S
Seller's Agent in 2025
Shawn Elliott
Nest Seekers LLC
38 Chestnut Hill Dr Oyster Bay, NY 11771
6
Beds
9
Baths
15,000
Sq Ft
5.12
Acres
Highlights
- Indoor Pool
- Eat-In Gourmet Kitchen
- Colonial Architecture
- Locust Valley High School Rated A
- 5.12 Acre Lot
- Main Floor Primary Bedroom
About This Home
As of June 2025Nestled in the cul-de-sac of Chestnut Hill Estates, one of Upper Brookville’s most sought-after developments, this 15,000 sq. ft. estate redefines luxury living on over 5 acres of impeccably manicured grounds.
A grand 30-foot marble-floored foyer with twin floating staircases makes an unforgettable first impression, highlighting masterful craftsmanship with intricate plaster moldings and marble flooring throughout.
The first floor is designed for both grand entertaining and intimate gatherings, featuring a 65-ft formal living room, formal dining room, sitting room, and family room — each with elegant marble fireplaces. The chef’s kitchen is a masterpiece with radiant heat, a Sub-Zero refrigerator and freezer, 60” Viking range, three Bosch dishwashers, and a butler’s pantry complete with a warming oven and additional dishwasher. A luxurious junior primary suite provides privacy and convenience, complemented by a full bath. Nearby, a dedicated spa area with a sauna offers the ultimate in relaxation.
The second-floor primary suite is a private sanctuary with a fireplace, 14-ft coffered ceilings, a kitchenette, office, and his-and-hers walk-in closets. Four additional en-suite bedrooms, each with walk-in closets, complete the upper level.
This estate’s 20x50 indoor/outdoor pool with a retractable roof, jacuzzi, and spa is a standout feature, seamlessly merging indoor luxury with outdoor tranquility. A media room on the main level and a state-of-the-art fitness center add to the home’s impressive amenities.
The 6,500 sq. ft. finished lower level, with marble flooring, features three guest suites and expansive gathering areas. Outside, formal gardens in the rear of the property provide a serene escape, enhancing the estate’s grandeur.
Additional highlights include an elevator servicing all three levels, a 10-car garage, and a third-floor cupola with breathtaking 360° views.
Located in one of Upper Brookville’s premier enclaves, this estate offers a rare blend of timeless elegance and cutting-edge design.
Last Agent to Sell the Property
Shawn Elliott
Nest Seekers LLC Brokerage Phone: 516-922-2878 License #10401350691 Listed on: 01/09/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $84,811
Year Built
- Built in 1998
Parking
- 10 Car Garage
Home Design
- Colonial Architecture
- Brick Exterior Construction
- Stucco
Interior Spaces
- 15,000 Sq Ft Home
- High Ceiling
- 6 Fireplaces
- Entrance Foyer
- Formal Dining Room
- Finished Basement
- Basement Fills Entire Space Under The House
- Dryer
Kitchen
- Eat-In Gourmet Kitchen
- Oven
- Range
- Dishwasher
- Granite Countertops
Bedrooms and Bathrooms
- 6 Bedrooms
- Primary Bedroom on Main
- En-Suite Primary Bedroom
- Walk-In Closet
Schools
- Contact Agent Elementary School
- Locust Valley Middle School
- Locust Valley High School
Utilities
- Central Air
- Baseboard Heating
- Cable TV Available
Additional Features
- Indoor Pool
- 5.12 Acre Lot
Listing and Financial Details
- Assessor Parcel Number 2427-24-E-00-1050-0
Ownership History
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Jan 9, 2025
Closed on
Jun 24, 2025
Sold by
182 188 Columbus Ave Llc
Bought by
38 Chestnut Hill Drive Llc
Seller's Agent
Shawn Elliott
Nest Seekers LLC
Buyer's Agent
Dee Dee Brix
Compass Greater NY LLC
List Price
$7,950,000
Sold Price
$7,250,000
Premium/Discount to List
-$700,000
-8.81%
Views
88
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
39.89%
Purchase Details
Closed on
May 10, 2007
Sold by
U S A
Purchase Details
Closed on
Mar 27, 2007
Sold by
Pescatore Michael
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Bargain Sale Deed | $7,250,000 | Advantage Title | |
| Deed | $8,300,000 | -- | |
| Deed | $8,300,000 | -- | |
| Deed | -- | -- | |
| Deed | -- | -- |
Source: Public Records
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 06/25/2025 06/25/25 | Sold | $7,250,000 | -8.8% | $483 / Sq Ft |
| 02/19/2025 02/19/25 | Pending | -- | -- | -- |
| 01/09/2025 01/09/25 | For Sale | $7,950,000 | -- | $530 / Sq Ft |
Source: OneKey® MLS
Tax History Compared to Growth
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $10,226 | $4,028 | $1,142 | $2,886 |
| 2024 | $10,226 | $3,800 | $1,038 | $2,762 |
| 2023 | $64,237 | $4,039 | $1,103 | $2,936 |
| 2022 | $64,237 | $4,180 | $1,142 | $3,038 |
| 2021 | $62,170 | $4,947 | $1,314 | $3,633 |
| 2020 | $77,263 | $7,420 | $3,184 | $4,236 |
| 2019 | $77,141 | $7,950 | $3,208 | $4,742 |
| 2018 | $77,569 | $8,454 | $0 | $0 |
| 2017 | $60,851 | $8,454 | $2,175 | $6,279 |
| 2016 | $74,987 | $11,272 | $2,899 | $8,373 |
| 2015 | $18,792 | $13,261 | $3,411 | $9,850 |
| 2014 | $18,792 | $13,261 | $3,411 | $9,850 |
| 2013 | $17,630 | $13,261 | $3,411 | $9,850 |
Source: Public Records
Agents Affiliated with this Home
-
-
Zach Elliott
Seller Co-Listing Agent in 2025
Zach Elliott
Nest Seekers LLC
(516) 922-2878
3 in this area
62 Total Sales
-
Dee Dee Brix
Buyer's Agent in 2025
Dee Dee Brix
Compass Greater NY LLC
(516) 551-5241
2 in this area
85 Total Sales
Map
Source: OneKey® MLS
MLS Number: 811272
APN: 2427-24-E-00-1050-0
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The data relating to real estate for sale or lease on this web site comes in part from OneKey® MLS. Real estate listings held by brokerage firms other than Ten-X are marked with the OneKey® MLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker.
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Information is deemed reliable but not guaranteed.
Copyright 2025 OneKey® MLS. All rights reserved.
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