2 Hamilton Dr, Chappaqua, NY 10514
OFF MARKET

2 Hamilton Dr
Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 3,474 sqft (on 1.45 acres)

$1,994,600

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $12,572/mo*
Refinance Your Home

$1,994,600

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $12,572/mo*
Refinance Your Home
4 Beds
4 Baths
3,474 sqft
(on 1.45 acres)

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1928
Lot Size
1.45 acres
Living Area
3,474 sqft
Price/Sqft
$574
Parking
Garage

Description

This single-family home is located at 2 Hamilton Dr, Chappaqua, NY. 2 Hamilton Dr is in Chappaqua, NY and in ZIP code 10514. This property has 4 bedrooms, 4 bathrooms and approximately 3,474 sqft of floor space. This property has a lot size of 1.45 acres and was built in 1928.
2 Hamilton Dr, Chappaqua, NY 10514 is a 4 bedroom, 4 bathroom, 3,474 sqft single-family home built in 1928. It is currently off market. The Trulia Estimate is $1,994,600, with a rent estimate of $7,345/month.

Home Details for 2 Hamilton Dr

Interior Features

Heating & Cooling
Heating: Other, OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: Single Family HomeArchitecture: mansion

Exterior Features

Exterior Home Features
Exterior: Stucco
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.45 acres

Market trends in Chappaqua

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
5MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$178,700
Home facts updated by county records

Comparable Sales for 2 Hamilton Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
35 Hamilton Road, Chappaqua, NY
0.10
Single-Family Home
$1,275,000
03/25/26
4
2
2,139
289 Hamilton Rd, Chappaqua, NY
0.26
Single-Family Home
$2,496,500
04/07/26
5
3
5,475
57 Hamilton Drive, Chappaqua, NY
0.24
Single-Family Home
$1,165,000
09/19/25
3
3
3,728
58 Spring Lane, Chappaqua, NY
0.47
Single-Family Home
$1,815,000
11/10/25
4
2.5
3,457
55 Kipp St, Chappaqua, NY
0.51
Single-Family Home
$1,900,000
09/05/25
4
3
3,231
10 Glen Terrace, Chappaqua, NY
0.60
Single-Family Home
$1,804,000
07/31/25
4
3.5
3,219
90 Prospect Drive, Chappaqua, NY
0.56
Single-Family Home
$1,815,090
08/28/25
4
2.5
3,087
24 Glen Terrace, Chappaqua, NY
0.49
Single-Family Home
$1,623,500
08/14/25
4
2.5
2,539
105 Douglas Road, Chappaqua, NY
0.22
Single-Family Home
$1,150,000
04/17/26
3
2.5
2,220
276 Quaker Road, Chappaqua, NY
0.30
Single-Family Home
$2,875,000
07/14/26
6
3.5
6,532

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Hamilton Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
    "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
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  • 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
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Homes for sale near 2 Hamilton Dr

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Off Market Homes Near 2 Hamilton Dr

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