For Sale
Single family home for sale at 31 Chestnut Hl Dr, Oyster Bay, NY 11771 | MLS# 1061123 | Listing updated on 2026-10-27
Photo 1 of Single family home for sale at 31 Chestnut Hl Dr, Oyster Bay, NY 11771 | MLS# 1061123 | Listing updated on 2026-10-27
Photo 2 of Single family home for sale at 31 Chestnut Hl Dr, Oyster Bay, NY 11771 | MLS# 1061123 | Listing updated on 2026-10-27
Photo 3 of Single family home for sale at 31 Chestnut Hl Dr, Oyster Bay, NY 11771 | MLS# 1061123 | Listing updated on 2026-10-27
Photo 4 of Single family home for sale at 31 Chestnut Hl Dr, Oyster Bay, NY 11771 | MLS# 1061123 | Listing updated on 2026-10-27
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$7,850,000

Monthly Est:$39,072

  • Beds Icon6 Beds
  • Beds Icon
    10 Baths
  • Beds Icon7,639sqft

31 Chestnut Hl Dr, Oyster Bay, NY 11771

$39,072/moEst:

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  • Single Family Residence

  • Built in 1989

  • $125/mo HOA

  • 5 acres lot

  • $1,028/sq.ft

Description

Introducing 31 Chestnut Hill Drive, an extraordinary contemporary estate situated on five private acres at the end of a prestigious cul-de-sac in Upper Brookville. Originally designed by renowned architect Gary Gallagher and comprehensively reimagined from 2023 to 2026 by award-winning architect Stuart Narofsky, this exceptional residence seamlessly blends striking modern architecture with sophisticated design, cutting-edge technology, and resort-style amenities.

Spanning over 10,000 square feet, the home features six bedrooms, six full and four half bathrooms, including a luxurious first-floor primary suite. Dramatic architectural details, including two custom floating
staircases with glass railings, expansive walls of glass, porcelain flooring, and polished white oak floors, create a remarkable sense of openness and light. Thoughtfully designed living and entertaining spaces are complemented by a state-of-the-art chef's kitchen featuring custom cabinetry, integrated Thermador appliances, specialty quartz countertops, and an expansive center island.

The home's extensive accommodations include multiple home offices, a library, and beautifully appointed guest suites. The fully finished lower level offers an exceptional collection of recreational and wellness amenities, including a Dolby Atmos home theater, custom wine room and tasting area, wet bar, fitness room, Finnish sauna, and dedicated yoga and massage space.

Outdoors, the estate unfolds into a private resort-like setting, complete with a newly rebuilt heated saline pool and spa, expansive porcelain patios, and a fully renovated guest/pool house with its own kitchen. An outdoor kitchen and beautifully landscaped grounds provide an ideal setting for both intimate gatherings and large-scale entertaining.

Additional highlights include a heated four-car garage, five-zone energy-efficient climate control, whole-house generator, and comprehensive smart-home technology managing lighting, security, motorized shades, and numerous additional systems. Offering exceptional privacy, architectural distinction, and an extraordinary level of modern luxury, 31 Chestnut Hill Drive represents a rare opportunity to experience contemporary estate living on Long Island's Gold Coast.

  • Houzeo last checked: 1 minute ago
  • Listing updated: October 27, 2026 at 7:38 pm
  • Listing Provided by: Jason P. Friedman (516) 236-6226 , Theodoros Kritikos | Daniel Gale Sothebys Intl Rlty (516) 626-7600
  • Source: OneKey MLS-NY as distributed by MLS GRID | MLS#: 1061123 OneKey MLS-NY as distributed by MLS GRID

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Nassau County

  • City

    Oyster Bay

  • Neighborhood

    --

  • Year Built

    1989

  • HOA Fees

    $125/mo

  • Finished Area

    7,639 sqft

  • Lot Size

    5 acres lot

  • Basement Area

    - sqft

  • MLS Name

    OneKey MLS

  • MLS Number

    1061123

  • MLS Status

    Active

  • Days on Market

    19

  • Cumulative Days on Market

    213

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Location

HOA Management

N/A

HOA Fees

$1,500/ Annually

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Snow Removal Snow Removal

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 6

    Bathrooms: 10

Interior

  • Appliances

    Dishwasher, Dryer, Electric Cooktop, Electric Oven, Exhaust Fan, Microwave, Refrigerator, Washer

  • Heating

    Electric, Forced Air

  • Exterior Features

    Balcony, Gas Grill, Lighting, Mailbox

  • Cooling

    Central Air

  • Interior Features

    First Floor Bedroom, First Floor Full Bath, Built In Features, Central Vacuum, Chefs Kitchen, Double Vanity, Eat In Kitchen, Entrance Foyer, Formal Dining, High Ceilings, High Speed Internet, His And Hers Closets, Kitchen Island, Open Floorplan, Primary Bathroom, Master Downstairs, Quartz/quartzite Counters, Recessed Lighting, Sauna, Smart Thermostat, Soaking Tub, Walk In Closet(s), Wet Bar

  • Window Features

    Casement, Double Pane Windows, Floor To Ceiling Windows, New Windows, Oversized Windows

  • Flooring

    Hardwood, Other

  • Sewer

    Cesspool

Construction

  • Year Built

    Year Built: 1989

  • Home type

    Single Family Residence

  • Property Condition

    Actual

  • Construction Materials

    Frame

  • Architectural Style

    Contemporary, Modern

Utilities & Energy

  • Parking Features

    Attached, Driveway, Garage, Garage Door Opener, Heated Garage

  • Utilities

    Electricity Connected, Propane, Trash Collection Private

  • Pool Features

    Fenced, In Ground, Pool Cover, Salt Water, Tile

  • Water Source

    Public

  • Laundry Features

    Laundry Room

  • Basement

    Partial, Walk Out Access

  • Security Features

    Building Security, Fire Alarm, Security Gate, Security Lights, Security System, Smoke Detector(s), Video Cameras

Other Features

  • Lot Features

    Back Yard, Cul De Sac, Landscaped, Sprinklers In Front, Sprinklers In Rear

  • Patio And Porch Features

    Patio

Price History

DateEventPrice

10/15/2026

Source: mls_logoOneKey MLS-NY #KEY1061123

Listed for Sale

$7,850,000 -12.73%

$1,028/sqft

10/01/2026

Source: mls_logoOneKey MLS-NY as distributed by MLS GRID #KEY970669

Listing Removed

$8,994,999

$1,178/sqft

09/02/2026

Source: mls_logoOneKey MLS-NY #KEY970669

Listed for Sale

$8,994,999

$1,178/sqft

07/16/2026

Source: mls_logoOneKey MLS-NY #KEY970669

Price Decreased

$8,995,000 -8.68%

$1,178/sqft

05/19/2026

Source: mls_logoOneKey MLS-NY #KEY970669

Price Decreased

$9,850,000 -8.37%

$1,289/sqft

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Nearby Homes

Based on information from OneKey MLS® through Nov 04, 2026, 01:01AM as submitted to and distributed by 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. 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. © 2026 OneKey MLS. All rights reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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