Jacqueline Jackson

8 Headley Way

Woodbury, NY
$ 5,000,000 Beds 5 Baths 5.5 Sq 6,696
Monthly Estimate* How much can I afford?

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.

Single Family

  • Price
  • $ 5,000,000
  • City
  • Woodbury
  • Bedrooms
  • 5
  • Full Bathrooms
  • 5
  • County
  • NASSAU
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 1 Acres
  • Zip
  • 11797
  • Sqr Footage
  • 6,696
  • Year Built
  • 2007
  • Taxes
  • $ 56711
  • Style
  • Colonial
  • MLS#
  • 1028542
Listed By: Property Professionals Realty
Data Source: Listings courtesy of OneKey® MLS as distributed by MLS GRID

Features

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 No
Garage Y/N Yes
Total Rooms 12
Full Baths 5
High School Syosset Senior High School
City Oyster Bay
Senior Community Y/N No
High School District Syosset
Carport Y/N No
Elementary School Walt Whitman Elementary School
Property Attached Y/N Yes
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
PostalCity Woodbury
AttributionContact 516-605-2700
Listing Appliances Dishwasher, Gas Range, Refrigerator, Washer

Interior Features

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) Yes
Fireplace Y/N Yes
Half Baths 1
Total Bedrooms 5
Total Baths 6
General Features First Floor Bedroom,First Floor Full Bath,Cathedral Ceiling(s),Chandelier,Chefs Kitchen,Entrance Foyer,In-Law Floorplan,Kitchen Island
Entrance Foyer Yes

Exterior Features

Parking Features Driveway,Garage
Water Source Public
Parking Features Driveway, Garage
Building Area Total 8797
Waterfront Y/N No

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Flushing, NY office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

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.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Walt Whitman Elementary School
Middle School H B Thompson Middle School
High School Syosset Senior High School

Price History

7/21/2026 Listed $5,000,000

Property vs Zip Code Average in 11797

Price
AVG $2.43M
$5M
Taxes
AVG $34,914
$56,711
Year Built
AVG 1983
2007
Visits
AVG 134
125
Data Provided by Inside Real Estate®

Areas That We Cover

8 Headley Way Woodbury, NY is a Single Family Home for sale at $5000000 with 6696 sqft and a lot size of 1 Acres Acre(s). 8 Headley Way Woodbury has 5 bedrooms, 5 baths and was built in 2007. The property's zip code is 11797 which is in Woodbury, NY

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: 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.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

Jacqueline Jackson

Jacqueline Jackson

Licensed Real Estate Salesperson

917-420-2177

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