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8 Headley WayWoodbury, NY 11797

For Sale

$5,000,000

Smart Buyer Rebate $50,000

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.

Listed by Khalidah Arifee

·

Property Professionals Realty

·

516-605-2700

Last updated July 26, 2026

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Source: OneKey #1028542

Listing Facts

  • TypeSingle-family
  • NeighborhoodWoodbury
  • Bedrooms5
  • Bathrooms6
  • Days on Prevu10
  • Taxes$56,711.85/year
  • Size6,696 sqft
  • Price per sqft$747

Amenities

  • Dishwasher
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

07/21/2026
Listed by Property Professionals Realty
$5,000,000

Property Details for 8 Headley Way

Exterior

Construction

  • Property Attached: Yes
  • Year Built: 2007
  • Architectural Style: Colonial
  • Construction Materials: Stone

Features

  • Pool Private: Yes

Measurements

  • Building Area Total: 8,797
  • Building Area Units: Square Feet
  • Lot Size Acres: 1.00
  • Lot Size Square Feet: 43,560

Financial

Taxes

  • Parcel Number: 2489-13-073-00-0010-0
  • Tax Annual Amount: $56,711.85
  • Tax Assessed Value: $2,281.00
  • Tax Year: 2024

Interior

Features

  • Appliances: Dishwasher, Gas Range, Refrigerator, Washer
  • Fireplace: Yes
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Cathedral Ceiling(s), Chandelier, Chefs Kitchen, Entrance Foyer, In-Law Floorplan, Kitchen Island

Measurements

  • Living Area: 6,696
  • Living Area Source: Public Records

Rooms

  • Basement: Full, Walk-Out Access
  • Has Basement: Yes
  • Bathrooms Full: 5
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 6
  • Bedrooms Total: 5
  • Rooms Total: 12

Parking

Parking

  • Garage Spaces: 3
  • Garage: Yes
  • Parking Features: Driveway, Garage

Schools

Elementary School

  • Elementary School: Walt Whitman Elementary School
  • Elementary School District: Syosset

High School

  • High School: Syosset Senior High School
  • High School District: Syosset

Middle or Junior School

  • Middle Or Junior School: H B Thompson Middle School
  • Middle Or Junior School District: Syosset

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Forced Air
  • Sewer: Public Sewer
  • Utilities: Electricity Connected, Natural Gas Connected
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 6 bathrooms in this single-family home at 8 Headley Way.

What schools are nearby to 8 Headley Way?

Nearby schools include the Walt Whitman Elementary School, H B Thompson Middle School, and Syosset Senior High School.

Does this single-family home have parking?

Yes, there are 3 parking spaces available for 8 Headley Way.

What are the annual taxes for 8 Headley Way?

Annual taxes for this single-family home are estimated at $56,711.

How does 8 Headley Way compare to other single-family homes in Woodbury?

This single-family home is listed 101% above the average price for single-family homes in Woodbury and has been on the market for 59 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 6,696 sqft.

8 Headley Way is a 5-bedroom, 6-bath single-family home for sale in Woodbury NY 11797. Listed on Prevu for 10 days at $5,000,000. This residence features 6,696 square feet of living space, located in Woodbury. The median listing price for single-family homes in this area is $2,250,000. Nearby schools include Walt Whitman Elementary School, H B Thompson Middle School, and Syosset Senior High School. The home offers dishwasher, air conditioning, parking, and washer/dryer. Explore more single-family home listings in Nassau County.

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey™ MLS. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. Information Copyright 2026, OneKey™ MLS. All Rights Reserved.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.