44 Pine Cliff Rd, Chappaqua, NY 10514
Property image
Property image
OFF MARKET

$1,750,900

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 2,960 sqft (on 0.74 acres)

44 Pine Cliff Rd, Chappaqua, NY 10514

Est. Refi. Payment $11,137/mo*
Refinance Your Home
Currently Off Market - Sold Mar 22, 2022 for $1,300,000

Home Value

Trulia Estimate
$1.75M
Since last month
Decreased$9K (-0.5%)
Since last year
Increased$139K (+8.6%)
Since last sale
Increased$452K (+34.7%)
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 +92% in the last 10 years
MonthEstimated value
2026
August 2026$1.75M
July 2026$1.76M
June 2026$1.74M
May 2026$1.68M
April 2026$1.63M
March 2026$1.64M
February 2026$1.61M
January 2026$1.61M
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
21 Kipp Street, Chappaqua, NY
0.30
Single-Family Home
$1,075,000
10/10/25
4
2.5
2,447
29 Meadow Lane, Chappaqua, NY
0.39
Single-Family Home
$1,300,033
03/27/26
4
2.5
2,445
45 Commodore Rd, Chappaqua, NY
0.23
Single-Family Home
$2,680,000
06/18/26
6
4
3,359
105 Douglas Road, Chappaqua, NY
0.34
Single-Family Home
$1,150,000
04/17/26
3
2.5
2,220
58 Spring Lane, Chappaqua, NY
0.15
Single-Family Home
$1,815,000
11/10/25
4
2.5
3,457
105 Cross Ridge, Chappaqua, NY
0.38
Single-Family Home
$1,950,000
08/07/26
4
3
2,953
14 Aldridge Road, Chappaqua, NY
0.55
Single-Family Home
$1,345,014
07/29/26
4
2.5
2,478
14 Crossways, Chappaqua, NY
0.49
Single-Family Home
$1,731,000
08/06/26
4
3.5
3,138
16 Mountain Peak Rd, Chappaqua, NY
0.38
Single-Family Home
$1,979,000
07/15/26
4
3.5
3,350
55 Kipp St, Chappaqua, NY
0.37
Single-Family Home
$1,900,000
09/05/25
4
3
3,231

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
111 Commodore Road, Chappaqua, NY 10514
0.12
$1,293,500
4
2.5
2,352
Off Market
58 Spring Lane, Chappaqua, NY 10514
0.15
$1,815,000
4
2.5
3,457
Recently Sold
275 Quaker Road, Chappaqua, NY 10514
0.16
$1,996,700
5
4
3,750
Off Market
9 Pine Cliff Road, Chappaqua, NY 10514
0.18
$1,612,800
3
3
1,812
Off Market
307 Quaker Road, Chappaqua, NY 10514
0.19
$1,950,000
5
3.5
3,806
Off Market
85 Commodore Road, Chappaqua, NY 10514
0.24
$2,091,600
5
3.5
3,432
Off Market
12 Spring Lane, Chappaqua, NY 10514
0.22
$1,088,700
2
2.5
2,440
Off Market
Leroy Road, Chappaqua, NY 10514
0.29
-
-
-
-
Off Market
Whippoorwill Road, Chappaqua, NY 10514
0.29
-
-
-
-
Off Market
Whippoorwill Road, Chappaqua, NY 10514
0.29
-
-
-
-
Off Market
256 Quaker Road, Chappaqua, NY 10514
0.23
$2,270,900
3
3.5
4,389
Off Market
71 Commodore Road, Chappaqua, NY 10514
0.29
$1,290,000
3
2
1,957
Recently Sold

Local Information

  • Map ViewExplore the area around 44 Pine Cliff Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1937
Lot Size
0.74 acres
Living Area
2,960 sqft
Price/Sqft
$592
Parking
Garage

About this House

Curb appeal! Everyone's favorite house in the neighborhood. Vintage 5BR, 3 1/2 bath, pre-war colonial offering charm, space and great layout. Level land, screened porch, patio, cul-de-sac location. Back stair case to 5th BR/bath, eat-in kitchen with Corian counters, desk area, new Frigidaire oven & generator. Solidly built with plaster walls and steel beams. New 1500 gallon septic tank and fields - 2016. Gas on street services generator, stove top and grill. Walking distance to Pine Cliff Audubon Park (7 acres of walking trails). Close to town, train & shops.
44 Pine Cliff Rd, Chappaqua, NY 10514 is a 5 bedroom, 4 bathroom, 2,960 sqft single-family home built in 1937. It last sold for $1,300,000 on Mar 22, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,750,900, with a rent estimate of $7,966/month.

Home Details for 44 Pine Cliff Rd

Interior Features

Heating & Cooling
Heating: Radiant, OilAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace
Security
Security System

Property Information

Year Built
Year Built: 1937
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Stone, WoodGardenPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.74 acres

Price and Tax history

DateEventPrice
Mar 22, 2022
Source: N/A
Sold
$1,300,000
May 5, 2016
Source: OneKey® MLS as distributed by MLS GRID #H4600930
Sold
$914,000
Feb 23, 2016
Source: Agent Provided
Pending
$925,000
Jan 15, 2016
Source: Agent Provided
Listed For Sale
$925,000

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 44 Pine Cliff Rd

  • What is 44 Pine Cliff Rd estimated to be worth?
    Trulia's estimated value for 44 Pine Cliff Rd in Chappaqua, NY is $1,750,900.
  • What is the price history for 44 Pine Cliff Rd?
    44 Pine Cliff Rd in Chappaqua, NY last sold for $1,300,000 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 44 Pine Cliff Rd have air conditioning?
    Yes, 44 Pine Cliff Rd in Chappaqua, NY has air conditioning.
  • How big is the lot at 44 Pine Cliff Rd?
    The lot at 44 Pine Cliff Rd in Chappaqua, NY is about 0.74 acres (32,237 sq ft).

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