Active
5 beds4,200 sqft$595/sqft
290 Windward Rd, Orient, NY 11957
Est: $13,928/moGet pre-approved
Single FamilyProperty Type
1.02 acresLot Size
2023Year Built
$595/sq ftPrice per sq ft
2 carsParking Spaces

Description

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...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.

Listing Agent

  1. Maureen Orientale

    Maureen Orientale

    Listing Agent

    Compass

    P: (516) 924-0729

    M: (516) 924-0729

551 days on Market
Last updated: 07/25/2026 01:09 PM • Source: ONEKEY as distributed by MLS GRID, MLS#: 828203

Location

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$13,928 per month

30 year fixed, 6.55% Interest

Principal and Interest

$12,707

Property Taxes

$1,221

HOA Dues

$0

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Property Information for 290 Windward Road

Property Details
  • Taxes: $14,652 / year
  • MLS Type: Single Family
  • City/Township: Southold
  • Architectural Style: Modern
  • Garage Spaces: 2
  • Waterfront: No
Building Information
  • Year Built: 2023
  • Lot Size: 1.02 AC / 44,431 SF
Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: Detached
  • State Or Province: NY
School Information
  • School District: Oysterponds, Greenport
  • Elementary School District: Oysterponds
  • Elementary School: Oysterponds Elementary School
  • Middle Or Junior School District: Greenport
  • Middle Or Junior School: Greenport High School
  • High School District: Greenport
  • High School: Greenport High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: Basement
  • Room Type: Office
Room 2 Information
  • Room Level: Basement
  • Room Type: Bathroom 5
Room 3 Information
  • Room Level: Basement
  • Room Type: Exercise Room
Room 4 Information
  • Room Level: Basement
  • Room Type: Lavatory
Room 5 Information
  • Room Level: Basement
  • Room Type: Family Room
Room 6 Information
  • Room Level: First
  • Room Type: Bedroom 1
Room 7 Information
  • Room Level: First
  • Room Type: Lavatory
Room 8 Information
  • Room Level: First
  • Room Type: Kitchen
Room 9 Information
  • Room Level: First
  • Room Type: Laundry
Room 10 Information
  • Room Level: First
  • Room Type: Living Room
Room 11 Information
  • Room Type: Dining Room
Room 12 Information
  • Room Level: Second
  • Room Type: Bedroom 4
Room 13 Information
  • Room Level: Second
  • Room Type: Bedroom 3
Room 14 Information
  • Room Level: Second
  • Room Type: Bedroom 2
Room 15 Information
  • Room Level: Second
  • Room Type: Bathroom 1
Room 16 Information
  • Room Level: Second
  • Room Type: Bathroom 2
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 1000-019-00-01-00-012-003
  • Tax Assessed Value: $7,500.00
  • Tax Source: Municipality
  • Tax Year: 2024
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, In Hall, Modern, Well, Wood Burning
  • Interior Features: First Floor Bedroom
  • Appliances: Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, ENERGY STAR Qualified Appliances, Freezer, Microwave, Refrigerator, Washer, Gas Water Heater, Wine Refrigerator
  • Total Rooms: 19
  • Basement: Finished, Full, Walk-Out Access
  • Attic Description: Partial
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Wood Burning
  • Location Amenities: Walk Out Basement, 1st Fl Master Bedroom
  • Laundry Features: In Hall
  • Living Area: 4200
  • Basement: Yes
Exterior Features
  • Elevation Certificate: No
  • Construction Materials: Advanced Framing Technique, Batts Insulation, Blown-In Insulation
Lot Information
  • Building Area Units: Square Feet
Parking
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Propane
  • Heat Fuel Type: Propane
  • Sewer: Cesspool
  • Water Source: Well
  • Utilities: Electricity Connected
Green Features
  • Green Features: Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, ENERGY STAR Qualified Appliances, Freezer, Microwave, Refrigerator, Washer, Gas Water Heater, Wine Refrigerator, Propane
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 290 Windward Road

DateEvent & SourcePriceAppreciation
Mar 26, 2026

Price Change

ONEKEY #828203

$2,499,999
Feb 27, 2026

Listed (Active)

ONEKEY #828203

Feb 26, 2026

Expired

ONEKEY #828203

$2,699,000
DateEvent & SourcePrice
03/26/2026

Price Change

ONEKEY #828203

$2,499,999
02/27/2026

Listed (Active)

ONEKEY #828203

02/26/2026

Expired

ONEKEY #828203

$2,699,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 290 Windward Road

Taxable ValueLand$1,500Additions$13,800Total$15,300
Tax Record2024$6,577 ($548 / month)
Home Facts
Beds0Lot Size44,431 SqFtStyleSingle Family ResidenceZoningR-80CountySUFFOLKAPN1000-019.00-01.00-012.003

Schools near 290 Windward Road

This home is within Oysterponds Union Free School District.
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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290 Windward Road is a single family home for sale in Orient, NY 11957. This property was listed for sale on February 25, 2025 by Compass, it's currently listed at $2,499,999. It has been on the market for a total of 551 days and was last sold on May 5, 2017. This listing's school district is Oysterponds Union Free School District. Nearby schools include Oysterponds Elementary School. 290 Windward Road is a 5-bed, 4-bath, 4,200 sqft single family home built in 2023.

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.

Based on information submitted to the MLS GRID as of 07/25/2026 01:09 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is 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. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.