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33 Greenbriar Drive

$2,249,000

Est. $15,642/mo

Chappaqua, NY 10514 · Westchester County

Beds
3
Baths
4
Sqft
6,115
Status
Active
On site
132 days

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About this home

Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods. This exceptional David Graham-designed 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 with Houlihan Lawrence Inc. · Wendy Nolan · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 3:09 PM ET. ©2026 One Key MLS.

Estimate Your Monthly Payment

Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and Private Mortgage Insurance.

$15,641.73Total / mo

Estimated Monthly Payment

Principal & interest
$11,077.98 (70.8%)
Taxes
$4,363.75 (27.9%)
Insurance
$200.00 (1.3%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

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Market Insights

The market around Chappaqua, NY

Current Listings

New in the last 30 days

8

Sep 2026

Average Price

Active listings

$1,857,441

Sep 2026

Average Days on Market

Active listings

92 days

Sep 2026

Computed from 34 active OneKey MLS listings in Chappaqua, NY.

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