56 High Way, Chappaqua, NY 10514
Property image
Property image
OFF MARKET

$2,053,200

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,763 sqft (on 1.24 acres)

56 High Way, Chappaqua, NY 10514

Est. Refi. Payment $13,645/mo*
Refinance Your Home
Currently Off Market - Sold Mar 24, 2022 for $1,375,000

Home Value

Trulia Estimate
$2.05M
Since last month
Decreased$29K (-1.4%)
Since last year
Increased$125K (+6.6%)
Since last sale
Increased$657K (+47.7%)
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 +93% in the last 10 years
MonthEstimated value
2026
September 2026$2.03M
August 2026$2.05M
July 2026$2.06M
June 2026$2.04M
May 2026$2.02M
April 2026$1.96M
March 2026$1.97M
February 2026$1.91M
January 2026$1.9M
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
16 Mountain Peak Rd, Chappaqua, NY
0.30
Single-Family Home
$1,979,000
07/15/26
4
3.5
3,350
33 High Way, Chappaqua, NY
0.09
Single-Family Home
$1,465,000
10/01/25
3
3.5
1,917
14 Crossways, Chappaqua, NY
0.17
Single-Family Home
$1,731,000
08/06/26
4
3.5
3,138
21 Kitchawan Drive, Chappaqua, NY
0.38
Single-Family Home
$1,850,000
06/01/26
4
2.5
3,956
105 Cross Ridge, Chappaqua, NY
0.46
Single-Family Home
$1,950,000
08/07/26
4
3
2,953
6 Algonquin Drive, Chappaqua, NY
0.67
Single-Family Home
$1,391,022
10/23/25
4
3.5
3,776
24 North Way, Chappaqua, NY
0.45
Single-Family Home
$2,375,000
06/24/26
3
3.5
3,638
24 North Way, Chappaqua, NY
0.45
Single-Family Home
$2,375,000
06/12/26
3
3.5
3,960
260 Mill River Road, Chappaqua, NY
0.50
Single-Family Home
$1,382,000
01/12/26
4
4.5
3,561
58 Spring Lane, Chappaqua, NY
0.53
Single-Family Home
$1,815,000
11/10/25
4
2.5
3,457

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
30 Lori Lane, Chappaqua, NY 10514
0.05
$1,351,400
4
3
2,288
Off Market
33 High Way, Chappaqua, NY 10514
0.09
$1,579,100
3
3.5
1,917
Off Market
45 Crossways, Chappaqua, NY 10514
0.10
$1,693,400
3
2.5
2,246
Off Market
29 Crossways, Chappaqua, NY 10514
0.13
$1,683,100
3
2.5
2,946
Off Market
2 West Way, Chappaqua, NY 10514
0.18
$1,735,000
4
3
2,369
Off Market
14 Crossways, Chappaqua, NY 10514
0.17
$1,731,000
4
3.5
3,138
Recently Sold
5 Crossways, Chappaqua, NY 10514
0.18
$1,380,600
4
2.5
2,212
Off Market
55 Shadow Brook Parkway, Chappaqua, NY 10514
0.19
$1,825,700
5
3
3,291
Off Market
339 N Greeley Avenue #339, Chappaqua, NY 10514
0.19
$678,400
2
2
1,563
Off Market
301 N Greeley Avenue, Chappaqua, NY 10514
0.20
$546,400
1
1.5
1,226
Off Market
324 N Greeley Avenue, Chappaqua, NY 10514
0.20
$651,700
2
2
1,608
Off Market
325 N Greeley Avenue, Chappaqua, NY 10514
0.20
$491,700
1
1.5
1,226
Off Market

Local Information

  • Map ViewExplore the area around 56 High Way.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1954
1.24 acre lot
3,763 sqft
$546/sqft
Garage

About this House

C.S. - NO MORE SHOWINGS. Inviting split level home in private Lawrence Farms South offering useable, park-like property, lots of space, light and storage. First floor 4-season porch + 4 levels of living area. Remodeled eat-in kitchen and baths. Potential expansion of 2nd primary suite on 4th level because of additional unfinished attic space. Potential to hook up to town sewer. Yearly homeowner fee of $1250 for maintenance of roads.
56 High Way, Chappaqua, NY 10514 is a 4 bedroom, 4 bathroom, 3,763 sqft single-family home built in 1954. It last sold for $1,375,000 on Mar 24, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,053,200, with a rent estimate of $8,689/month.

Home Details for 56 High Way

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: Central, WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1.7000000476837158
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1954
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 1.24 acres

Price and Tax history

DateEventPrice
Mar 24, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6161091
Sold
$1,375,000
Jan 21, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6161091
Pending
$1,099,000
Jan 17, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6161091
Listed For Sale
$1,099,000

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 56 High Way

  • What is 56 High Way estimated to be worth?
    Trulia's estimated value for 56 High Way in Chappaqua, NY is $2,053,200.
  • What is the price history for 56 High Way?
    56 High Way in Chappaqua, NY last sold for $1,375,000 in March 2022.
  • 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 56 High Way have air conditioning?
    Yes, 56 High Way in Chappaqua, NY has air conditioning.
  • Does 56 High Way have laundry facilities?
    Yes, 56 High Way in Chappaqua, NY has in-unit laundry.

Explore by feature - Air Conditioning

8 rentals with air conditioning in Chappaqua, NY

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Off Market Homes Near 56 High Way

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