2 Trails End, Chappaqua, NY 10514
Property image
Property image
OFF MARKET

$3,041,800

Trulia Estimate
  • 5 Beds
  • 6 Baths
  • 5,700 sqft (on 5.53 acres)

2 Trails End, Chappaqua, NY 10514

Est. Refi. Payment $20,196/mo*
Refinance Your Home
Currently Off Market - Sold Oct 5, 2012 for $2,025,000

Home Value

Trulia Estimate
$3.04M
Since last month
Increased$7K (+0.2%)
Since last year
Increased$224K (+7.9%)
Since last sale
Increased$1M (+50.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +61% in the last 10 years
MonthEstimated value
2026
September 2026$3.04M
August 2026$3.04M
July 2026$3.05M
June 2026$3.06M
May 2026$2.94M
April 2026$2.89M
March 2026$2.89M
February 2026$2.87M
January 2026$2.8M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Round Hill Place, Chappaqua, NY
0.40
Single-Family Home
$3,000,000
12/02/25
5
5
5,285
1 Hitching Post Lane, Chappaqua, NY
0.44
Single-Family Home
$2,310,018
08/25/26
5
4.5
4,489
45 Deerfield Rd, Chappaqua, NY
0.30
Single-Family Home
$1,877,300
01/08/26
5
3.5
3,085
2 Heathcote Drive, Mount Kisco, NY
0.81
Single-Family Home
$2,900,000
08/18/26
5
5.5
7,238
18 Hayrake Lane, Chappaqua, NY
0.50
Single-Family Home
$1,725,000
04/27/26
5
3
2,885
20 Cardinal Place, Mount Kisco, NY
0.79
Single-Family Home
$1,754,000
08/04/26
4
3
3,834
17 By Way, Chappaqua, NY
1.02
Single-Family Home
$3,080,000
08/06/26
5
5
4,675
32 North Way, Chappaqua, NY
0.91
Single-Family Home
$2,775,000
04/06/26
4
4.5
5,087
39 Mayberry Road, Chappaqua, NY
0.88
Single-Family Home
$1,550,000
06/26/26
4
3
3,761
56 Annandale Drive, Chappaqua, NY
1.03
Single-Family Home
$1,780,000
12/22/25
4
4.5
4,543

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
6 Trails End, Chappaqua, NY 10514
0.06
$2,966,000
5
6
7,624
Off Market
15 Paula Place, Chappaqua, NY 10514
0.06
$861,800
2
1
1,160
Off Market
3 Trails End, Chappaqua, NY 10514
0.07
$3,242,500
5
5.5
6,083
Off Market
50 Kerry Lane, Chappaqua, NY 10514
0.13
$2,046,800
4
4
4,051
Off Market
66 Kerry Lane, Chappaqua, NY 10514
0.19
$3,275,400
6
7.5
6,333
Off Market
6 Paula Place, Chappaqua, NY 10514
0.20
$1,876,700
4
3.5
5,272
Off Market
10 Paula Place, Chappaqua, NY 10514
0.21
$679,000
4
2
2,464
For Sale
24 Trails End, Chappaqua, NY 10514
0.25
$5,750,000
6
7.5
9,247
For Sale
140 Old Roaring Brook Road, Mount Kisco, NY 10549
0.32
$3,090,900
5
6.5
5,151
Off Market
58 Lawrence Farms Crossway, Chappaqua, NY 10514
0.36
$2,341,300
5
4.5
7,000
Off Market
15 Kerry Lane, Chappaqua, NY 10514
0.37
$2,588,800
4
4
5,534
Off Market
3 Round Hill Place, Chappaqua, NY 10514
0.40
$3,000,000
5
5
5,285
Recently Sold

Local Information

  • Map ViewExplore the area around 2 Trails End.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1991
5.53 acre lot
5,700 sqft
$534/sqft
Garage

About this House

Perfectly located on 5.5 park like acres in a private cul de sac of nine custom homes, this Colonial offers the perfect blend of elegant architectural detail with modern ammenities. Enjoy your own private retreat complete with heated pool and gracious pool house. Many amenities including gourmet kitchen, three fireplaces and a media room all set for your Super Bowl party. Pool house has a kitchen, bath and shower. This home is perfect for gracious entertaining and everyday living.
2 Trails End, Chappaqua, NY 10514 is a 5 bedroom, 6 bathroom, 5,700 sqft single-family home built in 1991. It last sold for $2,025,000 on Oct 5, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,041,800.

