290 Windward Rd

Orient, NY 11957

$2,699,000
Price
5
Beds
4,200 Sq. Ft.
$643 / Sq. Ft.
4,200
Sq. Ft.
$643
per Sq. Ft.
Listed By Compass
Listed By Compass
an aerial view of residential house with outdoor space and trees
an aerial view of a golf course with a lake view
a front view of a house with a yard
a front view of a house with a yard table and chairs
a view of a house with swimming pool and a porch
a view of a house with yard and tree s
an aerial view of a house with a yard table and chairs
view of a lake view
a kitchen with granite countertop lots of clutter and cabinets
a living room with furniture and a fireplace
a living room with furniture and a large window
a view of a dining room with furniture window and outside view
a dining room with furniture potted plants and a fireplace
a living room with stainless steel appliances granite countertop a sink and a large window
a kitchen with a large window and sink
a kitchen with stainless steel appliances granite countertop a sink a stove and a refrigerator
a view of a hallway with wooden floor and a potted plant
a bedroom with a bed and a couch
a bedroom with a bed and a potted plant
a living room with furniture and a flat screen tv
a view of an empty room with a window
a view of a room with gym equipment
a bathroom with a sink toilet and shower
a bathroom with a sink a toilet and shower
a bathroom with a bathtub sink and mirror
a bathroom with a sink toilet and mirror
a view of a house with a yard and sitting area
an aerial view of a house with a lake view
a view of a house with a backyard and a patio
a view of a yard with large trees

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.

Property Details for 290 Windward Road

City/Township
Southold
Architectural Style
Modern
Garage Spaces
2.00
Waterfront
No
LISTING UPDATED: 11/08/2025 03:09 PM

Property Details for 290 Windward Road

StatusActive
MLS #828203
Days on Market282
Taxes$14,652 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built2023
Lot Size1.02 AC / 44,431 SF
CountySuffolk County

Location

Listing Courtesy of: .

Add your commute

Building Information for 290 Windward Road

Stories-Year Built2023Building Size-Lot Size1.02 AC / 44,431 SF

Payment Calculator

$14,558 per month

30 year fixed, 6.28% Interest

Principal and Interest

$13,337

Property Taxes

$1,221

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 290 Windward Road

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: false
  • 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
  • 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
  • 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
May 5, 2017

Sold (Public Record)

Public Record #603350655

$300,000

-1.3% / yr

Dec 5, 2007

Sold (Public Record)

Public Record #230902126

$340,000—
DateEvent & SourcePrice
05/05/2017

Sold (Public Record)

Public Record #603350655

$300,000

-1.3% / yr

12/05/2007

Sold (Public Record)

Public Record #230902126

$340,000

For completeness, Compass 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
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
Oysterponds Elementary School
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.

Similar Homes

Similar Sold Homes

Explore Nearby Homes

More information about 290 Windward Road, Orient, NY 11957

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 $2,699,000. It has been on the market for a total of 282 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 descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/04/2025 10:51 PM. All data is obtained from various sources and may not have been verified by broker orMLS GRID. Supplied Open House Information is subject to change without notice. All informationshould be independently reviewed and verified for accuracy. Properties may or may not be listed bythe office/agent presenting the information.