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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.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1991
  • 9.078 Acre Lot
  • 3 Car Garage
  • 58 days on Market

  • Bedrooms
    6
  • Bathrooms
    7 full · 1 half
  • Year Built
    1991
  • Architectural Style
    Colonial, Estate
  • Construction Materials
    Frame, Brick
  • Garage Spaces
    3.0
  • Parking Features
    Attached
  • Living Area
    9247.0
  • Interior Features
    Cathedral Ceiling(s), Eat-in Kitchen, Walk-In Closet(s), Pantry, Entrance Foyer
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Washer, Cooktop, Oven, Freezer, Exhaust Fan
  • Exterior Features
    Balcony
  • Patio And Porch
    Patio, Deck, Porch
  • Pool Features
    In Ground, Pool/Spa Combo, Private
  • Security Features
    Security System
  • Cooling
    Central Air
  • Heating
    Forced Air, Baseboard, Radiant, Oil
  • Basement
    Finished, Full

  • Acres
    9.078
  • Lot Features
    Views, Landscaped
  • Water Front Features
    Waterfront Access
  • View
    Water
  • Water
    Public

  • County
    Westchester
  • City
    Chappaqua
  • Zip Code
    10514
  • High School
    Horace Greeley High School
  • Middle School
    Seven Bridges Middle School
  • Elementary School
    Roaring Brook

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Frequently Asked Questions

How do I schedule a tour of 24 Trail End?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 24 Trail End.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 24 Trail End?

Click Ask a Question to talk with our team. You already know it is a 6 bed, 7 bath, listed for $5,750,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Chappaqua, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 24 Trail End?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 24 Trail End at around $40,754. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 24 Trail End?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Westchester County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 24 Trail End?

In most cases, yes. Whether 24 Trail End is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Chappaqua's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 24 Trail End?

We can handle that for you. Our preferred local agent specializes in residentials in Chappaqua and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $5,750,000 with 9,247 sqft of space—that comes out to approximately $622 per square foot.

How long has this property been on the market?

24 Trail End was listed on September 14, 2026, which means it's been on the market for 58 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1991, making it approximately 35 years old.

What is the lot size of this property?

24 Trail End sits on a 9.08-acre lot, which is 395,525 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Roaring Brook
  • Middle: Seven Bridges Middle School
  • High: Horace Greeley High School

Want to see how these schools compare? Check out our Westchester County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 24 Trail End?

The most recent public record shows annual property taxes for 24 Trail End were approximately $96,392. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 24 Trail End still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.

Last Updated: November 11, 2026 at 08:05PM | Source: OneKey MLS | MLS#: 1017994