40 Smith Street, Chappaqua, NY 10514
SOLD
APR 28, 2026

$2,065,100

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,658 sqft (on 0.42 acres)

40 Smith Street, Chappaqua, NY 10514

Est. Refi. Payment $13,768/mo*
Refinance Your Home
Currently Off Market - Sold Apr 28, 2026 for $2,000,000 (38% above list price)

Home Value

Trulia Estimate
$2.06M
Since last month
Increased$27K (+1.3%)
Since last year
Increased$595K (+40.2%)
Since last sale
Increased$74K (+3.7%)
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 +161% in the last 10 years
MonthEstimated value
2026
September 2026$2.07M
August 2026$2.07M
July 2026$2.05M
June 2026$2.03M
May 2026$2.01M
April 2026$2M
January 2026$1.49M
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
74 Dogwood Lane, Pleasantville, NY
0.22
Single-Family Home
$1,602,000
07/09/26
4
3
3,656
31 Pierce Drive, Pleasantville, NY
0.30
Single-Family Home
$1,445,000
07/31/26
4
3.5
2,600
200 S Bedford Road, Chappaqua, NY
0.27
Single-Family Home
$1,350,000
04/10/26
3
3
2,364
14 Aldridge Road, Chappaqua, NY
0.38
Single-Family Home
$1,345,014
07/29/26
4
2.5
2,478
606 Washington Avenue, Pleasantville, NY
0.36
Single-Family Home
$840,000
07/11/26
5
2
2,124
23 Brookside Place, Pleasantville, NY
0.37
Single-Family Home
$880,000
12/11/25
4
2
1,690
35 Hamilton Road, Chappaqua, NY
0.41
Single-Family Home
$1,275,000
03/25/26
4
2
2,139

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
34 Glenside Place, Chappaqua, NY 10514
0.11
$1,192,100
3
2
1,880
Off Market
689 Washington Avenue, Pleasantville, NY 10570
0.19
$968,400
3
2.5
2,428
Off Market
679 Washington Avenue, Pleasantville, NY 10570
0.20
$879,600
3
2
1,830
Off Market
74 Dogwood Lane, Pleasantville, NY 10570
0.22
$1,602,000
4
3
3,656
Recently Sold
280 S Bedford Road, Chappaqua, NY 10514
0.21
$1,537,800
4
2.5
2,092
Off Market
40 Aldridge Road, Chappaqua, NY 10514
0.21
$2,218,600
4
4
3,541
Off Market
660 Washington Avenue, Pleasantville, NY 10570
0.27
$727,900
3
2
1,228
Off Market
31 Pierce Drive, Pleasantville, NY 10570
0.30
$1,445,000
4
3.5
2,600
Recently Sold
27 Bedford Road, Pleasantville, NY 10570
0.31
$836,500
5
4
2,916
Recently Sold
200 S Bedford Road, Chappaqua, NY 10514
0.27
$1,350,000
3
3
2,364
Recently Sold
624 Washington Avenue, Pleasantville, NY 10570
0.33
$750,000
3
1
1,326
Recently Sold

Local Information

  • Map ViewExplore the area around 40 Smith Street.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1927
0.42 acre lot
2,658 sqft
$752/sqft
Garage

About this House

Step into a story of timeless elegance in this enchanting 1920s village colonial, where the romantic allure of yesteryear meets the effortless luxury of modern living. Located in the heart of the village, this home offers a lifestyle of rare convenience—just a gentle stroll to vibrant shops, local cafes, and the morning train.
Inside, the home whispers of its storied past through beautifully preserved original details and handcrafted built-ins that exude warmth and character. At its heart lies a breathtaking chef’s eat-in kitchen—a masterfully designed "smart" addition that serves as the soul of the home. Bathed in light, this culinary sanctuary flows seamlessly into a lush, private backyard, creating an idyllic indoor-outdoor sanctuary for quiet morning coffees or alfresco summer evenings.
The journey continues upstairs to four serene bedrooms, plus an office, offering a peaceful retreat for every member of the household. Beyond the main residence, the detached two-car garage provides an unexpected bonus: an expansive second-level storage space with endless potential. Charming in every detail and situated in one of the village's most coveted locations, this is more than just a house; it is the remarkable home you’ve been waiting for. Welcome home.
40 Smith Street, Chappaqua, NY 10514 is a 4 bedroom, 3 bathroom, 2,658 sqft single-family home built in 1927. It last sold for $2,000,000 on Apr 28, 2026 (38% above the $1,450,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,065,100, with a rent estimate of $9,028/month.
Last check for updates: about 5 hours ago
Listed by Joanna Rizoulis, (917) 359-7885
Julia B Fee Sothebys Int. Rlty, (914) 234-0200
Amy Smith Sroka, (914) 523-0678
Julia B Fee Sothebys Int. Rlty, (914) 234-0200
Bought with: Cate A. Hegarty, (914) 582-9898, Compass Greater NY, LLC, (914) 238-0676
Co-Buyer's Agent: Carine Nowak, (914) 490-9877, Compass Greater NY, LLC, (914) 238-0676
Source: OneKey® MLS as distributed by MLS GRID, MLS#953539

Home Details for 40 Smith Street

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 9
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2658 Square Feet
Appliances & Utilities
Utilities: Natural Gas ConnectedAppliances: Dryer, Gas Cooktop, Microwave, Stainless Steel Appliance(s), WasherDryerMicrowaveWasher
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa

Exterior Features

Exterior Home Features
Patio / Porch: PatioFencing: Back YardOther Structures: Garage(s)No Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Detached,Driveway
Frontage
Responsible for Road Maintenance: Public Maintained Road
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses

Days on Market

Cumulative Days on Market: 7

Property Information

Year Built
Year Built: 1927
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Not Attached Property
Property Information
Parcel Number: 3600100015000010000041

Price & Status

Price
List Price: $1,450,000Price Per Sqft: $752/sqft
Status Change & Dates
Off Market Date: Fri Feb 27 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Chappaqua
School Information
Elementary School: Douglas G Grafflin SchoolJr High / Middle School: Robert E Bell SchoolHigh School: Horace Greeley High SchoolHigh School District: Chappaqua

Building

Building Area
Building Area: 2658 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.42 acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 953539Attic: Pull StairsShowing Requirements: Appointment Only

Price and Tax history

DateEventPrice
Apr 28, 2026
Source: OneKey® MLS as distributed by MLS GRID #953539
Sold
$2,000,000
Feb 27, 2026
Source: OneKey® MLS as distributed by MLS GRID #953539
Pending
$1,450,000
Feb 20, 2026
Source: OneKey® MLS as distributed by MLS GRID #953539
Listed For Sale
$1,450,000
Oct 11, 2005
Source: N/A
Sold
$1,107,000

Market trends in Chappaqua

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
14
13MoM

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

Based on information submitted to the MLS GRID as of 2026-09-18 01:03:35 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information

Frequently asked questions about 40 Smith Street

  • What is 40 Smith Street estimated to be worth?
    Trulia's estimated value for 40 Smith Street in Chappaqua, NY is $2,065,100.
  • What is the price history for 40 Smith Street?
    40 Smith Street in Chappaqua, NY last sold for $2,000,000 in April 2026.
  • 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 40 Smith Street have air conditioning?
    Yes, 40 Smith Street in Chappaqua, NY has air conditioning.
  • Does 40 Smith Street have laundry facilities?
    Yes, 40 Smith Street in Chappaqua, NY has in-unit laundry.

Explore by feature - Air Conditioning

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8 rentals with a washer/dryer in Chappaqua, NY

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