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$5,000,000
55 Days On Site

8 Headley Way
Woodbury, NY 11797

For Sale|Single Family Residence|Active
5
Beds
6
Total Baths
5
Full Baths
1
Partial Bath
6,696
SqFt
$747
/SqFt
2007
Built
County:
Nassau
Listing courtesy of Property Professionals Realty [email protected]

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8 Headley Way8 Headley Way8 Headley Way8 Headley Way
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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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Listing Snapshot
Price 
$5,000,000
Days On Site 
55 Days
Bedrooms 
5
Inside Area (SqFt) 
6,696 sqft
Total Baths 
6
Full Baths 
5
Partial Baths 
1
Lot Size 
1 Acre
Year Built 
2007
MLS® Number 
1028542
Status 
Active
Property Tax 
$56,711.85
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
2 months agoListing first seen on site
2 months agoListing updated with changes from the MLS®
General Features
Acres 
1
Garage 
Yes
Garage Spaces 
3
Parking 
DrivewayGarage
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
8797
Style 
Colonial
Utilities 
Natural Gas AvailableElectricity ConnectedNatural Gas Connected
Water Source 
Public
Interior Features
Appliances 
DishwasherGas RangeRefrigeratorWasher
Basement 
FullWalk-Out Access
Cooling 
Central Air
Fireplace 
Yes
Heating 
Forced Air
Interior 
Cathedral Ceiling(s)ChandelierEntrance FoyerIn-Law FloorplanKitchen Island
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Exterior Features
Construction Details 
Stone
Pool Features 
Private
Private Pool 
Yes
Community Features
School District 
Syosset
Schools
School District
Syosset
Elementary School
Walt Whitman Elementary School
Middle School
H B Thompson Middle School
High School
Syosset Senior High School
Listing courtesy of Property Professionals Realty [email protected]


Based on information submitted to the MLS GRID as of 2026-09-15 02:45 AM EDT. 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.

Neighborhood & Commute
Source: Walkscore
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