18 Paulding Dr, Chappaqua, NY 10514
Property image
Property image
OFF MARKET

$2,006,600

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 3,932 sqft (on 1.95 acres)

18 Paulding Dr, Chappaqua, NY 10514

Est. Refi. Payment $12,857/mo*
Refinance Your Home
Currently Off Market - Sold Dec 29, 2015 for $875,000

Home Value

Trulia Estimate
$2.01M
Since last month
Decreased$63K (-3%)
Since last year
Increased$291K (+17%)
Since last sale
Increased$1M (+129.3%)
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 +132% in the last 10 years
MonthEstimated value
2026
August 2026$2.01M
August 2026$1.99M
July 2026$2.07M
June 2026$2M
May 2026$1.91M
April 2026$1.83M
March 2026$1.81M
February 2026$1.76M
January 2026$1.77M
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
6 Algonquin Drive, Chappaqua, NY
0.28
Single-Family Home
$1,391,022
10/23/25
4
3.5
3,776
21 Kitchawan Drive, Chappaqua, NY
0.21
Single-Family Home
$1,850,000
06/01/26
4
2.5
3,956
35 Kings Ct, Chappaqua, NY
0.22
Single-Family Home
$1,330,000
08/14/26
4
4
3,314
211 Bedford Road, Chappaqua, NY
0.10
Single-Family Home
$2,850,000
05/07/26
4
6
5,536
14 Crossways, Chappaqua, NY
0.34
Single-Family Home
$1,731,000
08/06/26
4
3.5
3,138
58 Spring Lane, Chappaqua, NY
0.66
Single-Family Home
$1,815,000
11/10/25
4
2.5
3,457
100 Devoe Road, Chappaqua, NY
0.35
Single-Family Home
$1,510,000
08/18/26
3
2.5
2,010
59 Crest Road, Chappaqua, NY
0.22
Single-Family Home
$1,646,500
10/21/25
4
2.5
2,550
26 Kings Court, Chappaqua, NY
0.27
Single-Family Home
$1,298,000
12/18/25
4
2.5
2,060
33 High Way, Chappaqua, NY
0.41
Single-Family Home
$1,465,000
10/01/25
3
3.5
1,917

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
25 Paulding Drive, Chappaqua, NY 10514
0.05
$1,894,700
3
3
2,754
Off Market
211 Bedford Road, Chappaqua, NY 10514
0.10
$2,850,000
4
6
5,536
Recently Sold
28 Brevoort Road, Chappaqua, NY 10514
0.13
$3,516,000
6
4.5
4,949
Off Market
5 Brevoort Road, Chappaqua, NY 10514
0.15
$1,415,000
4
3
3,208
Off Market
40 Kings Court, Chappaqua, NY 10514
0.19
$2,025,000
3
2.5
3,121
Recently Sold
150 N Bedford Road #C9, Chappaqua, NY 10514
0.19
$458,000
1
1
980
Off Market
21 Kitchawan Drive, Chappaqua, NY 10514
0.21
$1,850,000
4
2.5
3,956
Recently Sold
59 Crest Road, Chappaqua, NY 10514
0.22
$1,760,600
4
2.5
2,550
Off Market
10 Algonquin Drive, Chappaqua, NY 10514
0.27
$1,533,500
4
3.5
2,384
Off Market
26 Kings Court, Chappaqua, NY 10514
0.27
$1,298,000
4
2.5
2,060
Recently Sold
6 Algonquin Drive, Chappaqua, NY 10514
0.28
$1,486,900
4
3.5
3,776
Off Market
8 Orchard Ridge Terrace, Chappaqua, NY 10514
0.24
$1,287,200
3
3
1,858
Off Market

Local Information

  • Map ViewExplore the area around 18 Paulding Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1929
1.95 acre lot
3,932 sqft
$510/sqft
Garage

About this House

Nestled in a park-like setting, this enchanting Circa 1929 residence captivates with its colonial charm. Bright, spacious interior features hardwood floors, elegant millwork, arched entryways, built-ins, large windows, and high ceilings. Generous layout highlighted by an updated eat-in-kitchen, gracious formal rooms, comfortable casual areas, and finished walk-out lower level. Mature property framed by stone walls offers delightful spaces for entertaining, play and relaxation, including an oversized deck with steps to a stone patio and fenced yard. A short pathway to town, shops and train.
18 Paulding Dr, Chappaqua, NY 10514 is a 4 bedroom, 5 bathroom, 3,932 sqft single-family home built in 1929. It last sold for $875,000 on Dec 29, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,006,600.

Home Details for 18 Paulding Dr

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1929
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 1.95 acres

Price and Tax history

DateEventPrice
Dec 29, 2015
Source: OneKey® MLS as distributed by MLS GRID #H4542047
Sold
$875,000
Sep 29, 2015
Source: Agent Provided
PriceChange
$929,000
Price decreased by 7%
Sep 15, 2015
Source: Agent Provided
PriceChange
$995,000
Price decreased by 9%
Jun 26, 2015
Source: Agent Provided
PriceChange
$1,095,000
Price decreased by 5%
Apr 14, 2015
Source: Agent Provided
Listed For Sale
$1,150,000

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 18 Paulding Dr

  • What is 18 Paulding Dr estimated to be worth?
    Trulia's estimated value for 18 Paulding Dr in Chappaqua, NY is $2,006,600.
  • What is the price history for 18 Paulding Dr?
    18 Paulding Dr in Chappaqua, NY last sold for $875,000 in December 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 18 Paulding Dr have air conditioning?
    Yes, 18 Paulding Dr in Chappaqua, NY has air conditioning.
  • Does 18 Paulding Dr have laundry facilities?
    Yes, 18 Paulding Dr in Chappaqua, NY has in-unit laundry.

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Off Market Homes Near 18 Paulding Dr

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