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33 Greenbriar DriveChappaqua, NY 10514

For Sale

$2,499,000

Smart Buyer Rebate $24,990

Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional luxury Colonial blends timeless architecture, designer finishes, and an unmatched indoor-outdoor lifestyle within the award-winning Chappaqua school district. Privately positioned against acres of preserved land, this premier Westchester County property offers both tranquility and convenience, just minutes to Metro North, downtown Chappaqua, and Chappaqua Crossing featuring Whole Foods Market and Life Time. Living like a 5-bedroom home, this luxury home for sale in Chappaqua showcases exceptional craftsmanship throughout with Juliet balconies, copper-topped cupolas, Belgian block-lined driveways, soaring ceilings, custom millwork, and walls of glass that flood the interiors with natural light. A dramatic curved staircase welcomes you into elegant yet comfortable living spaces designed for both everyday living and sophisticated entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and European mosaic tilework, seamlessly connecting to the formal and casual gathering spaces. Highlights include a sophisticated library with gas fireplace, a stunning vaulted family room, and an impressive entertainment lounge with a wood-burning fireplace, wet bar, Viking wine refrigerator, and custom built-ins. The luxurious primary suite offers a gas fireplace, oversized dressing room, and spa-inspired bath, delivering the ultimate private retreat.
Outside, the property lives like a private resort with a heated saltwater pool, outdoor fireplace, expansive patios, built-in grill, fire pit, poolside grotto with shower and changing area, gazebos, and a half basketball court with spotlighting. This exceptional Chappaqua estate offers luxury living, privacy, and resort-style amenities in one of Westchester’s most sought-after communities, known for top-rated schools, vibrant downtown, and easy NYC commute. A rare opportunity to experience estate-style living and the quintessential Chappaqua lifestyle at its finest.

Listed by Wendy Nolan

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Houlihan Lawrence Inc.

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914-238-4766

Last updated May 30, 2026

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Source: OneKey #973551

Listing Facts

  • TypeSingle-family
  • NeighborhoodNew Castle
  • Bedrooms3
  • Bathrooms4
  • Days on Prevu39
  • Taxes$52,365/year
  • Size6,115 sqft
  • Price per sqft$409

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

05/08/2026
Listed by Houlihan Lawrence Inc.
$2,499,000

Property Details for 33 Greenbriar Drive

Exterior

Construction

  • Window Features: Double Pane Windows, Drapes, Screens
  • Year Built: 1977
  • Architectural Style: Colonial
  • Construction Materials: Shingle Siding

Features

  • Other Structures: Gazebo
  • Patio And Porch Features: Patio, Terrace
  • Pool Features: Diving Board, Salt Water
  • Pool Private: Yes

Measurements

  • Building Area Total: 6,115
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.93
  • Lot Size Square Feet: 40,511

Financial

Taxes

  • Parcel Number: 3489-099-006-00002-006-0000
  • Tax Annual Amount: $52,365.00
  • Tax Assessed Value: $23,500.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Convection Oven, Cooktop, Dishwasher, Dryer, Gas Cooktop, Gas Range, Humidifier, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater, Wine Refrigerator
  • Fireplace Features: Bedroom, Gas, Wood Burning
  • Fireplace: Yes
  • Fireplaces Total: 4
  • Interior Features: Bidet, Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, Smart Thermostat, Storage, Walk-In Closet(s), Wet Bar
  • Spa: Yes

Measurements

  • Living Area: 6,115
  • Living Area Source: Public Records

Rooms

  • Basement: Finished
  • Has Basement: Yes
  • Bathrooms Full: 4
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 3
  • Rooms Total: 12

Other

General

  • Exclusions: Outdoor lamps, all chandeliers, and ceiling frescoes

Parking

Parking

  • Garage Spaces: 2
  • Garage: Yes
  • Parking Features: Driveway, Garage, Garage Door Opener

Schools

Elementary School

  • Elementary School: Roaring Brook
  • Elementary School District: Chappaqua

High School

  • High School: Horace Greeley High School
  • High School District: Chappaqua

Middle or Junior School

  • Middle Or Junior School: Robert E Bell School
  • Middle Or Junior School District: Chappaqua

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Baseboard
  • Other Equipment: Generator
  • Sewer: Septic Tank
  • Utilities: Cable Connected, Electricity Available, Natural Gas Connected, Propane, Water Available
  • Water Source: Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 3 bedrooms and 4 bathrooms in this single-family home at 33 Greenbriar Drive.

What schools are nearby to 33 Greenbriar Drive?

Nearby schools include the Roaring Brook Elementary School, Robert E Bell School Middle School, and Horace Greeley High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 33 Greenbriar Drive.

What are the annual taxes for 33 Greenbriar Drive?

Annual taxes for this single-family home are estimated at $52,365.

How does 33 Greenbriar Drive compare to other single-family homes in New Castle?

This single-family home is listed 18% above the average price for single-family homes in New Castle and has been on the market for 44 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 6,115 sqft.

33 Greenbriar Drive is a 3-bedroom, 4-bath single-family home for sale in Chappaqua NY 10514. Listed on Prevu for 39 days at $2,499,000. This residence features 6,115 square feet of living space, located in New Castle. The median listing price for single-family homes in this area is $1,589,000. Nearby schools include Roaring Brook Elementary School, Robert E Bell School Middle School, and Horace Greeley High School. Property amenities include private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. Browse more single-family home listings in Westchester County.

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey™ MLS. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. Information Copyright 2026, OneKey™ MLS. All Rights Reserved.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.