Home Details for 2 Trails End

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 2
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1991
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 5.53 acres

Price and Tax history

DateEventPrice
Oct 5, 2012
Source: OneKey® MLS as distributed by MLS GRID #H3208635
Sold
$2,025,000
May 2, 2012
Source: Agent Provided
PriceChange
$2,195,000
Price decreased by 8%
Mar 20, 2012
Source: Agent Provided
Listed For Sale
$2,395,000
Aug 13, 1997
Source: N/A
Sold
$1,300,000

Market trends in Chappaqua

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
14
13MoM

Around this home

What Locals Say about Chappaqua

At least 64 Trulia users voted on each feature.

  • 91 % Say it's quiet

  • 90 % Say car is needed

  • 86 % Say parking is easy

  • 85 % Say it's dog friendly

  • 78 % Say yards are well-kept

  • 75 % Say people would walk alone at night

  • 73 % Say there's wildlife

  • 72 % Say there's holiday spirit

  • 62 % Say neighbors are friendly

  • 61 % Say they plan to stay for at least 5 years

  • 54 % Say kids play outside

  • 50 % Say it's walkable to restaurants

  • 37 % Say there are community events

  • 35 % Say there are sidewalks

  • 32 % Say streets are well-lit

  • 26 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Plenty of areas that can walk dogs , quiet and safe"
    0
    Flag
  • Alvin Robert Colby
    "The community is relatively safe."
    0
    Flag
  • Trulia User
    "It’s a dog friendly place."
    0
    Flag
  • Chaarey
    "Easily accessible to all major roadways. I moved from one town over and absolutely love everything about it here. Shopping is amazing, food choices are plentiful, it’s clean but most of all, the people are amazing! "
    0
    Flag
  • Mereslavin
    "The commute is not too long and metro north is nice. Commuting into grand central is much nicer than commuting into penn."
    0
    Flag
  • Mereslavin
    "There’s Lots of space to play in and it’s very quiet. There’s lot of other animals which dogs might not like"
    1
    Flag
  • Marta V.
    "Very upscale. Safe. Family oriented. Clean. Good school district. Good for outdoors. Train to Manhattan makes it an easy and convenient commute. "
    0
    Flag
  • Jill B.
    "It’s great place to live, safe and friendly great neighborhood, easy commute to NYC. Lived here for 25 years, we have looked to downsize but can’t find a better place to live. "
    2
    Flag
  • Jill B.
    "Lived here for 18 years and love it, safe and friendly love my neighbors , perfect for country living and easy access to NYC great schools and community activities "
    0
    Flag
  • Trulia User
    "Feels safe and neighborhood friendly a golf course and great restaurant very pretty landescapes and trees beautiful houses "
    0
    Flag
  • Lizrappaport
    "It is very wooded with homes that are far apart from each other. There is no seeing into the neighbor’s kitchen, for example. The schools are excellent and the people are generally laid back. They are discerning and demanding, but not snobbish. "
    2
    Flag
  • Diane N. W.
    "My community has access to MetroNorth Station, buses, parks, bicycle paths, elite school system, restaurants, country setting...."
    0
    Flag
  • Elymiani
    "Amicable woodland safe all you need is her . Friendly. The best school are in chappaqua district . "
    1
    Flag
  • Carlosgamboan
    "I just moved in and already love the neighborhood. Great Schools, peaceful, lots of trees, friendly neighbors"
    1
    Flag
  • Christine R.
    "I grew up in Chappaqua, and lived there with my own children for several years. The Chappaqua schools are very highly rated, and the Park & Recreation department is very active as well. There is a small town feeling, but easily accessibility to NYC and White Plains via Metro North."
    0
    Flag
  • bal
    "i am so impressed with this litttle jewel of place in Chappaqua "
    0
    Flag
  • Susan S.
    "Incredible Old Farm Lake. Families, Singles and Couples all welcome. Convenient to the greatest schools, shopping and restaurants."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 2 Trails End

  • What is 2 Trails End estimated to be worth?
    Trulia's estimated value for 2 Trails End in Chappaqua, NY is $3,041,800.
  • What is the price history for 2 Trails End?
    2 Trails End in Chappaqua, NY last sold for $2,025,000 in October 2012.
  • Is Chappaqua a buyer's or seller's market?
    Chappaqua is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chappaqua?
    Residents describe Chappaqua, NY as quiet, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Chappaqua, NY.
  • Does 2 Trails End have air conditioning?
    Yes, 2 Trails End in Chappaqua, NY has air conditioning.
  • Does 2 Trails End have a pool?
    Yes, 2 Trails End in Chappaqua, NY has a pool.

Explore by feature - Air Conditioning

8 rentals with air conditioning in Chappaqua, NY

Explore by feature - Washer/dryer

9 rentals with a washer/dryer in Chappaqua, NY

Apartments for Rent

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Off Market Homes Near 2 Trails End

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