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

5 Pine Cliff Rd
Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 3,443 sqft (on 0.37 acres)

$1,624,200

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $10,311/mo*
Refinance Your Home

$1,624,200

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $10,311/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,443 sqft
(on 0.37 acres)

Local Information

  • Map ViewExplore the area around 5 Pine Cliff Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

LOCATION!LOCATION!LOCATION! Sidewalk stroll to town/train/shops. This graciously renovated circa 1920s spacious colonial seamlessly blends old world charm with modern day amenities - quality craftsmanship throughout. Ideal environment for easy living and entertaining, set in desirable neighborhood. Enjoy the privacy of the stone patio with lighted walkway , bordered by perennial gardens and lush level lawn as well as the screened porch. Renovations, additions, hardwood floors, plaster walls and so much more. Audubon Pinecliff Sanctuary at cul de sac's end... A REAL TREAT!
5 Pine Cliff Rd, Chappaqua, NY 10514 is a 4 bedroom, 3 bathroom, 3,443 sqft single-family home built in 1927. It last sold for $900,000 on Jun 3, 2019. It is currently off market. The Trulia Estimate is $1,624,200, with a rent estimate of $7,578/month.

Home Highlights

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

Home Details for 5 Pine Cliff Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: Other, OtherCooling System: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1927
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: 0.37 acres

Price History for 5 Pine Cliff Rd

DatePriceEventSource
06/03/2019$900,000Sold
OneKey® MLS as distributed by MLS GRID #H4839451
03/07/2019$997,500PendingAgent Provided
09/28/2018$997,500PriceChange
Agent Provided
09/13/2018$1,089,000Listed For SaleAgent Provided

Market trends in Chappaqua

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
7MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$160,308
Home facts updated by county records

Comparable Sales for 5 Pine Cliff Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
21 Kipp Street, Chappaqua, NY
0.17
Single-Family Home
$1,075,000
10/10/25
4
2.5
2,447
29 Meadow Lane, Chappaqua, NY
0.21
Single-Family Home
$1,300,033
03/27/26
4
2.5
2,445
26 Kipp St, Chappaqua, NY
0.23
Single-Family Home
$1,250,000
08/22/25
4
2
2,198
29 Begg Drive, Chappaqua, NY
0.38
Single-Family Home
$1,250,023
09/12/25
3
2.5
2,000
105 Douglas Road, Chappaqua, NY
0.30
Single-Family Home
$1,150,000
04/17/26
3
2.5
2,220
55 Kipp St, Chappaqua, NY
0.18
Single-Family Home
$1,900,000
09/05/25
4
3
3,231
375 Quaker Road, Chappaqua, NY
0.30
Single-Family Home
$752,000
08/19/25
3
2.5
2,084
31 Wynnewood Road, Chappaqua, NY
0.52
Single-Family Home
$1,530,000
09/12/25
4
3
2,420
12 Spring Lane, Chappaqua, NY
0.28
Single-Family Home
$999,999
07/14/25
2
2.5
2,440
12 Pond Hill Road, Chappaqua, NY
0.34
Single-Family Home
$1,445,000
08/07/25
3
3
2,652

Nearby homes

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Assigned Schools

These are the assigned schools for 5 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 63 Trulia users voted on each feature.

  • 91 % Say it's quiet

  • 90 % Say car is needed

  • 86 % Say it's dog friendly

  • 85 % Say parking is easy

  • 78 % Say yards are well-kept

  • 75 % Say people would walk alone at night

  • 73 % Say there's wildlife

  • 71 % Say there's holiday spirit

  • 62 % Say neighbors are friendly

  • 62 % 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

  • 33 % Say streets are well-lit

  • 27 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • 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
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  • 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
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  • 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
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  • 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 "
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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
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  • 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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Homes for sale near 5 Pine Cliff Rd

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Off Market Homes Near 5 Pine Cliff Rd

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