21 Buttonhook Rd, Chappaqua, NY 10514
Property image
Property image
OFF MARKET

21 Buttonhook Rd
Chappaqua, NY 10514

  • 5 Beds
  • 3 Baths
  • 3,222 sqft (on 1.01 acres)

$1,595,800

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $10,107/mo*
Refinance Your Home

$1,595,800

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $10,107/mo*
Refinance Your Home
5 Beds
3 Baths
3,222 sqft
(on 1.01 acres)

Local Information

  • Map ViewExplore the area around 21 Buttonhook Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1962
Lot Size
1.01 acres
Living Area
3,222 sqft
Price/Sqft
$495
Parking
Garage

About this House

Move right in to this immaculate, light filled home in sought-after neighborhood. Renovated custom Chef's kitchen with granite, stainless appliances and oversized island. Wonderful flow for entertaining with elegant living and dining rooms. Hardwood floors throughout. Lives like a 5 bedroom with additional office and 3 full renovated baths. Newly landscaped property with specimen plantings and walkway make this a must see! Westorchard Elementary. School bus stops in front of the house.
21 Buttonhook Rd, Chappaqua, NY 10514 is a 5 bedroom, 3 bathroom, 3,222 sqft single-family home built in 1962. It last sold for $868,000 on Aug 13, 2015. It is currently off market. The Trulia Estimate is $1,595,800, with a rent estimate of $7,968/month.

Home Details for 21 Buttonhook Rd

Interior Features

Interior Details
BasementNumber of Rooms: 11Types of Rooms: Walk In Closet, Family Room, Laundry Room, Master Bath, Mud Room, Office, Recreation Room
Heating & Cooling
Heating: Baseboard, OtherAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Stucco, WoodPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1962
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 1.01 acres

Price History for 21 Buttonhook Rd

DatePriceEventSource
08/13/2015$868,000Sold
OneKey® MLS as distributed by MLS GRID #H4505737
04/13/2015$899,000PriceChange
Agent Provided
03/20/2015$929,000PriceChange
Agent Provided
02/14/2015$959,000Listed For SaleAgent Provided
11/18/2014$999,000ListingRemovedAgent Provided
09/11/2014$999,000Listed For SaleAgent Provided
08/11/2014$1,029,000ListingRemovedN/A
06/14/2014$1,029,000PriceChange
N/A
06/13/2014$1,069,000Listed For SaleN/A
10/11/2013$665,000Sold
N/A
11/10/2010$665,000Sold
N/A
07/28/2010$499,000PriceChange
Agent Provided
07/01/2010$549,000PriceChange
Agent Provided
05/30/2010$599,900Listed For SaleAgent Provided
06/22/2007$1,200,000Sold
N/A
01/13/2006$765,000Sold
N/A

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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax
Assessment$164,300
Home facts updated by county records

Comparable Sales for 21 Buttonhook Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
26 Mayberry Road, Chappaqua, NY
0.33
Single-Family Home
$1,275,000
10/03/25
5
3
3,200
111 Seven Bridges Road, Chappaqua, NY
0.23
Single-Family Home
$1,375,000
04/20/26
4
2.5
2,069
86 Seven Bridges Road, Chappaqua, NY
0.25
Single-Family Home
$1,375,000
07/30/26
3
2.5
2,407
30 Hitching Post Ln, Chappaqua, NY
0.05
Single-Family Home
$2,250,000
08/26/25
5
3.5
4,178
9 Garey Dr, Chappaqua, NY
0.47
Single-Family Home
$1,240,000
03/09/26
4
4
2,900
74 Seven Bridges Road, Chappaqua, NY
0.29
Single-Family Home
$1,300,000
08/25/25
3
2
2,018
34 Turner Drive, Chappaqua, NY
0.49
Single-Family Home
$1,955,000
07/15/26
4
2.5
3,496
569 Millwood Road, Chappaqua, NY
0.76
Single-Family Home
$1,100,000
12/09/25
4
2.5
3,264
39 Mayberry Road, Chappaqua, NY
0.48
Single-Family Home
$1,550,000
06/26/26
4
3
3,761
18 Hayrake Lane, Chappaqua, NY
0.76
Single-Family Home
$1,725,000
04/27/26
5
3
2,885

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 21 Buttonhook Rd.
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
    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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Garage

Explore by feature - Air Conditioning

11 rentals with air conditioning in Chappaqua, NY

Explore by feature - Washer/dryer

10 rentals with a washer/dryer in Chappaqua, NY

Homes for sale near 21 Buttonhook Rd

Skip to last item
Skip to first item

Off Market Homes Near 21 Buttonhook Rd

Skip to last item
Skip to first item

Frequently asked questions about 21 Buttonhook Rd

  • What is 21 Buttonhook Rd estimated to be worth?
    Trulia's estimated value for 21 Buttonhook Rd in Chappaqua, NY is $1,595,800.
  • What is the price history for 21 Buttonhook Rd?
    21 Buttonhook Rd in Chappaqua, NY last sold for $868,000 in August 2015.
  • 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 21 Buttonhook Rd have air conditioning?
    Yes, 21 Buttonhook Rd in Chappaqua, NY has air conditioning.
  • Does 21 Buttonhook Rd have laundry facilities?
    Yes, 21 Buttonhook Rd in Chappaqua, NY has laundry facilities.