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290 Windward RoadOrient, NY 11957

For Sale

$2,699,000

Smart Buyer Rebate $26,990

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.

Listed by Maureen J. Orientale CBR

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Compass Greater NY LLC

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516-924-0729

Last updated February 27, 2026

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Source: OneKey #828203

Listing Facts

  • TypeSingle-family
  • NeighborhoodOrient
  • Bedrooms5
  • Bathrooms4
  • Days on Prevu385
  • Taxes$14,651.5/year
  • Size4,200 sqft
  • Price per sqft$643

Amenities

  • Dishwasher
  • Washer/Dryer
  • Air Conditioning

Location

Mortgage Calculator

Listing History

02/27/2026
Status changed to Active
$2,699,000
02/26/2026
Status changed to Expired
$2,699,000
02/25/2025
Listed by Compass Greater NY LLC
$2,699,000

Property Details for 290 Windward Road

Exterior

Construction

  • Year Built: 2023
  • Architectural Style: Modern
  • Construction Materials: Advanced Framing Technique, Batts Insulation, Blown-In Insulation

Measurements

  • Building Area Units: Square Feet
  • Lot Size Acres: 1.02
  • Lot Size Square Feet: 44,431

Financial

Taxes

  • Parcel Number: 1000-019-00-01-00-012-003
  • Tax Annual Amount: $14,651.50
  • Tax Assessed Value: $7,500.00
  • Tax Year: 2024

Interior

Features

  • Appliances: Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, ENERGY STAR Qualified Appliances, Freezer, Microwave, Refrigerator, Washer, Gas Water Heater, Wine Refrigerator
  • Fireplace Features: Wood Burning
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Interior Features: First Floor Bedroom

Measurements

  • Living Area: 4,200
  • Living Area Source: Plans

Rooms

  • Basement: Finished, Full, Walk-Out Access
  • Has Basement: Yes
  • Bathrooms Full: 4
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 5
  • Rooms Total: 19

Parking

Parking

  • Garage Spaces: 2
  • Garage: Yes

Schools

Elementary School

  • Elementary School: Oysterponds Elementary School
  • Elementary School District: Oysterponds

High School

  • High School: Greenport High School
  • High School District: Greenport

Middle or Junior School

  • Middle Or Junior School: Greenport High School
  • Middle Or Junior School District: Greenport

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Propane
  • Laundry Features: In Hall
  • Sewer: Cesspool
  • Utilities: Electricity Connected
  • Water Source: Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 4 bathrooms in this single-family home at 290 Windward Road.

What schools are nearby to 290 Windward Road?

Nearby schools include the Oysterponds Elementary School, Greenport High School Middle School, and Greenport High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 290 Windward Road.

What are the annual taxes for 290 Windward Road?

Annual taxes for this single-family home are estimated at $14,651.

How does 290 Windward Road compare to other single-family homes in Orient?

This single-family home is listed 11% above the average price for single-family homes in Orient and has been on the market for 229 more days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 4,200 sqft.

290 Windward Road is a 5-bedroom, 4-bath single-family home for sale in Orient NY 11957. Listed on Prevu for 385 days at $2,699,000. This home features 4,200 square feet of living space, located in Orient. The median listing price for single-family homes in this area is $2,397,000. Nearby schools include Oysterponds Elementary School, Greenport High School Middle School, and Greenport High School. Additional amenities include dishwasher, air conditioning, and washer/dryer. View other single-family home listings in Suffolk County.

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Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.