC

Contact: 516-924-0729

Listing updated: Jul 25, 2026 at 01:09pm

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #828203

Payment calculator

$14,568 per month

Principal and interest$12,972

Property taxes

$1,221

HOA dues

Home insurance

$375

Utilities

Add

5 minutes to get started. No credit impact.

Discover your buying power

Find out if this home is within budget

Down payment assistance

View down payment assistance programs for this home

See this home in person

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN FRI, 3PM TO 5PMVIDEO TOUR
$940,000
3 beds2 baths2,136 sq ft
311 Brightwater Rd, Old Lyme, CT 06371
OPEN SAT, 10AM TO 12PM
$1,690,000
3 beds2.5 baths1,900 sq ft
10 7th St, East Hampton, NY 11937
Listing by Brown Harris Stevens Hamptons
OPEN SAT, 11AM TO 2PM
$1,245,000
3 beds1 bath884 sq ft
24 W Shore Dr, Old Saybrook, CT 06475
OPEN SAT, 11:30AM TO 1PM
$2,200,000
3 beds3 baths2,600 sq ft
225 Lakeside Dr S, Southold, NY 11971
Listing by Daniel Gale Sothebys Intl Rlty
OPEN SAT, 11:30AM TO 1PM
$2,650,000
4 beds3.5 baths2,600 sq ft
195 Williamsburg Dr, Southold, NY 11971
Listing by Corcoran
OPEN SAT, 1PM TO 3PM
$799,000
2 beds2 baths1,100 sq ft
2820 Shipyard Ln Unit 1B2, East Marion, NY 11939
Listing by Douglas Elliman Real Estate
OPEN SAT, 1:15PM TO 3PM3D WALKTHROUGH
$1,249,000
3 beds3.5 baths1,700 sq ft
East Marion, NY 11939
Listing by William Raveis New York LLC
OPEN SUN, 9AM TO 10:30AM
$1,595,000
6 beds2 baths2,300 sq ft
430 1st St, Greenport, NY 11944
Listing by Daniel Gale Sothebys Intl Rlty
OPEN SUN, 11AM TO 1PM
$1,695,000
4 beds3 baths3,392 sq ft
90 Caiola Ct, Greenport, NY 11944
Listing by Daniel Gale Sothebys Intl Rlty
OPEN SUN, 12PM TO 2PM
$699,900
3 beds2 baths2,114 sq ft
18 Shepard St, Old Saybrook, CT 06475

Around this home

Schools

K - 12
Preschool & daycare

Oysterponds Elementary School

Public PreK-6 • Assigned • 1.7mi

4/10

Greenport High School

Public 7-12 • Assigned • 6.2mi

5/10

Provided by GreatSchools

About North

Fork

North Fork, located between Riverhead and Greenport, is a coastal and agricultural Calverton neighborhood with working vineyards and wide-open bayfront views. The mood concentrates around the Sound Avenue corridor near the Calverton hamlet center, where farm stands, tasting rooms, and low-key eateries set a weekend rhythm. Architectural character leans to shingled cottages, ranch homes, and barn-like outbuildings tied to the area’s farming roots. Macari Vineyards, Jamesport Farm Brewery, and Harbes Family Farm act as local pillars for tastings, seasonal events, and market-style shopping. Peconic Bay and the Long Island Sound frame the landscape with beaches, marinas, and long, flat roads made for cycling. The pace stays rural, with small clusters of storefronts separated by fields and rows of vines.

Provided by Walk Score and Local Logic

Market insights

290 Windward Rd · $2,499,999

DAYS ON MARKET

The average home goes pending in 24 days.

SALE-TO-LIST

Most homes are selling 3% above list price.

