38 Chestnut Hill Dr Upper Brookville, NY 11771

$7,950,000
6 beds
6 full, 3 partial
15,000 sqft
5.1 acres
$530 / sqft
House

Property details

About 38 Chestnut Hill Dr

Nestled 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.

Highlights

Home typeSingle Family Residence
HeatingBaseboard
StatusActive
CoolingCentral Air
Size15,000 sqft
BasementYes
Lot size5.12 Acres
Year built1998
MLS #811272
Garage10 spaces
Private poolYes

Summary

  • MLS Number: 811272
  • MLS Name: ONEKEY2
  • Office Name: Nest Seekers LLC
  • Office Phone: (516) 922-2878

IDX Listings courtesy of OneKey MLS as distributed by MLS GRID.

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IDXThe data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the OneKey™ MLS. Real Estate listings held by brokerage firms other than this broker are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers. This 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.

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Data displayed may be a portion of, and not a complete set of all listings published in the MLS.

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Last updated on: 2/1/2025, 10:56:48 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

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mediterranean / spanish-style home with a garage

$7,950,000

38 Chestnut Hill Dr

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Price information

Property sales

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Tax history

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Nearby schools

6

Vernon School

Public District 3-6

1.4 mi

880 Oyster Bay Rd

3

Margaret A. Connolly Elementary School

Public District 3-5

2.2 mi

100 Ridge Dr

7

Locust Valley Intermediate School

Public District 3-5

2.5 mi

96 Mountain Ave

School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.

All data from GreatSchools

Neighborhood

The neighbors living near this home have an average income of $145,270. The most common annual income of people living in Upper Brookville, NY is $200k+. Residents typically live in married, no kids family. Typical level of education for residents in this area is post secondary degree.

How much money do the neighbors make?

17%
<35k
20%
35k-100k
20%
100k-200k
43%
200k+

What level of education do the neighbors have?

High School Diploma
Post Secondary Degree
Masters Degree
Doctorate

What types of families live nearby?

23%
Single, No Kids
2%
Single, with Kids
41%
Married, No Kids
34%
Married, with Kids

Are the neighbors home owners or renters?

Home Owners
Renters

How old are people in this area?

13%
<11 yrs old
12%
12-17 yrs old
11%
18-34 yrs old
47%
35-64 yrs old
17%
65+ yrs old

What do the neighbors do for fun?

  • Skiing/snowboardingSkiing/snowboarding
  • PGA/LPGAPGA/LPGA
  • College FootballCollege Football

Where do the neighbors shop?

  • BJs Wholesale ClubBJs Wholesale Club
  • Stein MartStein Mart
  • Chico'sChico's

Where do the neighbors go to eat?

  • PaneraPanera
  • Cracker BarrelCracker Barrel
  • Bonefish GrillBonefish Grill

What do the neighbors drive?

  • InfinitiInfiniti
  • LexusLexus
  • CadillacCadillac

What do the neighbors listen to?

  • Adult HitsAdult Hits
  • OldiesOldies
  • ClassicalClassical
All data provided by Home Junction and Claritas

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Frequently asked questions

About 38 Chestnut Hill Dr

This home is located at 38 Chestnut Hill Dr in Upper Brookville, NY and zip code 11771 in the Town of Oyster Bay neighborhood. This 15,000 square foot home, which was built in 1998, sits on a 5.12 acre lot. Features: 6 bedrooms, 9 bathrooms. It has been listed on Rocket Homes since January 9, 2025 and is currently priced at $7,950,000.

In January 2025 in Upper Brookville, NY there were 26.7% more homes for sale than in December. The median list price of listings available in January 2025 was $3,100,000, while the average time on the real estate market was 180 days.

From Rocket Homes Real Estate and based on county public records data.

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