A One-of-a-Kind Custom EstateA 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 HighlightsArchitectural 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 faade 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 LivingFive 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
8 Headley Way | MLS# 1028542
This single family home located at 8 Headley Way , Woodbury, NY 11797 is currently listed for sale with an asking price of $5,000,000. This property was built in 2007 and has 5 bedrooms and 5 full and 1 partial baths with 6696 sq. ft. Headley Way is located within the Syosset school district. Search Woodbury real estate on irisbluth.laffey.com today.
Send an email with a link to 8 Headley Way , Woodbury, NY 11797.
REQUEST INFORMATIONx
Contact an agent to learn more about 8 Headley Way , Woodbury, NY 11797.
GET PRE-APPROVEDx
Disclaimer:
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 07/24/2026. The listing information on this page last changed on 07/24/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 07/24/2026 12:00:14 AM EST) or OneKey MLS (last updated Thu 07/23/2026 11:53:35 PM EST). Real estate listings held by brokerage firms other than Laffey Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. 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.
You are now registered to view virtual open houses for the listings.
Register to View this Listing
Why Create an Account?
If you're searching for your next home, or just curious about the market there is no better tool to help you quickly find homes that meet your needs and wants.
With an account you can:
Save your favorite listings
Save searches with your important parameters
Be emailed about new listings that meet your criteria
Be notified of changes to your saved listings such as a price reduction or when a property goes off the market
8 Headley Way | MLS# 1028542
This single family home located at 8 Headley Way , Woodbury, NY 11797 is currently listed for sale with an asking price of $5,000,000. This property was built in 2007 and has 5 bedrooms and 5 full and 1 partial baths with 6696 sq. ft. Headley Way is located within the Syosset school district. Search Woodbury real estate on irisbluth.laffey.com today.