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24 Trails End

$5,750,000

Est. $36,556/mo

Chappaqua, NY 10514 · Westchester County

Beds
6
Baths
7.5
Sqft
9,247
Status
Active
On site
50 days

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About this home

Welcome to 24 Trails End, an unparalleled private resort estate redefining luxury living on over 9 pristine, park-like acres. This majestic brick Colonial, quietly positioned at the end of a prestigious cul-de-sac, overlooks a scenic, spring-fed pond. Inside, classic architectural sophistication meets modern design, highlighted by a soaring double-height great room, dual home offices, and a rich mahogany billiard room with a wet bar and fireplace. The heart of the home is an expansive chef's kitchen, with an oversized marble island, and a sunny breakfast area. The lower level is an extraordinary recreation destination, boasting a 2600 sqft indoor sports court lined for basketball and pickleball, alongside a full home gym. Step outside to your private backyard paradise with an inviting heated Gunite pool, integrated spa, and a pool house/cabana surrounded by sprawling bluestone terraces and meandering walking trails. Two firepits located around the property and a serene pond with an island, an additional firepit and two docks for unmotorized boat usage complete this spectacular picture. An ultra-private lifestyle compound in the award winning Chappaqua schools, just under an hour from Manhattan.

Listed with Compass Greater NY, LLC · Brian Milton · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Nov 2, 2026, 8:07 PM ET. ©2026 One Key MLS.

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Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and private mortgage insurance.

$36,555.66Total / mo

Estimated monthly payment

Principal & interest
$28,322.99(77.5%)
Taxes
$8,032.67(22.0%)
Insurance
$200.00(0.5%)

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

5

Nov 2026

Average price

Active listings

$1,984,800

Nov 2026

Average days on market

Active listings

74 days

Nov 2026

Computed from 30 active OneKey MLS listings in Chappaqua, NY.

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