289 Hamilton Rd, Chappaqua, NY 10570
SOLD
APR 7, 2026

$2,592,700

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 5,475 sqft (on 1.33 acres)

289 Hamilton Rd, Chappaqua, NY 10570

Est. Refi. Payment $16,700/mo*
Refinance Your Home
Currently Off Market - Sold Apr 7, 2026 for $2,496,500

Home Value

Trulia Estimate
$2.59M
Since last month
Increased$24K (+0.9%)
Since last year
Increased$743K (+40.2%)
Since last sale
Increased$96K (+3.8%)
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 +107% in the last 10 years
MonthEstimated value
2026
August 2026$2.59M
August 2026$2.59M
July 2026$2.57M
June 2026$2.54M
May 2026$2.52M
April 2026$1.91M
March 2026$1.94M
February 2026$1.84M
January 2026$1.91M
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
5 Morning View Ct, Chappaqua, NY
0.33
Single-Family Home
$2,450,000
06/23/26
5
5
5,767
5 Morning View Court, Chappaqua, NY
0.33
Single-Family Home
$2,450,000
06/09/26
4
5
5,767
57 Hamilton Drive, Chappaqua, NY
0.11
Single-Family Home
$1,165,000
09/19/25
3
3
3,728
33 Aldridge Road, Chappaqua, NY
0.70
Single-Family Home
$2,621,000
07/10/26
5
3.5
5,247
74 Dogwood Lane, Pleasantville, NY
0.33
Single-Family Home
$1,602,000
07/09/26
4
3
3,656
790 Hardscrabble Road, Chappaqua, NY
0.52
Single-Family Home
$1,850,000
05/08/26
3
3.5
4,780
276 Quaker Road, Chappaqua, NY
0.53
Single-Family Home
$2,875,000
07/14/26
6
3.5
6,532
55 Kipp St, Chappaqua, NY
0.67
Single-Family Home
$1,900,000
09/05/25
4
3
3,231
35 Hamilton Road, Chappaqua, NY
0.34
Single-Family Home
$1,275,000
03/25/26
4
2
2,139

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
290 Hamilton Road, Chappaqua, NY 10514
0.05
$1,334,900
4
3.5
2,763
Off Market
57 Hamilton Drive, Chappaqua, NY 10514
0.11
$1,258,400
3
3
3,728
Off Market
188 Mill River Road, Chappaqua, NY 10514
0.14
$687,800
2
1.5
1,414
Off Market
10 Leroy Place, Chappaqua, NY 10514
0.12
$950,700
2
1.5
1,492
Off Market
254 Hamilton Road, Chappaqua, NY 10514
0.15
$2,716,200
5
5
3,842
Off Market
152 Mill River Road, Chappaqua, NY 10514
0.20
$1,043,000
3
2
2,079
Off Market
249 Mill River Road, Chappaqua, NY 10514
0.22
$849,999
4
2
2,100
For Sale
9 Peck Place, Chappaqua, NY 10514
0.20
$2,280,000
4
3.5
3,884
Off Market
219 Hamilton Road, Chappaqua, NY 10514
0.23
$2,820,900
6
4.5
4,692
Off Market
44 Hardscrabble Hill Road, Chappaqua, NY 10514
0.25
$1,250,900
3
4
3,440
Off Market
660 Washington Avenue, Pleasantville, NY 10570
0.27
$718,200
3
2
1,228
Off Market
27 Hardscrabble Hill Road, Chappaqua, NY 10514
0.25
$1,402,700
3
2.5
1,995
Off Market

Local Information

  • Map ViewExplore the area around 289 Hamilton Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1930
Lot Size
1.33 acres
Living Area
5,475 sqft
Price/Sqft
$456/sqft
Parking
Garage

About this House

This single-family home is located at 289 Hamilton Rd, Chappaqua, NY. 289 Hamilton Rd is in Chappaqua, NY and in ZIP code 10570. This property has 5 bedrooms, 3 bathrooms and approximately 5,475 sqft of floor space. The last sold price per dimension was $456/sqft. This property has a lot size of 1.33 acres and was built in 1930.
289 Hamilton Rd, Chappaqua, NY 10570 is a 5 bedroom, 3 bathroom, 5,475 sqft single-family home built in 1930. It last sold for $2,496,500 on Apr 7, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,592,700, with a rent estimate of $7,740/month.

Home Details for 289 Hamilton Rd

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2.5
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Stucco
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached

Price & Status

Price
Price Per Sqft: $456/sqft

Community

Units in Building: 1

Lot Information

Lot Area: 1.33 acres

Price and Tax history

DateEventPrice
Apr 7, 2026
Source: N/A
Sold
$2,496,500

Market trends in Chappaqua

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
5MoM

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 289 Hamilton Rd

  • What is 289 Hamilton Rd estimated to be worth?
    Trulia's estimated value for 289 Hamilton Rd in Chappaqua, NY is $2,592,700.
  • What is the price history for 289 Hamilton Rd?
    289 Hamilton Rd in Chappaqua, NY last sold for $2,496,500 in April 2026.
  • 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 289 Hamilton Rd have air conditioning?
    Yes, 289 Hamilton Rd in Chappaqua, NY has air conditioning.
  • How big is the lot at 289 Hamilton Rd?
    The lot at 289 Hamilton Rd in Chappaqua, NY is about 1.3 acres.

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