271 Hamilton Rd, Chappaqua, NY 10514
OFF MARKET

$1,844,700

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,858 sqft (on 1 acre)

271 Hamilton Rd, Chappaqua, NY 10514

Est. Refi. Payment $12,070/mo*
Refinance Your Home
Currently Off Market - Sold Mar 3, 1997 for $445,000

Home Value

Trulia Estimate
$1.84M
Since last month
Decreased$10K (-0.5%)
Since last year
Increased$251K (+15.7%)
Since last sale
Increased$1M (+314.5%)
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 +82% in the last 10 years
MonthEstimated value
2026
August 2026$1.84M
August 2026$1.84M
July 2026$1.85M
June 2026$1.85M
May 2026$1.81M
April 2026$1.7M
March 2026$1.72M
February 2026$1.67M
January 2026$1.64M
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
57 Hamilton Drive, Chappaqua, NY
0.15
Single-Family Home
$1,165,000
09/19/25
3
3
3,728
35 Hamilton Road, Chappaqua, NY
0.29
Single-Family Home
$1,275,000
03/25/26
4
2
2,139
289 Hamilton Rd, Chappaqua, NY
0.08
Single-Family Home
$2,496,500
04/07/26
5
3
5,475
105 Douglas Road, Chappaqua, NY
0.37
Single-Family Home
$1,150,000
04/17/26
3
2.5
2,220
21 Kipp Street, Chappaqua, NY
0.50
Single-Family Home
$1,075,000
10/10/25
4
2.5
2,447
31 Wynnewood Road, Chappaqua, NY
0.21
Single-Family Home
$1,530,000
09/12/25
4
3
2,420
676 Hardscrabble Rd, Chappaqua, NY
0.48
Single-Family Home
$595,000
11/14/25
3
2
2,420
14 Aldridge Road, Chappaqua, NY
0.62
Single-Family Home
$1,345,014
07/29/26
4
2.5
2,478
29 Begg Drive, Chappaqua, NY
0.28
Single-Family Home
$1,250,023
09/12/25
3
2.5
2,000
816 Hardscrabble Road, Chappaqua, NY
0.43
Single-Family Home
$1,299,000
08/24/26
3
3
2,444

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
0.10
$1,339,700
4
3.5
2,763
Off Market
254 Hamilton Road, Chappaqua, NY 10514
0.10
$2,703,800
5
5
3,842
Off Market
10 Leroy Place, Chappaqua, NY 10514
0.11
$938,800
2
1.5
1,492
Off Market
57 Hamilton Drive, Chappaqua, NY 10514
0.15
$1,252,800
3
3
3,728
Off Market
9 Peck Place, Chappaqua, NY 10514
0.12
$2,280,000
4
3.5
3,884
Off Market
188 Mill River Road, Chappaqua, NY 10514
0.19
$692,500
2
1.5
1,414
Off Market
219 Hamilton Road, Chappaqua, NY 10514
0.15
$2,820,900
6
4.5
4,692
Off Market
152 Mill River Road, Chappaqua, NY 10514
0.21
$1,043,000
3
2
2,079
Off Market
44 Wynnewood Road, Chappaqua, NY 10514
0.20
$1,242,100
2
2
1,922
Off Market
54 Spring Road, Chappaqua, NY 10514
0.20
$1,383,000
3
3.5
2,482
Off Market
31 Wynnewood Road, Chappaqua, NY 10514
0.21
$1,647,500
4
3
2,420
Off Market
45 Greenbriar Drive, Chappaqua, NY 10514
0.23
$1,574,500
3
3
2,585
Off Market

Local Information

  • Map ViewExplore the area around 271 Hamilton Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1941
1 acre lot
2,858 sqft
$645/sqft
Garage

About this House

This single-family home is located at 271 Hamilton Rd, Chappaqua, NY. 271 Hamilton Rd is in Chappaqua, NY and in ZIP code 10514. This property has 4 bedrooms, 3 bathrooms and approximately 2,858 sqft of floor space. This property has a lot size of 1 acre and was built in 1941.
271 Hamilton Rd, Chappaqua, NY 10514 is a 4 bedroom, 3 bathroom, 2,858 sqft single-family home built in 1941. It last sold for $445,000 on Mar 3, 1997. More recently, it was listed as a rental in May 2013 with an asking price of $6,500 per month. That rental listing was removed on July 2, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,844,700, with a rent estimate of $7,957/month.

Home Details for 271 Hamilton Rd

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: 1941
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price and Tax history

DateEventPrice
Jul 2, 2013
Source: Agent Provided
ListingRemoved
$6,200
Jun 16, 2013
Source: Agent Provided
PriceChange
$6,200
Price decreased by 5%
May 22, 2013
Source: Agent Provided
Listed For Rent
$6,500
Apr 12, 2013
Source: Agent Provided
ListingRemoved
$6,500
Mar 15, 2013
Source: Agent Provided
Listed For Rent
$6,500

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 271 Hamilton Rd

  • What is 271 Hamilton Rd estimated to be worth?
    Trulia's estimated value for 271 Hamilton Rd in Chappaqua, NY is $1,844,700.
  • What is the price history for 271 Hamilton Rd?
    271 Hamilton Rd in Chappaqua, NY last sold for $445,000 in March 1997.
  • 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 271 Hamilton Rd have air conditioning?
    Yes, 271 Hamilton Rd in Chappaqua, NY has air conditioning.
  • How big is the lot at 271 Hamilton Rd?
    The lot at 271 Hamilton Rd in Chappaqua, NY is about 1 acre.

Explore by feature - Air Conditioning

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Apartments for Rent

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Off Market Homes Near 271 Hamilton Rd

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