
35 Chestnut Hill Dr Oyster Bay, NY 11771
Highlights
- In Ground Pool
- Panoramic View
- 5 Acre Lot
- Locust Valley High School Rated A
- Estate
- Cathedral Ceiling
About This Home
As of March 2025Welcome to this exceptional 10,500 sq. ft. estate, located in the heart of Upper Brookville, New York. Fully redesigned in 2023, this custom Gold Coast residence showcases extraordinary craftsmanship and attention to detail throughout. Inside, you’ll find thick-cut millwork, stained glass windows, round-top doors, coffered ceilings, and hand-carved staircases that highlight the home’s unique character. With 7 bedrooms and 7.55 bathrooms, this estate features spacious formal entertaining areas, elegant stone gas fireplaces, and a sunlit eat-in kitchen. The kitchen boasts marble countertops, a Butler’s Pantry, high-end Viking and True appliances, and a cozy round breakfast nook filled with natural light. The primary suite offers high ceilings, an expansive walk-in closet, and a luxurious marble en-suite bathroom with His & Her’s vanities, a freestanding soaking tub, and a separate glass-enclosed shower. The exterior is a stunning example of North Shore architecture, constructed with brick, stone, slate, and cedar shake. Set on over 5 acres, the property features a private electric gate, Porte Cochere, a 4-car attached garage, and impeccably landscaped grounds. Outdoor amenities include a heated saltwater pool and spa, a built-in firepit, and a detached poolside cabana with a newly designed center-island kitchen. This estate blends timeless elegance with modern luxury, making it a truly distinctive offering in Upper Brookville.
Last Agent to Sell the Property
Shawn Elliott
Nest Seekers LLC Brokerage Phone: 516-922-2878 License #10401350691 Listed on: 01/17/2025

Home Details
Home Type
- Single Family
Est. Annual Taxes
- $75,104
Year Built
- Built in 1997
Parking
- 4 Car Garage
- 2 Carport Spaces
Home Design
- Estate
- Brick Exterior Construction
- Frame Construction
- Cedar
Interior Spaces
- 10,500 Sq Ft Home
- Central Vacuum
- Built-In Features
- Cathedral Ceiling
- Ceiling Fan
- Chandelier
- 5 Fireplaces
- Entrance Foyer
- Formal Dining Room
- Wood Flooring
- Panoramic Views
Kitchen
- Eat-In Kitchen
- Convection Oven
- Microwave
- Dishwasher
- Wine Refrigerator
- Granite Countertops
- Disposal
Bedrooms and Bathrooms
- 5 Bedrooms
- En-Suite Primary Bedroom
- Walk-In Closet
Laundry
- Dryer
- Washer
Finished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
- Basement Storage
Pool
- In Ground Pool
- Pool has a Solar Cover
Schools
- Ann Macarthur Primary Elementary School
- Locust Valley Middle School
- Locust Valley High School
Utilities
- Forced Air Heating and Cooling System
- Heating System Uses Oil
- Heating System Uses Propane
- Oil Water Heater
- Cesspool
- Cable TV Available
Additional Features
- Shed
- 5 Acre Lot
Listing and Financial Details
- Assessor Parcel Number 2427-24-E-00-1047-0
Ownership History
Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Purchase Details
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 | $5,650,000 | Commonwealth Land Ttl Ins Co | |
Bargain Sale Deed | $5,650,000 | Commonwealth Land Ttl Ins Co | |
Interfamily Deed Transfer | -- | Commonwealth Land Ttl Ins Co | |
Interfamily Deed Transfer | -- | Commonwealth Land Ttl Ins Co | |
Bargain Sale Deed | $4,050,000 | First American Title Ins Co | |
Bargain Sale Deed | $4,050,000 | First American Title Ins Co | |
Bargain Sale Deed | -- | -- | |
Bargain Sale Deed | -- | -- | |
Deed | $775,000 | -- | |
Deed | $775,000 | -- |
Mortgage History
Date | Status | Loan Amount | Loan Type |
---|---|---|---|
Previous Owner | $1,554,000 | New Conventional | |
Previous Owner | $2,561,500 | New Conventional |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
03/13/2025 03/13/25 | Sold | $5,650,000 | 0.0% | $538 / Sq Ft |
02/18/2025 02/18/25 | Pending | -- | -- | -- |
02/14/2025 02/14/25 | Off Market | $5,650,000 | -- | -- |
02/13/2025 02/13/25 | For Sale | $5,950,000 | +5.3% | $567 / Sq Ft |
02/13/2025 02/13/25 | Off Market | $5,650,000 | -- | -- |
01/17/2025 01/17/25 | For Sale | $5,950,000 | +46.9% | $567 / Sq Ft |
03/10/2022 03/10/22 | Sold | $4,050,000 | -18.9% | $380 / Sq Ft |
12/17/2021 12/17/21 | Pending | -- | -- | -- |
04/12/2021 04/12/21 | For Sale | $4,995,000 | +23.3% | $469 / Sq Ft |
11/06/2020 11/06/20 | Off Market | $4,050,000 | -- | -- |
06/15/2020 06/15/20 | For Sale | $4,995,000 | -- | $469 / Sq Ft |
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 | $10,569 | $3,672 | $773 | $2,899 |
2024 | $10,569 | $4,080 | $1,090 | $2,990 |
2023 | $85,682 | $5,059 | $1,352 | $3,707 |
2022 | $85,682 | $4,773 | $1,352 | $3,421 |
2021 | $77,718 | $4,291 | $1,384 | $2,907 |
2020 | $54,788 | $6,300 | $2,839 | $3,461 |
2019 | $11,993 | $6,750 | $2,852 | $3,898 |
2018 | $53,867 | $7,200 | $0 | $0 |
2017 | $55,064 | $7,650 | $2,706 | $4,944 |
2016 | $67,856 | $8,100 | $2,865 | $5,235 |
2015 | $12,187 | $8,600 | $2,708 | $5,892 |
2014 | $12,187 | $8,600 | $2,708 | $5,892 |
2013 | $11,433 | $8,600 | $2,709 | $5,891 |
Agents Affiliated with this Home
-
S
Seller's Agent in 2025
Shawn Elliott
Nest Seekers LLC
-
Seller Co-Listing Agent in 2025
Zach Elliott
Nest Seekers LLC
(516) 922-2878
3 in this area
63 Total Sales
-
Buyer's Agent in 2025
Connie Liappas
Compass Greater NY LLC
(516) 319-3274
1 in this area
98 Total Sales
-
Buyer Co-Listing Agent in 2025
Nicholas Liappas
Compass Greater NY LLC
(646) 741-1185
1 in this area
56 Total Sales
-
Seller's Agent in 2022
Maria Babaev
Douglas Elliman Real Estate
(516) 287-7716
8 in this area
177 Total Sales
Map
Source: OneKey® MLS
MLS Number: 811391

APN: 2427-24-E-00-1047-0
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