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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.

Highlights

  • Residential
  • Single Family Residence
  • Built in 2023
  • 1.02 Acre Lot
  • 2 Car Garage
  • 628 days on Market

  • Bedrooms
    5
  • Bathrooms
    4
  • Year Built
    2023
  • Architectural Style
    Modern
  • Construction Materials
    Blown-In Insulation, Batts Insulation
  • Garage Spaces
    2.0
  • Living Area
    4200.0
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Washer, Cooktop, Freezer, Gas Water Heater, Electric Oven, Wine Refrigerator, Electric Cooktop, ENERGY STAR Qualified Appliances
  • Cooling
    Central Air
  • Heating
    Propane
  • Basement
    Finished, Full, Walk-Out Access

  • Acres
    1.02
  • Utilities
    Electricity Connected
  • Water
    Private, Well

  • County
    Suffolk
  • City
    Orient
  • Zip Code
    11957
  • High School
    Greenport High School
  • Middle School
    Greenport High School
  • Elementary School
    Oysterponds Elementary School

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Frequently Asked Questions

How do I schedule a tour of 290 Windward?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 290 Windward.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 290 Windward?

Click Ask a Question to talk with our team. You already know it is a 5 bed, 4 bath, listed for $2,499,999. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Orient, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 290 Windward?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 290 Windward at around $15,448. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 290 Windward?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Suffolk County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 290 Windward?

In most cases, yes. Whether 290 Windward is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Orient's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 290 Windward?

We can handle that for you. Our preferred local agent specializes in residentials in Orient and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $2,499,999 with 4,200 sqft of space—that comes out to approximately $595 per square foot.

How long has this property been on the market?

290 Windward was listed on February 25, 2025, which means it's been on the market for 628 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 2023, making it approximately 3 years old.

What is the lot size of this property?

290 Windward sits on a 1.02-acre lot, which is 44,431 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Oysterponds Elementary School
  • Middle: Greenport High School
  • High: Greenport High School

Want to see how these schools compare? Check out our Suffolk County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 290 Windward?

The most recent public record shows annual property taxes for 290 Windward were approximately $14,652. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 290 Windward still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.

Last Updated: November 15, 2026 at 11:14AM | Source: OneKey MLS | MLS#: 828203