5 Crossways, Chappaqua, NY 10514
OFF MARKET

$1,380,600

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,212 sqft

5 Crossways, Chappaqua, NY 10514

Est. Refi. Payment $9,118/mo*
Refinance Your Home
Currently Off Market - Sold Sep 3, 2025 for $1,280,000

Home Value

Trulia Estimate
$1.38M
Since last month
Increased$23K (+1.7%)
Since last year
Increased$98K (+7.6%)
Since last sale
Increased$104K (+8.1%)
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 +125% in the last 10 years
MonthEstimated value
2026
September 2026$1.38M
August 2026$1.38M
July 2026$1.36M
June 2026$1.34M
May 2026$1.33M
March 2026$1.33M
February 2026$1.3M
January 2026$1.31M
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
59 Crest Road, Chappaqua, NY
0.17
Single-Family Home
$1,646,500
10/21/25
4
2.5
2,550
14 Crossways, Chappaqua, NY
0.03
Single-Family Home
$1,731,000
08/06/26
4
3.5
3,138
26 Kings Court, Chappaqua, NY
0.51
Single-Family Home
$1,298,000
12/18/25
4
2.5
2,060
80 Bischoff Avenue, Chappaqua, NY
0.32
Single-Family Home
$715,000
09/01/26
3
2.5
1,299
33 High Way, Chappaqua, NY
0.19
Single-Family Home
$1,465,000
10/01/25
3
3.5
1,917
40 Kings Court, Chappaqua, NY
0.46
Single-Family Home
$2,025,000
07/22/26
3
2.5
3,121
14 Aldridge Road, Chappaqua, NY
0.58
Single-Family Home
$1,345,014
07/29/26
4
2.5
2,478
21 Kitchawan Drive, Chappaqua, NY
0.31
Single-Family Home
$1,850,000
06/01/26
4
2.5
3,956

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
14 Crossways, Chappaqua, NY 10514
0.03
$1,731,000
4
3.5
3,138
Recently Sold
8 Orchard Ridge Terrace, Chappaqua, NY 10514
0.10
$1,287,200
3
3
1,858
Off Market
29 Crossways, Chappaqua, NY 10514
0.05
$1,671,000
3
2.5
2,946
Off Market
45 Crossways, Chappaqua, NY 10514
0.08
$1,693,400
3
2.5
2,246
Off Market
59 Crest Road, Chappaqua, NY 10514
0.17
$1,760,600
4
2.5
2,550
Off Market
94 Orchard Ridge Road, Chappaqua, NY 10514
0.17
$1,532,800
3
2.5
2,134
Off Market
30 Lori Lane, Chappaqua, NY 10514
0.14
$1,340,300
4
3
2,288
Off Market
9 Lori Lane, Chappaqua, NY 10514
0.14
$1,575,000
4
2.5
2,376
For Sale
339 N Greeley Avenue #339, Chappaqua, NY 10514
0.16
$678,400
2
2
1,563
Off Market
211 Bedford Road, Chappaqua, NY 10514
0.22
$2,850,000
4
6
5,536
Recently Sold
301 N Greeley Avenue, Chappaqua, NY 10514
0.16
$550,000
1
1.5
1,226
Off Market

Local Information

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

Home Highlights

Single-Family Home
Built in 1934
2,212 sqft
$624/sqft
Garage

About this House

Move right into this walk-to-town beautifully updated 4-bedroom, 2.5-bath Colonial that offers the perfect balance of classic charm and modern convenience. Just steps from the heart of Chappaqua, this home features an open-concept layout and flexible spaces ideal for everyday living and effortless entertaining.
Step through the storybook Dutch door to a light-filled, double-height entry with a skylight and elegant wraparound staircase. The open floorplan offers flexible spaces that can change and evolve with your lifestyle. The sun-drenched updated chef’s kitchen is the centerpiece of the home with generous custom recessed panel cabinetry, large center island seating and stainless steel appliances. It is open to the living and dining areas with custom built ins. Lovely architectural beamed ceilings and a charming fireplace add warmth and character to the living room.
On the first floor, a versatile bedroom (currently used as a den) boasts elegant French doors and an adjacent half bath. With room to add a shower, this space can easily be transformed into a guest suite or convenient first-floor primary.
Upstairs, the generously sized primary suite offers soaring vaulted ceilings, abundant natural light and a newly renovated ensuite bath with double vanity, whirlpool tub and skylight. The second bedroom also features vaulted ceilings and a cozy loft area that is perfect for a reading nook, study space, or creative hideaway. Another bedroom with expansive closets and a newly updated hall bath complete the upper level.
Tucked behind the home, a charming patio with high-end, easy-care turf and lush, vibrant plantings offers a serene spot to enjoy your morning coffee or unwind at the end of the day.
This home has been thoughtfully transformed with numerous recent upgrades including stunning newly refinished floors, fresh interior and exterior paint, lighting, mechanicals and more.
Don’t miss this special Chappaqua gem where charm, convenience, and turnkey living come together in perfect harmony.
5 Crossways, Chappaqua, NY 10514 is a 4 bedroom, 3 bathroom, 2,212 sqft single-family home built in 1934. It last sold for $1,280,000 on Sep 3, 2025 (16% above the $1,099,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,380,600, with a rent estimate of $6,502/month.
Last check for updates: about 4 hours ago
Listed by Jill Urban, (646) 245-8048
Compass Greater NY, LLC, (914) 238-0676
Bought with: Amy M. Singer, (914) 772-3526, Houlihan Lawrence Inc., (914) 273-9505
Source: OneKey® MLS as distributed by MLS GRID, MLS#844639

Home Details for 5 Crossways

Interior Features

Interior Details
Basement: Full,Storage SpaceNumber of Rooms: 10
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2212 Square Feet
Appliances & Utilities
Utilities: Natural Gas AvailableAppliances: Dishwasher, Dryer, Electric Cooktop, Freezer, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), WasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,Oil,See RemarksHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living Room, Wood BurningHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
No Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageParking Spaces: 1Parking: Garage
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 12

Property Information

Year Built
Year Built: 1934
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Construction Materials: Wood SidingNot Attached Property
Property Information
Included in Sale: Grill, Back patio table and chairsParcel Number: 3600092020000020000016

Price & Status

Price
List Price: $1,099,000
Status Change & Dates
Off Market Date: Tue May 13 2025

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: 2212 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 9148 sqft

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 844639Attic: CrawlAttribution Contact: 914-238-0676Showing Requirements: Appointment Only, Lockbox

Price and Tax history

DateEventPrice
Sep 3, 2025
Source: OneKey® MLS as distributed by MLS GRID #844639
Sold
$1,280,000
May 17, 2025
Source: OneKey® MLS as distributed by MLS GRID #844639
Pending
$1,099,000
May 13, 2025
Source: OneKey® MLS as distributed by MLS GRID #844639
ListingRemoved
$1,099,000
May 1, 2025
Source: OneKey® MLS as distributed by MLS GRID #844639
Listed For Sale
$1,099,000

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 2026-09-15 01:03:31 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 5 Crossways

  • What is 5 Crossways estimated to be worth?
    Trulia's estimated value for 5 Crossways in Chappaqua, NY is $1,380,600.
  • What is the price history for 5 Crossways?
    5 Crossways in Chappaqua, NY last sold for $1,280,000 in September 2025.
  • 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 5 Crossways have air conditioning?
    Yes, 5 Crossways in Chappaqua, NY has air conditioning.
  • Does 5 Crossways have laundry facilities?
    Yes, 5 Crossways in Chappaqua, NY has in-unit laundry.

Explore by feature - Air Conditioning

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