8 Headley Way Woodbury, NY $ 5,000,000
8 Headley Way
$ 5,000,000
Recently Listed
Open House 7/25 12:30pm - 2pm
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8 Headley Way

Woodbury, NY, 11797
$ 5,000,000
Bedrooms5 Baths5.1 Sq 6,696

Monthly Estimate*

$ 31,571

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Single Family Home for sale in Woodbury, NY

for $5,000,000 with 5 bedrooms and 5 full baths, 1 half bath. This 6,696 square foot home was built in 2007 on a lot size of 1.

A One-of-a-Kind Custom Estate A masterpiece of custom craftsmanship and timeless design, this extraordinary estate offers nearly 6,000 square feet of luxurious living space—exclusive of the basement and three-car garage. Conceived, designed, and meticulously built by its owners, every detail reflects an uncompromising commitment to quality, elegance, and enduring value. Exceptional Property Highlights Architectural Distinction – The home’s striking exterior is clad in exquisite natural Turkish stone, quarried in Turkey, precision-cut overseas, and imported by container exclusively for this residence, creating a timeless and distinguished façade rarely found in today’s luxury homes. Resort-Caliber Outdoor Living – A spectacular custom-designed swimming pool, completed in 2025, anchors an extraordinary outdoor oasis. Over $1.8 Million Invested Outdoors – The grounds have been transformed into a private resort with over $1.8 million invested in the backyard, featuring a luxury swimming pool and a professional multi-sport court designed for tennis, pickleball, and basketball. Complete Landscape & Engineering Transformation – Originally situated on a steep hillside, the entire backyard was professionally re-engineered, reconstructed, and regraded to create an expansive, level outdoor living space that seamlessly combines beauty, functionality, and exceptional usability. Comprehensive Drainage System – A professionally engineered French drain system extends throughout the property, ensuring superior drainage and long-term protection. Newly Constructed Grand Driveway – A beautifully designed driveway, completed in 2025, enhances the home’s impressive curb appeal and grand arrival. Three-Car Garage – A spacious three-car garage provides generous room for vehicles, storage, and everyday convenience. Grand Lower Level – The full basement boasts impressive 10-foot clear ceilings, offering exceptional scale and endless possibilities for additional living and entertainment space. It also includes a custom-built reinforced bomb/storm shelter, providing an added level of security and peace of mind. Sophisticated Interior Living Five generously proportioned bedrooms and five-and-a-half luxurious bathrooms, thoughtfully designed for both everyday living and elegant entertaining. Three private bedroom suites, each with its own full en-suite bathroom, offering exceptional comfort and privacy for family members or guests. Two additional en-suite bedrooms, creating a home where every bedroom enjoys the comfort and convenience of its own dedicated bath. Every inch of this remarkable residence was thoughtfully envisioned and custom crafted by its owners. From the imported natural stone exterior to the extensive structural enhancements and resort-inspired grounds, this is a home of exceptional quality, timeless elegance, and enduring craftsmanship—a truly rare offering in today’s luxury market.

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Open House

7/25/2026 12:30 PM - 2:00 PM
8 Headley Way Woodbury, NY
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 5,000,000

Bedrooms

5

Full Bath

5

Half Bath

1

Property Type

Single Family

Taxes

$ 56,711

Style

Colonial

Lot Size

1

Year Built

2007

Town/City

Woodbury

County/Region

Nassau

MLS | Web ID

1028542

Features
Interior
Interior Amenities First Floor Bedroom First Floor Full Bath Cathedral Ceiling(s) Chandelier Chefs Kitchen Entrance Foyer In-Law Floorplan Kitchen Island
Basement Full Walk-Out Access
Basement Features Full Walk-Out Access
Basement (Y/N) Y
Fireplace Y/N Y
Half Baths 1
Total Bedrooms 5
Total Baths 6
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General
Sewer Public Sewer
Heating Forced Air
Cooling Central Air
Utilities Electricity Connected Natural Gas Connected
Appliances Dishwasher Gas Range Refrigerator Washer
Garage Spaces 3
Architectural Style Colonial
Construction Materials Stone
Year Built 2007
Property Subtype Single Family Residence
Tax Year 2024
Parcel Number 2489-13-073-00-0010-0
County Nassau County
Property Type Residential
HOA N
Garage Y/N Y
Total Rooms 12
Full Baths 5
High School Syosset Senior High School
City Oyster Bay
Senior Community Y/N N
High School District Syosset
Carport Y/N N
Elementary School Walt Whitman Elementary School
Property Attached Y/N Y
Tax Annual Amount 56711.85
Middle/Junior High School H B Thompson Middle School
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Syosset
Elementary School District Syosset
Tax Assessed Value 2281
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Exterior
Parking Features Driveway Garage Driveway Garage
Water Source Public
Building Area Total 8797
Waterfront Y/N N
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Internal Only
Street Number 1 8
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* Excluded Features
List By
Khalidah Arifee

Listing Agent

Property Professionals Realty

Broker

516-605-2700

Contact

Affordability Calculator

$36,296
Per Month
87%
13%
0%
Monthly Principal & Interest
$31,571
Monthly Property Taxes
$4,726
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4099881 Elementary School
4101106 Middle School
Syosset Senior High School High School
Pricing History
DatePricePrice ChangeDescription
7/21/2026$5,000,000 Listed Price

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8 Headley Way, Woodbury, NY, 11797 is a Single Family Home for sale at $5,000,000 with 6,696 sqft and a lot size of 1. 8 Headley Way has 5 bedrooms, 5.1 baths, and was built in 2007. The property's zip code is 11797 which is in Woodbury, NY