44 Pine Cliff Rd, Chappaqua, NY 10514
OFF MARKET

44 Pine Cliff Rd
Chappaqua, NY 10514

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

$1,682,600

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $10,451/mo*
Refinance Your Home

$1,682,600

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $10,451/mo*
Refinance Your Home
5 Beds
3.5 Baths
2,960 sqft
(on 0.74 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

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 History for 44 Pine Cliff Rd

DatePriceEventSource
03/22/2022$1,300,000Sold
N/A
05/05/2016$914,000Sold
OneKey® MLS as distributed by MLS GRID #H4600930
02/23/2016$925,000PendingAgent Provided
01/15/2016$925,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax
Assessment$141,500
Home facts updated by county records

Comparable Sales for 44 Pine Cliff Rd

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
26 Kipp St, Chappaqua, NY
0.34
Single-Family Home
$1,250,000
08/22/25
4
2
2,198
105 Douglas Rd, Chappaqua, NY
0.34
Single-Family Home
$1,150,000
04/17/26
2
1.5
2,220
58 Spring Lane, Chappaqua, NY
0.15
Single-Family Home
$1,815,000
11/10/25
4
2.5
3,457
7 Oak Hill Road, Chappaqua, NY
0.61
Single-Family Home
$1,320,000
06/06/25
4
3
2,628
12 Pond Hill Road, Chappaqua, NY
0.53
Single-Family Home
$1,445,000
08/07/25
3
3
2,652
22 Mountain Peak Road, Chappaqua, NY
0.38
Single-Family Home
$1,850,000
07/15/25
5
4.5
4,419
375 Quaker Road, Chappaqua, NY
0.36
Single-Family Home
$752,000
08/19/25
3
2.5
2,084
55 Kipp St, Chappaqua, NY
0.37
Single-Family Home
$1,900,000
09/05/25
4
3
3,231

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Pine Cliff 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 62 Trulia users voted on each feature.

  • 90 % Say it's quiet

  • 90 % Say car is needed

  • 86 % Say it's dog friendly

  • 85 % Say parking is easy

  • 77 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 73 % Say there's wildlife

  • 71 % Say there's holiday spirit

  • 62 % Say neighbors are friendly

  • 61 % Say they plan to stay for at least 5 years

  • 53 % Say kids play outside

  • 50 % Say it's walkable to restaurants

  • 37 % Say there are community events

  • 36 % Say there are sidewalks

  • 33 % Say streets are well-lit

  • 27 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mereslavin
    "The commute is not too long and metro north is nice. Commuting into grand central is much nicer than commuting into penn."
    0
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  • 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
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  • Trulia User
    "Feels safe and neighborhood friendly a golf course and great restaurant very pretty landescapes and trees beautiful houses "
    0
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  • 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
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  • 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
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  • bal
    "i am so impressed with this litttle jewel of place in Chappaqua "
    0
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  • Susan S.
    "Incredible Old Farm Lake. Families, Singles and Couples all welcome. Convenient to the greatest schools, shopping and restaurants."
    0
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44 Pine Cliff Rd, Chappaqua, NY 10514 is a 5 bedroom, 4 bathroom, 2,960 sqft single-family home built in 1937. This property is not currently available for sale. 44 Pine Cliff Rd was last sold on Mar 22, 2022 for $1,300,000. The current Trulia Estimate for 44 Pine Cliff Rd is $1,682,600.