LIST PRICE

Median list price in this area is $722,500. (71% lower than this home)

PRICE DROP

15% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
First-floor bedroom
Finished full walk-out basement
Partial attic

Bedrooms
First-floor bedroom included

Bathrooms
4 full bathrooms

Kitchen
Cooktop
Electric cooktop
Electric oven
Dishwasher
Microwave
Refrigerator
Freezer
Wine refrigerator
ENERGY STAR qualified appliances

Laundry & utility
Washer
Dryer
Laundry located in hall
Gas water heater

Sale and tax history for 290 Windward Rd

Sale History
Tax History

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #828203

Mar 26, 2026

Price Changed

$2,499,999

$595/sq ft

Feb 27, 2026

Relisted

—

Feb 26, 2026

Listing Removed

—

Feb 25, 2025

Listed

$2,699,000

$643/sq ft

OneKey® MLS as Distributed by MLS Grid #L3582494

Feb 23, 2025

Listing Removed

—

Feb 23, 2024

Listed

$2,699,000

$643/sq ft

OneKey® MLS as Distributed by MLS Grid #3533473

Oct 2, 2024

Listing Removed

—

Jul 31, 2024

Price Changed

$2,699,000

$643/sq ft

Jun 18, 2024

Price Changed

$3,150,000

$750/sq ft

Mar 7, 2024

Listed

$3,499,999

$833/sq ft

Feb 23, 2024

Coming Soon

Public Records

Jun 2, 2017

Sold

$300,000

$71/sq ft

Public Records

Dec 17, 2007

Sold

$340,000

$81/sq ft

Public Records

Jun 4, 2002

Sold

$165,000

$39/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$15,123

$1,500 + $13,800

$15,300

2025

$15,123 (+3.2%)

$1,500 + $13,800

$15,300

2024

$14,652 (+122.8%)

$1,500 + $13,800

$15,300

2023

$6,577 (+907.6%)

$1,500 + $6,000

$7,500

2022

$653

$1,500 + $2,000

$3,500

2021

$653 (+2.9%)

$1,500

2020

$634 (−5.4%)

$1,500

2019

$670 (−48.9%)

$1,500

2018

$1,312 (+1.7%)

$1,500

2017

$1,290 (−1.6%)

$1,500

2016

$1,311 (+5.4%)

$1,500

2015

$1,244 (+2.6%)

$1,500

2014

$1,213 (+1.6%)

$1,500

2013

$1,194 (+1.8%)

$1,500

2012

$1,174 (+1.3%)

$1,500

2011

$1,158 (+2.0%)

$1,500

2010

$1,135 (−3.4%)

$1,500

2009

$1,176

$1,500

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

1.02 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Suffolk County

APN

1000019000100012003

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 21, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 91° expected this year, 19 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Orient, NY • 11957

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

97/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.1 hrs

6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 290 Windward Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $1,475,000 and $2,679,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.5M to $2.7M.

SOLD AUG 12, 2026
$1,475,000 Last sold price
4 beds4.5 baths2,900 sq ft
130 Sunset Ln, Greenport, NY 11944
Listing by Daniel Gale Sothebys Intl Rlty
$86/sq ft
smaller lot
2 years newer
SOLD JUN 12, 2026
$1,900,000 Last sold price
4 beds4 baths4,500 sq ft
435 Maple Ln, Greenport, NY 11944
Listing by Corcoran
$173/sq ft
larger lot
2 years newer
SOLD JAN 21, 2026
$2,679,000 Last sold price
4 beds3 baths3,420 sq ft
156 Ram Island Dr, Shelter Island Heights, NY 11964
Listing by Corcoran
$188/sq ft
larger lot
28 years older
SOLD SEP 9, 2025
$1,775,000 Last sold price
5 beds4.5 baths2,950 sq ft
1855 Greenway East, Orient, NY 11957
Listing by Corcoran Baer & McIntosh
$7/sq ft
1 year newer
unfinished basement
SOLD JAN 14, 2026
$1,725,000 Last sold price
3 beds2 baths3,170 sq ft
27 Country Club Dr, Shelter Island Heights, NY 11964
Listing by Daniel Gale Sothebys Intl Rlty
$51/sq ft
12 years older
unfinished basement
SOLD DEC 9, 2025
$1,800,000 Last sold price
4 beds2.5 baths2,264 sq ft
1075 Narrow River Rd, Orient, NY 11957
Listing by Douglas Elliman Real Estate
$200/sq ft
smaller lot
80 years older

Tour for free, no strings attached

Make a winning offer with the help of a local agent

Ask a question

(631) 336-2851