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MLS ID KEY828203Last updated Sep 30, 2026

Single Family

290 Windward Road

Active · Southold · Suffolk County, NY 11957

Bedrooms
5 Beds
Bathrooms
4 Baths
Year built
2023
Est. monthly taxes
$1,220.96
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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.

Listing snapshot

Days on site
59 days
Listed on MLS
Feb 25, 2025
Full baths
4
Half baths
0
Annual property tax (MLS)
$14,651.5
Tax year
2024
Area source (MLS)
Plans
Listing brokerage
Compass Greater NY LLC
MLS ID
KEY828203
Last updated
Sep 30, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
2023
Garage
Yes
Garage spaces
2
Water source
Well
Sewer
Cesspool
Utilities
Electricity Connected

Interior features

Basement
Finished, Full, Walk-Out Access
Heating
Propane
Cooling
Central Air
Interior
First Floor Bedroom
Appliances
Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, ENERGY STAR Qualified Appliances, Freezer, Microwave, Refrigerator, Washer, Gas Water Heater, Wine Refrigerator
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Modern
Construction materials
Advanced Framing Technique, Batts Insulation, Blown-In Insulation

Schools (MLS)

Elementary school
Oysterponds Elementary School
Elementary school district
Oysterponds
Middle school
Greenport High School
Middle school district
Greenport
High school
Greenport High School
High school district
Greenport

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. MLS status changed
  3. First seen on this site

Location

Southold · Suffolk County, NY 11957Show interactive map
290 Windward Road

Southold · Suffolk County, NY 11957

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Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.