11 Upland Dr, Chappaqua, NY 10514
OFF MARKET

$1,541,100

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,808 sqft (on 1.03 acres)

11 Upland Dr, Chappaqua, NY 10514

Est. Refi. Payment $9,892/mo*
Refinance Your Home
Currently Off Market - Sold Sep 27, 1991 for $450,000

Home Value

Trulia Estimate
$1.54M
Since last month
Decreased$15K (-1%)
Since last year
Increased$170K (+12.4%)
Since last sale
Increased$1M (+242.5%)
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 +49% in the last 10 years
MonthEstimated value
2026
August 2026$1.54M
August 2026$1.53M
July 2026$1.56M
June 2026$1.48M
May 2026$1.46M
April 2026$1.39M
March 2026$1.38M
February 2026$1.36M
January 2026$1.3M
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 Killington Street, Chappaqua, NY
0.29
Single-Family Home
$1,609,031
06/29/26
4
2.5
2,443
136 Roaring Brook Road, Chappaqua, NY
0.54
Single-Family Home
$700,000
11/21/25
4
5
2,875
4 Southview Road, Chappaqua, NY
0.41
Single-Family Home
$1,275,000
10/06/25
3
2.5
2,111
24 North Way, Chappaqua, NY
0.32
Single-Family Home
$2,375,000
06/24/26
3
3.5
3,638
24 North Way, Chappaqua, NY
0.32
Single-Family Home
$2,375,000
06/12/26
3
3.5
3,960
80 Roaring Brook Road, Chappaqua, NY
0.39
Single-Family Home
$1,290,000
05/22/26
3
3
3,421
21 Kitchawan Drive, Chappaqua, NY
0.51
Single-Family Home
$1,850,000
06/01/26
4
2.5
3,956
35 Overlook Drive, Chappaqua, NY
0.16
Single-Family Home
$2,700,000
11/04/25
4
6.5
5,354
50 Overlook Drive, Chappaqua, NY
0.22
Single-Family Home
$2,000,000
10/29/25
6
5
5,234
33 High Way, Chappaqua, NY
0.56
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
416 Bedford Road, Chappaqua, NY 10514
0.07
$1,486,800
3
3
2,356
Off Market
406 Bedford Road, Chappaqua, NY 10514
0.11
$1,800,000
4
3.5
2,913
For Sale
395 Bedford Road, Chappaqua, NY 10514
0.16
$1,746,900
5
3.5
3,041
Off Market
35 Overlook Drive, Chappaqua, NY 10514
0.16
$2,880,200
4
6.5
5,354
Off Market
50 Overlook Drive, Chappaqua, NY 10514
0.22
$2,135,600
6
5
5,234
Off Market
15 North Way, Chappaqua, NY 10514
0.27
$2,109,600
5
4.5
4,459
Off Market
24 North Way, Chappaqua, NY 10514
0.32
$2,375,000
3
3.5
3,960
Recently Sold
9 Killington Street, Chappaqua, NY 10514
0.28
$1,754,500
3
3
2,625
Off Market
17 Colony Row, Chappaqua, NY 10514
0.32
$2,814,500
4
5
5,680
Off Market
6 Killington Street, Chappaqua, NY 10514
0.29
$1,609,031
4
2.5
2,443
Recently Sold
28 North Way, Chappaqua, NY 10514
0.35
$2,992,400
5
4.5
3,775
Off Market
18 West Way, Chappaqua, NY 10514
0.39
$2,197,100
4
3.5
3,046
Off Market

Local Information

  • Map ViewExplore the area around 11 Upland Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1990
1.03 acre lot
2,808 sqft
$549/sqft
Garage

About this House

This single-family home is located at 11 Upland Dr, Chappaqua, NY. 11 Upland Dr is in Chappaqua, NY and in ZIP code 10514. This property has 4 bedrooms, 3 bathrooms and approximately 2,808 sqft of floor space. This property has a lot size of 1.03 acres and was built in 1990.
11 Upland Dr, Chappaqua, NY 10514 is a 4 bedroom, 3 bathroom, 2,808 sqft single-family home built in 1990. It last sold for $450,000 on Sep 27, 1991. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,541,100.

Home Details for 11 Upland Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Property Information

Year Built
Year Built: 1990
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: 1.03 acres

Price and Tax history

DateEventPrice
Sep 27, 1991
Source: N/A
Sold
$450,000

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 11 Upland Dr

  • What is 11 Upland Dr estimated to be worth?
    Trulia's estimated value for 11 Upland Dr in Chappaqua, NY is $1,541,100.
  • What is the price history for 11 Upland Dr?
    11 Upland Dr in Chappaqua, NY last sold for $450,000 in September 1991.
  • 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 11 Upland Dr have air conditioning?
    Yes, 11 Upland Dr in Chappaqua, NY has air conditioning.
  • How big is the lot at 11 Upland Dr?
    The lot at 11 Upland Dr in Chappaqua, NY is about 1 acre.

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